diff --git a/test/dynamo/test_dicts.py b/test/dynamo/test_dicts.py
index eae7dfcc6816..756d75972b6b 100644
--- a/test/dynamo/test_dicts.py
+++ b/test/dynamo/test_dicts.py
@@ -1538,6 +1538,19 @@ def test_type(self):
         self.assertIsInstance(d, self.thetype)
         self.assertIs(type(d), self.thetype)
 
+    @make_dynamo_test
+    def test_bool(self):
+        p = self.thetype()
+        q = self.thetype({"a": 1, "b": 2})
+        if p:
+            self.fail("empty mapping must compare to False")
+        if not q:
+            self.fail("full mapping must compare to True")
+        if bool(p):
+            self.fail("empty mapping must compare to False")
+        if not bool(q):
+            self.fail("full mapping must compare to True")
+
 
 class DictSubclassMethodsTests(DictMethodsTests):
     thetype = SimpleDict
diff --git a/test/dynamo_expected_failures/CPython313-test_dict-SubclassMappingTests.test_bool b/test/dynamo_expected_failures/CPython313-test_dict-SubclassMappingTests.test_bool
deleted file mode 100644
index e69de29bb2d1..000000000000
diff --git a/test/dynamo_expected_failures/CPython313-test_dict-SubclassMappingTests.test_read b/test/dynamo_expected_failures/CPython313-test_dict-SubclassMappingTests.test_read
deleted file mode 100644
index e69de29bb2d1..000000000000
diff --git a/test/dynamo_expected_failures/CPython313-test_ordered_dict-CPythonSubclassMappingTests.test_bool b/test/dynamo_expected_failures/CPython313-test_ordered_dict-CPythonSubclassMappingTests.test_bool
deleted file mode 100644
index e69de29bb2d1..000000000000
diff --git a/test/dynamo_expected_failures/CPython313-test_ordered_dict-CPythonSubclassMappingTests.test_read b/test/dynamo_expected_failures/CPython313-test_ordered_dict-CPythonSubclassMappingTests.test_read
deleted file mode 100644
index e69de29bb2d1..000000000000
diff --git a/torch/_dynamo/symbolic_convert.py b/torch/_dynamo/symbolic_convert.py
index bee1d88bc1c7..a8921a76ccb1 100644
--- a/torch/_dynamo/symbolic_convert.py
+++ b/torch/_dynamo/symbolic_convert.py
@@ -760,7 +760,7 @@ def inner(self: "InstructionTranslatorBase", inst: Instruction):
                     x = None
 
             # __bool__ or __len__ is function
-            if isinstance(x, UserMethodVariable):
+            if isinstance(x, (GetAttrVariable, UserMethodVariable)):
                 result = x.call_function(self, [], {})  # type: ignore[arg-type, assignment]
                 if isinstance(result, ConstantVariable) and isinstance(
                     result.value, (bool, int)
diff --git a/torch/_dynamo/variables/builtin.py b/torch/_dynamo/variables/builtin.py
index d2b5b8c40077..06c65d32214e 100644
--- a/torch/_dynamo/variables/builtin.py
+++ b/torch/_dynamo/variables/builtin.py
@@ -1493,6 +1493,9 @@ def call_bool(self, tx: "InstructionTranslator", arg):
             assert istype(arg.sym_num, (torch.SymInt, torch.SymFloat))
             return SymNodeVariable.create(tx, arg.as_proxy() != 0)
 
+        if isinstance(arg, (ConstDictVariable, UserDefinedDictVariable)):
+            return ConstantVariable.create(len(arg.items) > 0)
+
         # TODO handle more cases and merge this with this with `generic_jump`.
 
     def call_str(self, tx: "InstructionTranslator", arg):
@@ -2791,7 +2794,7 @@ def call_not_(self, tx: "InstructionTranslator", a):
         # Unwrap the underlying ConstDictVariable
         if isinstance(a, DictViewVariable):
             a = a.dv_dict
-        if isinstance(a, (ListVariable, ConstDictVariable)):
+        if isinstance(a, (ListVariable, ConstDictVariable, UserDefinedDictVariable)):
             return ConstantVariable.create(len(a.items) == 0)
 
         return None