diff --git a/src/renderer/src/components/editor/rich-markdown-extensions.ts b/src/renderer/src/components/editor/rich-markdown-extensions.ts
index d4b551d8355..f6e69f00862 100644
--- a/src/renderer/src/components/editor/rich-markdown-extensions.ts
+++ b/src/renderer/src/components/editor/rich-markdown-extensions.ts
@@ -39,6 +39,7 @@ import type { RichMarkdownHtmlSuperscriptLinkContext } from './rich-markdown-htm
 import { RichMarkdownOrderedList } from './rich-markdown-ordered-list'
 import { RichMarkdownCodeSpanPadding } from './rich-markdown-code-span-padding'
 import { RichMarkdownListItem } from './rich-markdown-list-item'
+import { RichMarkdownProseEntities } from './rich-markdown-prose-entities'
 import { RichMarkdownParagraph } from './rich-markdown-paragraph'
 import { RichMarkdownInlineMath } from './rich-markdown-inline-math'
 import { RichMarkdownCodeBlockLowlight } from './rich-markdown-lowlight'
@@ -255,6 +256,7 @@ export function createRichMarkdownExtensions({
       }
     }),
     RichMarkdownCodeSpanPadding,
+    RichMarkdownProseEntities,
     createRichMarkdownAnnotationHighlightExtension()
   ]
 
diff --git a/src/renderer/src/components/editor/rich-markdown-prose-entities.test.ts b/src/renderer/src/components/editor/rich-markdown-prose-entities.test.ts
new file mode 100644
index 00000000000..ed19fe95ca7
--- /dev/null
+++ b/src/renderer/src/components/editor/rich-markdown-prose-entities.test.ts
@@ -0,0 +1,75 @@
+import { Editor } from '@tiptap/core'
+import { describe, expect, it } from 'vitest'
+import { encodeRawMarkdownHtmlForRichEditor } from './raw-markdown-html'
+import { createRichMarkdownExtensions } from './rich-markdown-extensions'
+import { encodeProseTextForMarkdown } from './rich-markdown-prose-entities'
+import { createRichMarkdownEditorCodec } from './rich-markdown-source-transport'
+
+function roundTrip(source: string): string {
+  const codec = createRichMarkdownEditorCodec()
+  const editor = new Editor({
+    element: null,
+    extensions: createRichMarkdownExtensions({ codec }),
+    content: encodeRawMarkdownHtmlForRichEditor(source, codec),
+    contentType: 'markdown'
+  })
+  try {
+    return editor.getMarkdown().trimEnd()
+  } finally {
+    editor.destroy()
+  }
+}
+
+describe('encodeProseTextForMarkdown', () => {
+  it.each([
+    ['a < b && c'],
+    ['Finance > Invoices'],
+    ['F&B revenue'],
+    ['Copyright &copy; 2026'],
+    ['A &MadeUpEntity; here'],
+    ['5 <6 and 7> 8']
+  ])('leaves %j unescaped', (text) => {
+    expect(encodeProseTextForMarkdown(text)).toBe(text)
+  })
+
+  it.each([
+    ['Press <kbd>x</kbd>', 'Press &lt;kbd>x&lt;/kbd>'],
+    ['A <!-- comment --> here', 'A &lt;!-- comment --> here']
+  ])('escapes tag openings in %j', (text, expected) => {
+    expect(encodeProseTextForMarkdown(text)).toBe(expected)
+  })
+
+  it('encodes a block-quote marker only in the first column', () => {
+    expect(encodeProseTextForMarkdown('> quoted')).toBe('&gt; quoted')
+    expect(encodeProseTextForMarkdown('Finance > Invoices')).toBe('Finance > Invoices')
+  })
+})
+
+describe('prose entity round trip', () => {
+  it.each([
+    ['a < b && c'],
+    ['Finance > Invoices'],
+    ['F&B revenue'],
+    ['Copyright &copy; 2026'],
+    ['A &MadeUpEntity; here'],
+    ['5 <6 and 7> 8'],
+    ['Press <kbd>x</kbd> now.'],
+    ['`a < b && c` stays literal']
+  ])('preserves %j', (source) => {
+    expect(roundTrip(source)).toBe(source)
+  })
+
+  it('preserves prose entities inside a heading and a list item', () => {
+    const source = '# F&B > Revenue\n\n- a < b && c'
+    expect(roundTrip(source)).toBe(source)
+  })
+
+  it('is stable across three cycles', () => {
+    const source = 'Finance > Invoices, F&B, a < b && c, &copy; 2026'
+    let current = source
+    for (let cycle = 0; cycle < 3; cycle += 1) {
+      current = roundTrip(current)
+    }
+    expect(current).toBe(source)
+  })
+})
diff --git a/src/renderer/src/components/editor/rich-markdown-prose-entities.ts b/src/renderer/src/components/editor/rich-markdown-prose-entities.ts
new file mode 100644
index 00000000000..38440f3e353
--- /dev/null
+++ b/src/renderer/src/components/editor/rich-markdown-prose-entities.ts
@@ -0,0 +1,60 @@
+import { Extension } from '@tiptap/core'
+
+const TAG_OPENING = /^<(?:[a-zA-Z][a-zA-Z0-9-]*|\/[a-zA-Z][a-zA-Z0-9-]*|!|\?)/
+
+type MarkdownTextEncoder = {
+  encodeTextForMarkdown?: (text: string, node: unknown, parentNode?: unknown) => string
+}
+
+function isMarkdownTextEncoder(value: unknown): value is MarkdownTextEncoder {
+  return typeof value === 'object' && value !== null
+}
+
+function escapeMarkdownSyntax(text: string): string {
+  return text.replace(/([\\`*_[\]~])/g, '\\$1')
+}
+
+/** Keep prose punctuation literal unless its raw form would change Markdown parsing. */
+export function encodeProseTextForMarkdown(text: string): string {
+  let output = ''
+  let lineStart = true
+  for (let index = 0; index < text.length; index += 1) {
+    const character = text[index]
+    if (character === '<' && TAG_OPENING.test(text.slice(index))) {
+      output += '&lt;'
+    } else if (character === '>' && lineStart) {
+      output += '&gt;'
+    } else {
+      output += character
+    }
+    if (character === '\n') {
+      lineStart = true
+    } else if (lineStart && (character === ' ' || character === '\t')) {
+      lineStart = true
+    } else {
+      lineStart = false
+    }
+  }
+  return escapeMarkdownSyntax(output)
+}
+
+/** Restore prose entities after TipTap's serializer has classified code contexts. */
+export const RichMarkdownProseEntities = Extension.create({
+  name: 'richMarkdownProseEntities',
+  priority: 1,
+
+  onBeforeCreate() {
+    const managerValue: unknown = this.editor.markdown
+    if (!isMarkdownTextEncoder(managerValue)) {
+      return
+    }
+    const base = managerValue.encodeTextForMarkdown
+    if (typeof base !== 'function') {
+      return
+    }
+    managerValue.encodeTextForMarkdown = (text, node, parentNode) => {
+      const encoded = base.call(managerValue, text, node, parentNode)
+      return encoded === text ? text : encodeProseTextForMarkdown(text)
+    }
+  }
+})