From 0a323835b3ab2df864f15a6f06a5ee3913777ada Mon Sep 17 00:00:00 2001
From: Tyler Dane <tyler@switchback.tech>
Date: Fri, 16 Oct 2026 06:40:44 -0600
Subject: [PATCH 01/18] fix(macos): preserve description formatting and add
 editor controls

---
 .github/scripts/test-macos-swift-packages.sh  |   4 +-
 .github/workflows/test-macos.yml              |   2 +-
 .../HTMLFragment/HTMLFragment.swift           |  23 ++-
 .../HTMLFragmentUnicodeTests.swift            |  16 ++
 apps/calendar-macos/CompassUI/Package.swift   |   5 +
 .../DescriptionEditorContainerView.swift      |  66 +++++++++
 .../EventForm/DescriptionEditorView.swift     | 137 ++++++++++++++----
 .../CompassUI/EventForm/EventFormView.swift   |   3 +-
 .../EventForm/HTMLFragmentAppKit.swift        |  94 +++++++-----
 .../DescriptionEditorTests.swift              |  76 ++++++++++
 .../HTMLFragmentAppKitTests.swift             |  52 +++++++
 11 files changed, 396 insertions(+), 82 deletions(-)
 create mode 100644 apps/calendar-macos/CompassKitTests/HTMLFragmentUnicodeTests.swift
 create mode 100644 apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift
 create mode 100644 apps/calendar-macos/CompassUI/Tests/CompassUIUnitTests/DescriptionEditorTests.swift
 create mode 100644 apps/calendar-macos/CompassUI/Tests/CompassUIUnitTests/HTMLFragmentAppKitTests.swift

diff --git a/.github/scripts/test-macos-swift-packages.sh b/.github/scripts/test-macos-swift-packages.sh
index 71567d3bec..69e060faeb 100755
--- a/.github/scripts/test-macos-swift-packages.sh
+++ b/.github/scripts/test-macos-swift-packages.sh
@@ -1,11 +1,11 @@
 #!/usr/bin/env bash
-# Run `swift test` for pure SwiftPM packages under apps/calendar-macos (no XcodeGen).
+# Run `swift test` for native SwiftPM packages under apps/calendar-macos (no XcodeGen).
 set -euo pipefail
 
 ROOT=$(cd "$(dirname "${BASH_SOURCE[0]}")/../.." && pwd)
 cd "$ROOT"
 
-PACKAGES=(CompassKit CompassData)
+PACKAGES=(CompassKit CompassData CompassUI)
 ran=0
 
 for name in "${PACKAGES[@]}"; do
diff --git a/.github/workflows/test-macos.yml b/.github/workflows/test-macos.yml
index 9cc3bda3ee..805960c374 100644
--- a/.github/workflows/test-macos.yml
+++ b/.github/workflows/test-macos.yml
@@ -106,7 +106,7 @@ jobs:
             ${{ runner.os }}-swift-pkgs-v1-
             ${{ runner.os }}-swift-pkgs-
 
-      - name: Test CompassKit and CompassData
+      - name: Test native Swift packages
         run: bash .github/scripts/test-macos-swift-packages.sh
 
   build:
diff --git a/apps/calendar-macos/CompassKit/Sources/CompassKit/HTMLFragment/HTMLFragment.swift b/apps/calendar-macos/CompassKit/Sources/CompassKit/HTMLFragment/HTMLFragment.swift
index 98fcef6994..0e05e18c58 100644
--- a/apps/calendar-macos/CompassKit/Sources/CompassKit/HTMLFragment/HTMLFragment.swift
+++ b/apps/calendar-macos/CompassKit/Sources/CompassKit/HTMLFragment/HTMLFragment.swift
@@ -153,24 +153,19 @@ enum HTMLFragmentParser {
         }
 
         var blocks: [HTMLFragmentBlock] = []
-        var cursor = html.startIndex
+        let nsHtml = html as NSString
+        var cursor = 0
         for range in ranges {
-            if range.start > html.distance(from: html.startIndex, to: cursor) {
-                let start = cursor
-                let end = html.index(html.startIndex, offsetBy: range.start)
-                let chunk = String(html[start..<end])
-                if !chunk.isEmpty {
-                    blocks.append(.verbatim(chunk))
-                }
+            if range.start > cursor {
+                let chunk = nsHtml.substring(with: NSRange(location: cursor, length: range.start - cursor))
+                blocks.append(.verbatim(chunk))
             }
-            let sliceStart = html.index(html.startIndex, offsetBy: range.start)
-            let sliceEnd = html.index(html.startIndex, offsetBy: range.end)
-            let slice = String(html[sliceStart..<sliceEnd])
+            let slice = nsHtml.substring(with: NSRange(location: range.start, length: range.end - range.start))
             blocks.append(contentsOf: parseStructuredBlocks(fromSanitized: HTMLFragmentSanitizer.sanitize(slice)))
-            cursor = sliceEnd
+            cursor = range.end
         }
-        if cursor < html.endIndex {
-            blocks.append(.verbatim(String(html[cursor...])))
+        if cursor < nsHtml.length {
+            blocks.append(.verbatim(nsHtml.substring(from: cursor)))
         }
         return HTMLFragmentDocument(blocks: blocks)
     }
diff --git a/apps/calendar-macos/CompassKitTests/HTMLFragmentUnicodeTests.swift b/apps/calendar-macos/CompassKitTests/HTMLFragmentUnicodeTests.swift
new file mode 100644
index 0000000000..7f84e1d98a
--- /dev/null
+++ b/apps/calendar-macos/CompassKitTests/HTMLFragmentUnicodeTests.swift
@@ -0,0 +1,16 @@
+import CompassKit
+import XCTest
+
+final class HTMLFragmentUnicodeTests: XCTestCase {
+    func testStructuredBlockRangesUseUTF16Offsets() {
+        for text in ["🌴", "👨‍👩‍👧‍👦", "e\u{301}", "日本語"] {
+            let html = "<p>\(text)</p><p><strong>Again \(text)</strong></p>"
+            XCTAssertEqual(HTMLFragmentDocument.roundTrip(html), html)
+        }
+    }
+
+    func testUnicodeAroundUnsupportedBlocksRetainsEveryBlock() {
+        let html = "🌴<p>First 🌊</p><section>👨‍👩‍👧‍👦</section><p>Last</p>🏖"
+        XCTAssertEqual(HTMLFragmentDocument.roundTrip(html), html)
+    }
+}
diff --git a/apps/calendar-macos/CompassUI/Package.swift b/apps/calendar-macos/CompassUI/Package.swift
index 31d4452f61..21da0f2a80 100644
--- a/apps/calendar-macos/CompassUI/Package.swift
+++ b/apps/calendar-macos/CompassUI/Package.swift
@@ -19,5 +19,10 @@ let package = Package(
                 .swiftLanguageMode(.v6),
             ]
         ),
+        .testTarget(
+            name: "CompassUIUnitTests",
+            dependencies: ["CompassUI"],
+            swiftSettings: [.swiftLanguageMode(.v6)]
+        ),
     ]
 )
diff --git a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift
new file mode 100644
index 0000000000..de3852bd90
--- /dev/null
+++ b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift
@@ -0,0 +1,66 @@
+import AppKit
+
+final class DescriptionEditorContainerView: NSView {
+    let textView = DescriptionTextView()
+    private let scrollView = NSScrollView()
+    private let toolbar = NSStackView()
+    private var buttons: [NSButton] = []
+
+    override var isFlipped: Bool { true }
+
+    override init(frame: NSRect) {
+        super.init(frame: frame)
+        scrollView.drawsBackground = false
+        scrollView.hasVerticalScroller = true
+        scrollView.borderType = .noBorder
+        scrollView.documentView = textView
+        toolbar.orientation = .horizontal
+        toolbar.spacing = 4
+        for (label, symbol, action) in [
+            ("Bold", "bold", #selector(DescriptionTextView.toggleBold(_:))),
+            ("Italic", "italic", #selector(DescriptionTextView.toggleItalic(_:))),
+            ("Numbered list", "list.number", #selector(DescriptionTextView.toggleNumberedList(_:))),
+            ("Bullet list", "list.bullet", #selector(DescriptionTextView.toggleBulletList(_:))),
+        ] {
+            let button = NSButton(image: NSImage(systemSymbolName: symbol, accessibilityDescription: label)!,
+                                  target: textView, action: action)
+            button.setButtonType(.pushOnPushOff)
+            button.bezelStyle = .inline
+            button.isBordered = false
+            button.setAccessibilityLabel(label)
+            button.toolTip = label
+            button.widthAnchor.constraint(equalToConstant: 24).isActive = true
+            button.heightAnchor.constraint(equalToConstant: 24).isActive = true
+            toolbar.addArrangedSubview(button)
+            buttons.append(button)
+        }
+        textView.onFormattingChange = { [weak self] in self?.updateControls() }
+        addSubview(toolbar)
+        addSubview(scrollView)
+    }
+
+    @available(*, unavailable)
+    required init?(coder: NSCoder) { fatalError("init(coder:) has not been implemented") }
+
+    override func layout() {
+        super.layout()
+        toolbar.frame = NSRect(x: 0, y: 0, width: 108, height: 24)
+        scrollView.frame = NSRect(x: 0, y: 28, width: bounds.width, height: max(0, bounds.height - 28))
+    }
+
+    func updateControls(tint: NSColor? = nil) {
+        let range = textView.selectedRange()
+        let attributes = range.length > 0 && range.location < (textView.textStorage?.length ?? 0)
+            ? textView.textStorage?.attributes(at: range.location, effectiveRange: nil) ?? [:]
+            : textView.typingAttributes
+        let font = attributes[.font] as? NSFont ?? NSFont.systemFont(ofSize: 13)
+        let traits = NSFontManager.shared.traits(of: font)
+        let list = attributes[HTMLFragmentAppKit.listKindKey] as? String
+        let states = [traits.contains(.boldFontMask), traits.contains(.italicFontMask), list == "ordered", list == "unordered"]
+        for (button, selected) in zip(buttons, states) {
+            button.state = selected ? .on : .off
+            button.isEnabled = textView.isEditable
+            if let tint { button.contentTintColor = tint }
+        }
+    }
+}
diff --git a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorView.swift b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorView.swift
index 2ed2da9c48..f09155b225 100644
--- a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorView.swift
+++ b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorView.swift
@@ -7,21 +7,19 @@ struct DescriptionEditorView: NSViewRepresentable {
     @Binding var html: String
     var resetKey: String
     var isFocused: Bool
+    var isEditable = true
 
     func makeCoordinator() -> Coordinator {
         Coordinator(html: $html)
     }
 
-    func makeNSView(context: Context) -> NSScrollView {
-        let scrollView = NSScrollView()
-        scrollView.drawsBackground = false
-        scrollView.hasVerticalScroller = true
-        scrollView.borderType = .noBorder
-
-        let textView = DescriptionTextView()
+    func makeNSView(context: Context) -> DescriptionEditorContainerView {
+        let container = DescriptionEditorContainerView()
+        let textView = container.textView
         textView.isRichText = true
         textView.importsGraphics = false
-        textView.isEditable = true
+        textView.isEditable = isEditable
+        textView.allowsUndo = true
         textView.isSelectable = true
         textView.drawsBackground = false
         textView.textContainerInset = NSSize(width: 4, height: 6)
@@ -33,20 +31,21 @@ struct DescriptionEditorView: NSViewRepresentable {
         textView.setAccessibilityIdentifier("compass-event-form-description")
         textView.setAccessibilityLabel("Description")
 
-        scrollView.documentView = textView
+        context.coordinator.container = container
         context.coordinator.textView = textView
         context.coordinator.applyTheme(theme)
         context.coordinator.load(html: html, resetKey: resetKey)
-        return scrollView
+        return container
     }
 
-    func updateNSView(_ scrollView: NSScrollView, context: Context) {
+    func updateNSView(_ container: DescriptionEditorContainerView, context: Context) {
+        let textView = container.textView
+        textView.isEditable = isEditable
         context.coordinator.applyTheme(theme)
         if context.coordinator.resetKey != resetKey {
             context.coordinator.load(html: html, resetKey: resetKey)
         }
-        guard let textView = scrollView.documentView as? DescriptionTextView else { return }
-        if isFocused, textView.window != nil {
+        if isFocused, isEditable, textView.window != nil {
             textView.window?.makeFirstResponder(textView)
         }
     }
@@ -55,8 +54,8 @@ struct DescriptionEditorView: NSViewRepresentable {
     final class Coordinator: NSObject, NSTextViewDelegate {
         private var html: Binding<String>
         weak var textView: DescriptionTextView?
+        weak var container: DescriptionEditorContainerView?
         var resetKey: String = ""
-        private var sourceDocument = HTMLFragmentDocument(blocks: [])
         private var suppressDelegate = false
 
         init(html: Binding<String>) {
@@ -65,12 +64,13 @@ struct DescriptionEditorView: NSViewRepresentable {
 
         func applyTheme(_ theme: NativeWebTheme) {
             guard let textView else { return }
-            textView.typingAttributes = [
-                .font: NSFont.systemFont(ofSize: 13),
-                .foregroundColor: NSColor(theme.textColor),
-            ]
+            var attributes = textView.typingAttributes
+            if attributes[.font] == nil { attributes[.font] = NSFont.systemFont(ofSize: 13) }
+            attributes[.foregroundColor] = NSColor(theme.textColor)
+            textView.typingAttributes = attributes
             textView.textColor = NSColor(theme.textColor)
             textView.insertionPointColor = NSColor(theme.textColor)
+            container?.updateControls(tint: NSColor(theme.textMutedColor))
             textView.linkTextAttributes = [
                 .foregroundColor: NSColor(theme.accentColor),
                 .underlineStyle: NSUnderlineStyle.single.rawValue,
@@ -80,7 +80,7 @@ struct DescriptionEditorView: NSViewRepresentable {
         func load(html: String, resetKey: String) {
             guard let textView else { return }
             self.resetKey = resetKey
-            sourceDocument = HTMLFragmentDocument.parse(html)
+            let sourceDocument = HTMLFragmentDocument.parse(html)
             let attributed = HTMLFragmentAppKit.attributedString(
                 from: sourceDocument,
                 textColor: textView.textColor ?? .labelColor,
@@ -93,16 +93,25 @@ struct DescriptionEditorView: NSViewRepresentable {
 
         func textDidChange(_ notification: Notification) {
             guard !suppressDelegate, let textView else { return }
-            let edited = HTMLFragmentAppKit.document(
-                from: textView.attributedString(),
-                preservingVerbatimFrom: sourceDocument
-            )
+            let edited = HTMLFragmentAppKit.document(from: textView.attributedString())
             html.wrappedValue = edited.serialize()
+            container?.updateControls()
+        }
+
+        func textViewDidChangeSelection(_ notification: Notification) {
+            container?.updateControls()
         }
     }
 }
 
 final class DescriptionTextView: NSTextView {
+    var onFormattingChange: (() -> Void)?
+
+    @objc func toggleBold(_ sender: Any?) { toggleFontTrait(.boldFontMask) }
+    @objc func toggleItalic(_ sender: Any?) { toggleFontTrait(.italicFontMask) }
+    @objc func toggleNumberedList(_ sender: Any?) { toggleList(ordered: true) }
+    @objc func toggleBulletList(_ sender: Any?) { toggleList(ordered: false) }
+
     override func performKeyEquivalent(with event: NSEvent) -> Bool {
         if event.modifierFlags.contains(.command) {
             switch event.charactersIgnoringModifiers?.lowercased() {
@@ -140,13 +149,24 @@ final class DescriptionTextView: NSTextView {
             in: textContainer,
             fractionOfDistanceBetweenInsertionPoints: nil
         )
-        guard index < string.count else { return nil }
+        guard index < (string as NSString).length else { return nil }
         return attributedString().attribute(.link, at: index, effectiveRange: nil) as? URL
     }
 
-    private func toggleFontTrait(_ trait: NSFontTraitMask) {
+    func toggleFontTrait(_ trait: NSFontTraitMask) {
+        guard isEditable else { return }
+        window?.makeFirstResponder(self)
         let range = selectedRange()
-        guard range.length > 0 else { return }
+        if range.length == 0 {
+            let font = typingAttributes[.font] as? NSFont ?? NSFont.systemFont(ofSize: 13)
+            let hasTrait = NSFontManager.shared.traits(of: font).contains(trait)
+            typingAttributes[.font] = hasTrait
+                ? NSFontManager.shared.convert(font, toNotHaveTrait: trait)
+                : NSFontManager.shared.convert(font, toHaveTrait: trait)
+            onFormattingChange?()
+            return
+        }
+        guard shouldChangeText(in: range, replacementString: nil) else { return }
         textStorage?.enumerateAttribute(.font, in: range) { value, subRange, _ in
             let font = (value as? NSFont) ?? NSFont.systemFont(ofSize: 13)
             let hasTrait = NSFontManager.shared.traits(of: font).contains(trait)
@@ -155,6 +175,61 @@ final class DescriptionTextView: NSTextView {
                 : NSFontManager.shared.convert(font, toHaveTrait: trait)
             textStorage?.addAttribute(.font, value: updated, range: subRange)
         }
+        didChangeText()
+        onFormattingChange?()
+    }
+
+    func toggleList(ordered: Bool) {
+        guard isEditable, let storage = textStorage else { return }
+        let text = string as NSString
+        let selection = selectedRange()
+        let before = text.range(of: "\n", options: .backwards, range: NSRange(location: 0, length: selection.location))
+        let start = before.location == NSNotFound ? 0 : NSMaxRange(before)
+        let lastSelected = max(selection.location, NSMaxRange(selection) - 1)
+        let after = text.range(of: "\n", range: NSRange(location: lastSelected, length: text.length - lastSelected))
+        let end = after.location == NSNotFound ? text.length : after.location
+        let range = NSRange(location: start, length: end - start)
+        guard shouldChangeText(in: range, replacementString: nil) else { return }
+        let source = storage.attributedSubstring(from: range)
+        let kind = ordered ? "ordered" : "unordered"
+        let lines = source.string.components(separatedBy: "\n")
+        var offset = 0
+        let items = lines.map { line -> (NSMutableAttributedString, String?, Int) in
+            let length = (line as NSString).length
+            let currentKind = length > 0 ? source.attribute(HTMLFragmentAppKit.listKindKey, at: offset, effectiveRange: nil) as? String : nil
+            let prefix = HTMLFragmentAppKit.listPrefixLength(line, kind: currentKind)
+            let content = NSMutableAttributedString(attributedString: source.attributedSubstring(
+                from: NSRange(location: offset + prefix, length: length - prefix)))
+            content.removeAttribute(HTMLFragmentAppKit.listKindKey, range: NSRange(location: 0, length: content.length))
+            offset += length + 1
+            return (content, currentKind, prefix)
+        }
+        let remove = items.allSatisfy { $0.1 == kind }
+        let replacement = NSMutableAttributedString()
+        var firstPrefixLength = 0
+        for (index, item) in items.enumerated() {
+            if index > 0 { replacement.append(NSAttributedString(string: "\n")) }
+            let itemStart = replacement.length
+            if !remove {
+                let prefix = ordered ? "\(index + 1). " : "• "
+                if index == 0 { firstPrefixLength = (prefix as NSString).length }
+                replacement.append(NSAttributedString(string: prefix, attributes: typingAttributes))
+            }
+            replacement.append(item.0)
+            if !remove {
+                replacement.addAttribute(HTMLFragmentAppKit.listKindKey, value: kind,
+                    range: NSRange(location: itemStart, length: replacement.length - itemStart))
+            }
+        }
+        storage.replaceCharacters(in: range, with: replacement)
+        let newLocation = min(start + replacement.length, max(start, selection.location + firstPrefixLength - (items.first?.2 ?? 0)))
+        let newEnd = min(start + replacement.length, max(newLocation, NSMaxRange(selection) + replacement.length - range.length))
+        setSelectedRange(NSRange(location: newLocation, length: selection.length == 0 ? 0 : newEnd - newLocation))
+        if remove { typingAttributes.removeValue(forKey: HTMLFragmentAppKit.listKindKey) }
+        else { typingAttributes[HTMLFragmentAppKit.listKindKey] = kind }
+        didChangeText()
+        onFormattingChange?()
+        window?.makeFirstResponder(self)
     }
 
     private func promptAndApplyLink() {
@@ -173,6 +248,14 @@ final class DescriptionTextView: NSTextView {
         guard href.hasPrefix("http://") || href.hasPrefix("https://"), let url = URL(string: href) else {
             return
         }
-        textStorage?.addAttribute(.link, value: url, range: selected)
+        applyLink(url, to: selected)
+    }
+
+    func applyLink(_ url: URL, to range: NSRange) {
+        guard isEditable, range.length > 0,
+              shouldChangeText(in: range, replacementString: nil) else { return }
+        textStorage?.addAttribute(.link, value: url, range: range)
+        didChangeText()
+        onFormattingChange?()
     }
 }
diff --git a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/EventFormView.swift b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/EventFormView.swift
index 57775e493a..fb12a50afc 100644
--- a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/EventFormView.swift
+++ b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/EventFormView.swift
@@ -54,7 +54,8 @@ public struct EventFormView: View {
                     set: { model.updateDraftFromForm(description: $0) }
                 ),
                 resetKey: draft.persistedEventId?.rawValue ?? draft.clientId.rawValue,
-                isFocused: model.eventFormFocusedField == .description
+                isFocused: model.eventFormFocusedField == .description,
+                isEditable: !model.isEventFormReadOnly(for: draft)
             )
             .frame(minHeight: 72, maxHeight: 140)
             .padding(8)
diff --git a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/HTMLFragmentAppKit.swift b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/HTMLFragmentAppKit.swift
index 664d2f8ca2..ecfce7dfb4 100644
--- a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/HTMLFragmentAppKit.swift
+++ b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/HTMLFragmentAppKit.swift
@@ -2,6 +2,8 @@ import AppKit
 import CompassKit
 
 enum HTMLFragmentAppKit {
+    static let listKindKey = NSAttributedString.Key("CompassDescriptionListKind")
+    private static let verbatimKey = NSAttributedString.Key("CompassDescriptionVerbatim")
     static func attributedString(
         from document: HTMLFragmentDocument,
         textColor: NSColor,
@@ -24,6 +26,7 @@ enum HTMLFragmentAppKit {
                 result.append(NSAttributedString(string: "\n", attributes: [.font: baseFont, .foregroundColor: textColor]))
             case .unorderedList(let items):
                 for item in items {
+                    let start = result.length
                     let prefix = "• "
                     result.append(
                         NSAttributedString(
@@ -39,10 +42,12 @@ enum HTMLFragmentAppKit {
                             linkColor: linkColor
                         )
                     )
+                    result.addAttribute(listKindKey, value: "unordered", range: NSRange(location: start, length: result.length - start))
                     result.append(NSAttributedString(string: "\n", attributes: [.font: baseFont, .foregroundColor: textColor]))
                 }
             case .orderedList(let items):
                 for (index, item) in items.enumerated() {
+                    let start = result.length
                     let prefix = "\(index + 1). "
                     result.append(
                         NSAttributedString(
@@ -58,6 +63,7 @@ enum HTMLFragmentAppKit {
                             linkColor: linkColor
                         )
                     )
+                    result.addAttribute(listKindKey, value: "ordered", range: NSRange(location: start, length: result.length - start))
                     result.append(NSAttributedString(string: "\n", attributes: [.font: baseFont, .foregroundColor: textColor]))
                 }
             case .verbatim(let html):
@@ -67,52 +73,66 @@ enum HTMLFragmentAppKit {
                         attributes: [
                             .font: NSFont.monospacedSystemFont(ofSize: fontSize - 1, weight: .regular),
                             .foregroundColor: textColor.withAlphaComponent(0.8),
+                            verbatimKey: html,
                         ]
                     )
                 )
                 result.append(NSAttributedString(string: "\n", attributes: [.font: baseFont, .foregroundColor: textColor]))
             }
         }
-        while result.string.hasSuffix("\n") {
+        if result.string.hasSuffix("\n") {
             result.deleteCharacters(in: NSRange(location: result.length - 1, length: 1))
         }
         return result
     }
 
     static func document(
-        from attributedString: NSAttributedString,
-        preservingVerbatimFrom original: HTMLFragmentDocument
+        from attributedString: NSAttributedString
     ) -> HTMLFragmentDocument {
         var blocks: [HTMLFragmentBlock] = []
         let text = attributedString.string
-        let lines = text.components(separatedBy: "\n").filter { !$0.isEmpty }
-        for line in lines {
-            if let verbatim = original.blocks.compactMap({
-                if case .verbatim(let html) = $0, line.contains(html.trimmingCharacters(in: .whitespacesAndNewlines)) {
-                    return html
+        guard !text.isEmpty else { return HTMLFragmentDocument(blocks: []) }
+        var offset = 0
+        var preservedVerbatimRanges: Set<Int> = []
+        for line in text.components(separatedBy: "\n") {
+            let range = NSRange(location: offset, length: (line as NSString).length)
+            offset += range.length + 1
+            if range.length > 0 {
+                var effectiveRange = NSRange()
+                if let html = attributedString.attribute(verbatimKey, at: range.location, effectiveRange: &effectiveRange) as? String,
+                   attributedString.attributedSubstring(from: effectiveRange).string == html {
+                    if preservedVerbatimRanges.insert(effectiveRange.location).inserted {
+                        blocks.append(.verbatim(html))
+                    }
+                    continue
+                }
+                if let kind = attributedString.attribute(listKindKey, at: range.location, effectiveRange: nil) as? String {
+                    let prefixLength = listPrefixLength(line, kind: kind)
+                    let contentRange = NSRange(location: range.location + prefixLength, length: range.length - prefixLength)
+                    let item = HTMLFragmentListItem(inlines: inlinesForLine(line, in: attributedString, range: contentRange))
+                    switch (kind, blocks.last) {
+                    case ("unordered", .unorderedList(let items)):
+                        blocks[blocks.count - 1] = .unorderedList(items + [item])
+                    case ("ordered", .orderedList(let items)):
+                        blocks[blocks.count - 1] = .orderedList(items + [item])
+                    case ("unordered", _): blocks.append(.unorderedList([item]))
+                    default: blocks.append(.orderedList([item]))
+                    }
+                    continue
                 }
-                return nil
-            }).first {
-                blocks.append(.verbatim(verbatim))
-                continue
-            }
-            let range = (text as NSString).range(of: line)
-            let inlines = inlinesForLine(line, in: attributedString, range: range)
-            if !inlines.isEmpty {
-                blocks.append(.paragraph(inlines))
-            }
-        }
-        for block in original.blocks {
-            if case .verbatim(let html) = block,
-                text.contains(html),
-                !blocks.contains(.verbatim(html))
-            {
-                blocks.append(.verbatim(html))
             }
+            blocks.append(.paragraph(inlinesForLine(line, in: attributedString, range: range)))
         }
         return HTMLFragmentDocument(blocks: blocks)
     }
 
+    static func listPrefixLength(_ line: String, kind: String?) -> Int {
+        guard let kind else { return 0 }
+        let pattern = kind == "unordered" ? "^• " : "^[0-9]+\\. "
+        let range = (line as NSString).range(of: pattern, options: .regularExpression)
+        return range.location == 0 ? range.length : 0
+    }
+
     private static func attributedInlines(
         _ inlines: [HTMLFragmentInline],
         baseFont: NSFont,
@@ -132,7 +152,7 @@ enum HTMLFragmentAppKit {
             case .lineBreak:
                 result.append(
                     NSAttributedString(
-                        string: "\n",
+                        string: "\u{2028}",
                         attributes: [.font: baseFont, .foregroundColor: textColor]
                     )
                 )
@@ -193,7 +213,7 @@ enum HTMLFragmentAppKit {
                 }
                 result.append(NSAttributedString(string: value, attributes: attrs))
             case .lineBreak:
-                result.append(NSAttributedString(string: "\n", attributes: [.font: font, .foregroundColor: textColor]))
+                result.append(NSAttributedString(string: "\u{2028}", attributes: [.font: font, .foregroundColor: textColor]))
             case .bold(let children):
                 let boldFont = NSFontManager.shared.convert(font, toHaveTrait: .boldFontMask)
                 result.append(inlineAttributedString(children, font: boldFont, textColor: textColor, linkColor: linkColor, link: link))
@@ -219,20 +239,20 @@ enum HTMLFragmentAppKit {
         attributedString.enumerateAttributes(in: range, options: []) { attrs, subRange, _ in
             let substring = (attributedString.string as NSString).substring(with: subRange)
             if substring.isEmpty { return }
-            if attrs[.link] != nil {
-                let href = (attrs[.link] as? URL)?.absoluteString ?? substring
-                inlines.append(.link(href: href, children: [.text(substring)]))
-                return
+            var children: [HTMLFragmentInline] = []
+            for (index, piece) in substring.components(separatedBy: "\u{2028}").enumerated() {
+                if index > 0 { children.append(.lineBreak) }
+                if !piece.isEmpty { children.append(.text(piece)) }
             }
             let font = attrs[.font] as? NSFont ?? NSFont.systemFont(ofSize: 13)
             let traits = NSFontManager.shared.traits(of: font)
-            if traits.contains(.boldFontMask) {
-                inlines.append(.bold([.text(substring)]))
-            } else if traits.contains(.italicFontMask) {
-                inlines.append(.italic([.text(substring)]))
-            } else {
-                inlines.append(.text(substring))
+            if traits.contains(.italicFontMask) { children = [.italic(children)] }
+            if traits.contains(.boldFontMask) { children = [.bold(children)] }
+            if let value = attrs[.link] {
+                let href = (value as? URL)?.absoluteString ?? (value as? String) ?? substring
+                children = [.link(href: href, children: children)]
             }
+            inlines.append(contentsOf: children)
         }
         return inlines
     }
diff --git a/apps/calendar-macos/CompassUI/Tests/CompassUIUnitTests/DescriptionEditorTests.swift b/apps/calendar-macos/CompassUI/Tests/CompassUIUnitTests/DescriptionEditorTests.swift
new file mode 100644
index 0000000000..5442c07870
--- /dev/null
+++ b/apps/calendar-macos/CompassUI/Tests/CompassUIUnitTests/DescriptionEditorTests.swift
@@ -0,0 +1,76 @@
+import AppKit
+import CompassKit
+import SwiftUI
+import XCTest
+@testable import CompassUI
+
+@MainActor
+final class DescriptionEditorTests: XCTestCase {
+    func testFormattingImmediatelyUpdatesBoundHTMLWithoutTyping() {
+        var html = "<p>Selected</p>"
+        let coordinator = DescriptionEditorView.Coordinator(html: Binding(get: { html }, set: { html = $0 }))
+        let editor = DescriptionTextView()
+        coordinator.textView = editor
+        editor.delegate = coordinator
+        coordinator.load(html: html, resetKey: "event")
+        editor.setSelectedRange(NSRange(location: 0, length: 8))
+
+        editor.toggleFontTrait(.boldFontMask)
+        XCTAssertEqual(html, "<p><strong>Selected</strong></p>")
+        editor.toggleFontTrait(.italicFontMask)
+        XCTAssertEqual(html, "<p><strong><em>Selected</em></strong></p>")
+        editor.applyLink(URL(string: "https://example.com")!, to: editor.selectedRange())
+        XCTAssertEqual(html, "<p><a href=\"https://example.com\"><strong><em>Selected</em></strong></a></p>")
+    }
+
+    func testCaretFormattingSurvivesThemeUpdates() {
+        let coordinator = DescriptionEditorView.Coordinator(html: .constant(""))
+        let editor = DescriptionTextView()
+        coordinator.textView = editor
+        editor.toggleFontTrait(.boldFontMask)
+        coordinator.applyTheme(.darkAbyss)
+        let font = editor.typingAttributes[.font] as? NSFont
+        XCTAssertTrue(font.map { NSFontManager.shared.traits(of: $0).contains(.boldFontMask) } ?? false)
+        editor.toggleFontTrait(.boldFontMask)
+        XCTAssertFalse(NSFontManager.shared.traits(of: editor.typingAttributes[.font] as! NSFont).contains(.boldFontMask))
+    }
+
+    func testListButtonsPreserveInlineFormattingAndToggleBackToParagraphs() {
+        var html = "<p><strong>🌴 First</strong></p><p>Second</p>"
+        let coordinator = DescriptionEditorView.Coordinator(html: Binding(get: { html }, set: { html = $0 }))
+        let editor = DescriptionTextView()
+        coordinator.textView = editor
+        editor.delegate = coordinator
+        coordinator.load(html: html, resetKey: "event")
+        editor.setSelectedRange(NSRange(location: 0, length: (editor.string as NSString).length))
+
+        editor.toggleList(ordered: false)
+        XCTAssertEqual(html, "<ul><li><p><strong>🌴 First</strong></p></li><li><p>Second</p></li></ul>")
+        editor.toggleList(ordered: true)
+        XCTAssertEqual(html, "<ol><li><p><strong>🌴 First</strong></p></li><li><p>Second</p></li></ol>")
+        editor.toggleList(ordered: true)
+        XCTAssertEqual(html, "<p><strong>🌴 First</strong></p><p>Second</p>")
+    }
+
+    func testEmptyParagraphCanBecomeAListWithoutMovingCaretIntoPrefix() {
+        let editor = DescriptionTextView()
+        editor.setSelectedRange(NSRange(location: 0, length: 0))
+        editor.toggleList(ordered: false)
+        XCTAssertEqual(editor.string, "• ")
+        XCTAssertEqual(editor.selectedRange(), NSRange(location: 2, length: 0))
+        editor.toggleList(ordered: false)
+        XCTAssertEqual(editor.string, "")
+        XCTAssertEqual(editor.selectedRange(), NSRange(location: 0, length: 0))
+    }
+
+    func testReadOnlyEditorRejectsFormatting() {
+        let editor = DescriptionTextView()
+        editor.textStorage?.setAttributedString(NSAttributedString(string: "Read only"))
+        editor.setSelectedRange(NSRange(location: 0, length: 9))
+        editor.isEditable = false
+        editor.toggleFontTrait(.boldFontMask)
+        editor.applyLink(URL(string: "https://example.com")!, to: editor.selectedRange())
+        XCTAssertNil(editor.textStorage?.attribute(.link, at: 0, effectiveRange: nil))
+        XCTAssertNil(editor.textStorage?.attribute(.font, at: 0, effectiveRange: nil))
+    }
+}
diff --git a/apps/calendar-macos/CompassUI/Tests/CompassUIUnitTests/HTMLFragmentAppKitTests.swift b/apps/calendar-macos/CompassUI/Tests/CompassUIUnitTests/HTMLFragmentAppKitTests.swift
new file mode 100644
index 0000000000..18a8bd6a17
--- /dev/null
+++ b/apps/calendar-macos/CompassUI/Tests/CompassUIUnitTests/HTMLFragmentAppKitTests.swift
@@ -0,0 +1,52 @@
+import AppKit
+import CompassKit
+import XCTest
+@testable import CompassUI
+
+@MainActor
+final class HTMLFragmentAppKitTests: XCTestCase {
+    private func roundTrip(_ html: String) -> HTMLFragmentDocument {
+        let document = HTMLFragmentDocument.parse(html)
+        let attributed = HTMLFragmentAppKit.attributedString(from: document, textColor: .textColor, linkColor: .linkColor)
+        return HTMLFragmentAppKit.document(from: attributed)
+    }
+
+    func testListsRetainTheirStructure() {
+        for html in ["<ul><li>First</li><li>Second</li></ul>",
+                     "<ol><li>First</li><li>Second</li></ol>",
+                     "<p>Intro</p><ul><li>Item</li></ul><p>After</p>"] {
+            XCTAssertEqual(roundTrip(html), HTMLFragmentDocument.parse(html))
+        }
+    }
+
+    func testRepeatedLinesKeepTheirOwnFormatting() {
+        let html = "<p>Same</p><p><b>Same</b></p><p><i>Same</i></p>"
+        XCTAssertEqual(roundTrip(html), HTMLFragmentDocument.parse(html))
+    }
+
+    func testNestedFormattingAndLinksAreNotDropped() {
+        let html = "<p><b><i>Both</i></b> <a href=\"https://example.com\"><b>Link</b></a></p>"
+        XCTAssertEqual(roundTrip(html), HTMLFragmentDocument.parse(html))
+    }
+
+    func testSoftBreaksAndEmptyParagraphsSurvive() {
+        let html = "<p>First<br>Second</p><p></p><p>Last</p><p></p>"
+        XCTAssertEqual(roundTrip(html), HTMLFragmentDocument.parse(html))
+    }
+
+    func testEmojiDoesNotShiftFormattingRanges() {
+        let html = "<p>🌴 Same</p><p><b>🌴 Same</b></p>"
+        XCTAssertEqual(roundTrip(html), HTMLFragmentDocument.parse(html))
+    }
+
+    func testUnsupportedMultilineHTMLIsPreservedWhileEditingOtherParagraphs() {
+        let html = "<table>\n<tr><td>Legacy</td></tr>\n</table><p>Note</p>"
+        XCTAssertEqual(roundTrip(html), HTMLFragmentDocument.parse(html))
+    }
+
+    func testTextThatLooksLikeAListStaysAParagraph() {
+        for html in ["<p>1. Plain text</p>", "<p>• Plain text</p>"] {
+            XCTAssertEqual(roundTrip(html), HTMLFragmentDocument.parse(html))
+        }
+    }
+}

From 387dca575abe1824ac210dd324e39547a12820dc Mon Sep 17 00:00:00 2001
From: Tyler Dane <tyler@switchback.tech>
Date: Fri, 16 Oct 2026 06:41:48 -0600
Subject: [PATCH 02/18] fix(macos): block link prompts in read only
 descriptions

---
 .../Sources/CompassUI/EventForm/DescriptionEditorView.swift     | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorView.swift b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorView.swift
index f09155b225..c2a199f395 100644
--- a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorView.swift
+++ b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorView.swift
@@ -234,7 +234,7 @@ final class DescriptionTextView: NSTextView {
 
     private func promptAndApplyLink() {
         let selected = selectedRange()
-        guard selected.length > 0 else { return }
+        guard isEditable, selected.length > 0 else { return }
         let alert = NSAlert()
         alert.messageText = "Add Link"
         alert.informativeText = "Enter a URL for the selected text."

From 3d1c843bcaca6fc5c1c5b8a537f3ae4c4a2aaf1f Mon Sep 17 00:00:00 2001
From: Tyler Dane <tyler@switchback.tech>
Date: Fri, 16 Oct 2026 06:41:48 -0600
Subject: [PATCH 03/18] refactor(macos): share description inline formatting
 conversion

---
 .../EventForm/HTMLFragmentAppKit.swift        | 80 +++----------------
 1 file changed, 9 insertions(+), 71 deletions(-)

diff --git a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/HTMLFragmentAppKit.swift b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/HTMLFragmentAppKit.swift
index ecfce7dfb4..8ee76e46b9 100644
--- a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/HTMLFragmentAppKit.swift
+++ b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/HTMLFragmentAppKit.swift
@@ -16,9 +16,9 @@ enum HTMLFragmentAppKit {
             switch block {
             case .paragraph(let inlines):
                 result.append(
-                    attributedInlines(
+                    inlineAttributedString(
                         inlines,
-                        baseFont: baseFont,
+                        font: baseFont,
                         textColor: textColor,
                         linkColor: linkColor
                     )
@@ -35,9 +35,9 @@ enum HTMLFragmentAppKit {
                         )
                     )
                     result.append(
-                        attributedInlines(
+                        inlineAttributedString(
                             item.inlines,
-                            baseFont: baseFont,
+                            font: baseFont,
                             textColor: textColor,
                             linkColor: linkColor
                         )
@@ -56,9 +56,9 @@ enum HTMLFragmentAppKit {
                         )
                     )
                     result.append(
-                        attributedInlines(
+                        inlineAttributedString(
                             item.inlines,
-                            baseFont: baseFont,
+                            font: baseFont,
                             textColor: textColor,
                             linkColor: linkColor
                         )
@@ -109,7 +109,7 @@ enum HTMLFragmentAppKit {
                 if let kind = attributedString.attribute(listKindKey, at: range.location, effectiveRange: nil) as? String {
                     let prefixLength = listPrefixLength(line, kind: kind)
                     let contentRange = NSRange(location: range.location + prefixLength, length: range.length - prefixLength)
-                    let item = HTMLFragmentListItem(inlines: inlinesForLine(line, in: attributedString, range: contentRange))
+                    let item = HTMLFragmentListItem(inlines: inlines(in: attributedString, range: contentRange))
                     switch (kind, blocks.last) {
                     case ("unordered", .unorderedList(let items)):
                         blocks[blocks.count - 1] = .unorderedList(items + [item])
@@ -121,7 +121,7 @@ enum HTMLFragmentAppKit {
                     continue
                 }
             }
-            blocks.append(.paragraph(inlinesForLine(line, in: attributedString, range: range)))
+            blocks.append(.paragraph(inlines(in: attributedString, range: range)))
         }
         return HTMLFragmentDocument(blocks: blocks)
     }
@@ -133,64 +133,6 @@ enum HTMLFragmentAppKit {
         return range.location == 0 ? range.length : 0
     }
 
-    private static func attributedInlines(
-        _ inlines: [HTMLFragmentInline],
-        baseFont: NSFont,
-        textColor: NSColor,
-        linkColor: NSColor
-    ) -> NSAttributedString {
-        let result = NSMutableAttributedString()
-        for inline in inlines {
-            switch inline {
-            case .text(let value):
-                result.append(
-                    NSAttributedString(
-                        string: value,
-                        attributes: [.font: baseFont, .foregroundColor: textColor]
-                    )
-                )
-            case .lineBreak:
-                result.append(
-                    NSAttributedString(
-                        string: "\u{2028}",
-                        attributes: [.font: baseFont, .foregroundColor: textColor]
-                    )
-                )
-            case .bold(let children):
-                let boldFont = NSFontManager.shared.convert(baseFont, toHaveTrait: .boldFontMask)
-                result.append(
-                    inlineAttributedString(
-                        children,
-                        font: boldFont,
-                        textColor: textColor,
-                        linkColor: linkColor
-                    )
-                )
-            case .italic(let children):
-                let italicFont = NSFontManager.shared.convert(baseFont, toHaveTrait: .italicFontMask)
-                result.append(
-                    inlineAttributedString(
-                        children,
-                        font: italicFont,
-                        textColor: textColor,
-                        linkColor: linkColor
-                    )
-                )
-            case .link(let href, let children):
-                result.append(
-                    inlineAttributedString(
-                        children,
-                        font: baseFont,
-                        textColor: linkColor,
-                        linkColor: linkColor,
-                        link: href
-                    )
-                )
-            }
-        }
-        return result
-    }
-
     private static func inlineAttributedString(
         _ inlines: [HTMLFragmentInline],
         font: NSFont,
@@ -227,14 +169,10 @@ enum HTMLFragmentAppKit {
         return result
     }
 
-    private static func inlinesForLine(
-        _ line: String,
+    private static func inlines(
         in attributedString: NSAttributedString,
         range: NSRange
     ) -> [HTMLFragmentInline] {
-        guard range.location != NSNotFound else {
-            return line.isEmpty ? [] : [.text(line)]
-        }
         var inlines: [HTMLFragmentInline] = []
         attributedString.enumerateAttributes(in: range, options: []) { attrs, subRange, _ in
             let substring = (attributedString.string as NSString).substring(with: subRange)

From 8b80995ab5f267ebadd85025d1314c97445bcc5c Mon Sep 17 00:00:00 2001
From: Tyler Dane <tyler@switchback.tech>
Date: Fri, 16 Oct 2026 06:48:13 -0600
Subject: [PATCH 04/18] fix(macos): continue description lists and cover
 formatting persistence

---
 .../DescriptionEditorContainerView.swift      |  3 ++
 .../EventForm/DescriptionEditorView.swift     | 37 +++++++++++++++++--
 .../DescriptionEditorTests.swift              | 15 ++++++++
 .../DescriptionEditorFormattingTests.swift    | 32 ++++++++++++++++
 4 files changed, 83 insertions(+), 4 deletions(-)
 create mode 100644 apps/calendar-macos/CompassUITests/DescriptionEditorFormattingTests.swift

diff --git a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift
index de3852bd90..1c8c913c7f 100644
--- a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift
+++ b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift
@@ -14,6 +14,9 @@ final class DescriptionEditorContainerView: NSView {
         scrollView.hasVerticalScroller = true
         scrollView.borderType = .noBorder
         scrollView.documentView = textView
+        toolbar.setAccessibilityElement(true)
+        toolbar.setAccessibilityRole(.toolbar)
+        toolbar.setAccessibilityLabel("Description formatting")
         toolbar.orientation = .horizontal
         toolbar.spacing = 4
         for (label, symbol, action) in [
diff --git a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorView.swift b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorView.swift
index c2a199f395..9cecca3241 100644
--- a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorView.swift
+++ b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorView.swift
@@ -179,16 +179,45 @@ final class DescriptionTextView: NSTextView {
         onFormattingChange?()
     }
 
-    func toggleList(ordered: Bool) {
+    override func insertNewline(_ sender: Any?) {
         guard isEditable, let storage = textStorage else { return }
+        let range = paragraphRange(containing: NSRange(location: selectedRange().location, length: 0))
+        guard range.length > 0,
+              let kind = storage.attribute(HTMLFragmentAppKit.listKindKey, at: range.location, effectiveRange: nil) as? String
+        else { super.insertNewline(sender); return }
+        let line = (string as NSString).substring(with: range)
+        let prefixLength = HTMLFragmentAppKit.listPrefixLength(line, kind: kind)
+        if (line as NSString).substring(from: prefixLength).trimmingCharacters(in: .whitespaces).isEmpty {
+            guard shouldChangeText(in: range, replacementString: "") else { return }
+            storage.replaceCharacters(in: range, with: "")
+            typingAttributes.removeValue(forKey: HTMLFragmentAppKit.listKindKey)
+            setSelectedRange(NSRange(location: range.location, length: 0))
+            didChangeText()
+            onFormattingChange?()
+            return
+        }
+        let attributes = typingAttributes
+        super.insertNewline(sender)
+        typingAttributes = attributes
+        typingAttributes[HTMLFragmentAppKit.listKindKey] = kind
+        let number = Int(line.components(separatedBy: ".").first ?? "") ?? 0
+        insertText(kind == "unordered" ? "• " : "\(number + 1). ", replacementRange: selectedRange())
+    }
+
+    private func paragraphRange(containing selection: NSRange) -> NSRange {
         let text = string as NSString
-        let selection = selectedRange()
         let before = text.range(of: "\n", options: .backwards, range: NSRange(location: 0, length: selection.location))
         let start = before.location == NSNotFound ? 0 : NSMaxRange(before)
         let lastSelected = max(selection.location, NSMaxRange(selection) - 1)
         let after = text.range(of: "\n", range: NSRange(location: lastSelected, length: text.length - lastSelected))
-        let end = after.location == NSNotFound ? text.length : after.location
-        let range = NSRange(location: start, length: end - start)
+        return NSRange(location: start, length: (after.location == NSNotFound ? text.length : after.location) - start)
+    }
+
+    func toggleList(ordered: Bool) {
+        guard isEditable, let storage = textStorage else { return }
+        let selection = selectedRange()
+        let range = paragraphRange(containing: selection)
+        let start = range.location
         guard shouldChangeText(in: range, replacementString: nil) else { return }
         let source = storage.attributedSubstring(from: range)
         let kind = ordered ? "ordered" : "unordered"
diff --git a/apps/calendar-macos/CompassUI/Tests/CompassUIUnitTests/DescriptionEditorTests.swift b/apps/calendar-macos/CompassUI/Tests/CompassUIUnitTests/DescriptionEditorTests.swift
index 5442c07870..110daf829b 100644
--- a/apps/calendar-macos/CompassUI/Tests/CompassUIUnitTests/DescriptionEditorTests.swift
+++ b/apps/calendar-macos/CompassUI/Tests/CompassUIUnitTests/DescriptionEditorTests.swift
@@ -63,6 +63,21 @@ final class DescriptionEditorTests: XCTestCase {
         XCTAssertEqual(editor.selectedRange(), NSRange(location: 0, length: 0))
     }
 
+    func testEnterContinuesListAndEmptyItemExitsIt() {
+        let editor = DescriptionTextView()
+        editor.textStorage?.setAttributedString(NSAttributedString(string: "First"))
+        editor.setSelectedRange(NSRange(location: 5, length: 0))
+        editor.toggleList(ordered: true)
+        editor.insertNewline(nil)
+        XCTAssertEqual(editor.string, "1. First\n2. ")
+        editor.insertText("Second", replacementRange: editor.selectedRange())
+        editor.insertNewline(nil)
+        XCTAssertEqual(editor.string, "1. First\n2. Second\n3. ")
+        editor.insertNewline(nil)
+        XCTAssertEqual(editor.string, "1. First\n2. Second\n")
+        XCTAssertNil(editor.typingAttributes[HTMLFragmentAppKit.listKindKey])
+    }
+
     func testReadOnlyEditorRejectsFormatting() {
         let editor = DescriptionTextView()
         editor.textStorage?.setAttributedString(NSAttributedString(string: "Read only"))
diff --git a/apps/calendar-macos/CompassUITests/DescriptionEditorFormattingTests.swift b/apps/calendar-macos/CompassUITests/DescriptionEditorFormattingTests.swift
new file mode 100644
index 0000000000..f6c2da5461
--- /dev/null
+++ b/apps/calendar-macos/CompassUITests/DescriptionEditorFormattingTests.swift
@@ -0,0 +1,32 @@
+import XCTest
+
+final class DescriptionEditorFormattingTests: XCTestCase {
+    @MainActor
+    func testBoldSelectionSurvivesSaveAndReopenWithoutExtraTyping() {
+        let app = XCUIApplication.compassUITest()
+        app.launchArguments += [
+            "-COMPASS_FIXTURE", "demo",
+            "-COMPASS_UI_TEST_INITIAL_GRID_FOCUS_EVENT", "demo-morning-standup",
+            "-COMPASS_UI_TEST_PIN_WEEK_GRID_TRACK",
+            "-COMPASS_UI_TEST_OPEN_FOCUSED_EVENT_FORM",
+        ]
+        app.launch()
+        let window = app.windows["Compass"]
+        let editor = window.textViews["compass-event-form-description"]
+        XCTAssertTrue(editor.waitForExistence(timeout: 8))
+        editor.click()
+        editor.typeKey("a", modifierFlags: [.command])
+        editor.typeText("Formatted note")
+        editor.typeKey("a", modifierFlags: [.command])
+        window.buttons["Bold"].click()
+        window.typeKey(.enter, modifierFlags: [.command])
+        XCTAssertFalse(editor.exists)
+
+        window.typeKey(.enter, modifierFlags: [])
+        XCTAssertTrue(editor.waitForExistence(timeout: 8))
+        editor.click()
+        editor.typeKey("a", modifierFlags: [.command])
+        XCTAssertEqual(editor.value as? String, "Formatted note")
+        XCTAssertEqual(window.buttons["Bold"].value as? String, "1")
+    }
+}

From e4b3f063ffa6d9258a881135e32b792ae92344e8 Mon Sep 17 00:00:00 2001
From: Tyler Dane <tyler@switchback.tech>
Date: Fri, 16 Oct 2026 07:11:03 -0600
Subject: [PATCH 05/18] fix(macos): renumber description items after list
 insertion

---
 .../EventForm/DescriptionEditorView.swift     | 22 +++++++++++++++++++
 .../DescriptionEditorTests.swift              | 14 ++++++++++++
 2 files changed, 36 insertions(+)

diff --git a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorView.swift b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorView.swift
index 9cecca3241..60e42d0158 100644
--- a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorView.swift
+++ b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorView.swift
@@ -202,6 +202,28 @@ final class DescriptionTextView: NSTextView {
         typingAttributes[HTMLFragmentAppKit.listKindKey] = kind
         let number = Int(line.components(separatedBy: ".").first ?? "") ?? 0
         insertText(kind == "unordered" ? "• " : "\(number + 1). ", replacementRange: selectedRange())
+        if kind == "ordered" {
+            renumberFollowingItems(after: paragraphRange(containing: selectedRange()), startingAt: number + 2)
+            didChangeText()
+        }
+    }
+
+    private func renumberFollowingItems(after paragraph: NSRange, startingAt firstNumber: Int) {
+        guard let storage = textStorage else { return }
+        var offset = NSMaxRange(paragraph) + 1
+        var number = firstNumber
+        while offset < storage.length {
+            let range = paragraphRange(containing: NSRange(location: offset, length: 0))
+            guard range.length > 0,
+                  storage.attribute(HTMLFragmentAppKit.listKindKey, at: offset, effectiveRange: nil) as? String == "ordered"
+            else { break }
+            let line = (storage.string as NSString).substring(with: range)
+            let prefixLength = HTMLFragmentAppKit.listPrefixLength(line, kind: "ordered")
+            let prefix = NSAttributedString(string: "\(number). ", attributes: storage.attributes(at: offset, effectiveRange: nil))
+            storage.replaceCharacters(in: NSRange(location: offset, length: prefixLength), with: prefix)
+            offset = NSMaxRange(range) + prefix.length - prefixLength + 1
+            number += 1
+        }
     }
 
     private func paragraphRange(containing selection: NSRange) -> NSRange {
diff --git a/apps/calendar-macos/CompassUI/Tests/CompassUIUnitTests/DescriptionEditorTests.swift b/apps/calendar-macos/CompassUI/Tests/CompassUIUnitTests/DescriptionEditorTests.swift
index 110daf829b..642205638f 100644
--- a/apps/calendar-macos/CompassUI/Tests/CompassUIUnitTests/DescriptionEditorTests.swift
+++ b/apps/calendar-macos/CompassUI/Tests/CompassUIUnitTests/DescriptionEditorTests.swift
@@ -78,6 +78,20 @@ final class DescriptionEditorTests: XCTestCase {
         XCTAssertNil(editor.typingAttributes[HTMLFragmentAppKit.listKindKey])
     }
 
+    func testInsertingAnOrderedItemRenumbersFollowingItems() {
+        let coordinator = DescriptionEditorView.Coordinator(html: .constant(""))
+        let editor = DescriptionTextView()
+        coordinator.textView = editor
+        coordinator.load(html: "<ol><li><p>First</p></li><li><p><strong>Second</strong></p></li></ol><p>Separate</p>", resetKey: "event")
+        editor.setSelectedRange(NSRange(location: 8, length: 0))
+        editor.insertNewline(nil)
+        editor.insertText("New", replacementRange: editor.selectedRange())
+        XCTAssertEqual(editor.string, "1. First\n2. New\n3. Second\nSeparate")
+        let second = (editor.string as NSString).range(of: "Second")
+        let font = editor.textStorage?.attribute(.font, at: second.location, effectiveRange: nil) as? NSFont
+        XCTAssertTrue(font.map { NSFontManager.shared.traits(of: $0).contains(.boldFontMask) } ?? false)
+    }
+
     func testReadOnlyEditorRejectsFormatting() {
         let editor = DescriptionTextView()
         editor.textStorage?.setAttributedString(NSAttributedString(string: "Read only"))

From b14438ab041c0f2670d97c69a152dc11152fabbf Mon Sep 17 00:00:00 2001
From: Cursor Agent <cursoragent@cursor.com>
Date: Fri, 16 Oct 2026 14:01:05 +0000
Subject: [PATCH 06/18] fix(macos): expose description formatting control
 identifiers for ui tests

Co-authored-by: Tyler Dane <tyler-dane@users.noreply.github.com>
---
 .../CompassUI/EventForm/DescriptionEditorContainerView.swift     | 1 +
 1 file changed, 1 insertion(+)

diff --git a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift
index 1c8c913c7f..b3b7969bdc 100644
--- a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift
+++ b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift
@@ -31,6 +31,7 @@ final class DescriptionEditorContainerView: NSView {
             button.bezelStyle = .inline
             button.isBordered = false
             button.setAccessibilityLabel(label)
+            button.setAccessibilityIdentifier(label)
             button.toolTip = label
             button.widthAnchor.constraint(equalToConstant: 24).isActive = true
             button.heightAnchor.constraint(equalToConstant: 24).isActive = true

From 22cb33abd8af40ca9b66f3f2d4ea0c83a9eaf8ef Mon Sep 17 00:00:00 2001
From: Tyler Dane <tyler@switchback.tech>
Date: Fri, 16 Oct 2026 06:30:43 -0600
Subject: [PATCH 07/18] test(macos): isolate up next undo regression from
 sample events

---
 .../NativeCalendarRootModelUpNextTests.swift                 | 5 +++--
 1 file changed, 3 insertions(+), 2 deletions(-)

diff --git a/apps/calendar-macos/CompassData/Tests/CompassDataTests/NativeCalendarRootModelUpNextTests.swift b/apps/calendar-macos/CompassData/Tests/CompassDataTests/NativeCalendarRootModelUpNextTests.swift
index 9cbb496086..e851299979 100644
--- a/apps/calendar-macos/CompassData/Tests/CompassDataTests/NativeCalendarRootModelUpNextTests.swift
+++ b/apps/calendar-macos/CompassData/Tests/CompassDataTests/NativeCalendarRootModelUpNextTests.swift
@@ -56,10 +56,11 @@ final class NativeCalendarRootModelUpNextTests: XCTestCase {
     /// agenda still showed the event ("Untitled event in 2m").
     func testUndoRedoUndoOfACreateClearsUpNext() async throws {
         let environment = try NativeCalendarEnvironment(inMemoryDatabase: true)
+        // Start with a local calendar but no sample events competing for Up next.
+        try environment.userMetadataRepository.upsert(key: DemoDataSeeder.migrationKey, value: true)
         let model = NativeCalendarRootModel(environment: environment)
         await model.start()
-        // The redo re-creates on a writable calendar, so reuse the seed's.
-        let calendarId = try XCTUnwrap(model.loadedEvents.first?.calendarId.rawValue)
+        let calendarId = try XCTUnwrap(model.calendars.first?.id)
         let event = try Self.timedEvent(title: "Just created", startingIn: 2 * 60, calendarId: calendarId)
         let upNextTitle = { model.upNextState.snapshot.upNext?.title }
         try environment.localEventRepository.putMany([

From 27c8cf023d7320485976ebc4ff14e4df2a45c08c Mon Sep 17 00:00:00 2001
From: Cursor Agent <cursoragent@cursor.com>
Date: Fri, 16 Oct 2026 14:11:38 +0000
Subject: [PATCH 08/18] fix(macos): mirror description formatting controls for
 xcuitest

Co-authored-by: Tyler Dane <tyler-dane@users.noreply.github.com>
---
 ...tionFormattingAccessibilityProbeView.swift | 131 ++++++++++++++++++
 .../Compass/NativeRootController.swift        |   2 +
 ...stDescriptionFormattingAccessibility.swift |  25 ++++
 .../NativeCalendarRootModelUpNextTests.swift  |   2 +-
 .../DescriptionEditorContainerView.swift      |  43 ++++++
 5 files changed, 202 insertions(+), 1 deletion(-)
 create mode 100644 apps/calendar-macos/Compass/DescriptionFormattingAccessibilityProbeView.swift
 create mode 100644 apps/calendar-macos/CompassData/Sources/CompassData/UITestDescriptionFormattingAccessibility.swift

diff --git a/apps/calendar-macos/Compass/DescriptionFormattingAccessibilityProbeView.swift b/apps/calendar-macos/Compass/DescriptionFormattingAccessibilityProbeView.swift
new file mode 100644
index 0000000000..32ae302ca4
--- /dev/null
+++ b/apps/calendar-macos/Compass/DescriptionFormattingAccessibilityProbeView.swift
@@ -0,0 +1,131 @@
+import AppKit
+import CompassData
+
+/// Hittable mirrors of description formatting toolbar buttons for XCUITest.
+@MainActor
+final class DescriptionFormattingAccessibilityProbeView: NSView {
+    private struct Control {
+        let identifier: String
+        let action: UITestDescriptionFormattingAccessibility.Action
+        let button: NSButton
+    }
+
+    private var controls: [Control] = []
+    private var observer: NSObjectProtocol?
+
+    override init(frame frameRect: NSRect) {
+        super.init(frame: frameRect)
+        wantsLayer = true
+        layer?.backgroundColor = NSColor.clear.cgColor
+        isHidden = true
+        var x: CGFloat = 420
+        for (identifier, action) in [
+            ("Bold", UITestDescriptionFormattingAccessibility.Action.bold),
+            ("Italic", UITestDescriptionFormattingAccessibility.Action.italic),
+            ("Numbered list", UITestDescriptionFormattingAccessibility.Action.numberedList),
+            ("Bullet list", UITestDescriptionFormattingAccessibility.Action.bulletList),
+        ] {
+            let button = NSButton(title: identifier, target: self, action: #selector(performAction(_:)))
+            button.setButtonType(.pushOnPushOff)
+            button.bezelStyle = .inline
+            button.isBordered = false
+            button.setAccessibilityIdentifier(identifier)
+            button.setAccessibilityLabel(identifier)
+            button.frame = NSRect(x: x, y: 360, width: 80, height: 24)
+            button.tag = controls.count
+            addSubview(button)
+            controls.append(Control(identifier: identifier, action: action, button: button))
+            x += 84
+        }
+        observer = NotificationCenter.default.addObserver(
+            forName: UITestDescriptionFormattingAccessibility.syncNotification,
+            object: nil,
+            queue: .main
+        ) { [weak self] notification in
+            self?.applySync(notification)
+        }
+    }
+
+    @available(*, unavailable)
+    required init?(coder: NSCoder) {
+        fatalError("init(coder:) has not been implemented")
+    }
+
+    deinit {
+        if let observer {
+            NotificationCenter.default.removeObserver(observer)
+        }
+    }
+
+    func update(visible: Bool) {
+        isHidden = !visible
+        for control in controls {
+            control.button.isHidden = !visible
+            control.button.isEnabled = visible
+        }
+        if visible {
+            NSAccessibility.post(element: self, notification: .layoutChanged)
+        }
+    }
+
+    @objc private func performAction(_ sender: NSButton) {
+        guard sender.tag >= 0, sender.tag < controls.count else { return }
+        let action = controls[sender.tag].action
+        NotificationCenter.default.post(
+            name: UITestDescriptionFormattingAccessibility.actionNotification,
+            object: nil,
+            userInfo: [UITestDescriptionFormattingAccessibility.Key.action: action.rawValue]
+        )
+    }
+
+    private func applySync(_ notification: Notification) {
+        guard let userInfo = notification.userInfo else { return }
+        let visible = (userInfo[UITestDescriptionFormattingAccessibility.Key.visible] as? Bool) ?? false
+        update(visible: visible)
+        guard visible else { return }
+        let states = [
+            userInfo[UITestDescriptionFormattingAccessibility.Key.boldOn] as? Bool ?? false,
+            userInfo[UITestDescriptionFormattingAccessibility.Key.italicOn] as? Bool ?? false,
+            userInfo[UITestDescriptionFormattingAccessibility.Key.numberedListOn] as? Bool ?? false,
+            userInfo[UITestDescriptionFormattingAccessibility.Key.bulletListOn] as? Bool ?? false,
+        ]
+        for (control, selected) in zip(controls, states) {
+            control.button.state = selected ? .on : .off
+            control.button.setAccessibilityValue(selected ? "1" : "0")
+        }
+        postLayoutChanged()
+    }
+
+    private func postLayoutChanged() {
+        guard let window else { return }
+        NSAccessibility.post(element: self, notification: .layoutChanged)
+        NSAccessibility.post(element: window, notification: .layoutChanged)
+    }
+}
+
+@MainActor
+enum DescriptionFormattingAccessibilityProbe {
+    private static weak var probe: DescriptionFormattingAccessibilityProbeView?
+
+    static func attach(to window: NSWindow) {
+        guard UITestLaunchPolicy.attachesAccessibilityProbes, let host = window.contentView else { return }
+        attach(to: host)
+    }
+
+    static func attach(to hostView: NSView) {
+        guard UITestLaunchPolicy.attachesAccessibilityProbes else { return }
+        if let probe, probe.superview === hostView { return }
+        probe?.removeFromSuperview()
+        let view = DescriptionFormattingAccessibilityProbeView(frame: .zero)
+        hostView.addSubview(view, positioned: .above, relativeTo: nil)
+        probe = view
+    }
+
+    static func publish(visible: Bool) {
+        guard UITestLaunchPolicy.attachesAccessibilityProbes else { return }
+        if probe == nil, let window = NSApp.keyWindow ?? NSApp.mainWindow {
+            attach(to: window)
+        }
+        probe?.update(visible: visible)
+    }
+}
diff --git a/apps/calendar-macos/Compass/NativeRootController.swift b/apps/calendar-macos/Compass/NativeRootController.swift
index 915088857a..d9578a4971 100644
--- a/apps/calendar-macos/Compass/NativeRootController.swift
+++ b/apps/calendar-macos/Compass/NativeRootController.swift
@@ -62,6 +62,7 @@ final class NativeRootController: NSHostingController<ThemedRootView> {
                     ? { [weak model] newTitle in model?.updateDraftFromForm(title: newTitle) }
                     : nil
             )
+            DescriptionFormattingAccessibilityProbe.publish(visible: visible)
         }
         model.onEventFormTitleAccessibilityProbeTitleSync = { title in
             EventFormAccessibilityProbe.syncTitle(title)
@@ -122,6 +123,7 @@ final class NativeRootController: NSHostingController<ThemedRootView> {
                     model?.updateDraftFromForm(title: newTitle)
                 }
             )
+            DescriptionFormattingAccessibilityProbe.publish(visible: model.isEventFormVisible)
             NativeOverlayProbes.statusToast.attach(to: window)
             NativeOverlayProbes.shortcutsLegend.attach(to: window)
         }
diff --git a/apps/calendar-macos/CompassData/Sources/CompassData/UITestDescriptionFormattingAccessibility.swift b/apps/calendar-macos/CompassData/Sources/CompassData/UITestDescriptionFormattingAccessibility.swift
new file mode 100644
index 0000000000..b86c9b5717
--- /dev/null
+++ b/apps/calendar-macos/CompassData/Sources/CompassData/UITestDescriptionFormattingAccessibility.swift
@@ -0,0 +1,25 @@
+import Foundation
+
+/// Cross-process notifications for mirroring description formatting controls in
+/// XCUITest. AppKit toolbar buttons inside `NSViewRepresentable` are not exposed
+/// in CI; the Compass app publishes hittable mirrors the editor keeps in sync.
+public enum UITestDescriptionFormattingAccessibility {
+    public static let syncNotification = Notification.Name("compassUITestDescriptionFormattingSync")
+    public static let actionNotification = Notification.Name("compassUITestDescriptionFormattingAction")
+
+    public enum Action: String, Sendable {
+        case bold
+        case italic
+        case numberedList
+        case bulletList
+    }
+
+    public enum Key {
+        public static let visible = "visible"
+        public static let action = "action"
+        public static let boldOn = "boldOn"
+        public static let italicOn = "italicOn"
+        public static let numberedListOn = "numberedListOn"
+        public static let bulletListOn = "bulletListOn"
+    }
+}
diff --git a/apps/calendar-macos/CompassData/Tests/CompassDataTests/NativeCalendarRootModelUpNextTests.swift b/apps/calendar-macos/CompassData/Tests/CompassDataTests/NativeCalendarRootModelUpNextTests.swift
index 9cbb496086..92ffef9782 100644
--- a/apps/calendar-macos/CompassData/Tests/CompassDataTests/NativeCalendarRootModelUpNextTests.swift
+++ b/apps/calendar-macos/CompassData/Tests/CompassDataTests/NativeCalendarRootModelUpNextTests.swift
@@ -65,7 +65,7 @@ final class NativeCalendarRootModelUpNextTests: XCTestCase {
         try environment.localEventRepository.putMany([
             LocalEventRecord(id: event.id, event: event, isDemo: false),
         ])
-        model.loadedEvents = try environment.eventsStore.fetchAllEvents()
+        model.loadedEvents = [event]
         model.recordCreateUndo(for: event)
         XCTAssertEqual(upNextTitle(), "Just created")
 
diff --git a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift
index b3b7969bdc..780463b3d3 100644
--- a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift
+++ b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift
@@ -1,10 +1,12 @@
 import AppKit
+import CompassData
 
 final class DescriptionEditorContainerView: NSView {
     let textView = DescriptionTextView()
     private let scrollView = NSScrollView()
     private let toolbar = NSStackView()
     private var buttons: [NSButton] = []
+    private var formattingActionObserver: NSObjectProtocol?
 
     override var isFlipped: Bool { true }
 
@@ -39,6 +41,13 @@ final class DescriptionEditorContainerView: NSView {
             buttons.append(button)
         }
         textView.onFormattingChange = { [weak self] in self?.updateControls() }
+        formattingActionObserver = NotificationCenter.default.addObserver(
+            forName: UITestDescriptionFormattingAccessibility.actionNotification,
+            object: nil,
+            queue: .main
+        ) { [weak self] notification in
+            self?.performFormattingAction(notification)
+        }
         addSubview(toolbar)
         addSubview(scrollView)
     }
@@ -46,6 +55,12 @@ final class DescriptionEditorContainerView: NSView {
     @available(*, unavailable)
     required init?(coder: NSCoder) { fatalError("init(coder:) has not been implemented") }
 
+    deinit {
+        if let formattingActionObserver {
+            NotificationCenter.default.removeObserver(formattingActionObserver)
+        }
+    }
+
     override func layout() {
         super.layout()
         toolbar.frame = NSRect(x: 0, y: 0, width: 108, height: 24)
@@ -66,5 +81,33 @@ final class DescriptionEditorContainerView: NSView {
             button.isEnabled = textView.isEditable
             if let tint { button.contentTintColor = tint }
         }
+        publishFormattingProbeSync(states: states)
+    }
+
+    private func publishFormattingProbeSync(states: [Bool]) {
+        guard UITestLaunchPolicy.attachesAccessibilityProbes else { return }
+        NotificationCenter.default.post(
+            name: UITestDescriptionFormattingAccessibility.syncNotification,
+            object: textView,
+            userInfo: [
+                UITestDescriptionFormattingAccessibility.Key.visible: !textView.isHidden,
+                UITestDescriptionFormattingAccessibility.Key.boldOn: states[0],
+                UITestDescriptionFormattingAccessibility.Key.italicOn: states[1],
+                UITestDescriptionFormattingAccessibility.Key.numberedListOn: states[2],
+                UITestDescriptionFormattingAccessibility.Key.bulletListOn: states[3],
+            ]
+        )
+    }
+
+    private func performFormattingAction(_ notification: Notification) {
+        guard let raw = notification.userInfo?[UITestDescriptionFormattingAccessibility.Key.action] as? String,
+              let action = UITestDescriptionFormattingAccessibility.Action(rawValue: raw)
+        else { return }
+        switch action {
+        case .bold: textView.toggleBold(nil)
+        case .italic: textView.toggleItalic(nil)
+        case .numberedList: textView.toggleNumberedList(nil)
+        case .bulletList: textView.toggleBulletList(nil)
+        }
     }
 }

From 8722d11ac1a32f8684304692c82674fce08939c4 Mon Sep 17 00:00:00 2001
From: Cursor Agent <cursoragent@cursor.com>
Date: Fri, 16 Oct 2026 14:31:41 +0000
Subject: [PATCH 09/18] fix(macos): satisfy swift 6 ui test hooks and stabilize
 up next test

Co-authored-by: Tyler Dane <tyler-dane@users.noreply.github.com>
---
 .../CompassDataTests/NativeCalendarRootModelUpNextTests.swift | 3 +++
 .../CompassUI/EventForm/DescriptionEditorContainerView.swift  | 4 +++-
 2 files changed, 6 insertions(+), 1 deletion(-)

diff --git a/apps/calendar-macos/CompassData/Tests/CompassDataTests/NativeCalendarRootModelUpNextTests.swift b/apps/calendar-macos/CompassData/Tests/CompassDataTests/NativeCalendarRootModelUpNextTests.swift
index 92ffef9782..247f9a6022 100644
--- a/apps/calendar-macos/CompassData/Tests/CompassDataTests/NativeCalendarRootModelUpNextTests.swift
+++ b/apps/calendar-macos/CompassData/Tests/CompassDataTests/NativeCalendarRootModelUpNextTests.swift
@@ -60,6 +60,9 @@ final class NativeCalendarRootModelUpNextTests: XCTestCase {
         await model.start()
         // The redo re-creates on a writable calendar, so reuse the seed's.
         let calendarId = try XCTUnwrap(model.loadedEvents.first?.calendarId.rawValue)
+        let demoIds = try environment.localEventRepository.fetchAll().filter(\.isDemo).map(\.id)
+        try environment.localEventRepository.delete(ids: demoIds)
+        model.loadedEvents = model.loadedEvents.filter { !demoIds.contains($0.id) }
         let event = try Self.timedEvent(title: "Just created", startingIn: 2 * 60, calendarId: calendarId)
         let upNextTitle = { model.upNextState.snapshot.upNext?.title }
         try environment.localEventRepository.putMany([
diff --git a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift
index 780463b3d3..634f7e6cd9 100644
--- a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift
+++ b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift
@@ -46,7 +46,9 @@ final class DescriptionEditorContainerView: NSView {
             object: nil,
             queue: .main
         ) { [weak self] notification in
-            self?.performFormattingAction(notification)
+            guard let raw = notification.userInfo?[UITestDescriptionFormattingAccessibility.Key.action] as? String
+            else { return }
+            self?.performFormattingAction(raw)
         }
         addSubview(toolbar)
         addSubview(scrollView)

From 6f43041d29e9a939c92448870fc03d2079a95162 Mon Sep 17 00:00:00 2001
From: Cursor Agent <cursoragent@cursor.com>
Date: Fri, 16 Oct 2026 14:31:52 +0000
Subject: [PATCH 10/18] fix(macos): move formatting observer teardown off
 deinit

Co-authored-by: Tyler Dane <tyler-dane@users.noreply.github.com>
---
 .../EventForm/DescriptionEditorContainerView.swift   | 12 ++++++------
 1 file changed, 6 insertions(+), 6 deletions(-)

diff --git a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift
index 634f7e6cd9..24634d6b94 100644
--- a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift
+++ b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift
@@ -57,10 +57,12 @@ final class DescriptionEditorContainerView: NSView {
     @available(*, unavailable)
     required init?(coder: NSCoder) { fatalError("init(coder:) has not been implemented") }
 
-    deinit {
-        if let formattingActionObserver {
+    override func willMove(toWindow newWindow: NSWindow?) {
+        if newWindow == nil, let formattingActionObserver {
             NotificationCenter.default.removeObserver(formattingActionObserver)
+            self.formattingActionObserver = nil
         }
+        super.willMove(toWindow: newWindow)
     }
 
     override func layout() {
@@ -101,10 +103,8 @@ final class DescriptionEditorContainerView: NSView {
         )
     }
 
-    private func performFormattingAction(_ notification: Notification) {
-        guard let raw = notification.userInfo?[UITestDescriptionFormattingAccessibility.Key.action] as? String,
-              let action = UITestDescriptionFormattingAccessibility.Action(rawValue: raw)
-        else { return }
+    private func performFormattingAction(_ raw: String) {
+        guard let action = UITestDescriptionFormattingAccessibility.Action(rawValue: raw) else { return }
         switch action {
         case .bold: textView.toggleBold(nil)
         case .italic: textView.toggleItalic(nil)

From fcc1daca7262fb705f8846e284a4f59666e4410b Mon Sep 17 00:00:00 2001
From: Cursor Agent <cursoragent@cursor.com>
Date: Fri, 16 Oct 2026 15:06:55 +0000
Subject: [PATCH 11/18] ci(macos): retrigger workflow after ci fixes

Co-authored-by: Tyler Dane <tyler-dane@users.noreply.github.com>

From c3b5f6d1e491fdde0fed2e020066670fdbdea7b5 Mon Sep 17 00:00:00 2001
From: Cursor Agent <cursoragent@cursor.com>
Date: Fri, 16 Oct 2026 15:25:31 +0000
Subject: [PATCH 12/18] ci(macos): touch macos paths to run workflow

Co-authored-by: Tyler Dane <tyler-dane@users.noreply.github.com>
---
 .../CompassData/UITestDescriptionFormattingAccessibility.swift   | 1 +
 1 file changed, 1 insertion(+)

diff --git a/apps/calendar-macos/CompassData/Sources/CompassData/UITestDescriptionFormattingAccessibility.swift b/apps/calendar-macos/CompassData/Sources/CompassData/UITestDescriptionFormattingAccessibility.swift
index b86c9b5717..8c26bb5385 100644
--- a/apps/calendar-macos/CompassData/Sources/CompassData/UITestDescriptionFormattingAccessibility.swift
+++ b/apps/calendar-macos/CompassData/Sources/CompassData/UITestDescriptionFormattingAccessibility.swift
@@ -23,3 +23,4 @@ public enum UITestDescriptionFormattingAccessibility {
         public static let bulletListOn = "bulletListOn"
     }
 }
+

From 460225a5f84d810a56937249d75184ae83c505fd Mon Sep 17 00:00:00 2001
From: Tyler Dane <tyler@switchback.tech>
Date: Fri, 16 Oct 2026 11:31:29 -0600
Subject: [PATCH 13/18] test(macos): query description formatting as named
 toggle controls

---
 .../CompassUITests/DescriptionEditorFormattingTests.swift     | 4 ++--
 1 file changed, 2 insertions(+), 2 deletions(-)

diff --git a/apps/calendar-macos/CompassUITests/DescriptionEditorFormattingTests.swift b/apps/calendar-macos/CompassUITests/DescriptionEditorFormattingTests.swift
index f6c2da5461..db13fecf61 100644
--- a/apps/calendar-macos/CompassUITests/DescriptionEditorFormattingTests.swift
+++ b/apps/calendar-macos/CompassUITests/DescriptionEditorFormattingTests.swift
@@ -18,7 +18,7 @@ final class DescriptionEditorFormattingTests: XCTestCase {
         editor.typeKey("a", modifierFlags: [.command])
         editor.typeText("Formatted note")
         editor.typeKey("a", modifierFlags: [.command])
-        window.buttons["Bold"].click()
+        window.descendants(matching: .any)["Bold"].click()
         window.typeKey(.enter, modifierFlags: [.command])
         XCTAssertFalse(editor.exists)
 
@@ -27,6 +27,6 @@ final class DescriptionEditorFormattingTests: XCTestCase {
         editor.click()
         editor.typeKey("a", modifierFlags: [.command])
         XCTAssertEqual(editor.value as? String, "Formatted note")
-        XCTAssertEqual(window.buttons["Bold"].value as? String, "1")
+        XCTAssertEqual(window.descendants(matching: .any)["Bold"].value as? String, "1")
     }
 }

From 90112f7ec6e57289f8c386f9574141209366be89 Mon Sep 17 00:00:00 2001
From: Tyler Dane <tyler@switchback.tech>
Date: Fri, 16 Oct 2026 11:32:54 -0600
Subject: [PATCH 14/18] fix(macos): preserve native editor input during
 interaction tests

---
 .../Compass/NativeGridKeyboardRouter.swift               | 4 ++++
 .../Notifications/CompassNotificationCenter.swift        | 3 +++
 .../Sources/CompassData/UITestLaunchPolicy.swift         | 9 +++++++++
 .../Tests/CompassDataTests/UITestLaunchPolicyTests.swift | 6 ++++++
 .../EventForm/DescriptionEditorContainerView.swift       | 1 +
 .../DescriptionEditorFormattingTests.swift               | 2 +-
 6 files changed, 24 insertions(+), 1 deletion(-)

diff --git a/apps/calendar-macos/Compass/NativeGridKeyboardRouter.swift b/apps/calendar-macos/Compass/NativeGridKeyboardRouter.swift
index 487b746f12..26776e0a30 100644
--- a/apps/calendar-macos/Compass/NativeGridKeyboardRouter.swift
+++ b/apps/calendar-macos/Compass/NativeGridKeyboardRouter.swift
@@ -316,6 +316,10 @@ final class NativeGridKeyboardRouter {
     /// Probes mirror via `EventFormAccessibilityProbeView` when `-COMPASS_UI_TEST` is set.
     private func handleUITestEventFormTyping(_ keyEvent: KeyEvent) -> Bool {
         guard UITestLaunchPolicy.mirrorsEventFormTitleTyping else { return false }
+        // The title probe is a fallback, never a replacement for a real text editor.
+        if let editor = NSApp.keyWindow?.firstResponder as? NSTextView, editor.isEditable {
+            return false
+        }
         if keyEvent.modifiers == [.command],
             case .character(let char) = keyEvent.key,
             char.lowercased() == "v",
diff --git a/apps/calendar-macos/Compass/Notifications/CompassNotificationCenter.swift b/apps/calendar-macos/Compass/Notifications/CompassNotificationCenter.swift
index 57c97da62a..3d02b288d8 100644
--- a/apps/calendar-macos/Compass/Notifications/CompassNotificationCenter.swift
+++ b/apps/calendar-macos/Compass/Notifications/CompassNotificationCenter.swift
@@ -1,4 +1,5 @@
 import AppKit
+import CompassData
 import CompassKit
 import UserNotifications
 
@@ -25,6 +26,7 @@ final class CompassNotificationCenter {
     }
 
     func requestAuthorizationIfNeeded() async {
+        guard UITestLaunchPolicy.allowsSystemNotifications else { return }
         let center = UNUserNotificationCenter.current()
         let settings = await center.notificationSettings()
         if permissionString(for: settings) == "default", !didRequestAuthorization {
@@ -35,6 +37,7 @@ final class CompassNotificationCenter {
 
     @discardableResult
     func showNative(_ payload: DesktopNotificationPayload) async -> Bool {
+        guard UITestLaunchPolicy.allowsSystemNotifications else { return false }
         let center = UNUserNotificationCenter.current()
         let settings = await center.notificationSettings()
         guard permissionString(for: settings) == "granted" else {
diff --git a/apps/calendar-macos/CompassData/Sources/CompassData/UITestLaunchPolicy.swift b/apps/calendar-macos/CompassData/Sources/CompassData/UITestLaunchPolicy.swift
index 1521d551ff..e9f2a034b1 100644
--- a/apps/calendar-macos/CompassData/Sources/CompassData/UITestLaunchPolicy.swift
+++ b/apps/calendar-macos/CompassData/Sources/CompassData/UITestLaunchPolicy.swift
@@ -17,6 +17,15 @@ public enum UITestLaunchPolicy {
         arguments.contains(uiTestLaunchArgument)
     }
 
+    /// Fixture interaction tests must not prompt for or post real system notifications.
+    public static var allowsSystemNotifications: Bool {
+        allowsSystemNotifications(arguments: ProcessInfo.processInfo.arguments)
+    }
+
+    public static func allowsSystemNotifications(arguments: [String]) -> Bool {
+        !arguments.contains(uiTestLaunchArgument)
+    }
+
     /// When set, focuses this grid event once the demo fixture layout is ready (no pointer hint).
     public static var initialGridFocusEventId: String? {
         let args = ProcessInfo.processInfo.arguments
diff --git a/apps/calendar-macos/CompassData/Tests/CompassDataTests/UITestLaunchPolicyTests.swift b/apps/calendar-macos/CompassData/Tests/CompassDataTests/UITestLaunchPolicyTests.swift
index 8a6368193b..7a3435f25c 100644
--- a/apps/calendar-macos/CompassData/Tests/CompassDataTests/UITestLaunchPolicyTests.swift
+++ b/apps/calendar-macos/CompassData/Tests/CompassDataTests/UITestLaunchPolicyTests.swift
@@ -19,6 +19,12 @@ final class UITestLaunchPolicyTests: XCTestCase {
                 arguments: ["Compass", "-COMPASS_UI_TEST", "-COMPASS_UI_TEST_OPEN_FOCUSED_EVENT_FORM"]))
     }
 
+    func testOnlyInteractionTestsSuppressSystemNotificationSideEffects() {
+        XCTAssertTrue(UITestLaunchPolicy.allowsSystemNotifications(arguments: ["/Applications/Compass.app"]))
+        XCTAssertTrue(UITestLaunchPolicy.allowsSystemNotifications(arguments: ["Compass", "-COMPASS_FIXTURE", "demo"]))
+        XCTAssertFalse(UITestLaunchPolicy.allowsSystemNotifications(arguments: ["Compass", "-COMPASS_UI_TEST"]))
+    }
+
     func testUITestLaunchAttachesAccessibilityProbes() {
         XCTAssertTrue(
             UITestLaunchPolicy.attachesAccessibilityProbes(arguments: ["Compass", "-COMPASS_UI_TEST"]))
diff --git a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift
index 1c8c913c7f..54faa9a164 100644
--- a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift
+++ b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift
@@ -14,6 +14,7 @@ final class DescriptionEditorContainerView: NSView {
         scrollView.hasVerticalScroller = true
         scrollView.borderType = .noBorder
         scrollView.documentView = textView
+        toolbar.frame = NSRect(x: 0, y: 0, width: 108, height: 24)
         toolbar.setAccessibilityElement(true)
         toolbar.setAccessibilityRole(.toolbar)
         toolbar.setAccessibilityLabel("Description formatting")
diff --git a/apps/calendar-macos/CompassUITests/DescriptionEditorFormattingTests.swift b/apps/calendar-macos/CompassUITests/DescriptionEditorFormattingTests.swift
index db13fecf61..9d422a2df9 100644
--- a/apps/calendar-macos/CompassUITests/DescriptionEditorFormattingTests.swift
+++ b/apps/calendar-macos/CompassUITests/DescriptionEditorFormattingTests.swift
@@ -20,7 +20,7 @@ final class DescriptionEditorFormattingTests: XCTestCase {
         editor.typeKey("a", modifierFlags: [.command])
         window.descendants(matching: .any)["Bold"].click()
         window.typeKey(.enter, modifierFlags: [.command])
-        XCTAssertFalse(editor.exists)
+        XCTAssertTrue(editor.waitForNonExistence(timeout: 8))
 
         window.typeKey(.enter, modifierFlags: [])
         XCTAssertTrue(editor.waitForExistence(timeout: 8))

From 3ebcc7c53cf167ab2841278b6e42c2663059bfca Mon Sep 17 00:00:00 2001
From: Tyler Dane <tyler@switchback.tech>
Date: Fri, 16 Oct 2026 11:41:55 -0600
Subject: [PATCH 15/18] fix(macos): scroll to form fields and normalize keypad
 enter

---
 .../Compass/NSEvent+KeyEvent.swift            |   6 +-
 .../CompassKitTests/NativeKeyEventTests.swift |  17 +++
 .../CompassUI/EventForm/EventFormView.swift   | 140 ++++++++++--------
 .../DescriptionEditorFormattingTests.swift    |  17 ++-
 apps/calendar-macos/project.yml               |   1 +
 5 files changed, 114 insertions(+), 67 deletions(-)
 create mode 100644 apps/calendar-macos/CompassKitTests/NativeKeyEventTests.swift

diff --git a/apps/calendar-macos/Compass/NSEvent+KeyEvent.swift b/apps/calendar-macos/Compass/NSEvent+KeyEvent.swift
index 2fbde94a3c..fff9801616 100644
--- a/apps/calendar-macos/Compass/NSEvent+KeyEvent.swift
+++ b/apps/calendar-macos/Compass/NSEvent+KeyEvent.swift
@@ -25,7 +25,7 @@ extension KeyToken {
     init?(nsEvent: NSEvent) {
         switch nsEvent.keyCode {
         case 53: self = .named(.escape)
-        case 36: self = .named(.enter)
+        case 36, 76: self = .named(.enter)
         case 48: self = .named(.tab)
         case 126: self = .named(.arrowUp)
         case 125: self = .named(.arrowDown)
@@ -38,7 +38,9 @@ extension KeyToken {
             guard let chars = nsEvent.charactersIgnoringModifiers?.lowercased(), let first = chars.first else {
                 return nil
             }
-            if first.isLetter || first.isNumber {
+            if first == "\r" || first == "\n" || first == "\u{3}" {
+                self = .named(.enter)
+            } else if first.isLetter || first.isNumber {
                 self = .character(first)
             } else {
                 self = .punctuation(String(first))
diff --git a/apps/calendar-macos/CompassKitTests/NativeKeyEventTests.swift b/apps/calendar-macos/CompassKitTests/NativeKeyEventTests.swift
new file mode 100644
index 0000000000..a8e1a1bd4d
--- /dev/null
+++ b/apps/calendar-macos/CompassKitTests/NativeKeyEventTests.swift
@@ -0,0 +1,17 @@
+import AppKit
+import CompassKit
+import XCTest
+
+final class NativeKeyEventTests: XCTestCase {
+    func testReturnAndKeypadEnterBothReachTheSaveChord() throws {
+        for (code, characters) in [(UInt16(36), "\r"), (UInt16(76), "\u{3}"), (UInt16(0), "\r"), (UInt16(0), "\u{3}")] {
+            let event = try XCTUnwrap(NSEvent.keyEvent(
+                with: .keyDown, location: .zero, modifierFlags: [.command, .numericPad],
+                timestamp: 0, windowNumber: 0, context: nil, characters: characters,
+                charactersIgnoringModifiers: characters, isARepeat: false, keyCode: code))
+            let normalized = try XCTUnwrap(KeyEvent(nsEvent: event))
+            XCTAssertEqual(normalized.key, .named(.enter))
+            XCTAssertTrue(normalized.matches(KeyChord(modifiers: [.command], token: .named(.enter))))
+        }
+    }
+}
diff --git a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/EventFormView.swift b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/EventFormView.swift
index c53ae6913f..a7df078d93 100644
--- a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/EventFormView.swift
+++ b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/EventFormView.swift
@@ -48,70 +48,84 @@ public struct EventFormView: View {
             .accessibilityIdentifier("compass-event-form-title")
             .pageJumpChipAnchor(id: "form-title")
 
-            ScrollView {
-                VStack(alignment: .leading, spacing: 12) {
-                    EventFormScheduleSection(
-                        model: model,
-                        draft: draft,
-                        focusField: model.eventFormFocusedField
-                    )
-                    EventFormRecurrenceSection(
-                        model: model,
-                        draft: draft,
-                        focusField: model.eventFormFocusedField
-                    )
-                    EventFormCalendarSection(
-                        model: model,
-                        draft: draft,
-                        focusField: model.eventFormFocusedField
-                    )
-                    EventFormColorSection(
-                        model: model,
-                        draft: draft,
-                        focusField: model.eventFormFocusedField
-                    )
-                    EventFormLocationField(
-                        model: model,
-                        draft: draft,
-                        focusField: model.eventFormFocusedField
-                    )
-                    DescriptionEditorView(
-                        html: Binding(
-                            get: { draft.description },
-                            set: { model.updateDraftFromForm(description: $0) }
-                        ),
-                        resetKey: draft.persistedEventId?.rawValue ?? draft.clientId.rawValue,
-                        isFocused: model.eventFormFocusedField == .description,
-                        isEditable: !model.isEventFormReadOnly(for: draft)
-                    )
-                    .frame(minHeight: 72, maxHeight: 140)
-                    .padding(8)
-                    .background(theme.surfacePanelColor)
-                    .clipShape(RoundedRectangle(cornerRadius: 8))
-                    .overlay(
-                        RoundedRectangle(cornerRadius: 8)
-                            .stroke(
-                                model.eventFormFocusedField == .description ? theme.accentColor : theme.borderColor,
-                                lineWidth: 1
-                            )
-                    )
-                    .pageJumpChipAnchor(id: "form-description")
+            ScrollViewReader { proxy in
+                ScrollView {
+                    VStack(alignment: .leading, spacing: 12) {
+                        EventFormScheduleSection(
+                            model: model,
+                            draft: draft,
+                            focusField: model.eventFormFocusedField
+                        )
+                        .id(EventFormField.start) .id(EventFormField.end)
+                        EventFormRecurrenceSection(
+                            model: model,
+                            draft: draft,
+                            focusField: model.eventFormFocusedField
+                        )
+                        .id(EventFormField.recurrence)
+                        EventFormCalendarSection(
+                            model: model,
+                            draft: draft,
+                            focusField: model.eventFormFocusedField
+                        )
+                        .id(EventFormField.calendar)
+                        EventFormColorSection(
+                            model: model,
+                            draft: draft,
+                            focusField: model.eventFormFocusedField
+                        )
+                        .id(EventFormField.color)
+                        EventFormLocationField(
+                            model: model,
+                            draft: draft,
+                            focusField: model.eventFormFocusedField
+                        )
+                        .id(EventFormField.location)
+                        DescriptionEditorView(
+                            html: Binding(
+                                get: { draft.description },
+                                set: { model.updateDraftFromForm(description: $0) }
+                            ),
+                            resetKey: draft.persistedEventId?.rawValue ?? draft.clientId.rawValue,
+                            isFocused: model.eventFormFocusedField == .description,
+                            isEditable: !model.isEventFormReadOnly(for: draft)
+                        )
+                        .frame(minHeight: 72, maxHeight: 140)
+                        .padding(8)
+                        .background(theme.surfacePanelColor)
+                        .clipShape(RoundedRectangle(cornerRadius: 8))
+                        .overlay(
+                            RoundedRectangle(cornerRadius: 8)
+                                .stroke(
+                                    model.eventFormFocusedField == .description ? theme.accentColor : theme.borderColor,
+                                    lineWidth: 1
+                                )
+                        )
+                        .pageJumpChipAnchor(id: "form-description")
+                        .id(EventFormField.description)
 
-                    EventFormConferenceSection(
-                        model: model,
-                        draft: draft,
-                        focusField: model.eventFormFocusedField
-                    )
-                    EventFormAttendeesSection(
-                        model: model,
-                        draft: draft,
-                        focusField: model.eventFormFocusedField
-                    )
-                    EventFormRsvpSection(
-                        model: model,
-                        draft: draft,
-                        focusField: model.eventFormFocusedField
-                    )
+                        EventFormConferenceSection(
+                            model: model,
+                            draft: draft,
+                            focusField: model.eventFormFocusedField
+                        )
+                        .id(EventFormField.conference)
+                        EventFormAttendeesSection(
+                            model: model,
+                            draft: draft,
+                            focusField: model.eventFormFocusedField
+                        )
+                        .id(EventFormField.attendees)
+                        EventFormRsvpSection(
+                            model: model,
+                            draft: draft,
+                            focusField: model.eventFormFocusedField
+                        )
+                        .id(EventFormField.rsvp)
+                    }
+                }
+                .onChange(of: model.eventFormFocusedField) { _, field in
+                    proxy.scrollTo(field, anchor: .center)
                 }
             }
             if !model.isEventFormReadOnly(for: draft) {
diff --git a/apps/calendar-macos/CompassUITests/DescriptionEditorFormattingTests.swift b/apps/calendar-macos/CompassUITests/DescriptionEditorFormattingTests.swift
index 9d422a2df9..a8e25964b5 100644
--- a/apps/calendar-macos/CompassUITests/DescriptionEditorFormattingTests.swift
+++ b/apps/calendar-macos/CompassUITests/DescriptionEditorFormattingTests.swift
@@ -12,21 +12,34 @@ final class DescriptionEditorFormattingTests: XCTestCase {
         ]
         app.launch()
         let window = app.windows["Compass"]
+        defer {
+            if (testRun?.failureCount ?? 0) > 0 {
+                let hierarchy = XCTAttachment(string: window.debugDescription)
+                hierarchy.lifetime = .keepAlways
+                add(hierarchy)
+                let screenshot = XCTAttachment(screenshot: app.screenshot())
+                screenshot.lifetime = .keepAlways
+                add(screenshot)
+            }
+        }
         let editor = window.textViews["compass-event-form-description"]
         XCTAssertTrue(editor.waitForExistence(timeout: 8))
+        window.typeKey("9", modifierFlags: [.command])
         editor.click()
         editor.typeKey("a", modifierFlags: [.command])
         editor.typeText("Formatted note")
+        XCTAssertEqual(editor.value as? String, "Formatted note")
         editor.typeKey("a", modifierFlags: [.command])
-        window.descendants(matching: .any)["Bold"].click()
+        window.checkBoxes["Bold"].click()
         window.typeKey(.enter, modifierFlags: [.command])
         XCTAssertTrue(editor.waitForNonExistence(timeout: 8))
 
         window.typeKey(.enter, modifierFlags: [])
         XCTAssertTrue(editor.waitForExistence(timeout: 8))
+        window.typeKey("9", modifierFlags: [.command])
         editor.click()
         editor.typeKey("a", modifierFlags: [.command])
         XCTAssertEqual(editor.value as? String, "Formatted note")
-        XCTAssertEqual(window.descendants(matching: .any)["Bold"].value as? String, "1")
+        XCTAssertEqual(String(describing: window.checkBoxes["Bold"].value ?? ""), "1")
     }
 }
diff --git a/apps/calendar-macos/project.yml b/apps/calendar-macos/project.yml
index a5dd974c8b..f79654cb6b 100644
--- a/apps/calendar-macos/project.yml
+++ b/apps/calendar-macos/project.yml
@@ -61,6 +61,7 @@ targets:
         MACOSX_DEPLOYMENT_TARGET: "14.0"
     sources:
       - CompassKitTests
+      - Compass/NSEvent+KeyEvent.swift
     resources:
       - path: CompassKitTests/Fixtures
         type: folder

From 1d6a73ba77dd55e1d025e052ca0884b5aea55361 Mon Sep 17 00:00:00 2001
From: Tyler Dane <tyler@switchback.tech>
Date: Fri, 16 Oct 2026 11:43:20 -0600
Subject: [PATCH 16/18] test(macos): keep appkit adapter coverage in the native
 test target

---
 .../NativeKeyEventTests.swift                                     | 0
 1 file changed, 0 insertions(+), 0 deletions(-)
 rename apps/calendar-macos/{CompassKitTests => CompassNativeTests}/NativeKeyEventTests.swift (100%)

diff --git a/apps/calendar-macos/CompassKitTests/NativeKeyEventTests.swift b/apps/calendar-macos/CompassNativeTests/NativeKeyEventTests.swift
similarity index 100%
rename from apps/calendar-macos/CompassKitTests/NativeKeyEventTests.swift
rename to apps/calendar-macos/CompassNativeTests/NativeKeyEventTests.swift

From 77667e291c69fba72a71b0920d199071e13a3653 Mon Sep 17 00:00:00 2001
From: Tyler Dane <tyler@switchback.tech>
Date: Fri, 16 Oct 2026 11:43:28 -0600
Subject: [PATCH 17/18] test(macos): include native adapter tests in the xcode
 target

---
 apps/calendar-macos/project.yml | 1 +
 1 file changed, 1 insertion(+)

diff --git a/apps/calendar-macos/project.yml b/apps/calendar-macos/project.yml
index f79654cb6b..f0da360e70 100644
--- a/apps/calendar-macos/project.yml
+++ b/apps/calendar-macos/project.yml
@@ -61,6 +61,7 @@ targets:
         MACOSX_DEPLOYMENT_TARGET: "14.0"
     sources:
       - CompassKitTests
+      - CompassNativeTests
       - Compass/NSEvent+KeyEvent.swift
     resources:
       - path: CompassKitTests/Fixtures

From 44075d32e2b254cb7e12eb595f4727b56d973ecd Mon Sep 17 00:00:00 2001
From: Tyler Dane <tyler@switchback.tech>
Date: Fri, 16 Oct 2026 11:47:52 -0600
Subject: [PATCH 18/18] refactor(macos): test description formatting through
 its native controls

---
 ...tionFormattingAccessibilityProbeView.swift | 131 ------------------
 .../Compass/NativeRootController.swift        |   2 -
 ...stDescriptionFormattingAccessibility.swift |  26 ----
 .../DescriptionEditorContainerView.swift      |  45 ------
 4 files changed, 204 deletions(-)
 delete mode 100644 apps/calendar-macos/Compass/DescriptionFormattingAccessibilityProbeView.swift
 delete mode 100644 apps/calendar-macos/CompassData/Sources/CompassData/UITestDescriptionFormattingAccessibility.swift

diff --git a/apps/calendar-macos/Compass/DescriptionFormattingAccessibilityProbeView.swift b/apps/calendar-macos/Compass/DescriptionFormattingAccessibilityProbeView.swift
deleted file mode 100644
index 32ae302ca4..0000000000
--- a/apps/calendar-macos/Compass/DescriptionFormattingAccessibilityProbeView.swift
+++ /dev/null
@@ -1,131 +0,0 @@
-import AppKit
-import CompassData
-
-/// Hittable mirrors of description formatting toolbar buttons for XCUITest.
-@MainActor
-final class DescriptionFormattingAccessibilityProbeView: NSView {
-    private struct Control {
-        let identifier: String
-        let action: UITestDescriptionFormattingAccessibility.Action
-        let button: NSButton
-    }
-
-    private var controls: [Control] = []
-    private var observer: NSObjectProtocol?
-
-    override init(frame frameRect: NSRect) {
-        super.init(frame: frameRect)
-        wantsLayer = true
-        layer?.backgroundColor = NSColor.clear.cgColor
-        isHidden = true
-        var x: CGFloat = 420
-        for (identifier, action) in [
-            ("Bold", UITestDescriptionFormattingAccessibility.Action.bold),
-            ("Italic", UITestDescriptionFormattingAccessibility.Action.italic),
-            ("Numbered list", UITestDescriptionFormattingAccessibility.Action.numberedList),
-            ("Bullet list", UITestDescriptionFormattingAccessibility.Action.bulletList),
-        ] {
-            let button = NSButton(title: identifier, target: self, action: #selector(performAction(_:)))
-            button.setButtonType(.pushOnPushOff)
-            button.bezelStyle = .inline
-            button.isBordered = false
-            button.setAccessibilityIdentifier(identifier)
-            button.setAccessibilityLabel(identifier)
-            button.frame = NSRect(x: x, y: 360, width: 80, height: 24)
-            button.tag = controls.count
-            addSubview(button)
-            controls.append(Control(identifier: identifier, action: action, button: button))
-            x += 84
-        }
-        observer = NotificationCenter.default.addObserver(
-            forName: UITestDescriptionFormattingAccessibility.syncNotification,
-            object: nil,
-            queue: .main
-        ) { [weak self] notification in
-            self?.applySync(notification)
-        }
-    }
-
-    @available(*, unavailable)
-    required init?(coder: NSCoder) {
-        fatalError("init(coder:) has not been implemented")
-    }
-
-    deinit {
-        if let observer {
-            NotificationCenter.default.removeObserver(observer)
-        }
-    }
-
-    func update(visible: Bool) {
-        isHidden = !visible
-        for control in controls {
-            control.button.isHidden = !visible
-            control.button.isEnabled = visible
-        }
-        if visible {
-            NSAccessibility.post(element: self, notification: .layoutChanged)
-        }
-    }
-
-    @objc private func performAction(_ sender: NSButton) {
-        guard sender.tag >= 0, sender.tag < controls.count else { return }
-        let action = controls[sender.tag].action
-        NotificationCenter.default.post(
-            name: UITestDescriptionFormattingAccessibility.actionNotification,
-            object: nil,
-            userInfo: [UITestDescriptionFormattingAccessibility.Key.action: action.rawValue]
-        )
-    }
-
-    private func applySync(_ notification: Notification) {
-        guard let userInfo = notification.userInfo else { return }
-        let visible = (userInfo[UITestDescriptionFormattingAccessibility.Key.visible] as? Bool) ?? false
-        update(visible: visible)
-        guard visible else { return }
-        let states = [
-            userInfo[UITestDescriptionFormattingAccessibility.Key.boldOn] as? Bool ?? false,
-            userInfo[UITestDescriptionFormattingAccessibility.Key.italicOn] as? Bool ?? false,
-            userInfo[UITestDescriptionFormattingAccessibility.Key.numberedListOn] as? Bool ?? false,
-            userInfo[UITestDescriptionFormattingAccessibility.Key.bulletListOn] as? Bool ?? false,
-        ]
-        for (control, selected) in zip(controls, states) {
-            control.button.state = selected ? .on : .off
-            control.button.setAccessibilityValue(selected ? "1" : "0")
-        }
-        postLayoutChanged()
-    }
-
-    private func postLayoutChanged() {
-        guard let window else { return }
-        NSAccessibility.post(element: self, notification: .layoutChanged)
-        NSAccessibility.post(element: window, notification: .layoutChanged)
-    }
-}
-
-@MainActor
-enum DescriptionFormattingAccessibilityProbe {
-    private static weak var probe: DescriptionFormattingAccessibilityProbeView?
-
-    static func attach(to window: NSWindow) {
-        guard UITestLaunchPolicy.attachesAccessibilityProbes, let host = window.contentView else { return }
-        attach(to: host)
-    }
-
-    static func attach(to hostView: NSView) {
-        guard UITestLaunchPolicy.attachesAccessibilityProbes else { return }
-        if let probe, probe.superview === hostView { return }
-        probe?.removeFromSuperview()
-        let view = DescriptionFormattingAccessibilityProbeView(frame: .zero)
-        hostView.addSubview(view, positioned: .above, relativeTo: nil)
-        probe = view
-    }
-
-    static func publish(visible: Bool) {
-        guard UITestLaunchPolicy.attachesAccessibilityProbes else { return }
-        if probe == nil, let window = NSApp.keyWindow ?? NSApp.mainWindow {
-            attach(to: window)
-        }
-        probe?.update(visible: visible)
-    }
-}
diff --git a/apps/calendar-macos/Compass/NativeRootController.swift b/apps/calendar-macos/Compass/NativeRootController.swift
index d9578a4971..915088857a 100644
--- a/apps/calendar-macos/Compass/NativeRootController.swift
+++ b/apps/calendar-macos/Compass/NativeRootController.swift
@@ -62,7 +62,6 @@ final class NativeRootController: NSHostingController<ThemedRootView> {
                     ? { [weak model] newTitle in model?.updateDraftFromForm(title: newTitle) }
                     : nil
             )
-            DescriptionFormattingAccessibilityProbe.publish(visible: visible)
         }
         model.onEventFormTitleAccessibilityProbeTitleSync = { title in
             EventFormAccessibilityProbe.syncTitle(title)
@@ -123,7 +122,6 @@ final class NativeRootController: NSHostingController<ThemedRootView> {
                     model?.updateDraftFromForm(title: newTitle)
                 }
             )
-            DescriptionFormattingAccessibilityProbe.publish(visible: model.isEventFormVisible)
             NativeOverlayProbes.statusToast.attach(to: window)
             NativeOverlayProbes.shortcutsLegend.attach(to: window)
         }
diff --git a/apps/calendar-macos/CompassData/Sources/CompassData/UITestDescriptionFormattingAccessibility.swift b/apps/calendar-macos/CompassData/Sources/CompassData/UITestDescriptionFormattingAccessibility.swift
deleted file mode 100644
index 8c26bb5385..0000000000
--- a/apps/calendar-macos/CompassData/Sources/CompassData/UITestDescriptionFormattingAccessibility.swift
+++ /dev/null
@@ -1,26 +0,0 @@
-import Foundation
-
-/// Cross-process notifications for mirroring description formatting controls in
-/// XCUITest. AppKit toolbar buttons inside `NSViewRepresentable` are not exposed
-/// in CI; the Compass app publishes hittable mirrors the editor keeps in sync.
-public enum UITestDescriptionFormattingAccessibility {
-    public static let syncNotification = Notification.Name("compassUITestDescriptionFormattingSync")
-    public static let actionNotification = Notification.Name("compassUITestDescriptionFormattingAction")
-
-    public enum Action: String, Sendable {
-        case bold
-        case italic
-        case numberedList
-        case bulletList
-    }
-
-    public enum Key {
-        public static let visible = "visible"
-        public static let action = "action"
-        public static let boldOn = "boldOn"
-        public static let italicOn = "italicOn"
-        public static let numberedListOn = "numberedListOn"
-        public static let bulletListOn = "bulletListOn"
-    }
-}
-
diff --git a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift
index 8101aafd5a..5581087cb4 100644
--- a/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift
+++ b/apps/calendar-macos/CompassUI/Sources/CompassUI/EventForm/DescriptionEditorContainerView.swift
@@ -1,12 +1,10 @@
 import AppKit
-import CompassData
 
 final class DescriptionEditorContainerView: NSView {
     let textView = DescriptionTextView()
     private let scrollView = NSScrollView()
     private let toolbar = NSStackView()
     private var buttons: [NSButton] = []
-    private var formattingActionObserver: NSObjectProtocol?
 
     override var isFlipped: Bool { true }
 
@@ -42,15 +40,6 @@ final class DescriptionEditorContainerView: NSView {
             buttons.append(button)
         }
         textView.onFormattingChange = { [weak self] in self?.updateControls() }
-        formattingActionObserver = NotificationCenter.default.addObserver(
-            forName: UITestDescriptionFormattingAccessibility.actionNotification,
-            object: nil,
-            queue: .main
-        ) { [weak self] notification in
-            guard let raw = notification.userInfo?[UITestDescriptionFormattingAccessibility.Key.action] as? String
-            else { return }
-            self?.performFormattingAction(raw)
-        }
         addSubview(toolbar)
         addSubview(scrollView)
     }
@@ -58,14 +47,6 @@ final class DescriptionEditorContainerView: NSView {
     @available(*, unavailable)
     required init?(coder: NSCoder) { fatalError("init(coder:) has not been implemented") }
 
-    override func willMove(toWindow newWindow: NSWindow?) {
-        if newWindow == nil, let formattingActionObserver {
-            NotificationCenter.default.removeObserver(formattingActionObserver)
-            self.formattingActionObserver = nil
-        }
-        super.willMove(toWindow: newWindow)
-    }
-
     override func layout() {
         super.layout()
         toolbar.frame = NSRect(x: 0, y: 0, width: 108, height: 24)
@@ -86,31 +67,5 @@ final class DescriptionEditorContainerView: NSView {
             button.isEnabled = textView.isEditable
             if let tint { button.contentTintColor = tint }
         }
-        publishFormattingProbeSync(states: states)
-    }
-
-    private func publishFormattingProbeSync(states: [Bool]) {
-        guard UITestLaunchPolicy.attachesAccessibilityProbes else { return }
-        NotificationCenter.default.post(
-            name: UITestDescriptionFormattingAccessibility.syncNotification,
-            object: textView,
-            userInfo: [
-                UITestDescriptionFormattingAccessibility.Key.visible: !textView.isHidden,
-                UITestDescriptionFormattingAccessibility.Key.boldOn: states[0],
-                UITestDescriptionFormattingAccessibility.Key.italicOn: states[1],
-                UITestDescriptionFormattingAccessibility.Key.numberedListOn: states[2],
-                UITestDescriptionFormattingAccessibility.Key.bulletListOn: states[3],
-            ]
-        )
-    }
-
-    private func performFormattingAction(_ raw: String) {
-        guard let action = UITestDescriptionFormattingAccessibility.Action(rawValue: raw) else { return }
-        switch action {
-        case .bold: textView.toggleBold(nil)
-        case .italic: textView.toggleItalic(nil)
-        case .numberedList: textView.toggleNumberedList(nil)
-        case .bulletList: textView.toggleBulletList(nil)
-        }
     }
 }