diff --git a/tests/parser/exceptions/test_invalid_type_exception.py b/tests/parser/exceptions/test_invalid_type_exception.py
index 8cf7f9d6ff..450e6f4ae7 100644
--- a/tests/parser/exceptions/test_invalid_type_exception.py
+++ b/tests/parser/exceptions/test_invalid_type_exception.py
@@ -1,7 +1,5 @@
 import pytest
-from pytest import raises
 
-from vyper import compiler
 from vyper.exceptions import InvalidType, UnknownType
 
 fail_list = [
@@ -25,9 +23,8 @@
 
 
 @pytest.mark.parametrize("bad_code", fail_list)
-def test_unknown_type_exception(bad_code):
-    with raises(UnknownType):
-        compiler.compile_code(bad_code)
+def test_unknown_type_exception(bad_code, get_contract, assert_compile_failed):
+    assert_compile_failed(lambda: get_contract(bad_code), UnknownType)
 
 
 invalid_list = [
@@ -68,10 +65,13 @@ def mint(_to: address, _value: uint256):
     """
 b: HashMap[(int128, decimal), int128]
     """,
+    # Address literal must be checksummed
+    """
+a: constant(address) = 0x3cd751e6b0078be393132286c442345e5dc49699
+    """,
 ]
 
 
 @pytest.mark.parametrize("bad_code", invalid_list)
-def test_invalid_type_exception(bad_code):
-    with raises(InvalidType):
-        compiler.compile_code(bad_code)
+def test_invalid_type_exception(bad_code, get_contract, assert_compile_failed):
+    assert_compile_failed(lambda: get_contract(bad_code), InvalidType)
diff --git a/vyper/semantics/validation/utils.py b/vyper/semantics/validation/utils.py
index b140dcb1de..fe4c027db9 100644
--- a/vyper/semantics/validation/utils.py
+++ b/vyper/semantics/validation/utils.py
@@ -25,8 +25,11 @@
     DynamicArrayDefinition,
     TupleDefinition,
 )
+from vyper.semantics.types.value.address import AddressDefinition
 from vyper.semantics.types.value.boolean import BoolDefinition
+from vyper.semantics.types.value.bytes_fixed import Bytes20Definition  # type: ignore
 from vyper.semantics.validation.levenshtein_utils import get_levenshtein_error_suggestions
+from vyper.utils import checksum_encode
 
 
 def _validate_op(node, types_list, validation_fn_name):
@@ -456,9 +459,16 @@ def validate_expected_type(node, expected_type):
             types_str = sorted(str(i) for i in given_types)
             given_str = f"{', '.join(types_str[:1])} or {types_str[-1]}"
 
+        suggestion_str = ""
+        if isinstance(expected_type[0], AddressDefinition) and isinstance(
+            given_types[0], Bytes20Definition
+        ):
+            suggestion_str = f" Did you mean {checksum_encode(node.value)}?"
+
         # CMC 2022-02-14 maybe TypeMismatch would make more sense here
         raise InvalidType(
-            f"Expected {expected_str} but literal can only be cast as {given_str}", node
+            f"Expected {expected_str} but literal can only be cast as {given_str}.{suggestion_str}",
+            node,
         )