diff --git a/flytepropeller/pkg/compiler/validators/typing.go b/flytepropeller/pkg/compiler/validators/typing.go
index 388cb32123..669bca0e5d 100644
--- a/flytepropeller/pkg/compiler/validators/typing.go
+++ b/flytepropeller/pkg/compiler/validators/typing.go
@@ -356,9 +356,27 @@ func getTypeChecker(t *flyte.LiteralType) typeChecker {
 	}
 }
 
-func AreTypesCastable(upstreamType, downstreamType *flyte.LiteralType) bool {
+func isTypeAny(t *flyte.LiteralType) bool {
+	if t.GetMetadata() != nil {
+		if t.GetMetadata().GetFields() != nil {
+			pythonClassName := t.GetMetadata().GetFields()["python_class_name"]
+			if pythonClassName != nil {
+				if strVal, ok := pythonClassName.GetKind().(*structpb.Value_StringValue); ok && strVal.StringValue == "typing.Any" {
+					return true
+				}
+			}
+		}
+	}
+	return false
+}
+
+func AreTypesCastable(upstreamType *flyte.LiteralType, downstreamType *flyte.LiteralType) bool {
 	typeChecker := getTypeChecker(downstreamType)
 
+	if isTypeAny(upstreamType) || isTypeAny(downstreamType) {
+		return true
+	}
+
 	// if upstream is a singular union we check if the downstream type is castable from the union variant
 	if upstreamType.GetUnionType() != nil && len(upstreamType.GetUnionType().GetVariants()) == 1 {
 		variants := upstreamType.GetUnionType().GetVariants()