diff --git a/python/src/com/jetbrains/python/psi/types/PyTypeChecker.java b/python/src/com/jetbrains/python/psi/types/PyTypeChecker.java
index 88ba5d387bca..08b3988cb7c0 100644
--- a/python/src/com/jetbrains/python/psi/types/PyTypeChecker.java
+++ b/python/src/com/jetbrains/python/psi/types/PyTypeChecker.java
@@ -80,6 +80,7 @@ public class PyTypeChecker {
       }
     }
     if (expected instanceof PyInstantiableType && actual instanceof PyInstantiableType
+        && !(expected instanceof PyGenericType && typeVarAcceptsBothClassAndInstanceTypes((PyGenericType)expected)) 
         && ((PyInstantiableType)expected).isDefinition() ^ ((PyInstantiableType)actual).isDefinition()) {
       return false;
     }
@@ -288,6 +289,10 @@ public class PyTypeChecker {
     return matchNumericTypes(expected, actual);
   }
 
+  private static boolean typeVarAcceptsBothClassAndInstanceTypes(@NotNull PyGenericType typeVar) {
+    return !typeVar.isDefinition() && typeVar.getBound() == null;
+  }
+
   private static boolean consistsOfSameElementNumberTuples(@NotNull PyUnionType unionType, int elementCount) {
     for (PyType type : unionType.getMembers()) {
       if (type instanceof PyTupleType) {
diff --git a/python/testData/inspections/PyTypeCheckerInspection/UnboundTypeVarsMatchClassObjectTypes.py b/python/testData/inspections/PyTypeCheckerInspection/UnboundTypeVarsMatchClassObjectTypes.py
new file mode 100644
index 000000000000..05f1376366ea
--- /dev/null
+++ b/python/testData/inspections/PyTypeCheckerInspection/UnboundTypeVarsMatchClassObjectTypes.py
@@ -0,0 +1,38 @@
+from typing import TypeVar
+
+T = TypeVar('T')
+B = TypeVar('B', str)
+
+
+def f1(p: T):
+    return p
+
+
+f1(str)
+
+
+def f2(p: B):
+    return p
+
+
+f2(<warning descr="Expected type 'TypeVar('B', str)', got 'Type[str]' instead">str</warning>)
+
+
+def g1(p):
+    """
+    :type p: T 
+    """
+
+
+g1(str)
+
+
+def g2(p):
+    """
+    :type p: T <= str 
+    """
+
+
+g2(<warning descr="Expected type 'TypeVar('T', str)', got 'Type[str]' instead">str</warning>)
+
+xs = list([str])
diff --git a/python/testSrc/com/jetbrains/python/PyTypingTest.java b/python/testSrc/com/jetbrains/python/PyTypingTest.java
index 9342dd00adfe..12420ba99c6e 100644
--- a/python/testSrc/com/jetbrains/python/PyTypingTest.java
+++ b/python/testSrc/com/jetbrains/python/PyTypingTest.java
@@ -868,6 +868,30 @@ public class PyTypingTest extends PyTestCase {
            "    expr = x");
   }
 
+  // PY-23053
+  public void testUnboundGenericMatchesClassObjectTypes() {
+    doTest("Type[str]",
+           "from typing import Generic, TypeVar\n" +
+           "\n" +
+           "T = TypeVar('T')\n" +
+           "\n" +
+           "class Holder(Generic[T]):\n" +
+           "    def __init__(self, value: T):\n" +
+           "        self._value = value\n" +
+           "\n" +
+           "    def get(self) -> T:\n" +
+           "        return self._value\n" +
+           "\n" +
+           "expr = Holder(str).get()\n");
+  }
+
+  // PY-23053
+  public void testListContainingClasses() {
+    doTest("Type[str]", 
+           "xs = [str]\n" +
+           "expr = xs.pop()");
+  }
+
   private void doTestNoInjectedText(@NotNull String text) {
     myFixture.configureByText(PythonFileType.INSTANCE, text);
     final InjectedLanguageManager languageManager = InjectedLanguageManager.getInstance(myFixture.getProject());
diff --git a/python/testSrc/com/jetbrains/python/inspections/Py3TypeCheckerInspectionTest.java b/python/testSrc/com/jetbrains/python/inspections/Py3TypeCheckerInspectionTest.java
index 9de54dc04f70..a86c8023dfde 100644
--- a/python/testSrc/com/jetbrains/python/inspections/Py3TypeCheckerInspectionTest.java
+++ b/python/testSrc/com/jetbrains/python/inspections/Py3TypeCheckerInspectionTest.java
@@ -223,4 +223,9 @@ public class Py3TypeCheckerInspectionTest extends PyTestCase {
   public void testReplaceCalledOnUnionOfStrAndBytesWithStrArguments() {
     doTest();
   }
+
+  // PY-23053
+  public void testUnboundTypeVarsMatchClassObjectTypes() {
+    doTest();
+  }
 }