diff --git a/sjsonnet/src/sjsonnet/Evaluator.scala b/sjsonnet/src/sjsonnet/Evaluator.scala
index 5f99b43b..5dd31baf 100644
--- a/sjsonnet/src/sjsonnet/Evaluator.scala
+++ b/sjsonnet/src/sjsonnet/Evaluator.scala
@@ -894,9 +894,10 @@ class Evaluator(
         val ll = visitExprAsDouble(e.lhs).toSafeLong(pos)
         val rr = visitExprAsDouble(e.rhs).toSafeLong(pos)
         if (rr < 0) Error.fail("Shift by negative exponent", pos)
-        if (rr >= 1 && math.abs(ll) >= (1L << (63 - rr)))
+        val masked = (rr % 64).toInt
+        if (masked >= 1 && math.abs(ll) >= (1L << (63 - masked)))
           Error.fail("Numeric value outside safe integer range for bitwise operation", pos)
-        (ll << rr).toDouble
+        (ll << masked).toDouble
       case Expr.BinaryOp.OP_>> =>
         val ll = visitExprAsDouble(e.lhs).toSafeLong(pos)
         val rr = visitExprAsDouble(e.rhs).toSafeLong(pos)
diff --git a/sjsonnet/test/resources/new_test_suite/leftshift_fast_path_masking.jsonnet b/sjsonnet/test/resources/new_test_suite/leftshift_fast_path_masking.jsonnet
new file mode 100644
index 00000000..7ffe5f75
--- /dev/null
+++ b/sjsonnet/test/resources/new_test_suite/leftshift_fast_path_masking.jsonnet
@@ -0,0 +1,9 @@
+std.assertEqual((1 << 64) * 1, 1) &&
+std.assertEqual(((1 << 64) + 0) * 1, 1) &&
+std.assertEqual((1 << 65) * 1, 2) &&
+std.assertEqual((1 << 128) * 1, 1) &&
+std.assertEqual((0 << 128) * 1, 0) &&
+std.assertEqual(((-1) << 64) * 1, -1) &&
+std.assertEqual(((-2) << 65) * 1, -4) &&
+std.assertEqual(((-3) << 128) * 1, -3) &&
+true
diff --git a/sjsonnet/test/resources/new_test_suite/leftshift_fast_path_masking.jsonnet.golden b/sjsonnet/test/resources/new_test_suite/leftshift_fast_path_masking.jsonnet.golden
new file mode 100644
index 00000000..27ba77dd
--- /dev/null
+++ b/sjsonnet/test/resources/new_test_suite/leftshift_fast_path_masking.jsonnet.golden
@@ -0,0 +1 @@
+true