diff --git a/frontend/src/components/shared/markdown-editor/markdown-editor-paste.test.ts b/frontend/src/components/shared/markdown-editor/markdown-editor-paste.test.ts
index 0e353be1..5b0655fa 100644
--- a/frontend/src/components/shared/markdown-editor/markdown-editor-paste.test.ts
+++ b/frontend/src/components/shared/markdown-editor/markdown-editor-paste.test.ts
@@ -31,10 +31,30 @@ describe('shouldParseMarkdownOnPaste — markdown-parse plain text, defer rich s
         expect(shouldParseMarkdownOnPaste('# x', html, false)).toBe(false);
     });
 
-    it('still parses when the HTML is only styled-inline (e.g. a VS Code span, no block tags)', () => {
+    it('still parses when the HTML is only styled-inline but the text IS markdown (VS Code markdown copy)', () => {
         expect(shouldParseMarkdownOnPaste('**x**', '<span style="color:red">**x**</span>', false)).toBe(true);
     });
 
+    it.each([
+        ['# heading', '<span># heading</span>'],
+        ['- item one\n- item two', '<span>- item one<br>- item two</span>'],
+        ['| a | b |', '<span>| a | b |</span>'],
+        ['```\ncode\n```', '<span>```</span>'],
+        ['> quoted', '<span>&gt; quoted</span>'],
+        ['see [docs](https://x.dev)', '<span>see [docs](https://x.dev)</span>'],
+        ['1. first', '<span>1. first</span>'],
+    ])('parses markdown-looking text %s despite an inline-only HTML wrapper', (text, html) => {
+        expect(shouldParseMarkdownOnPaste(text, html, false)).toBe(true);
+    });
+
+    it.each([
+        ['hello world', '<b style="font-weight:700">hello world</b>'], // Google Docs bold paragraph
+        ['see the docs', '<a href="https://example.com">see the docs</a>'], // inline link
+        ['plain sentence', '<span style="font-style:italic">plain sentence</span>'], // Word italic
+    ])('defers inline-formatted HTML whose text %s has no markdown (native parse keeps the marks)', (text, html) => {
+        expect(shouldParseMarkdownOnPaste(text, html, false)).toBe(false);
+    });
+
     it('keeps a paste inside a code context literal', () => {
         expect(shouldParseMarkdownOnPaste('# x', '', true)).toBe(false);
     });
@@ -78,4 +98,10 @@ describe('MarkdownPaste — the parsed payload matches load (same tuned markdown
 
         expect(html).not.toContain('<h1>');
     });
+
+    it('defers inline-formatted HTML with markdown-free text (plugin inserts nothing)', () => {
+        const html = pasteHtml('hello bold world', '<b>hello bold world</b>');
+
+        expect(html).not.toContain('hello bold world');
+    });
 });
diff --git a/frontend/src/components/shared/markdown-editor/markdown-editor-paste.ts b/frontend/src/components/shared/markdown-editor/markdown-editor-paste.ts
index 9560bb07..955f1631 100644
--- a/frontend/src/components/shared/markdown-editor/markdown-editor-paste.ts
+++ b/frontend/src/components/shared/markdown-editor/markdown-editor-paste.ts
@@ -3,13 +3,27 @@ import { Plugin, PluginKey } from '@tiptap/pm/state';
 
 // @tiptap/markdown parses markdown for load/insertContent but never for the clipboard, so a paste of block
 // markdown (# ## - 1. | >) would land as literal text (only StarterKit's inline mark paste-rules fire).
-// Route plain-text pastes through the same markdown layer as load; defer to ProseMirror's own path for rich
-// sources — an in-editor copy (carries `data-pm-slice`) or web/Office HTML (block tags) — so their fidelity
-// survives, and keep pastes inside code literal.
+// Route markdown-looking plain-text pastes through the same markdown layer as load; defer to ProseMirror's
+// own path for rich sources — an in-editor copy (carries `data-pm-slice`), web/Office HTML (block tags), or
+// inline-formatted HTML whose text carries no markdown — so their fidelity survives, and keep pastes inside
+// code literal.
 const RICH_HTML_BLOCK = /<(?:h[1-6]|ul|ol|li|table|thead|tbody|tr|td|th|blockquote|pre|img|hr)\b/i;
 
+const MARKDOWN_CUES = [
+    /^#{1,6}\s/m, // heading
+    /\*\*[^*]+\*\*/, // bold
+    /\[.+\]\(.+\)/, // link
+    /^[-*+]\s/m, // bullet item
+    /^\d+\.\s/m, // ordered item
+    /^ {0,3}(?:```|~~~)/m, // fence
+    /^\|/m, // table row
+    /^>\s/m, // blockquote
+];
+
+const looksLikeMarkdown = (text: string): boolean => MARKDOWN_CUES.some((cue) => cue.test(text));
+
 export const shouldParseMarkdownOnPaste = (text: string, html: string, isCodeContext: boolean): boolean => {
-    if (!text.trim()) {
+    if (!text.trim() || isCodeContext) {
         return false;
     }
 
@@ -17,7 +31,16 @@ export const shouldParseMarkdownOnPaste = (text: string, html: string, isCodeCon
         return false;
     }
 
-    return !isCodeContext;
+    // Inline-only rich HTML (a Google Docs/Word/mail single paragraph: <b>, <a href>, styled spans) whose
+    // text/plain carries no markdown: defer to ProseMirror's native HTML parse — it runs the clipboard HTML
+    // through the schema, so bold/italic/links survive as marks. Markdown-looking text still wins the
+    // markdown parse: a VS Code copy of markdown source arrives wrapped in syntax-color spans, and parsing
+    // its text/plain (not the span noise) is the point of this plugin.
+    if (html && !looksLikeMarkdown(text)) {
+        return false;
+    }
+
+    return true;
 };
 
 export const MarkdownPaste = Extension.create({