diff --git a/vyper/ast/nodes.py b/vyper/ast/nodes.py
index 3e753cae2d..ffd442f89a 100644
--- a/vyper/ast/nodes.py
+++ b/vyper/ast/nodes.py
@@ -979,13 +979,11 @@ def evaluate(self, left, right) -> ExprNode:
             raise UnfoldableNode("Node contains invalid field(s) for evaluation")
 
         # this validation is performed to prevent the compiler from hanging
-        # on very large shifts and improve the error message for negative
-        # values.
+        # on very large shifts. the actual error is handled downstream.
         if isinstance(self.op, (LShift, RShift)) and not (0 <= right.value <= 256):
-            raise InvalidLiteral("Shift bits must be between 0 and 256", right)
+            raise UnfoldableNode
 
         value = self.op._op(left.value, right.value)
-        _validate_numeric_bounds(self, value)
         return type(left).from_node(self, value=value)
 
 
diff --git a/vyper/semantics/analysis/local.py b/vyper/semantics/analysis/local.py
index 9cdd32e339..b865c8461a 100644
--- a/vyper/semantics/analysis/local.py
+++ b/vyper/semantics/analysis/local.py
@@ -635,7 +635,11 @@ def visit_BinOp(self, node: vy_ast.BinOp, typ: VyperType) -> None:
         self.visit(node.left, typ)
 
         rtyp = typ
+        right = get_folded_value(node.right)
         if isinstance(node.op, (vy_ast.LShift, vy_ast.RShift)):
+            if isinstance(right, vy_ast.Int) and not (0 <= right.value <= 256):
+                raise InvalidLiteral("Shift bits must be between 0 and 256", right)
+
             rtyp = get_possible_types_from_node(node.right).pop()
 
         validate_expected_type(node.right, rtyp)