diff --git a/src/telegram/format.ts b/src/telegram/format.ts
index f82921fa5fb..777ac3aaec6 100644
--- a/src/telegram/format.ts
+++ b/src/telegram/format.ts
@@ -20,7 +20,57 @@ function escapeHtmlAttr(text: string): string {
   return escapeHtml(text).replace(/"/g, """);
 }
 
-function buildTelegramLink(link: MarkdownLinkSpan, _text: string) {
+/**
+ * File extensions that share TLDs and commonly appear in code/documentation.
+ * These are wrapped in <code> tags to prevent Telegram from generating
+ * spurious domain registrar previews.
+ */
+const FILE_EXTENSIONS_WITH_TLD = new Set([
+  // High priority - commonly referenced in messages
+  "md", // Markdown (Moldova)
+  "go", // Go language
+  "py", // Python (Paraguay)
+  "pl", // Perl (Poland)
+  "ai", // Adobe Illustrator (Anguilla)
+  "sh", // Shell (Saint Helena)
+  // Medium priority - sometimes referenced
+  "io", // Tuvalu (often used for tech projects)
+  "tv", // Tuvalu (video files)
+  "fm", // Federated States of Micronesia (audio)
+  "am", // Armenia
+  "at", // Austria
+  "be", // Belgium
+  "cc", // Cocos Islands
+  "co", // Colombia
+]);
+
+/** Detects when markdown-it linkify auto-generated a link from a bare filename (e.g. README.md → http://README.md) */
+function isAutoLinkedFileRef(href: string, label: string): boolean {
+  const stripped = href.replace(/^https?:\/\//i, "");
+  if (stripped !== label) {
+    return false;
+  }
+  const dotIndex = label.lastIndexOf(".");
+  if (dotIndex < 1) {
+    return false;
+  }
+  const ext = label.slice(dotIndex + 1).toLowerCase();
+  if (!FILE_EXTENSIONS_WITH_TLD.has(ext)) {
+    return false;
+  }
+  // Reject if any path segment before the filename contains a dot (looks like a domain)
+  const segments = label.split("/");
+  if (segments.length > 1) {
+    for (let i = 0; i < segments.length - 1; i++) {
+      if (segments[i].includes(".")) {
+        return false;
+      }
+    }
+  }
+  return true;
+}
+
+function buildTelegramLink(link: MarkdownLinkSpan, text: string) {
   const href = link.href.trim();
   if (!href) {
     return null;
@@ -28,6 +78,11 @@ function buildTelegramLink(link: MarkdownLinkSpan, _text: string) {
   if (link.start === link.end) {
     return null;
   }
+  // Suppress auto-linkified file references (e.g. README.md → http://README.md)
+  const label = text.slice(link.start, link.end);
+  if (isAutoLinkedFileRef(href, label)) {
+    return null;
+  }
   const safeHref = escapeHtmlAttr(href);
   return {
     start: link.start,
@@ -69,30 +124,6 @@ export function markdownToTelegramHtml(
   return html;
 }
 
-/**
- * File extensions that share TLDs and commonly appear in code/documentation.
- * These are wrapped in <code> tags to prevent Telegram from generating
- * spurious domain registrar previews.
- */
-const FILE_EXTENSIONS_WITH_TLD = new Set([
-  // High priority - commonly referenced in messages
-  "md", // Markdown (Moldova)
-  "go", // Go language
-  "py", // Python (Paraguay)
-  "pl", // Perl (Poland)
-  "ai", // Adobe Illustrator (Anguilla)
-  "sh", // Shell (Saint Helena)
-  // Medium priority - sometimes referenced
-  "io", // Tuvalu (often used for tech projects)
-  "tv", // Tuvalu (video files)
-  "fm", // Federated States of Micronesia (audio)
-  "am", // Armenia
-  "at", // Austria
-  "be", // Belgium
-  "cc", // Cocos Islands
-  "co", // Colombia
-]);
-
 /**
  * Wraps standalone file references (with TLD extensions) in <code> tags.
  * This prevents Telegram from treating them as URLs and generating
@@ -104,6 +135,18 @@ const FILE_EXTENSIONS_WITH_TLD = new Set([
 export function wrapFileReferencesInHtml(html: string): string {
   // Build regex pattern for all tracked extensions
   const extensionsPattern = Array.from(FILE_EXTENSIONS_WITH_TLD).join("|");
+
+  // Safety-net: de-linkify auto-generated anchors where href="http://<label>" (defense in depth for textMode: "html")
+  const autoLinkedAnchor = new RegExp(`<a\\s+href="https?://([^"]+)"\\s*>([^<]+)</a>`, "gi");
+  html = html.replace(autoLinkedAnchor, (_match, href: string, label: string) => {
+    if (href !== label) {
+      return _match;
+    }
+    if (!isAutoLinkedFileRef(`http://${href}`, label)) {
+      return _match;
+    }
+    return `<code>${label}</code>`;
+  });
   const filePattern = new RegExp(
     `(^|>|[\\s])([a-zA-Z0-9_.\\-./]+\\.(?:${extensionsPattern}))(?=$|[\\s<])`,
     "gi",
@@ -123,7 +166,7 @@ export function wrapFileReferencesInHtml(html: string): string {
   while ((match = tagPattern.exec(html)) !== null) {
     const tagStart = match.index;
     const tagEnd = tagPattern.lastIndex;
-    const isClosing = match[1] === "/";
+    const isClosing = match[1] === "</";
     const tagName = match[2].toLowerCase();
 
     // Process text before this tag
@@ -183,10 +226,8 @@ export function renderTelegramHtmlText(
     // For HTML mode, still wrap file references in the HTML
     return wrapFileReferencesInHtml(text);
   }
-  const html = markdownToTelegramHtml(text, { tableMode: options.tableMode });
-  // Wrap file references after markdown→HTML conversion
-  // This ensures we only transform text nodes, not HTML attributes
-  return wrapFileReferencesInHtml(html);
+  // markdownToTelegramHtml already wraps file references by default
+  return markdownToTelegramHtml(text, { tableMode: options.tableMode });
 }
 
 export function markdownToTelegramChunks(
diff --git a/src/telegram/format.wrap-md.test.ts b/src/telegram/format.wrap-md.test.ts
index 5ef7d1297c6..917fb78898b 100644
--- a/src/telegram/format.wrap-md.test.ts
+++ b/src/telegram/format.wrap-md.test.ts
@@ -1,5 +1,6 @@
 import { describe, expect, it } from "vitest";
 import {
+  markdownToTelegramChunks,
   markdownToTelegramHtml,
   renderTelegramHtmlText,
   wrapFileReferencesInHtml,
@@ -25,6 +26,10 @@ describe("wrapFileReferencesInHtml", () => {
     expect(wrapFileReferencesInHtml("Check backup.pl")).toContain("Check <code>backup.pl</code>");
   });
 
+  it("wraps .sh filenames", () => {
+    expect(wrapFileReferencesInHtml("Run backup.sh")).toContain("Run <code>backup.sh</code>");
+  });
+
   it("wraps file paths", () => {
     expect(wrapFileReferencesInHtml("Look at squad/friday/HEARTBEAT.md")).toContain(
       "Look at <code>squad/friday/HEARTBEAT.md</code>",
@@ -50,10 +55,10 @@ describe("wrapFileReferencesInHtml", () => {
     expect(result).toBe(input);
   });
 
-  it("does not wrap in URLs", () => {
-    const result = wrapFileReferencesInHtml("Visit https://example.com/README.md");
-    expect(result).toContain('href="https://example.com/README.md"');
-    expect(result).not.toContain("<code>README.md</code>");
+  it("does not wrap file refs inside real URL anchor tags", () => {
+    const input = 'Visit <a href="https://example.com/README.md">example.com/README.md</a>';
+    const result = wrapFileReferencesInHtml(input);
+    expect(result).toBe(input);
   });
 
   it("handles mixed content correctly", () => {
@@ -67,6 +72,27 @@ describe("wrapFileReferencesInHtml", () => {
     expect(wrapFileReferencesInHtml("File.md at start")).toContain("<code>File.md</code>");
     expect(wrapFileReferencesInHtml("Ends with file.md")).toContain("<code>file.md</code>");
   });
+
+  it("de-linkifies auto-linkified file ref anchors", () => {
+    const input = '<a href="http://README.md">README.md</a>';
+    expect(wrapFileReferencesInHtml(input)).toBe("<code>README.md</code>");
+  });
+
+  it("de-linkifies auto-linkified path anchors", () => {
+    const input = '<a href="http://squad/friday/HEARTBEAT.md">squad/friday/HEARTBEAT.md</a>';
+    expect(wrapFileReferencesInHtml(input)).toBe("<code>squad/friday/HEARTBEAT.md</code>");
+  });
+
+  it("preserves explicit links where label differs from href", () => {
+    const input = '<a href="http://README.md">click here</a>';
+    expect(wrapFileReferencesInHtml(input)).toBe(input);
+  });
+
+  it("wraps file ref after closing anchor tag", () => {
+    const input = '<a href="https://example.com">link</a> then README.md';
+    const result = wrapFileReferencesInHtml(input);
+    expect(result).toContain("</a> then <code>README.md</code>");
+  });
 });
 
 describe("renderTelegramHtmlText - file reference wrapping", () => {
@@ -98,4 +124,35 @@ describe("markdownToTelegramHtml - file reference wrapping", () => {
     const result = markdownToTelegramHtml("Check README.md", { wrapFileRefs: false });
     expect(result).not.toContain("<code>README.md</code>");
   });
+
+  it("wraps multiple file types in a single message", () => {
+    const result = markdownToTelegramHtml("Edit main.go and script.py");
+    expect(result).toContain("<code>main.go</code>");
+    expect(result).toContain("<code>script.py</code>");
+  });
+
+  it("preserves real URLs as anchor tags", () => {
+    const result = markdownToTelegramHtml("Visit https://example.com");
+    expect(result).toContain('<a href="https://example.com">');
+  });
+
+  it("preserves explicit markdown links even when href looks like a file ref", () => {
+    const result = markdownToTelegramHtml("[docs](http://README.md)");
+    expect(result).toContain('<a href="http://README.md">docs</a>');
+  });
+
+  it("wraps file ref after real URL in same message", () => {
+    const result = markdownToTelegramHtml("Visit https://example.com and README.md");
+    expect(result).toContain('<a href="https://example.com">');
+    expect(result).toContain("<code>README.md</code>");
+  });
+});
+
+describe("markdownToTelegramChunks - file reference wrapping", () => {
+  it("wraps file references in chunked output", () => {
+    const chunks = markdownToTelegramChunks("Check README.md and backup.sh", 4096);
+    expect(chunks.length).toBeGreaterThan(0);
+    expect(chunks[0].html).toContain("<code>README.md</code>");
+    expect(chunks[0].html).toContain("<code>backup.sh</code>");
+  });
 });