diff --git a/src/Platform/Microsoft.Testing.Platform/Requests/TreeNodeFilter/TreeNodeFilter.cs b/src/Platform/Microsoft.Testing.Platform/Requests/TreeNodeFilter/TreeNodeFilter.cs
index 3bc210353c..1b8f468f16 100644
--- a/src/Platform/Microsoft.Testing.Platform/Requests/TreeNodeFilter/TreeNodeFilter.cs
+++ b/src/Platform/Microsoft.Testing.Platform/Requests/TreeNodeFilter/TreeNodeFilter.cs
@@ -50,6 +50,12 @@ internal TreeNodeFilter(string filter)
     /// OP = '&' | '|'
     /// NODE_VALUE = TOKEN | TOKEN '[' FILTER_EXPR ']'
     /// TOKEN = string
+    ///
+    /// OR expressions are supported for a single path segment, for example:
+    /// <c>/A/B/C/(Test1|Test2)</c>.
+    ///
+    /// OR expressions over full paths are not supported, for example:
+    /// <c>(/A/B/C/Test1)|(/A/B/C/Test2)</c>.
     /// </code>
     /// </remarks>
     /// <exception cref="InvalidOperationException">
@@ -97,14 +103,14 @@ private static List<FilterExpression> ParseFilter(string filter)
                         _ => throw ApplicationStateGuard.Unreachable(),
                     };
 
-                    ProcessHigherPrecedenceOperators(expressionStack, operatorStack, currentOp);
+                    ProcessHigherPrecedenceOperators(expressionStack, operatorStack, currentOp, filter);
 
                     isOperatorAllowed = false;
                     isPropAllowed = false;
                     break;
 
                 case "/":
-                    ProcessHigherPrecedenceOperators(expressionStack, operatorStack, OperatorKind.Separator);
+                    ProcessHigherPrecedenceOperators(expressionStack, operatorStack, OperatorKind.Separator, filter);
 
                     isOperatorAllowed = false;
                     isPropAllowed = false;
@@ -147,7 +153,7 @@ private static List<FilterExpression> ParseFilter(string filter)
                             break;
                         }
 
-                        ProcessStackOperator(topStackOperator, expressionStack, operatorStack);
+                        ProcessStackOperator(topStackOperator, expressionStack, operatorStack, filter);
                     }
 
                     isOperatorAllowed = true;
@@ -179,7 +185,7 @@ private static List<FilterExpression> ParseFilter(string filter)
                             break;
                         }
 
-                        ProcessStackOperator(topStackOperator, expressionStack, operatorStack);
+                        ProcessStackOperator(topStackOperator, expressionStack, operatorStack, filter);
                     }
 
                     // We should end up with an expression and a property.
@@ -244,7 +250,7 @@ private static List<FilterExpression> ParseFilter(string filter)
         while (operatorStack.Count > 0 && operatorStack.Peek() != OperatorKind.Separator)
         {
             topStackOperator = operatorStack.Pop();
-            ProcessStackOperator(topStackOperator, expressionStack, operatorStack);
+            ProcessStackOperator(topStackOperator, expressionStack, operatorStack, filter);
         }
 
         var parsedFilter = expressionStack.Reverse().ToList();
@@ -265,12 +271,13 @@ private static List<FilterExpression> ParseFilter(string filter)
         static void ProcessHigherPrecedenceOperators(
             Stack<FilterExpression> expressionStack,
             Stack<OperatorKind> operatorStack,
-            OperatorKind currentOp)
+            OperatorKind currentOp,
+            string currentFilter)
         {
             while (operatorStack.Count != 0 && operatorStack.Peek() > currentOp)
             {
                 OperatorKind topStackOperator = operatorStack.Pop();
-                ProcessStackOperator(topStackOperator, expressionStack, operatorStack);
+                ProcessStackOperator(topStackOperator, expressionStack, operatorStack, currentFilter);
                 break;
             }
 
@@ -303,7 +310,7 @@ private static void ValidateExpression(FilterExpression expr, bool isMatchAllAll
         }
     }
 
-    private static void ProcessStackOperator(OperatorKind op, Stack<FilterExpression> expr, Stack<OperatorKind> ops)
+    private static void ProcessStackOperator(OperatorKind op, Stack<FilterExpression> expr, Stack<OperatorKind> ops, string filter)
     {
         switch (op)
         {
@@ -325,14 +332,14 @@ private static void ProcessStackOperator(OperatorKind op, Stack<FilterExpression
                     subexprs.Add(expr.Pop());
                 }
 
-                FilterOperator filter = op switch
+                FilterOperator filterOperator = op switch
                 {
                     OperatorKind.And => FilterOperator.And,
                     OperatorKind.Or => FilterOperator.Or,
                     _ => throw ApplicationStateGuard.Unreachable(),
                 };
 
-                expr.Push(new OperatorExpression(filter, subexprs));
+                expr.Push(new OperatorExpression(filterOperator, subexprs));
                 break;
 
             case OperatorKind.FilterEquals:
@@ -364,7 +371,9 @@ private static void ProcessStackOperator(OperatorKind op, Stack<FilterExpression
                 // Note: Handling of other operations in valid scenarios should be handled by the caller.
                 //       Reaching this code for instance means that we're trying to process / operator
                 //       in the middle of a ( expression ).
-                throw new InvalidOperationException(PlatformResources.TreeNodeFilterUnexpectedSlashOperatorErrorMessage);
+                throw new InvalidOperationException(
+                    $"{PlatformResources.TreeNodeFilterUnexpectedSlashOperatorErrorMessage} "
+                    + $"Filter: '{filter}'. To combine alternatives for one path segment, use syntax like '/A/B/C/(X|Y)'.");
         }
     }
 
diff --git a/test/UnitTests/Microsoft.Testing.Platform.UnitTests/Requests/TreeNodeFilterTests.cs b/test/UnitTests/Microsoft.Testing.Platform.UnitTests/Requests/TreeNodeFilterTests.cs
index ebfdbdbb22..84fce56c5e 100644
--- a/test/UnitTests/Microsoft.Testing.Platform.UnitTests/Requests/TreeNodeFilterTests.cs
+++ b/test/UnitTests/Microsoft.Testing.Platform.UnitTests/Requests/TreeNodeFilterTests.cs
@@ -70,6 +70,34 @@ public void OrExpression_WorksForLiteralStrings()
         Assert.IsFalse(filter.MatchesFilter("/C", new PropertyBag()));
     }
 
+    [TestMethod]
+    public void OrExpression_WorksForSinglePathSegmentInsideParentheses()
+    {
+        TreeNodeFilter filter = new("/*/*/*/(MyTest1|MyTest2)");
+
+        Assert.IsTrue(filter.MatchesFilter("/A/B/C/MyTest1", new PropertyBag()));
+        Assert.IsTrue(filter.MatchesFilter("/A/B/C/MyTest2", new PropertyBag()));
+        Assert.IsFalse(filter.MatchesFilter("/A/B/C/MyTest3", new PropertyBag()));
+    }
+
+    [TestMethod]
+    public void ExactMatch_DoesNotMatchAdditionalSuffixUnlessWildcardIsUsed()
+    {
+        TreeNodeFilter filter = new("/*/*/*/(MyTest1|MyTest2)");
+
+        Assert.IsFalse(filter.MatchesFilter("/A/B/C/MyTest1()", new PropertyBag()));
+        Assert.IsFalse(filter.MatchesFilter("/A/B/C/MyTest2()", new PropertyBag()));
+    }
+
+    [TestMethod]
+    public void FullPathOrInsideParenthesizedExpressions_IsNotSupported_ThrowsActionableMessage()
+    {
+        InvalidOperationException exception = Assert.ThrowsExactly<InvalidOperationException>(
+            () => _ = new TreeNodeFilter("(/*/*/*/MyTest1)|(/*/*/*/MyTest2)"));
+
+        Assert.IsTrue(exception.Message.Contains("/A/B/C/(X|Y)", StringComparison.Ordinal));
+    }
+
     [TestMethod]
     public void AndExpression()
     {