diff --git a/src/Analysis/Ast/Impl/Analyzer/Evaluation/ExpressionEval.Hints.cs b/src/Analysis/Ast/Impl/Analyzer/Evaluation/ExpressionEval.Hints.cs
index 55d9e25b7..b12e08072 100644
--- a/src/Analysis/Ast/Impl/Analyzer/Evaluation/ExpressionEval.Hints.cs
+++ b/src/Analysis/Ast/Impl/Analyzer/Evaluation/ExpressionEval.Hints.cs
@@ -79,7 +79,7 @@ public IPythonType GetTypeFromPepHint(Node node) {
             }
 
             // Type alone is not a valid syntax, so we need to simulate the annotation.
-            var typeString = content.Substring(hintStart, i - hintStart);
+            var typeString = content.Substring(hintStart, i - hintStart).Trim();
             return GetTypeFromString(typeString);
         }
 
@@ -88,7 +88,8 @@ public IPythonType GetTypeFromString(string typeString) {
             typeString = $"x: {typeString}";
             using (var sr = new StringReader(typeString)) {
                 var sink = new CollectingErrorSink();
-                var parser = Parser.CreateParser(sr, Module.Interpreter.LanguageVersion, new ParserOptions { ErrorSink = sink });
+                // Always use Python 3 since expression is an annotation which is 3.x
+                var parser = Parser.CreateParser(sr, PythonLanguageVersion.V36, new ParserOptions { ErrorSink = sink });
                 var ast = parser.ParseFile();
                 var exprStatement = (ast?.Body as SuiteStatement)?.Statements?.FirstOrDefault() as ExpressionStatement;
                 if (!(Statement.GetExpression(exprStatement) is ExpressionWithAnnotation annExpr) || sink.Errors.Count > 0) {
diff --git a/src/Analysis/Ast/Test/PepHintTests.cs b/src/Analysis/Ast/Test/PepHintTests.cs
index 8e1e04bcb..91db0df13 100644
--- a/src/Analysis/Ast/Test/PepHintTests.cs
+++ b/src/Analysis/Ast/Test/PepHintTests.cs
@@ -19,6 +19,7 @@
 using Microsoft.Python.Analysis.Tests.FluentAssertions;
 using Microsoft.Python.Analysis.Types;
 using Microsoft.Python.Analysis.Values;
+using Microsoft.Python.Parsing.Tests;
 using Microsoft.Python.Tests.Utilities.FluentAssertions;
 using Microsoft.VisualStudio.TestTools.UnitTesting;
 using TestUtilities;
@@ -76,5 +77,18 @@ class Response: # truncated
             c.Should().HaveMember<IPythonInstance>("elapsed")
                 .Which.Should().HaveSameMembersAs(timedelta);
         }
+
+        [TestMethod, Priority(0)]
+        public async Task HintsInPython2() {
+            const string code = @"
+def func(x):
+    y = x # type: int
+";
+            var analysis = await GetAnalysisAsync(code, PythonVersions.LatestAvailable2X);
+
+            analysis.Should().HaveFunction("func")
+                .Which.Should().HaveVariable("y")
+                .Which.Should().HaveType(BuiltinTypeId.Int);
+        }
     }
 }