diff --git a/core/vm.cpp b/core/vm.cpp
index 667f9e1c..b90ed8d4 100644
--- a/core/vm.cpp
+++ b/core/vm.cpp
@@ -3246,7 +3246,8 @@ class Interpreter {
                                 case UOP_MINUS: scratch = makeNumber(-scratch.v.d); break;
 
                                 case UOP_BITWISE_NOT:
-                                    scratch = makeNumber(~(long)(scratch.v.d));
+                                    scratch = makeNumber(
+                                        ~safeDoubleToInt64(scratch.v.d, ast.location));
                                     break;
 
                                 default:
diff --git a/test_suite/error.integer_bitwise_not.jsonnet b/test_suite/error.integer_bitwise_not.jsonnet
new file mode 100644
index 00000000..b433aaf4
--- /dev/null
+++ b/test_suite/error.integer_bitwise_not.jsonnet
@@ -0,0 +1,3 @@
+// Value just beyond MAX_SAFE_INTEGER (2^53 - 1)
+local beyond_max = 9007199254740992;  // 2^53
+~beyond_max  // Should throw error "numeric value outside safe integer range for bitwise operation"
diff --git a/test_suite/error.integer_bitwise_not.jsonnet.golden b/test_suite/error.integer_bitwise_not.jsonnet.golden
new file mode 100644
index 00000000..69b96c76
--- /dev/null
+++ b/test_suite/error.integer_bitwise_not.jsonnet.golden
@@ -0,0 +1,2 @@
+RUNTIME ERROR: numeric value outside safe integer range for bitwise operation.
+	error.integer_bitwise_not.jsonnet:3:1-12