diff --git a/apps/calendar-web/src/index.css b/apps/calendar-web/src/index.css
index 266b5cdf48..582077c539 100644
--- a/apps/calendar-web/src/index.css
+++ b/apps/calendar-web/src/index.css
@@ -1348,28 +1348,23 @@
   & .timepicker__single-value {
     color: var(--text);
   }
-  & .timepicker__menu {
-    min-width: 150px;
-    border: 1px solid var(--color-border);
-    border-radius: 2px;
-    background: var(--surface);
-  }
-  & .timepicker__menu-list {
-    padding: 0;
-    font-size: var(--font-size-m);
-    transition: var(--transition-default);
-  }
-  & .timepicker__menu-list::-webkit-scrollbar {
-    width: 8px;
-  }
-  & .timepicker__menu-list::-webkit-scrollbar-thumb {
-    border-radius: var(--radius-default);
-    background: var(--color-border);
-  }
-  & .timepicker__menu-list::-webkit-scrollbar-thumb:hover {
-    background: var(--color-border-strong);
-    transition: background-color 0.2s;
-  }
+}
+
+/*
+ * Time picker menus portal to document.body, outside .c-time-picker. Menu
+ * chrome lives in TimePicker's react-select styles; only pseudo-elements,
+ * which style objects can't reach, stay here.
+ */
+.timepicker__menu-list::-webkit-scrollbar {
+  width: 8px;
+}
+.timepicker__menu-list::-webkit-scrollbar-thumb {
+  border-radius: var(--radius-default);
+  background: var(--color-border);
+}
+.timepicker__menu-list::-webkit-scrollbar-thumb:hover {
+  background: var(--color-border-strong);
+  transition: background-color 0.2s;
 }
 
 /*
diff --git a/apps/calendar-web/src/views/Forms/EventForm/DateControlsSection/DateTimeSection/EventFormDateField.test.tsx b/apps/calendar-web/src/views/Forms/EventForm/DateControlsSection/DateTimeSection/EventFormDateField.test.tsx
index a85e16eb3d..8773811071 100644
--- a/apps/calendar-web/src/views/Forms/EventForm/DateControlsSection/DateTimeSection/EventFormDateField.test.tsx
+++ b/apps/calendar-web/src/views/Forms/EventForm/DateControlsSection/DateTimeSection/EventFormDateField.test.tsx
@@ -68,6 +68,55 @@ describe("EventFormDateField", () => {
     expect(onCommit.mock.calls[0]?.[0].getDate()).toBe(17);
   });
 
+  it("commits a typed date on Tab instead of discarding it", async () => {
+    const user = userEvent.setup();
+    const onCommit = mock();
+    render(<Harness onCommit={onCommit} />);
+
+    const input = screen.getByTitle("Pick Start Date");
+    await user.click(input);
+    await user.clear(input);
+    await user.type(input, "10.20.26");
+    await user.tab();
+
+    expect(onCommit).toHaveBeenCalledTimes(1);
+    expect(onCommit.mock.calls[0]?.[0].getDate()).toBe(20);
+  });
+
+  it("commits a typed date when focus leaves the field", async () => {
+    const user = userEvent.setup();
+    const onCommit = mock();
+    render(
+      <>
+        <Harness onCommit={onCommit} />
+        <button type="button">Elsewhere</button>
+      </>,
+    );
+
+    const input = screen.getByTitle("Pick Start Date");
+    await user.click(input);
+    await user.clear(input);
+    await user.type(input, "10.21.26");
+    await user.click(screen.getByRole("button", { name: "Elsewhere" }));
+
+    expect(onCommit).toHaveBeenCalledTimes(1);
+    expect(onCommit.mock.calls[0]?.[0].getDate()).toBe(21);
+  });
+
+  it("restores the date when Enter is pressed on an empty field", async () => {
+    const user = userEvent.setup();
+    const onCommit = mock();
+    render(<Harness onCommit={onCommit} />);
+
+    const input = screen.getByTitle("Pick Start Date");
+    await user.click(input);
+    await user.clear(input);
+    await user.keyboard("{Enter}");
+
+    expect(onCommit).not.toHaveBeenCalled();
+    expect(input).toHaveValue(formatEventFormDateLabel(START));
+  });
+
   it("nudges one day with arrow keys when the calendar is closed", async () => {
     const user = userEvent.setup();
     const onCommit = mock();
diff --git a/apps/calendar-web/src/views/Forms/EventForm/DateControlsSection/DateTimeSection/EventFormDateField.tsx b/apps/calendar-web/src/views/Forms/EventForm/DateControlsSection/DateTimeSection/EventFormDateField.tsx
index 2e34478bb4..cf33712cbb 100644
--- a/apps/calendar-web/src/views/Forms/EventForm/DateControlsSection/DateTimeSection/EventFormDateField.tsx
+++ b/apps/calendar-web/src/views/Forms/EventForm/DateControlsSection/DateTimeSection/EventFormDateField.tsx
@@ -50,10 +50,19 @@ export const EventFormDateField = ({
   selectedRef.current = selected;
   const containerRef = useRef<HTMLDivElement>(null);
 
+  const shownDateRef = useRef<number | null>(null);
+
   useEffect(() => {
     if (isOpen) return;
     const input = containerRef.current?.querySelector("input");
     if (!input) return;
+    // Closing the calendar (outside click, Escape) must not wipe a date the
+    // user is still typing; blur commits or reverts it.
+    const isDraft =
+      input === document.activeElement &&
+      shownDateRef.current === selected.getTime();
+    if (isDraft) return;
+    shownDateRef.current = selected.getTime();
     input.value = formatEventFormDateLabel(selected);
   }, [isOpen, selected]);
 
@@ -68,6 +77,31 @@ export const EventFormDateField = ({
     target.value = formatEventFormDateLabel(selectedRef.current);
   };
 
+  /**
+   * Enter, Tab, and blur all land here: commit a typed date that changes the
+   * day, quietly restore an emptied field, and explain anything unparseable.
+   * Returns false when nothing was committed.
+   */
+  const commitOrRevert = (target: HTMLInputElement) => {
+    const value = target.value.trim();
+    const parsed = value ? parseUserDate(value, dayjs()) : null;
+    if (parsed && !parsed.isSame(selectedRef.current, "day")) {
+      const date = parsed.startOf("day").toDate();
+      // Optimistic until the parent re-renders, so a blur right after Enter
+      // doesn't commit the same draft twice.
+      selectedRef.current = date;
+      onCommit(date);
+      return true;
+    }
+    if (value && !parsed) {
+      showErrorToast(
+        `Sorry, IDK what to do with a ${sideLabel} date of '${value}'. Try 10.17.26, 17.10.26, 10/17/2026, or 2026-10-17.`,
+      );
+    }
+    revertInput(target);
+    return false;
+  };
+
   const nudgeDays = (deltaDays: number) => {
     onCommit(dayjs(selectedRef.current).add(deltaDays, "day").toDate());
   };
@@ -119,11 +153,7 @@ export const EventFormDateField = ({
       case event.key === "Enter": {
         event.stopPropagation();
         event.preventDefault();
-        if (!commitTypedDate(typedValue)) {
-          showErrorToast(
-            `Sorry, IDK what to do with a ${sideLabel} date of '${typedValue}'. Try 10.17.26, 17.10.26, 10/17/2026, or 2026-10-17.`,
-          );
-        }
+        if (!commitOrRevert(target)) onCalendarClose();
         break;
       }
       case event.key === "Escape": {
@@ -137,7 +167,7 @@ export const EventFormDateField = ({
         break;
       }
       case event.key === "Tab": {
-        onCalendarClose();
+        if (!commitOrRevert(target)) onCalendarClose();
         break;
       }
     }
@@ -156,6 +186,16 @@ export const EventFormDateField = ({
       ref={containerRef}
       className={DATE_FIELD_CLASSNAME}
       id={jumpId}
+      onBlur={(event) => {
+        // react-datepicker skips onBlur while its calendar is open, so listen
+        // on the wrapper. Moving into the calendar is not leaving the field.
+        const next = event.relatedTarget;
+        if (next instanceof Element && next.closest(".react-datepicker"))
+          return;
+        if (event.target instanceof HTMLInputElement) {
+          commitOrRevert(event.target);
+        }
+      }}
       onMouseDown={stopPropagation}
       onMouseUp={stopPropagation}
       tabIndex={-1}
@@ -172,6 +212,9 @@ export const EventFormDateField = ({
         onCalendarOpen={onCalendarOpen}
         onChange={() => null}
         onInputClick={onCalendarOpen}
+        onFocus={(event) => {
+          if (event.target instanceof HTMLInputElement) event.target.select();
+        }}
         onKeyDown={handleKeyDown}
         onSelect={(date) => {
           if (!date) return;
diff --git a/apps/calendar-web/src/views/Forms/EventForm/DateControlsSection/DateTimeSection/TimePicker/TimePicker.tsx b/apps/calendar-web/src/views/Forms/EventForm/DateControlsSection/DateTimeSection/TimePicker/TimePicker.tsx
index 238cb63372..05b4ae8e5d 100644
--- a/apps/calendar-web/src/views/Forms/EventForm/DateControlsSection/DateTimeSection/TimePicker/TimePicker.tsx
+++ b/apps/calendar-web/src/views/Forms/EventForm/DateControlsSection/DateTimeSection/TimePicker/TimePicker.tsx
@@ -40,6 +40,21 @@ const timePickerTextStyles = {
   singleValue: themeColor("var(--text)"),
   input: themeColor("var(--text)"),
   placeholder: themeColor("var(--text-muted)"),
+  // The menu portals to document.body, outside .c-time-picker, so its
+  // chrome lives here. Fit the longest label ("12:45 PM") without wrapping.
+  menu: (base: CSSObjectWithLabel): CSSObjectWithLabel => ({
+    ...base,
+    width: "max-content",
+    minWidth: "100%",
+    border: "1px solid var(--color-border)",
+    borderRadius: 2,
+    backgroundColor: "var(--surface)",
+  }),
+  menuList: (base: CSSObjectWithLabel): CSSObjectWithLabel => ({
+    ...base,
+    padding: 0,
+    fontSize: "var(--font-size-m)",
+  }),
   menuPortal: (base: CSSObjectWithLabel): CSSObjectWithLabel => ({
     ...base,
     zIndex: Z_INDEX_FLOATING_MENU,
@@ -49,6 +64,7 @@ const timePickerTextStyles = {
     { isFocused, isSelected }: { isFocused: boolean; isSelected: boolean },
   ): CSSObjectWithLabel => ({
     ...base,
+    whiteSpace: "nowrap",
     color: isFocused ? "var(--on-accent)" : "var(--text)",
     backgroundColor: isFocused
       ? "var(--accent)"
@@ -69,6 +85,13 @@ const MENU_NAV_KEYS = new Set([
   "PageDown",
 ]);
 
+/** The menu portals to document.body, so reach it through the combobox. */
+function menuListbox(container: HTMLElement | null): HTMLElement | null {
+  const combobox = container?.querySelector<HTMLElement>('[role="combobox"]');
+  const listboxId = combobox?.getAttribute("aria-controls");
+  return listboxId ? document.getElementById(listboxId) : null;
+}
+
 function optionFromFocusedMenu(
   container: HTMLElement | null,
   options: TimeOption[] | undefined,
@@ -78,7 +101,9 @@ function optionFromFocusedMenu(
   const activeId = combobox?.getAttribute("aria-activedescendant");
   const focusedEl = activeId
     ? document.getElementById(activeId)
-    : container?.getElementsByClassName(`${TIMEPICKER}__option--is-focused`)[0];
+    : menuListbox(container)?.getElementsByClassName(
+        `${TIMEPICKER}__option--is-focused`,
+      )[0];
   const focusedLabel = focusedEl?.textContent?.trim();
   if (!focusedLabel) return undefined;
 
@@ -131,10 +156,10 @@ export const TimePicker = ({
     scrollRafRef.current = requestAnimationFrame(() => {
       scrollRafRef.current = requestAnimationFrame(() => {
         scrollRafRef.current = null;
-        const defaultOpt = containerRef.current?.getElementsByClassName(
-          `${TIMEPICKER}__option--is-selected`,
-        )[0];
-        defaultOpt?.scrollIntoView();
+        const defaultOpt = menuListbox(
+          containerRef.current,
+        )?.getElementsByClassName(`${TIMEPICKER}__option--is-selected`)[0];
+        defaultOpt?.scrollIntoView({ block: "center" });
       });
     });
   };
diff --git a/apps/calendar-web/src/views/Forms/EventForm/EventForm.tsx b/apps/calendar-web/src/views/Forms/EventForm/EventForm.tsx
index a218c216b0..2bf1dc0b6c 100644
--- a/apps/calendar-web/src/views/Forms/EventForm/EventForm.tsx
+++ b/apps/calendar-web/src/views/Forms/EventForm/EventForm.tsx
@@ -863,7 +863,7 @@ export const EventForm: React.FC<GridEventFormProps> = memo(
           onPointerDown={onFormPointerDown}
           onFocusCapture={onFormFocusIn}
         >
-          <div className="sticky top-0 z-10 shrink-0 bg-surface-panel px-4 pt-1 pb-2">
+          <div className="sticky top-0 z-10 shrink-0 bg-surface-panel px-4 pt-3 pb-2">
             <FormActionsRow
               ref={formActionsRef}
               bookingLinks={bookingLinks}