diff --git a/python/python-psi-impl/src/com/jetbrains/python/psi/types/PyTypeChecker.java b/python/python-psi-impl/src/com/jetbrains/python/psi/types/PyTypeChecker.java
index 2f5e32da5e03..10432517871a 100644
--- a/python/python-psi-impl/src/com/jetbrains/python/psi/types/PyTypeChecker.java
+++ b/python/python-psi-impl/src/com/jetbrains/python/psi/types/PyTypeChecker.java
@@ -215,7 +215,7 @@ public class PyTypeChecker {
       context.substitutions.put(expected, actual);
     }
     else if (bound != null) {
-      context.substitutions.put(expected, bound);
+      context.substitutions.put(expected, PyUnionType.createWeakType(bound));
     }
 
     return true;
diff --git a/python/testSrc/com/jetbrains/python/PyTypeTest.java b/python/testSrc/com/jetbrains/python/PyTypeTest.java
index e1c286f4c2ac..637f4d76f5e5 100644
--- a/python/testSrc/com/jetbrains/python/PyTypeTest.java
+++ b/python/testSrc/com/jetbrains/python/PyTypeTest.java
@@ -636,7 +636,7 @@ public class PyTypeTest extends PyTestCase {
   }
 
   public void testUpperBoundGeneric() {
-    doTest("Union[int, str]",
+    doTest("Union[Union[int, str], Any]",
            "def foo(x):\n" +
            "    '''\n" +
            "    :type x: T <= int or str\n" +
diff --git a/python/testSrc/com/jetbrains/python/PyTypingTest.java b/python/testSrc/com/jetbrains/python/PyTypingTest.java
index 1f9608495a03..58af95f1312d 100644
--- a/python/testSrc/com/jetbrains/python/PyTypingTest.java
+++ b/python/testSrc/com/jetbrains/python/PyTypingTest.java
@@ -239,7 +239,7 @@ public class PyTypingTest extends PyTestCase {
   }
 
   public void testAnyStrForUnknown() {
-    doTest("Union[str, bytes]",
+    doTest("Union[Union[str, bytes], Any]",
            "from typing import AnyStr\n" +
            "\n" +
            "def foo(x: AnyStr) -> AnyStr:\n" +