diff --git a/vyper/semantics/analysis/local.py b/vyper/semantics/analysis/local.py
index 3d1e9b8ef1..618b5c9d2c 100644
--- a/vyper/semantics/analysis/local.py
+++ b/vyper/semantics/analysis/local.py
@@ -37,6 +37,7 @@
     TYPE_T,
     AddressT,
     BoolT,
+    BytesT,
     DArrayT,
     EnumT,
     EventT,
@@ -232,7 +233,7 @@ def visit_AnnAssign(self, node):
             )
 
         typ = type_from_annotation(node.annotation, DataLocation.MEMORY)
-        validate_expected_type(node.value, typ)
+        #validate_expected_type(node.value, typ)
 
         try:
             self.namespace[name] = VarInfo(typ, location=DataLocation.MEMORY)
@@ -262,7 +263,6 @@ def visit_Assign(self, node):
                 "Left-hand side of assignment cannot be a HashMap without a key", node
             )
 
-        validate_expected_type(node.value, target.typ)
         target.validate_modification(node, self.func.mutability)
 
         self.expr_visitor.visit(node.value, target.typ)
@@ -691,7 +691,11 @@ def visit_Compare(self, node: vy_ast.Compare, typ: VyperType) -> None:
             self.visit(node.right, rtyp)
 
     def visit_Constant(self, node: vy_ast.Constant, typ: VyperType) -> None:
-        validate_expected_type(node, typ)
+        if typ in (BytesT, StringT):
+            typ = typ.from_literal(node)
+            node._metadata["type"] = typ
+
+        typ.validate_literal(node)
 
     def visit_Index(self, node: vy_ast.Index, typ: VyperType) -> None:
         validate_expected_type(node.value, typ)
diff --git a/vyper/semantics/types/bytestrings.py b/vyper/semantics/types/bytestrings.py
index 09130626aa..b422832b44 100644
--- a/vyper/semantics/types/bytestrings.py
+++ b/vyper/semantics/types/bytestrings.py
@@ -60,10 +60,9 @@ def maxlen(self):
 
     def validate_literal(self, node: vy_ast.Constant) -> None:
         super().validate_literal(node)
-
-        if len(node.value) != self.length:
+        if len(node.value) > self.length:
             # should always be constructed with correct length
-            # at the point that validate_literal is calle.d
+            # at the point that validate_literal is called
             raise CompilerPanic("unreachable")
 
     @property