diff --git a/scripts/cbmc_json_parser.py b/scripts/cbmc_json_parser.py
index 955d83031145..9a0d58387f04 100755
--- a/scripts/cbmc_json_parser.py
+++ b/scripts/cbmc_json_parser.py
@@ -205,7 +205,7 @@ def postprocess_results(properties):
     annotate_properties_with_reach_results(properties, reach_checks)
 
     for property in properties:
-        if has_reachable_unsupported_constructs:
+        if has_reachable_unsupported_constructs or has_failed_unwinding_asserts:
             # Change SUCCESS to UNDETERMINED for all properties
             if property["status"] == "SUCCESS":
                 property["status"] = "UNDETERMINED"
@@ -213,7 +213,6 @@ def postprocess_results(properties):
             # Change SUCCESS to UNREACHABLE
             assert property["status"] == "SUCCESS", "** ERROR: Expecting an unreachable property to have a status of \"SUCCESS\""
             property["status"] = "UNREACHABLE"
-        # TODO: Handle unwinding assertion failure
 
     messages = ""
     if has_reachable_unsupported_constructs:
diff --git a/tests/expected/report/insufficient_unwind/expected b/tests/expected/report/insufficient_unwind/expected
new file mode 100644
index 000000000000..5dd5d65f0953
--- /dev/null
+++ b/tests/expected/report/insufficient_unwind/expected
@@ -0,0 +1,3 @@
+UNDETERMINED
+[Kani] info: Verification output shows one or more unwinding failures.
+[Kani] tip: Consider increasing the unwinding value or disabling `--unwinding-assertions`.
diff --git a/tests/expected/report/insufficient_unwind/test.rs b/tests/expected/report/insufficient_unwind/test.rs
new file mode 100644
index 000000000000..32921baea6f4
--- /dev/null
+++ b/tests/expected/report/insufficient_unwind/test.rs
@@ -0,0 +1,18 @@
+// Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
+// SPDX-License-Identifier: Apache-2.0 OR MIT
+
+// This test checks that Kani reports UNDETERMINED if the specified unwinding is
+// insufficient. The minimum required unwinding is 7.
+
+// kani-flags: --unwind 6
+
+fn main() {
+    let x: bool = kani::any();
+    let v = if x { vec![1, 2, 3] } else { vec![1, 1, 1, 1, 1, 1] };
+
+    let mut sum = 0;
+    for i in v {
+        sum += i;
+    }
+    assert!(sum == 6);
+}
diff --git a/tests/expected/unwind_tip/expected b/tests/expected/unwind_tip/expected
index cb7e4f45d9a0..5dd5d65f0953 100644
--- a/tests/expected/unwind_tip/expected
+++ b/tests/expected/unwind_tip/expected
@@ -1,2 +1,3 @@
+UNDETERMINED
 [Kani] info: Verification output shows one or more unwinding failures.
 [Kani] tip: Consider increasing the unwinding value or disabling `--unwinding-assertions`.