Stage

app/editor-webview/page.tsx

@@ -255,6 +255,12 @@ export default function EditorWebViewPage() {
     }
   }
 
+  const handleSelectionChange = (hasSelection: boolean) => {
+    if (window.ReactNativeWebView) {
+      window.ReactNativeWebView.postMessage(JSON.stringify({ type: 'SELECTION_CHANGE', payload: hasSelection }))
+    }
+  }
+
   return (
     <div className="h-screen w-screen overflow-auto bg-background">
       <RichTextEditorWebView
@@ -263,6 +269,7 @@ export default function EditorWebViewPage() {
         onContentChange={handleChange}
         onFocus={handleFocus}
         onBlur={handleBlur}
+        onSelectionChange={handleSelectionChange}
       />
     </div>
   )

core/services/smartPaste.ts

@@ -95,46 +95,60 @@ export const SmartPasteService = {
     return { type: 'plain', confidence: 0.6, reasons, warnings }
   },
 
-  resolvePaste(payload: PastePayload, options: SmartPasteOptions = {}): PasteResult {
+  resolvePaste(
+    payload: PastePayload,
+    options: SmartPasteOptions = {},
+    forcedType?: PasteType,
+  ): PasteResult {
     const config = { ...DEFAULT_OPTIONS, ...options }
-    const detection = SmartPasteService.detectPasteType(payload, config)
-    const warnings = [...detection.warnings]
-
-    try {
-      if (detection.type === 'html' && payload.html) {
-        const sanitized = sanitizePasteHtml(payload.html)
-        const html = unwrapSingleParagraph(sanitized)
-        return { html, type: 'html', warnings, detection }
+    const detection: PasteDetection = forcedType
+      ? { type: forcedType, confidence: 1.0, reasons: ['forced-by-user'], warnings: [] }
+      : SmartPasteService.detectPasteType(payload, config)
+    return resolvePasteInternal(payload, detection, config)
+  },
+}
+
+function resolvePasteInternal(
+  payload: PastePayload,
+  detection: PasteDetection,
+  config: Required<SmartPasteOptions>,
+): PasteResult {
+  const warnings = [...detection.warnings]
+
+  try {
+    if (detection.type === 'html' && payload.html) {
+      const sanitized = sanitizePasteHtml(payload.html)
+      const html = unwrapSingleParagraph(sanitized)
+      return { html, type: 'html', warnings, detection }
+    }
+
+    if (detection.type === 'markdown' && payload.text) {
+      if (payload.text.length > config.maxLength) {
+        warnings.push('plain:oversized-text')
+        const html = plainTextToHtml(payload.text)
+        return { html: sanitizePasteHtml(html), type: 'plain', warnings, detection }
       }
 
-      if (detection.type === 'markdown' && payload.text) {
-        if (payload.text.length > config.maxLength) {
-          warnings.push('plain:oversized-text')
-          const html = plainTextToHtml(payload.text)
-          return { html: sanitizePasteHtml(html), type: 'plain', warnings, detection }
-        }
-
-        if (containsUnsupportedMarkdown(payload.text)) {
-          warnings.push('plain:unsupported-markdown')
-          // Fallback to plain text wrapper without stripping characters (Strategy 2)
-          const html = plainTextToHtml(payload.text)
-          return { html: sanitizePasteHtml(html), type: 'plain', warnings, detection }
-        }
-
-        const rendered = markdown.render(payload.text)
-        return { html: sanitizePasteHtml(rendered), type: 'markdown', warnings, detection }
+      if (containsUnsupportedMarkdown(payload.text)) {
+        warnings.push('plain:unsupported-markdown')
+        // Fallback to plain text wrapper without stripping characters (Strategy 2)
+        const html = plainTextToHtml(payload.text)
+        return { html: sanitizePasteHtml(html), type: 'plain', warnings, detection }
       }
 
-      const text = payload.text ?? SanitizationService.stripHtml(payload.html ?? '')
-      const plainHtml = plainTextToHtml(text)
-      return { html: sanitizePasteHtml(plainHtml), type: 'plain', warnings, detection }
-    } catch {
-      warnings.push('plain:parse-failed')
-      const fallbackText = payload.text ?? safeStripHtml(payload.html ?? '')
-      const fallbackHtml = plainTextToHtml(fallbackText)
-      return { html: fallbackHtml, type: 'plain', warnings, detection }
+      const rendered = markdown.render(payload.text)
+      return { html: sanitizePasteHtml(rendered), type: 'markdown', warnings, detection }
     }
-  },
+
+    const text = payload.text ?? SanitizationService.stripHtml(payload.html ?? '')
+    const plainHtml = plainTextToHtml(text)
+    return { html: sanitizePasteHtml(plainHtml), type: 'plain', warnings, detection }
+  } catch {
+    warnings.push('plain:parse-failed')
+    const fallbackText = payload.text ?? safeStripHtml(payload.html ?? '')
+    const fallbackHtml = plainTextToHtml(fallbackText)
+    return { html: fallbackHtml, type: 'plain', warnings, detection }
+  }
 }
 
 function safeStripHtml(html: string): string {

core/tests/fixtures/clipboard/force-markdown.txt

@@ -0,0 +1,5 @@
+Project notes
+
+- Buy milk
+- Call dentist
+- Review PR

cypress/component/editor/RichTextEditorApplyMarkdown.cy.tsx

@@ -0,0 +1,110 @@
+import React from 'react'
+import RichTextEditor from '../../../ui/web/components/RichTextEditor'
+
+function mountEditor(content = '') {
+  const spy = cy.spy().as('onChange')
+  cy.mount(
+    <RichTextEditor
+      initialContent={content}
+      onContentChange={spy}
+    />
+  )
+}
+
+describe('RichTextEditor — Apply as Markdown button', () => {
+  describe('button state', () => {
+    it('renders the MD button in the toolbar', () => {
+      mountEditor('')
+      cy.get('[data-cy="apply-markdown-button"]').should('be.visible')
+    })
+
+    it('is disabled when no text is selected', () => {
+      mountEditor('<p>Some text</p>')
+      cy.get('[data-cy="apply-markdown-button"]').should('be.disabled')
+    })
+
+    it('becomes enabled after selecting text', () => {
+      mountEditor('<p>Some text</p>')
+      cy.get('[data-cy="editor-content"]').click()
+      cy.get('.ProseMirror').type('{selectall}')
+      cy.get('[data-cy="apply-markdown-button"]').should('not.be.disabled')
+    })
+
+    it('becomes disabled again after deselecting (pressing Escape)', () => {
+      mountEditor('<p>Some text</p>')
+      cy.get('[data-cy="editor-content"]').click()
+      cy.get('.ProseMirror').type('{selectall}')
+      cy.get('[data-cy="apply-markdown-button"]').should('not.be.disabled')
+      cy.get('.ProseMirror').type('{end}')
+      cy.get('[data-cy="apply-markdown-button"]').should('be.disabled')
+    })
+  })
+
+  describe('markdown rendering', () => {
+    it('converts selected low-score markdown text to rendered list', () => {
+      // This text scores below the auto-detection threshold (bullet list only = 2pts < 3)
+      // so without forcedType it would be detected as plain text
+      mountEditor('<p>Project notes\n\n- Buy milk\n- Call dentist\n- Review PR</p>')
+
+      cy.get('[data-cy="editor-content"]').click()
+      cy.get('.ProseMirror').type('{selectall}')
+      cy.get('[data-cy="apply-markdown-button"]').click()
+
+      cy.get('[data-cy="editor-content"]').find('ul').should('exist')
+      cy.get('[data-cy="editor-content"]').find('li').should('have.length.gte', 3)
+      cy.get('[data-cy="editor-content"]').should('contain.text', 'Buy milk')
+    })
+
+    it('converts selected heading markdown to h1 element', () => {
+      mountEditor('<p># Main Title\n\nContent below</p>')
+
+      cy.get('[data-cy="editor-content"]').click()
+      cy.get('.ProseMirror').type('{selectall}')
+      cy.get('[data-cy="apply-markdown-button"]').click()
+
+      cy.get('[data-cy="editor-content"]').find('h1').should('exist').and('contain.text', 'Main Title')
+    })
+
+    it('strips XSS tags from forced markdown input', () => {
+      mountEditor('<p># Title\n\n<script>alert(1)</script>\n\nParagraph</p>')
+
+      cy.get('[data-cy="editor-content"]').click()
+      cy.get('.ProseMirror').type('{selectall}')
+      cy.get('[data-cy="apply-markdown-button"]').click()
+
+      cy.get('[data-cy="editor-content"]').should('not.contain.html', '<script>')
+      cy.get('[data-cy="editor-content"]').find('h1').should('exist')
+      cy.get('[data-cy="editor-content"]').should('contain.text', 'Paragraph')
+    })
+
+    it('calls onContentChange after applying markdown', () => {
+      mountEditor('<p>- Item one\n- Item two</p>')
+
+      cy.get('[data-cy="editor-content"]').click()
+      cy.get('.ProseMirror').type('{selectall}')
+      cy.get('[data-cy="apply-markdown-button"]').click()
+
+      cy.get('@onChange').should('have.been.called')
+    })
+
+    it('text without markdown syntax remains as paragraph without crashing', () => {
+      mountEditor('<p>Just plain text with no markdown</p>')
+
+      cy.get('[data-cy="editor-content"]').click()
+      cy.get('.ProseMirror').type('{selectall}')
+      cy.get('[data-cy="apply-markdown-button"]').click()
+
+      // No crash, text still present
+      cy.get('[data-cy="editor-content"]').should('contain.text', 'Just plain text with no markdown')
+    })
+  })
+
+  describe('early returns — no crash', () => {
+    it('clicking disabled button (no selection) does not modify content', () => {
+      mountEditor('<p>Unchanged</p>')
+      cy.get('[data-cy="apply-markdown-button"]').click({ force: true })
+      cy.get('[data-cy="editor-content"]').should('contain.text', 'Unchanged')
+      cy.get('@onChange').should('not.have.been.called')
+    })
+  })
+})