diff --git a/lang/en/fieldtypes.php b/lang/en/fieldtypes.php
index d1d6792579c..444f862ea81 100644
--- a/lang/en/fieldtypes.php
+++ b/lang/en/fieldtypes.php
@@ -140,6 +140,7 @@
     'list.title' => 'List',
     'markdown.config.automatic_line_breaks' => 'Enables automatic line breaks.',
     'markdown.config.automatic_links' => 'Enables automatic linking of any URLs.',
+    'markdown.config.buttons' => 'Choose which buttons to show in the toolbar. Drag to rearrange.',
     'markdown.config.container' => 'Choose which asset container to use for this field.',
     'markdown.config.escape_markup' => 'Escapes inline HTML markup (e.g. `<div>` to `&lt;div&gt;`).',
     'markdown.config.folder' => 'Specify the initial directory.',
diff --git a/resources/js/components/fieldtypes/markdown/MarkdownButtonsSettingFieldtype.vue b/resources/js/components/fieldtypes/markdown/MarkdownButtonsSettingFieldtype.vue
index 5f41895aa98..f6422c79f42 100644
--- a/resources/js/components/fieldtypes/markdown/MarkdownButtonsSettingFieldtype.vue
+++ b/resources/js/components/fieldtypes/markdown/MarkdownButtonsSettingFieldtype.vue
@@ -4,8 +4,12 @@
             <button
                 v-for="button in buttons"
                 :key="button.name"
+                type="button"
                 v-tooltip="button.text"
+                class="relative hover:bg-white/10!"
                 :class="{ active: enabled(button.name) }"
+                :aria-label="button.text"
+                :aria-pressed="enabled(button.name)"
                 @click="toggleButton(button.name)"
             >
                 <ui-icon :name="button.svg" />
@@ -91,6 +95,17 @@ export default {
                 swapAnimation: { horizontal: true },
                 plugins: [Plugins.SwapAnimation],
                 distance: 10,
+                classes: {
+                    'source:dragging': [
+                        'draggable-source--is-dragging',
+                        'bg-gray-800!',
+                        'opacity-100!',
+                        'shadow-lg',
+                        'ring-1',
+                        'ring-white/15',
+                        'z-10',
+                    ],
+                },
             })
                 .on('sortable:stop', (e) => {
                     this.buttons.splice(e.newIndex, 0, this.buttons.splice(e.oldIndex, 1)[0]);
diff --git a/resources/js/components/fieldtypes/markdown/MarkdownFieldtype.vue b/resources/js/components/fieldtypes/markdown/MarkdownFieldtype.vue
index c140ecfd078..1376f9979bd 100644
--- a/resources/js/components/fieldtypes/markdown/MarkdownFieldtype.vue
+++ b/resources/js/components/fieldtypes/markdown/MarkdownFieldtype.vue
@@ -392,6 +392,26 @@ export default {
             return text.slice(delimiter.length, -delimiter.length);
         },
 
+        toggleHeading(level) {
+            const startPoint = this.codemirror.getCursor('start');
+            const endPoint = this.codemirror.getCursor('end');
+            const pattern = /^(\s*)(#{1,6})(?:\s+|$)/;
+            const delimiter = '#'.repeat(level);
+            const prefix = delimiter + ' ';
+
+            for (let i = startPoint.line; i <= endPoint.line; i++) {
+                const text = this.codemirror.getLine(i);
+                const heading = text.match(pattern);
+                const newText = heading
+                    ? text.replace(pattern, heading[2] === delimiter ? '$1' : '$1' + prefix)
+                    : text.replace(/^(\s*)/, '$1' + prefix);
+
+                this.codemirror.replaceRange(newText, { line: i, ch: 0 }, { line: i, ch: Infinity });
+            }
+
+            this.codemirror.focus();
+        },
+
         toggleLine(type) {
             const startPoint = this.codemirror.getCursor('start');
             const endPoint = this.codemirror.getCursor('end');
diff --git a/resources/js/components/fieldtypes/markdown/buttons.js b/resources/js/components/fieldtypes/markdown/buttons.js
index d7d277c5925..bbd946a48a3 100644
--- a/resources/js/components/fieldtypes/markdown/buttons.js
+++ b/resources/js/components/fieldtypes/markdown/buttons.js
@@ -1,4 +1,40 @@
 const availableButtons = () => [
+    {
+        name: 'h1',
+        text: __('Heading 1'),
+        command: (editor) => editor.toggleHeading(1),
+        svg: 'h1',
+    },
+    {
+        name: 'h2',
+        text: __('Heading 2'),
+        command: (editor) => editor.toggleHeading(2),
+        svg: 'h2',
+    },
+    {
+        name: 'h3',
+        text: __('Heading 3'),
+        command: (editor) => editor.toggleHeading(3),
+        svg: 'h3',
+    },
+    {
+        name: 'h4',
+        text: __('Heading 4'),
+        command: (editor) => editor.toggleHeading(4),
+        svg: 'h4',
+    },
+    {
+        name: 'h5',
+        text: __('Heading 5'),
+        command: (editor) => editor.toggleHeading(5),
+        svg: 'h5',
+    },
+    {
+        name: 'h6',
+        text: __('Heading 6'),
+        command: (editor) => editor.toggleHeading(6),
+        svg: 'h6',
+    },
     { name: 'bold', text: __('Bold'), command: (editor) => editor.toggleInline('bold'), svg: 'text-bold' },
     { name: 'italic', text: __('Italic'), command: (editor) => editor.toggleInline('italic'), svg: 'text-italic' },
     { name: 'strikethrough', text: __('Strikethrough'), command: (editor) => editor.toggleInline('strikethrough'), svg: 'text-strike-through' },
diff --git a/resources/js/tests/components/fieldtypes/MarkdownFieldtype.test.js b/resources/js/tests/components/fieldtypes/MarkdownFieldtype.test.js
index ffb0f6a3d2b..21052b23792 100644
--- a/resources/js/tests/components/fieldtypes/MarkdownFieldtype.test.js
+++ b/resources/js/tests/components/fieldtypes/MarkdownFieldtype.test.js
@@ -1,9 +1,11 @@
 import { mount } from '@vue/test-utils';
-import { expect, test } from 'vitest';
+import { expect, test, vi } from 'vitest';
+import CodeMirror from 'codemirror';
 import { computed, ref } from 'vue';
 import * as Globals from '@/bootstrap/globals';
 import MarkdownFieldtype from '@/components/fieldtypes/markdown/MarkdownFieldtype.vue';
 import { containerContextKey } from '@/components/ui/Publish/Container.vue';
+import { availableButtons } from '@/components/fieldtypes/markdown/buttons';
 
 Object.keys(Globals).forEach((fn) => (window[fn] = Globals[fn]));
 window.cp_url = (url) => url;
@@ -59,3 +61,32 @@ test('the preview pane gets the content direction', async () => {
     // dir attribute can be asserted without switching into preview mode.
     expect(wrapper.find('.markdown-preview').attributes('dir')).toBe('rtl');
 });
+
+function headingEditor(text) {
+    const codemirror = new CodeMirror.Doc(text);
+    codemirror.focus = vi.fn();
+
+    return { codemirror, toggleHeading: MarkdownFieldtype.methods.toggleHeading };
+}
+
+test.each([1, 2, 3, 4, 5, 6])('the H%i button toggles its heading level', (level) => {
+    const editor = headingEditor('hello world');
+    const button = availableButtons().find((button) => button.name === `h${level}`);
+
+    editor.codemirror.setCursor({ line: 0, ch: 5 });
+    button.command(editor);
+    expect(editor.codemirror.getValue()).toBe(`${'#'.repeat(level)} hello world`);
+
+    button.command(editor);
+    expect(editor.codemirror.getValue()).toBe('hello world');
+
+    expect(editor.codemirror.focus).toHaveBeenCalledTimes(2);
+});
+
+test('heading buttons replace existing levels across selected lines', () => {
+    const editor = headingEditor('# First\n  ### Second\nPlain text\n####### Not a heading');
+    editor.codemirror.setSelection({ line: 0, ch: 0 }, { line: 3, ch: 24 });
+    editor.toggleHeading(2);
+
+    expect(editor.codemirror.getValue()).toBe('## First\n  ## Second\n## Plain text\n## ####### Not a heading');
+});
diff --git a/src/Fieldtypes/Markdown.php b/src/Fieldtypes/Markdown.php
index 4b82a98c41a..02360c06ae7 100644
--- a/src/Fieldtypes/Markdown.php
+++ b/src/Fieldtypes/Markdown.php
@@ -53,8 +53,9 @@ protected function configFieldItems(): array
                 'fields' => [
                     'buttons' => [
                         'display' => __('Buttons'),
-                        'instructions' => __('statamic::fieldtypes.bard.config.buttons'),
+                        'instructions' => __('statamic::fieldtypes.markdown.config.buttons'),
                         'type' => 'markdown_buttons_setting',
+                        'full_width_setting' => true,
                         'default' => [
                             'bold',
                             'italic',
@@ -65,7 +66,6 @@ protected function configFieldItems(): array
                             'image',
                             'table',
                         ],
-                        'width' => 66,
                     ],
                     'toolbar_mode' => [
                         'display' => __('Toolbar Mode'),
diff --git a/tests/Fieldtypes/MarkdownTest.php b/tests/Fieldtypes/MarkdownTest.php
index cca36bfd157..ce2cf050297 100644
--- a/tests/Fieldtypes/MarkdownTest.php
+++ b/tests/Fieldtypes/MarkdownTest.php
@@ -16,6 +16,28 @@ class MarkdownTest extends TestCase
 {
     use PreventSavingStacheItemsToDisk;
 
+    #[Test]
+    public function heading_buttons_are_opt_in()
+    {
+        $buttons = (new Markdown)->configFields()->get('buttons');
+
+        $this->assertSame([
+            'bold', 'italic', 'unorderedlist', 'orderedlist', 'quote', 'link', 'image', 'table',
+        ], $buttons->defaultValue());
+        $this->assertTrue($buttons->get('full_width_setting'));
+    }
+
+    #[Test]
+    public function existing_button_selections_and_order_are_preserved()
+    {
+        foreach ([[], ['table', 'bold'], ['h6', 'h1', 'italic']] as $buttons) {
+            $fieldtype = $this->fieldtype(['buttons' => $buttons]);
+
+            $this->assertSame($buttons, $fieldtype->config('buttons'));
+            $this->assertSame($buttons, $fieldtype->config()['buttons']);
+        }
+    }
+
     #[Test]
     public function it_augments_to_html()
     {