diff --git a/src/telegram/format.ts b/src/telegram/format.ts
index 2972acb9845..501b6ac776f 100644
--- a/src/telegram/format.ts
+++ b/src/telegram/format.ts
@@ -222,14 +222,17 @@ export function wrapFileReferencesInHtml(html: string): string {
     `([^a-zA-Z0-9]|^)([A-Za-z]\\.(?:${extensionsPattern}))(?=[^a-zA-Z0-9/]|$)`,
     "g",
   );
-  result = result.replace(orphanedTldPattern, (m, prefix, tld, offset) => {
+  // Snapshot for offset calculations (offset is relative to pre-replacement string)
+  // Note: replace() doesn't mutate, but snapshot makes intent explicit
+  const snapshot = result;
+  result = snapshot.replace(orphanedTldPattern, (m, prefix, tld, offset) => {
     // Skip if prefix is > (right after a tag close)
     if (prefix === ">") {
       return m;
     }
     // Skip if we're inside an HTML tag (between < and >)
-    const lastOpen = result.lastIndexOf("<", offset);
-    const lastClose = result.lastIndexOf(">", offset);
+    const lastOpen = snapshot.lastIndexOf("<", offset);
+    const lastClose = snapshot.lastIndexOf(">", offset);
     if (lastOpen > lastClose) {
       return m; // Inside a tag
     }
diff --git a/src/telegram/format.wrap-md.test.ts b/src/telegram/format.wrap-md.test.ts
index 413b91c1576..96b7628f71d 100644
--- a/src/telegram/format.wrap-md.test.ts
+++ b/src/telegram/format.wrap-md.test.ts
@@ -341,4 +341,22 @@ describe("edge cases", () => {
     const result = wrapFileReferencesInHtml(input);
     expect(result).toBe(input);
   });
+
+  it("handles multiple orphaned TLDs with HTML tags (offset stability)", () => {
+    // This tests the bug where offset is relative to pre-replacement string
+    // but we were checking against the mutating result string
+    const input = '<a href="http://A.md">link</a> B.md <span title="C.sh">text</span> D.py';
+    const result = wrapFileReferencesInHtml(input);
+    // A.md in href should NOT be wrapped (inside attribute)
+    // B.md outside tags SHOULD be wrapped
+    // C.sh in title attribute should NOT be wrapped
+    // D.py outside tags SHOULD be wrapped
+    expect(result).toContain("<code>B.md</code>");
+    expect(result).toContain("<code>D.py</code>");
+    expect(result).not.toContain("<code>A.md</code>");
+    expect(result).not.toContain("<code>C.sh</code>");
+    // Attributes should be unchanged
+    expect(result).toContain('href="http://A.md"');
+    expect(result).toContain('title="C.sh"');
+  });
 });