diff --git a/tracer/src/Datadog.Trace/Ci/CodeOwners.cs b/tracer/src/Datadog.Trace/Ci/CodeOwners.cs
index ef1d69d2bd54..ae2f821962fe 100644
--- a/tracer/src/Datadog.Trace/Ci/CodeOwners.cs
+++ b/tracer/src/Datadog.Trace/Ci/CodeOwners.cs
@@ -137,13 +137,18 @@ private static bool TryParseSectionHeader(string raw, [NotNullWhen(true)] out Se
         /// </summary>
         private static Regex CompileGlob(string pattern)
         {
+            var patternWithoutLeadingGlobstar = pattern.StartsWith("**/", StringComparison.Ordinal)
+                                                    ? pattern.Substring(3)
+                                                    : pattern;
+
             // Escape regex metachars first.
-            var rx = Regex.Escape(pattern);
+            var rx = Regex.Escape(patternWithoutLeadingGlobstar);
+
+            // A globstar surrounded by slashes matches zero or more directories.
+            rx = rx.Replace("/\\*\\*/", "/(?:[^/]+/)*");
 
-            // Temporary sentinel for ** that we restore after dealing with single *.
-            rx = rx.Replace("\\*\\*", "§§DOUBLESTAR§§");
+            rx = rx.Replace("\\*\\*", ".*"); // multi-level wildcard
             rx = rx.Replace("\\*", "[^/]*"); // single‑level wildcard
-            rx = rx.Replace("§§DOUBLESTAR§§", ".*"); // multi‑level wildcard
             rx = rx.Replace("\\?", "."); // single char
 
             if (pattern.EndsWith("/"))
diff --git a/tracer/test/Datadog.Trace.ClrProfiler.IntegrationTests/CI/CodeOwnersTests.cs b/tracer/test/Datadog.Trace.ClrProfiler.IntegrationTests/CI/CodeOwnersTests.cs
index c13f2001fd95..e609eebc2bf2 100644
--- a/tracer/test/Datadog.Trace.ClrProfiler.IntegrationTests/CI/CodeOwnersTests.cs
+++ b/tracer/test/Datadog.Trace.ClrProfiler.IntegrationTests/CI/CodeOwnersTests.cs
@@ -51,6 +51,26 @@ public CodeOwnersTests()
         // New GitHub quirks
         [InlineData("/x/logs/error.txt", "[\"@octo-org/octocats\"]")] // **/logs pattern
         [InlineData("docs/getting-started.md", "[\"docs@example.com\"]")] // docs/* pattern
+        [InlineData("/globstar/target", "[\"@globstar-owner\"]")]
+        [InlineData("/globstar/one/target", "[\"@globstar-owner\"]")]
+        [InlineData("/globstar/one/two/target", "[\"@globstar-owner\"]")]
+        [InlineData("/globstar/one/not-target", "[\"@global-owner1\",\"@global-owner2\"]")]
+        // Leading globstar
+        [InlineData("foo", "[\"@foo-owner\"]")]
+        [InlineData("one/foo", "[\"@foo-owner\"]")]
+        [InlineData("one/two/foo", "[\"@foo-owner\"]")]
+        [InlineData("foo/bar", "[\"@foo-bar-owner\"]")]
+        [InlineData("one/foo/bar", "[\"@foo-bar-owner\"]")]
+        [InlineData("one/two/foo/bar", "[\"@foo-bar-owner\"]")]
+        [InlineData("foobar", "[\"@global-owner1\",\"@global-owner2\"]")]
+        // Trailing globstar
+        [InlineData("abc/file", "[\"@abc-owner\"]")]
+        [InlineData("abc/one/file", "[\"@abc-owner\"]")]
+        [InlineData("abc/one/two/file", "[\"@abc-owner\"]")]
+        [InlineData("abc", "[\"@global-owner1\",\"@global-owner2\"]")]
+        [InlineData("abcd/file", "[\"@global-owner1\",\"@global-owner2\"]")]
+        // An embedded **/ must not receive leading-globstar semantics
+        [InlineData("prefixtarget", "[\"@global-owner1\",\"@global-owner2\"]")]
         public void CheckGithubCodeOwners(string value, string expected)
         {
             var match = _githubCodeOwners.Match(value);
diff --git a/tracer/test/Datadog.Trace.ClrProfiler.IntegrationTests/CI/Data/CODEOWNERS_GITHUB b/tracer/test/Datadog.Trace.ClrProfiler.IntegrationTests/CI/Data/CODEOWNERS_GITHUB
index afbd198dcf9c..f13213c8c0f3 100644
--- a/tracer/test/Datadog.Trace.ClrProfiler.IntegrationTests/CI/Data/CODEOWNERS_GITHUB
+++ b/tracer/test/Datadog.Trace.ClrProfiler.IntegrationTests/CI/Data/CODEOWNERS_GITHUB
@@ -51,4 +51,17 @@ apps/ @octocat
 # directory in the root of your repository except for the `/apps/github`
 # subdirectory, as its owners are left empty.
 /apps/ @octocat
-/apps/github
\ No newline at end of file
+/apps/github
+
+# A globstar between slashes matches zero or more directories.
+/globstar/**/target @globstar-owner
+
+# A leading globstar matches at any depth, including the repository root.
+**/foo @foo-owner
+**/foo/bar @foo-bar-owner
+
+# A trailing globstar matches everything inside the directory.
+abc/** @abc-owner
+
+# Consecutive stars outside a globstar position are not a leading globstar.
+prefix**/target @embedded-star-owner