diff --git a/tools/code-owners-parser/CodeOwnersParser/MatchedCodeOwnerEntry.cs b/tools/code-owners-parser/CodeOwnersParser/MatchedCodeOwnerEntry.cs
index 268b5868ff8..9a870666fb2 100644
--- a/tools/code-owners-parser/CodeOwnersParser/MatchedCodeOwnerEntry.cs
+++ b/tools/code-owners-parser/CodeOwnersParser/MatchedCodeOwnerEntry.cs
@@ -27,20 +27,9 @@ internal class MatchedCodeOwnerEntry
         public readonly CodeOwnerEntry Value;
 
         /// <summary>
-        /// The entry is valid if it obeys following conditions:
-        /// - The Value was obtained with a call to Azure.Sdk.Tools.CodeOwnersParser.CodeOwnersFile.ParseContent().
-        ///   - As a consequence, in the case of no match, the entry is not valid.
-        /// - the Value.PathExpression starts with "/".
-        ///
-        /// Once the validation described in the following issue is implemented:
-        /// https://github.com/Azure/azure-sdk-tools/issues/4859
-        /// To be valid, the entry will also have to obey following conditions:
-        /// - if the Value.PathExpression ends with "/", at least one corresponding
-        /// directory exists in the repository
-        /// - if the Value.PathExpression does not end with "/", at least one corresponding
-        /// file exists in the repository.
+        /// See comment on IsCodeOwnersPathValid
         /// </summary>
-        public bool IsValid => this.Value.PathExpression.StartsWith("/");
+        public bool IsValid => IsCodeOwnersPathValid(this.Value.PathExpression);
 
         /// <summary>
         /// Any CODEOWNERS path with these characters will be skipped.
@@ -132,12 +121,7 @@ private static string NormalizeTargetPath(string targetPath, string codeownersPa
 
         private static Regex ConvertToRegex(string codeownersPath)
         {
-            // CODEOWNERS paths that do not start with "/" are relative and considered invalid.
-            // However, here we handle such cases to accomodate for parsing CODEOWNERS file
-            // paths that somehow slipped through validation. We do so by instead treating
-            // such paths as if they were absolute to repository root, i.e. starting with "/".
-            if (!codeownersPath.StartsWith("/"))
-                codeownersPath = "/" + codeownersPath;
+            codeownersPath = ConvertPathIfInvalid(codeownersPath);
 
             string pattern = codeownersPath;
 
@@ -148,29 +132,64 @@ private static Regex ConvertToRegex(string codeownersPath)
 
             pattern = Regex.Escape(pattern);
 
-            // Denote that all paths are absolute by prepending "beginning of string" symbol.
+            pattern = AddStringAnchors(pattern);
+
+            // Note that the "/**/" case is implicitly covered by "**/".
+            pattern = pattern.Replace("_DOUBLE_STAR_/", "(.*)");
+            // This case is necessary to cover suffix case, e.g. "/foo/bar/**".
+            pattern = pattern.Replace("/_DOUBLE_STAR_", "(.*)");
+            // This case is necessary to cover inline **, e.g. "/a**b/".
+            pattern = pattern.Replace("_DOUBLE_STAR_", "(.*)");
+            pattern = pattern.Replace("_SINGLE_STAR_", "([^/]*)");
+            return new Regex(pattern);
+        }
+
+        private static string ConvertPathIfInvalid(string codeownersPath)
+        {
+            // CODEOWNERS paths that do not start with "/" are relative and considered invalid.
+            // However, here we handle such cases to accomodate for parsing CODEOWNERS file
+            // paths that somehow slipped through validation. We do so by instead treating
+            // such paths as if they were absolute to repository root, i.e. starting with "/".
+            if (!IsCodeOwnersPathValid(codeownersPath))
+                codeownersPath = "/" + codeownersPath;
+            return codeownersPath;
+        }
+
+        private static string AddStringAnchors(string pattern)
+        {
+            // Denote that all paths are absolute by pre-pending "beginning of string" symbol.
             pattern = "^" + pattern;
 
             // Lack of slash at the end denotes the path is a path to a file,
             // per our validation logic.
-            // Note we assume this is the case even if the path is invalid,
-            // even though in such case it might not necessarily be true.
-            if (!(pattern.EndsWith("/") 
-                  || pattern.EndsWith("_DOUBLE_STAR_")))
+            // Note we assume this is path to a file even if the path is invalid,
+            // even though in such case the path might be a path to a directory.
+            if (!pattern.EndsWith("/"))
             {
                 // Append "end of string", symbol, denoting the match has to be exact,
                 // not a substring, as we are dealing with a file.
                 pattern += "$";
             }
 
-            // Note that the "/**/" case is implicitly covered by "**/".
-            pattern = pattern.Replace("_DOUBLE_STAR_/", "(.*)");
-            // This case is necessary to cover suffix case, e.g. "/foo/bar/**".
-            pattern = pattern.Replace("/_DOUBLE_STAR_", "(.*)");
-            // This case is necessary to cover inline **, e.g. "/a**b/".
-            pattern = pattern.Replace("_DOUBLE_STAR_", "(.*)");
-            pattern = pattern.Replace("_SINGLE_STAR_", "([^/]*)");
-            return new Regex(pattern);
+            return pattern;
         }
+
+        /// <summary>
+        /// The entry is valid if it obeys following conditions:
+        /// - The Value was obtained with a call to
+        ///   Azure.Sdk.Tools.CodeOwnersParser.CodeOwnersFile.ParseContent().
+        ///   - As a consequence, in the case of no match, the entry is not valid.
+        /// - the Value.PathExpression starts with "/".
+        ///
+        /// Once the validation described in the following issue is implemented:
+        /// https://github.com/Azure/azure-sdk-tools/issues/4859
+        /// To be valid, the entry will also have to obey following conditions:
+        /// - if the Value.PathExpression ends with "/", at least one corresponding
+        /// directory exists in the repository
+        /// - if the Value.PathExpression does not end with "/", at least one corresponding
+        /// file exists in the repository.
+        /// </summary>
+        private static bool IsCodeOwnersPathValid(string codeownersPath)
+            => codeownersPath.StartsWith("/");
     }
 }