diff --git a/src/telegram/format.ts b/src/telegram/format.ts
index 7feab62aeadf..c970e6f8ce8f 100644
--- a/src/telegram/format.ts
+++ b/src/telegram/format.ts
@@ -41,7 +41,6 @@ const FILE_EXTENSIONS_WITH_TLD = new Set([
   "at", // Assembly (Austria)
   "be", // Backend files (Belgium)
   "cc", // C++ source (Cocos Islands)
-  "co", // Configuration (Colombia)
 ]);
 
 /** Detects when markdown-it linkify auto-generated a link from a bare filename (e.g. README.md → http://README.md) */
@@ -150,7 +149,7 @@ export function wrapFileReferencesInHtml(html: string): string {
     return `<code>${escapeHtml(label)}</code>`;
   });
   const filePattern = new RegExp(
-    `(^|>|[\\s])([a-zA-Z0-9_.\\-./]+\\.(?:${extensionsPattern}))(?=$|[\\s<])`,
+    `(^|[^a-zA-Z0-9_\\-/])([a-zA-Z0-9_.\\-./]+\\.(?:${extensionsPattern}))(?=$|[^a-zA-Z0-9_\\-/])`,
     "gi",
   );
 
@@ -173,11 +172,18 @@ export function wrapFileReferencesInHtml(html: string): string {
 
     // Process text before this tag
     const textBefore = html.slice(lastIndex, tagStart);
-    result += textBefore.replace(filePattern, (m, prefix, filename) => {
+    result += textBefore.replace(filePattern, (m, prefix, filename, offset, source) => {
       // Skip if inside protected tags or if it's a URL
       if (codeDepth > 0 || preDepth > 0 || anchorDepth > 0) {
         return m;
       }
+      // Skip if we're inside any HTML tag (e.g., attributes on tags other than code/pre/a)
+      const filenameOffset = Number(offset) + String(prefix).length;
+      const lastOpen = String(source).lastIndexOf("<", filenameOffset);
+      const lastClose = String(source).lastIndexOf(">", filenameOffset);
+      if (lastOpen > lastClose) {
+        return m;
+      }
       if (filename.startsWith("//")) {
         return m;
       }
@@ -203,10 +209,16 @@ export function wrapFileReferencesInHtml(html: string): string {
 
   // Process remaining text
   const remainingText = html.slice(lastIndex);
-  result += remainingText.replace(filePattern, (m, prefix, filename) => {
+  result += remainingText.replace(filePattern, (m, prefix, filename, offset, source) => {
     if (codeDepth > 0 || preDepth > 0 || anchorDepth > 0) {
       return m;
     }
+    const filenameOffset = Number(offset) + String(prefix).length;
+    const lastOpen = String(source).lastIndexOf("<", filenameOffset);
+    const lastClose = String(source).lastIndexOf(">", filenameOffset);
+    if (lastOpen > lastClose) {
+      return m;
+    }
     if (filename.startsWith("//")) {
       return m;
     }
diff --git a/src/telegram/format.wrap-md.test.ts b/src/telegram/format.wrap-md.test.ts
index e882ef837b70..9fc3e386f323 100644
--- a/src/telegram/format.wrap-md.test.ts
+++ b/src/telegram/format.wrap-md.test.ts
@@ -73,6 +73,13 @@ describe("wrapFileReferencesInHtml", () => {
     expect(wrapFileReferencesInHtml("Ends with file.md")).toContain("<code>file.md</code>");
   });
 
+  it("wraps file refs with punctuation boundaries", () => {
+    expect(wrapFileReferencesInHtml("See README.md.")).toContain("<code>README.md</code>.");
+    expect(wrapFileReferencesInHtml("See README.md,")).toContain("<code>README.md</code>,");
+    expect(wrapFileReferencesInHtml("(README.md)")).toContain("(<code>README.md</code>)");
+    expect(wrapFileReferencesInHtml("README.md:")).toContain("<code>README.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>");
@@ -193,15 +200,12 @@ describe("edge cases", () => {
     expect(result).toBe("README.md");
   });
 
-  it("wraps supported TLD extensions (.am, .at, .be, .cc, .co)", () => {
-    const result = markdownToTelegramHtml(
-      "Makefile.am and code.at and app.be and main.cc and config.co",
-    );
+  it("wraps supported TLD extensions (.am, .at, .be, .cc)", () => {
+    const result = markdownToTelegramHtml("Makefile.am and code.at and app.be and main.cc");
     expect(result).toContain("<code>Makefile.am</code>");
     expect(result).toContain("<code>code.at</code>");
     expect(result).toContain("<code>app.be</code>");
     expect(result).toContain("<code>main.cc</code>");
-    expect(result).toContain("<code>config.co</code>");
   });
 
   it("does not wrap popular domain TLDs (.ai, .io, .tv, .fm)", () => {
@@ -214,6 +218,14 @@ describe("edge cases", () => {
     expect(result).toContain('<a href="http://radio.fm">');
   });
 
+  it("keeps .co domains as links", () => {
+    const result = markdownToTelegramHtml("Visit t.co and openclaw.co");
+    expect(result).toContain('<a href="http://t.co">');
+    expect(result).toContain('<a href="http://openclaw.co">');
+    expect(result).not.toContain("<code>t.co</code>");
+    expect(result).not.toContain("<code>openclaw.co</code>");
+  });
+
   it("does not wrap non-TLD extensions", () => {
     const result = markdownToTelegramHtml("image.png and style.css and script.js");
     expect(result).not.toContain("<code>image.png</code>");