diff --git a/packages/app/e2e/browser/assistant-selection-copy.spec.ts b/packages/app/e2e/browser/assistant-selection-copy.spec.ts
index ad05e2af7..3c9440fdb 100644
--- a/packages/app/e2e/browser/assistant-selection-copy.spec.ts
+++ b/packages/app/e2e/browser/assistant-selection-copy.spec.ts
@@ -118,11 +118,18 @@ async function selectAssistantText(page: Page, text: string): Promise<void> {
   await selectAssistantTextRange(page, text, text);
 }
 
-async function doubleClickAssistantText(page: Page, text: string): Promise<void> {
+async function doubleClickAssistantMarkdownText(
+  page: Page,
+  tag: "code" | "strong",
+  text: string,
+): Promise<void> {
   const assistantMessage = page.getByTestId("assistant-message").filter({
     hasText: "Direct matches:",
   });
-  await assistantMessage.getByText(text, { exact: true }).dblclick();
+  await assistantMessage
+    .locator(`[data-paseo-markdown-tag="${tag}"]`)
+    .filter({ hasText: text })
+    .dblclick({ position: { x: 5, y: 5 } });
 }
 
 async function selectAssistantTextRange(
@@ -333,13 +340,20 @@ test("copying an assistant selection preserves Markdown structure and links", as
     expect(clipboard.html).toContain('<th style="text-align:right">Right</th>');
     expect(clipboard.html).toContain('<th style="text-align:center">Center</th>');
 
-    await doubleClickAssistantText(page, "apply_patch");
+    await doubleClickAssistantMarkdownText(page, "code", "apply_patch");
     await copySelection(page);
 
     const doubleClickedCodeClipboard = await readRichClipboard(page);
     expect(doubleClickedCodeClipboard.plainText).toBe("apply_patch");
     expect(doubleClickedCodeClipboard.html).not.toContain("<code>");
 
+    await doubleClickAssistantMarkdownText(page, "strong", "strong prose");
+    await copySelection(page);
+
+    const doubleClickedBoldClipboard = await readRichClipboard(page);
+    expect(doubleClickedBoldClipboard.plainText).toBe("strong");
+    expect(doubleClickedBoldClipboard.html).not.toContain("<strong>");
+
     await selectAssistantTextRange(
       page,
       "P1 — High-value UI behavior",
@@ -395,30 +409,21 @@ test("copying an assistant selection preserves Markdown structure and links", as
     await copySelection(page);
 
     const titledLinkClipboard = await readRichClipboard(page);
-    expect(titledLinkClipboard.plainText).toBe('[docs](https://docs.example.com "Reference")');
-    expect(titledLinkClipboard.html).toContain(
-      '<a href="https://docs.example.com/" title="Reference">docs</a>',
-    );
+    expect(titledLinkClipboard.plainText).toBe("docs");
+    expect(titledLinkClipboard.html).not.toContain("<a ");
 
     await selectAssistantText(page, "https://autolink.example.com");
     await copySelection(page);
 
     const autolinkClipboard = await readRichClipboard(page);
-    expect(autolinkClipboard.plainText).toBe(
-      "[https://autolink.example.com](https://autolink.example.com)",
-    );
-    expect(autolinkClipboard.html).toContain(
-      '<a href="https://autolink.example.com/">https://autolink.example.com</a>',
-    );
+    expect(autolinkClipboard.plainText).toBe("https://autolink.example.com");
 
     await selectAssistantText(page, "workspace file");
     await copySelection(page);
 
     const fileLinkClipboard = await readRichClipboard(page);
-    expect(fileLinkClipboard.plainText).toBe("[workspace file](file:///tmp/paseo%20notes.md#L4)");
-    expect(fileLinkClipboard.html).toContain(
-      '<a href="file:///tmp/paseo%20notes.md#L4">workspace file</a>',
-    );
+    expect(fileLinkClipboard.plainText).toBe("workspace file");
+    expect(fileLinkClipboard.html).not.toContain("<a ");
 
     await selectAssistantTextRange(page, "Seventh item", "Eighth item");
     await copySelection(page);
diff --git a/packages/app/src/assistant-selection-copy/content.browser.test.ts b/packages/app/src/assistant-selection-copy/content.browser.test.ts
index f46505c2b..df3269017 100644
--- a/packages/app/src/assistant-selection-copy/content.browser.test.ts
+++ b/packages/app/src/assistant-selection-copy/content.browser.test.ts
@@ -155,15 +155,19 @@ describe("assistant selection copy ranges", () => {
     },
   );
 
-  it("retains strong delimiters when its complete contents are selected", () => {
-    const message = mountFixture();
-    const element = fixtureElement(message, '[data-paseo-markdown-tag="strong"]');
-    const content = createAssistantSelectionClipboardContent(
-      selectText(element, 0, textNode(element).length),
-    );
-    expect(content?.plainText).toBe("**bold text**");
-    expect(content?.html).toContain("<strong>");
-  });
+  it.each(["strong", "em", "s", "h2", "blockquote"])(
+    "copies all content selected from inside a %s element without its syntax",
+    (tag) => {
+      const message = mountFixture();
+      const element = fixtureElement(message, '[data-paseo-markdown-tag="strong"]');
+      element.setAttribute("data-paseo-markdown-tag", tag);
+      const content = createAssistantSelectionClipboardContent(
+        selectText(element, 0, textNode(element).length),
+      );
+      expect(content?.plainText).toBe("bold text");
+      expect(content?.html).not.toContain(`<${tag}>`);
+    },
+  );
 
   it("copies complete inline code without delimiters when the selection stays inside", () => {
     const message = mountFixture();
diff --git a/packages/app/src/assistant-selection-copy/content.web.ts b/packages/app/src/assistant-selection-copy/content.web.ts
index ac157039d..6678e4a5b 100644
--- a/packages/app/src/assistant-selection-copy/content.web.ts
+++ b/packages/app/src/assistant-selection-copy/content.web.ts
@@ -278,6 +278,13 @@ function shouldPreserveSemanticElement(range: Range, element: Element): boolean
   if (tag === "p" || isTableStructure(tag)) {
     return true;
   }
+  const isSelectableSemantic = tag !== null && tag !== "ol" && tag !== "ul";
+  if (
+    (isSelectableSemantic || element.tagName === "A") &&
+    selectionStaysInsideElement(range, element)
+  ) {
+    return false;
+  }
   if (tag === "ol" || tag === "ul") {
     const selectedItems = selectedListItems(element, range);
     return selectedItems.some((item) => hasSelectedAllContents(range, item, true));
@@ -285,6 +292,15 @@ function shouldPreserveSemanticElement(range: Range, element: Element): boolean
   return hasSelectedAllContents(range, element, tag === "li");
 }
 
+function selectionStaysInsideElement(range: Range, element: Element): boolean {
+  return (
+    range.startContainer !== element &&
+    range.endContainer !== element &&
+    element.contains(range.startContainer) &&
+    element.contains(range.endContainer)
+  );
+}
+
 function selectedListItems(list: Element, range: Range): Element[] {
   return Array.from(list.children).filter(
     (child) =>