diff --git a/src/renderer/src/components/editor/markdown-rich-mode.test.ts b/src/renderer/src/components/editor/markdown-rich-mode.test.ts
index 1c05d3ef1b9..5e581b23ae9 100644
--- a/src/renderer/src/components/editor/markdown-rich-mode.test.ts
+++ b/src/renderer/src/components/editor/markdown-rich-mode.test.ts
@@ -244,6 +244,17 @@ describe('getMarkdownRichModeUnsupportedMessage', () => {
   })
 
   describe('reference-style link definitions', () => {
+    it('blocks a definition whose label contains an escaped closing bracket', () => {
+      expect(
+        getMarkdownRichModeUnsupportedMessage('[foo\\]]: https://example.com\n')
+      ).not.toBeNull()
+    })
+
+    it('blocks an escaped-bracket definition in an oversized document', () => {
+      const content = `${'a'.repeat(50_001)}\n\n[foo\\]]: https://example.com\n`
+      expect(getMarkdownRichModeUnsupportedMessage(content)).not.toBeNull()
+    })
+
     it('blocks a real link reference definition', () => {
       expect(getMarkdownRichModeUnsupportedMessage('[id]: https://example.com\n')).not.toBeNull()
     })
diff --git a/src/renderer/src/components/editor/markdown-rich-mode.ts b/src/renderer/src/components/editor/markdown-rich-mode.ts
index 73a565db071..82a86171a3b 100644
--- a/src/renderer/src/components/editor/markdown-rich-mode.ts
+++ b/src/renderer/src/components/editor/markdown-rich-mode.ts
@@ -80,7 +80,7 @@ const UNSUPPORTED_PATTERNS: UnsupportedMatch[] = [
     // container nesting produces (e.g. `1) [x]:`); `[label]: ` also opens
     // ordinary prose, so `hasLinkReferenceDefinition` confirms a real
     // definition per CommonMark.
-    pattern: /^[ \t>*+\-\d.)]*\[[^\]]+\]:/m
+    pattern: /^[ \t>*+\-\d.)]*\[(?:\\.|[^\]\\\n])+\]:/m
   },
   {
     reason: 'footnotes',
@@ -196,7 +196,7 @@ function hasLinkReferenceDefinition(content: string): boolean {
   // Definitions inside transported HTML comments are comment text, not
   // Markdown definitions. Remove complete comments before the bounded probe.
   const commentStripped = content.replace(/<!--[\s\S]*?-->/g, '')
-  if (!/^[ \t>*+\-\d.)]*\[[^\]]+\]:/m.test(commentStripped)) {
+  if (!/^[ \t>*+\-\d.)]*\[(?:\\.|[^\]\\\n])+\]:/m.test(commentStripped)) {
     return false
   }
   if (commentStripped.length > 50_000) {
@@ -205,7 +205,7 @@ function hasLinkReferenceDefinition(content: string): boolean {
       .split(/\r?\n[ \t]*\r?\n/)
       .some(
         (block) =>
-          /^[ \t>*+\-\d.)]*\[[^\]]+\]:/m.test(block) &&
+          /^[ \t>*+\-\d.)]*\[(?:\\.|[^\]\\\n])+\]:/m.test(block) &&
           containsDefinitionNode(linkReferenceDefinitionProcessor.parse(block))
       )
   }
diff --git a/src/renderer/src/components/editor/rich-markdown-attribute-encoding.test.ts b/src/renderer/src/components/editor/rich-markdown-attribute-encoding.test.ts
new file mode 100644
index 00000000000..9df34cabaf1
--- /dev/null
+++ b/src/renderer/src/components/editor/rich-markdown-attribute-encoding.test.ts
@@ -0,0 +1,43 @@
+import { Editor } from '@tiptap/core'
+import { describe, expect, it } from 'vitest'
+import { createRichMarkdownExtensions } from './rich-markdown-extensions'
+import { createRichMarkdownEditorCodec } from './rich-markdown-source-transport'
+import { encodeRawMarkdownHtmlForRichEditor } from './raw-markdown-html'
+
+function open(source: string): Editor {
+  const codec = createRichMarkdownEditorCodec()
+  return new Editor({
+    element: null,
+    extensions: createRichMarkdownExtensions({ codec }),
+    content: encodeRawMarkdownHtmlForRichEditor(source, codec),
+    contentType: 'markdown'
+  })
+}
+
+for (const text of ['two "" quotes', 'slash\\"quote', 'two\\\\', '[brackets]\\', '中文 😀']) {
+  describe(`attribute ${JSON.stringify(text)}`, () => {
+    it.each(['title', 'alt'])('preserves image %s through editing and reopening', (attribute) => {
+      const editor = open('![image](image.png)')
+      try {
+        const image = editor.state.doc.nodeAt(1)
+        expect(image?.type.name).toBe('image')
+        editor.view.dispatch(
+          editor.state.tr.setNodeMarkup(1, undefined, { ...image?.attrs, [attribute]: text })
+        )
+        let saved = editor.getMarkdown()
+        for (let revision = 0; revision < 3; revision += 1) {
+          const reopened = open(saved)
+          try {
+            reopened.state.doc.check()
+            expect(reopened.state.doc.nodeAt(1)?.attrs[attribute]).toBe(text)
+            saved = reopened.getMarkdown()
+          } finally {
+            reopened.destroy()
+          }
+        }
+      } finally {
+        editor.destroy()
+      }
+    })
+  })
+}
diff --git a/src/renderer/src/components/editor/rich-markdown-clipboard-serialization.test.ts b/src/renderer/src/components/editor/rich-markdown-clipboard-serialization.test.ts
index e71cea2aaa9..0b8f54644bb 100644
--- a/src/renderer/src/components/editor/rich-markdown-clipboard-serialization.test.ts
+++ b/src/renderer/src/components/editor/rich-markdown-clipboard-serialization.test.ts
@@ -1,33 +1,80 @@
 import { Editor } from '@tiptap/core'
-import { describe, expect, it } from 'vitest'
+import { Slice } from '@tiptap/pm/model'
+import { describe, expect, it, vi } from 'vitest'
 import { encodeRawMarkdownHtmlForRichEditor } from './raw-markdown-html'
 import { createRichMarkdownExtensions } from './rich-markdown-extensions'
 import { serializeRichMarkdownSliceAsMarkdown } from './rich-markdown-clipboard-serialization'
 import { createRichMarkdownEditorCodec } from './rich-markdown-source-transport'
 
 describe('rich Markdown clipboard serialization', () => {
-  it('serializes a selected slice as Markdown source', () => {
+  it.each([
+    'First paragraph.\n\nSecond paragraph.',
+    '# Heading\n\nA **bold** paragraph with a [link](https://example.com).',
+    '# Heading\n\n- First item\n- Second item\n\nLast paragraph.'
+  ])('preserves block boundaries when copying %s', (source) => {
     const codec = createRichMarkdownEditorCodec()
     const editor = new Editor({
       element: null,
       extensions: createRichMarkdownExtensions({ codec }),
-      content: encodeRawMarkdownHtmlForRichEditor(
-        '# Heading\n\nA **bold** paragraph with a [link](https://example.com).\n',
-        codec
-      ),
+      content: encodeRawMarkdownHtmlForRichEditor(source, codec),
       contentType: 'markdown'
     })
     try {
       const slice = editor.state.doc.slice(0, editor.state.doc.content.size)
+      const original = editor.state.doc
+      const manager = editor.markdown
+      if (!manager) {
+        throw new Error('Markdown manager is required')
+      }
       const markdown = serializeRichMarkdownSliceAsMarkdown(slice, (content) =>
-        editor.markdown!.serialize(content)
+        manager.serialize(content)
       )
-      expect(markdown).toContain('# Heading')
-      expect(markdown).toContain('**bold**')
-      expect(markdown).toContain('[link](https://example.com)')
-      expect(markdown).not.toContain('\n\n\n')
+      expect(markdown).toBe(source)
+      editor.commands.setContent(encodeRawMarkdownHtmlForRichEditor(markdown, codec), {
+        contentType: 'markdown'
+      })
+      expect(editor.state.doc.eq(original)).toBe(true)
     } finally {
       editor.destroy()
     }
   })
+
+  it('copies only the selected inline text and retains its mark', () => {
+    const codec = createRichMarkdownEditorCodec()
+    const editor = new Editor({
+      element: null,
+      extensions: createRichMarkdownExtensions({ codec }),
+      content: encodeRawMarkdownHtmlForRichEditor('A **bold** paragraph.', codec),
+      contentType: 'markdown'
+    })
+    try {
+      const slice = editor.state.doc.slice(3, 7)
+      const manager = editor.markdown
+      if (!manager) {
+        throw new Error('Markdown manager is required')
+      }
+      const markdown = serializeRichMarkdownSliceAsMarkdown(slice, (content) =>
+        manager.serialize(content)
+      )
+      expect(markdown).toBe('**bold**')
+      editor.commands.setContent(markdown, { contentType: 'markdown' })
+      expect(editor.getJSON()).toEqual({
+        type: 'doc',
+        content: [
+          {
+            type: 'paragraph',
+            content: [{ type: 'text', text: 'bold', marks: [{ type: 'bold' }] }]
+          }
+        ]
+      })
+    } finally {
+      editor.destroy()
+    }
+  })
+
+  it('returns empty text without serializing an empty selection', () => {
+    const serialize = vi.fn(() => 'unexpected content')
+    expect(serializeRichMarkdownSliceAsMarkdown(Slice.empty, serialize)).toBe('')
+    expect(serialize).not.toHaveBeenCalled()
+  })
 })
diff --git a/src/renderer/src/components/editor/rich-markdown-clipboard-serialization.ts b/src/renderer/src/components/editor/rich-markdown-clipboard-serialization.ts
index ed4360b2cb1..b8ba718a902 100644
--- a/src/renderer/src/components/editor/rich-markdown-clipboard-serialization.ts
+++ b/src/renderer/src/components/editor/rich-markdown-clipboard-serialization.ts
@@ -24,5 +24,5 @@ export function serializeRichMarkdownSliceAsMarkdown(
   serialize: MarkdownSliceSerializer
 ): string {
   const content = slice.content.toJSON()
-  return Array.isArray(content) ? serialize(content) : ''
+  return Array.isArray(content) ? serialize({ type: 'doc', content }) : ''
 }
diff --git a/src/renderer/src/components/editor/rich-markdown-code-span-padding.test.ts b/src/renderer/src/components/editor/rich-markdown-code-span-padding.test.ts
index 4fe833311d3..05d5dd69348 100644
--- a/src/renderer/src/components/editor/rich-markdown-code-span-padding.test.ts
+++ b/src/renderer/src/components/editor/rich-markdown-code-span-padding.test.ts
@@ -36,7 +36,21 @@ describe('maskCodeSpanPadding', () => {
       { type: 'text', text: ' code ', marks: [{ type: 'code' }] }
     ])
     expect(masked.nodes[0]?.text).not.toContain(' ')
-    expect(restoreCodeSpanPadding(masked.nodes[0]?.text ?? '', masked.placeholder)).toBe(' code ')
+    expect(
+      restoreCodeSpanPadding(masked.nodes[0]?.text ?? '', masked.placeholder, masked.replacements)
+    ).toBe(' code ')
+  })
+
+  it('restores the exact whitespace bytes at code-span boundaries', () => {
+    const leading = '\t\u00a0 '
+    const trailing = ' \u00a0\t'
+    const masked = maskCodeSpanPadding([
+      { type: 'text', text: `${leading}code${trailing}`, marks: [{ type: 'code' }] }
+    ])
+
+    expect(
+      restoreCodeSpanPadding(masked.nodes[0]?.text ?? '', masked.placeholder, masked.replacements)
+    ).toBe(`${leading}code${trailing}`)
   })
 })
 
@@ -49,7 +63,8 @@ describe('code span padding round trip', () => {
     ['`a\uE000b` and ` padded`'],
     ['**bold** and `code` and *it*'],
     ['`a` and `b`'],
-    ['[`label`](https://example.com)']
+    ['[`label`](https://example.com)'],
+    ['Read `\tcode\u00a0` and write up.']
   ])('preserves %j', (source) => {
     expect(roundTrip(source)).toBe(source)
   })
diff --git a/src/renderer/src/components/editor/rich-markdown-code-span-padding.ts b/src/renderer/src/components/editor/rich-markdown-code-span-padding.ts
index 4ad7c0e10bd..507622a8f0c 100644
--- a/src/renderer/src/components/editor/rich-markdown-code-span-padding.ts
+++ b/src/renderer/src/components/editor/rich-markdown-code-span-padding.ts
@@ -40,8 +40,15 @@ function paddingPlaceholder(nodes: MarkdownNodeLike[]): string {
 export function maskCodeSpanPadding(nodes: MarkdownNodeLike[]): {
   nodes: MarkdownNodeLike[]
   placeholder: string
+  replacements: readonly (readonly [string, string])[]
 } {
   const placeholder = paddingPlaceholder(nodes)
+  const replacements: [string, string][] = []
+  const mask = (padding: string): string => {
+    const token = `${placeholder}${replacements.length}${placeholder}`
+    replacements.push([token, padding])
+    return token
+  }
   const masked = nodes.map((node) => {
     if (node?.type !== 'text' || !hasCodeMark(node)) {
       return node
@@ -55,14 +62,22 @@ export function maskCodeSpanPadding(nodes: MarkdownNodeLike[]): {
     const body = text.slice(leading.length, trailing ? text.length - trailing.length : text.length)
     return {
       ...node,
-      text: placeholder.repeat(leading.length) + body + placeholder.repeat(trailing.length)
+      text: (leading ? mask(leading) : '') + body + (trailing ? mask(trailing) : '')
     }
   })
-  return { nodes: masked, placeholder }
+  return { nodes: masked, placeholder, replacements }
 }
 
-export function restoreCodeSpanPadding(markdown: string, placeholder: string): string {
-  return markdown.split(placeholder).join(' ')
+export function restoreCodeSpanPadding(
+  markdown: string,
+  placeholder: string,
+  replacements: readonly (readonly [string, string])[]
+): string {
+  const padding = new Map(replacements)
+  return markdown.replace(
+    new RegExp(`${placeholder}\\d+${placeholder}`, 'g'),
+    (token) => padding.get(token) ?? token
+  )
 }
 
 /**
@@ -92,7 +107,7 @@ export const RichMarkdownCodeSpanPadding = Extension.create({
       const masked = maskCodeSpanPadding(nodes ?? [])
       const rendered = walk.call(this, masked.nodes, ...rest)
       return typeof rendered === 'string'
-        ? restoreCodeSpanPadding(rendered, masked.placeholder)
+        ? restoreCodeSpanPadding(rendered, masked.placeholder, masked.replacements)
         : rendered
     }
   }
diff --git a/src/renderer/src/components/editor/rich-markdown-inline-math.test.ts b/src/renderer/src/components/editor/rich-markdown-inline-math.test.ts
index cf28bebf79a..90ff5bf3c25 100644
--- a/src/renderer/src/components/editor/rich-markdown-inline-math.test.ts
+++ b/src/renderer/src/components/editor/rich-markdown-inline-math.test.ts
@@ -62,3 +62,34 @@ describe('inline math delimiters', () => {
     expect(countInlineMath('A line with US$ 5,000 here\nand another with R$ 40,000 there.')).toBe(0)
   })
 })
+
+it.each([
+  '$x$ then \\$HOME',
+  '\\$HOME then $x$',
+  '$x$ and \\$a\\$b',
+  '<span>x</span> \\$HOME and \\$PATH'
+])('preserves literal dollars beside math or HTML: %s', (source) => {
+  withEditor(source, (editor) => {
+    const expectedText = editor.state.doc.textContent
+    const expectedMath: string[] = []
+    editor.state.doc.descendants((node) => {
+      if (node.type.name === 'inlineMath') {
+        expectedMath.push(node.attrs.latex)
+      }
+    })
+    let saved = editor.getMarkdown()
+    for (let revision = 0; revision < 3; revision += 1) {
+      saved = withEditor(saved, (reopened) => {
+        const math: string[] = []
+        reopened.state.doc.descendants((node) => {
+          if (node.type.name === 'inlineMath') {
+            math.push(node.attrs.latex)
+          }
+        })
+        expect(reopened.state.doc.textContent).toBe(expectedText)
+        expect(math).toEqual(expectedMath)
+        return reopened.getMarkdown()
+      })
+    }
+  })
+})
diff --git a/src/renderer/src/components/editor/rich-markdown-literal-serialization.ts b/src/renderer/src/components/editor/rich-markdown-literal-serialization.ts
index 0cbdde67c75..9f4466ee7f1 100644
--- a/src/renderer/src/components/editor/rich-markdown-literal-serialization.ts
+++ b/src/renderer/src/components/editor/rich-markdown-literal-serialization.ts
@@ -39,19 +39,6 @@ function escapeBare(markdown: string, chars: string): string {
   return parts.join('')
 }
 
-function hasBare(markdown: string, chars: string): boolean {
-  let oddBackslash = false
-  for (let i = 0; i < markdown.length; i += 1) {
-    const character = markdown[i] ?? ''
-    const bare = !oddBackslash
-    oddBackslash = character === '\\' ? !oddBackslash : false
-    if (chars.includes(character) && bare) {
-      return true
-    }
-  }
-  return false
-}
-
 function destNeedsEscape(dest: string): boolean {
   let depth = 0
   let oddBackslash = false
@@ -150,8 +137,8 @@ function attrNeedsRepair(
   const dest = kind === 'image' ? attrs.src : attrs.href
   return (
     (typeof dest === 'string' && destNeedsEscape(dest)) ||
-    (typeof attrs.title === 'string' && hasBare(attrs.title, '"')) ||
-    (kind === 'image' && typeof attrs.alt === 'string' && hasBare(attrs.alt, '[]\\'))
+    (typeof attrs.title === 'string' && /["\\]/.test(attrs.title)) ||
+    (kind === 'image' && typeof attrs.alt === 'string' && /[\\[\]]/.test(attrs.alt))
   )
 }
 
@@ -172,11 +159,11 @@ function escapeLinkAndImageAttributes(node: JSONContent): void {
     if (typeof dest === 'string' && destNeedsEscape(dest)) {
       attrs[destKey] = escapeBare(dest, '()')
     }
-    if (typeof attrs.title === 'string' && hasBare(attrs.title, '"')) {
-      attrs.title = escapeBare(attrs.title, '"')
+    if (typeof attrs.title === 'string' && /["\\]/.test(attrs.title)) {
+      attrs.title = attrs.title.replace(/["\\]/g, '\\$&')
     }
-    if (kind === 'image' && typeof attrs.alt === 'string' && hasBare(attrs.alt, '[]\\')) {
-      attrs.alt = escapeBare(attrs.alt, '[]\\')
+    if (kind === 'image' && typeof attrs.alt === 'string' && /[\\[\]]/.test(attrs.alt)) {
+      attrs.alt = attrs.alt.replace(/[\\[\]]/g, '\\$&')
     }
   })
 }
diff --git a/src/renderer/src/components/editor/rich-markdown-prose-entities.ts b/src/renderer/src/components/editor/rich-markdown-prose-entities.ts
index 38440f3e353..9b7c524ce7e 100644
--- a/src/renderer/src/components/editor/rich-markdown-prose-entities.ts
+++ b/src/renderer/src/components/editor/rich-markdown-prose-entities.ts
@@ -1,9 +1,9 @@
-import { Extension } from '@tiptap/core'
+import { Extension, type JSONContent } 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
+  encodeTextForMarkdown?: (text: string, node: JSONContent, parentNode?: JSONContent) => string
 }
 
 function isMarkdownTextEncoder(value: unknown): value is MarkdownTextEncoder {
@@ -54,7 +54,13 @@ export const RichMarkdownProseEntities = Extension.create({
     }
     managerValue.encodeTextForMarkdown = (text, node, parentNode) => {
       const encoded = base.call(managerValue, text, node, parentNode)
-      return encoded === text ? text : encodeProseTextForMarkdown(text)
+      const prose = encoded === text ? text : encodeProseTextForMarkdown(text)
+      const insideCode =
+        parentNode?.type === 'codeBlock' || node.marks?.some((mark) => mark.type === 'code')
+      const hasInlineSyntax = parentNode?.content?.some(
+        (child) => child.type === 'inlineMath' || child.type === 'rawMarkdownHtmlInline'
+      )
+      return !insideCode && hasInlineSyntax ? prose.replace(/\$/g, '\\$&') : prose
     }
   }
 })
diff --git a/src/renderer/src/components/editor/tiptap-marked-facade.ts b/src/renderer/src/components/editor/tiptap-marked-facade.ts
index 534c2fffb58..bb8d9b02270 100644
--- a/src/renderer/src/components/editor/tiptap-marked-facade.ts
+++ b/src/renderer/src/components/editor/tiptap-marked-facade.ts
@@ -19,7 +19,10 @@ export function createTiptapMarkedFacade(): typeof marked {
     tokenizer: {
       link(src) {
         const token = Tokenizer.prototype.link.call(this, src)
-        const label = token?.type === 'link' ? this.rules.inline.link.exec(src)?.[1] : undefined
+        const label = token ? this.rules.inline.link.exec(src)?.[1] : undefined
+        if (token?.type === 'image' && label !== undefined) {
+          token.text = label.replace(/\\([!"#$%&'()*+,\-./:;<=>?@[\]\\^_`{|}~])/g, '$1')
+        }
         if (token?.type === 'link' && label && /\\(?:\[|\])/.test(label)) {
           // Preserve label escapes before nested inline parsing can reinterpret them as links.
           const wasInLink = this.lexer.state.inLink
diff --git a/tests/e2e/markdown-copy-formatting.spec.ts b/tests/e2e/markdown-copy-formatting.spec.ts
index 5ef99daf431..8ea3a3e638e 100644
--- a/tests/e2e/markdown-copy-formatting.spec.ts
+++ b/tests/e2e/markdown-copy-formatting.spec.ts
@@ -53,6 +53,30 @@ test('copying a rich selection preserves Markdown formatting', async ({ orcaPage
     expect(copied.html).toContain('<strong>bold</strong>')
     await expect(editor.locator('p')).toHaveText('A bold paragraph with a link.')
     await testInfo.attach('copied-markdown', { body: copied.text, contentType: 'text/markdown' })
+
+    await editor.evaluate((element) => {
+      const range = document.createRange()
+      range.selectNodeContents(element)
+      const selection = window.getSelection()
+      selection?.removeAllRanges()
+      selection?.addRange(range)
+      element.focus()
+      document.dispatchEvent(new Event('selectionchange'))
+    })
+    await expect
+      .poll(() => orcaPage.evaluate(() => window.getSelection()?.toString()))
+      .toContain('Copy formatting')
+    const copiedBlocks = await editor.evaluate((element) => {
+      const clipboardData = new DataTransfer()
+      element.dispatchEvent(
+        new ClipboardEvent('copy', { clipboardData, bubbles: true, cancelable: true })
+      )
+      return clipboardData.getData('text/plain')
+    })
+    expect(copiedBlocks).toBe(
+      '# Copy formatting\n\nA **bold** paragraph with a [link](https://example.com).'
+    )
+    await testInfo.attach('copied-blocks', { body: copiedBlocks, contentType: 'text/markdown' })
   } finally {
     await cleanupMarkdownFixture(filePath)
   }