diff --git a/packages/app/src/components/markdown/html-ish.test.ts b/packages/app/src/components/markdown/html-ish.test.ts
index d8b45ae415..f8606d2714 100644
--- a/packages/app/src/components/markdown/html-ish.test.ts
+++ b/packages/app/src/components/markdown/html-ish.test.ts
@@ -3,6 +3,71 @@ import { describe, expect, it } from "vitest";
 import { normalizeHtmlishMarkdown, splitHtmlishMarkdown } from "./html-ish";
 
 describe("splitHtmlishMarkdown", () => {
+  it("renders heading text beside a linked picture without literal heading tags", () => {
+    const source =
+      '<h2><a href="https://example.com/r"><picture><source srcset="https://example.com/d.svg"><img alt="Retrigger" src="https://example.com/l.svg"></picture></a>Confidence Score: 5/5</h2>';
+
+    expect(splitHtmlishMarkdown(source)).toEqual([
+      {
+        kind: "inlineImage",
+        alt: "Retrigger",
+        src: "https://example.com/l.svg",
+        href: "https://example.com/r",
+        flowsWithText: true,
+      },
+      { kind: "markdown", text: "Confidence Score: 5/5" },
+    ]);
+  });
+
+  it.each(["h1", "h2", "h3", "h4", "h5", "h6"])(
+    "keeps a mixed %s heading together after preceding markdown",
+    (heading) => {
+      const source = `Intro\n\n<${heading}><img alt="Icon" src="https://example.com/icon.svg">Caption</${heading}>\n\nOutro`;
+
+      expect(splitHtmlishMarkdown(source)).toEqual([
+        { kind: "markdown", text: "Intro\n\n" },
+        {
+          kind: "inlineImage",
+          alt: "Icon",
+          src: "https://example.com/icon.svg",
+          flowsWithText: true,
+        },
+        { kind: "markdown", text: "Caption\n\nOutro" },
+      ]);
+    },
+  );
+
+  it("preserves formatted text before and after images in a details heading", () => {
+    const source =
+      '<details><summary>More</summary><h2><strong>Before</strong><img alt="Icon" src="https://example.com/icon.svg"><em>After</em></h2></details>';
+
+    expect(splitHtmlishMarkdown(source)).toEqual([
+      {
+        kind: "details",
+        summary: "More",
+        body: "**Before***After*",
+        bodyParts: [
+          { kind: "markdown", text: "**Before**" },
+          { kind: "inlineImage", alt: "Icon", src: "https://example.com/icon.svg" },
+          { kind: "markdown", text: "*After*" },
+        ],
+      },
+    ]);
+  });
+
+  it("keeps mixed HTML headings literal in code examples", () => {
+    const heading = '<h2><img src="https://example.com/icon.svg">Caption</h2>';
+    const source = `Use \`${heading}\`\n\n\`\`\`html\n${heading}\n\`\`\``;
+
+    expect(splitHtmlishMarkdown(source)).toEqual([{ kind: "markdown", text: source }]);
+  });
+
+  it("preserves unknown wrappers around text-only headings", () => {
+    expect(splitHtmlishMarkdown("<section><h2>Heading</h2></section>")).toEqual([
+      { kind: "markdown", text: "<section>Heading</section>" },
+    ]);
+  });
+
   const inlineImageBody = [
     '<a href="#"><img alt="Priority" src="https://example.com/assets/priority.svg?v=9" align="top"></a> Spoofed browser User-Agent allows access control bypass',
     "",
diff --git a/packages/app/src/components/markdown/html-ish.ts b/packages/app/src/components/markdown/html-ish.ts
index bd095c60b3..94eb7cab5b 100644
--- a/packages/app/src/components/markdown/html-ish.ts
+++ b/packages/app/src/components/markdown/html-ish.ts
@@ -125,9 +125,20 @@ function splitHtmlishTokens(tokens: HtmlToken[]): MarkdownDisplayPart[] {
       continue;
     }
 
-    const nextDetailsIndex = findNextOpenTag(tokens, cursor + 1, "details");
-    const nextInlineImageIndex = findNextInlineImageIndex(tokens, cursor + 1);
-    const end = Math.min(nextDetailsIndex ?? tokens.length, nextInlineImageIndex ?? tokens.length);
+    if (isHeadingTag(token)) {
+      const closeIndex = findMixedHeadingClose(tokens, cursor);
+      if (closeIndex !== null) {
+        // Headings render as their contents. Split those contents together so an
+        // embedded image cannot strand the opening heading tag in a text slice.
+        for (const part of splitHtmlishTokens(tokens.slice(cursor + 1, closeIndex))) {
+          appendDisplayPart(parts, part);
+        }
+        cursor = closeIndex + 1;
+        continue;
+      }
+    }
+
+    const end = findNextDisplayPartIndex(tokens, cursor + 1) ?? tokens.length;
     appendMarkdownPart(parts, renderInlineTokens(tokens.slice(cursor, end)));
     cursor = end;
   }
@@ -259,15 +270,44 @@ function flowsWithFollowingText(tokens: HtmlToken[], start: number, end: number)
   return false;
 }
 
-function findNextInlineImageIndex(tokens: HtmlToken[], start: number): number | null {
+function findNextDisplayPartIndex(tokens: HtmlToken[], start: number): number | null {
   for (let index = start; index < tokens.length; index += 1) {
-    if (parseInlineImageAt(tokens, index)) {
+    if (
+      isOpenTag(tokens[index], "details") ||
+      findMixedHeadingClose(tokens, index) !== null ||
+      parseInlineImageAt(tokens, index)
+    ) {
       return index;
     }
   }
   return null;
 }
 
+function findMixedHeadingClose(tokens: HtmlToken[], start: number): number | null {
+  const token = tokens[start];
+  if (!isHeadingTag(token)) {
+    return null;
+  }
+  const closeIndex = findMatchingClose(tokens, start, token.name);
+  if (closeIndex === null) {
+    return null;
+  }
+  for (let index = start + 1; index < closeIndex; index += 1) {
+    if (parseInlineImageAt(tokens, index)) {
+      return closeIndex;
+    }
+  }
+  return null;
+}
+
+function appendDisplayPart(parts: MarkdownDisplayPart[], part: MarkdownDisplayPart): void {
+  if (part.kind === "markdown") {
+    appendMarkdownPart(parts, part.text);
+  } else {
+    parts.push(part);
+  }
+}
+
 function appendMarkdownPart(parts: MarkdownDisplayPart[], text: string): void {
   if (!text) {
     return;