diff --git a/src/scancode/cli.py b/src/scancode/cli.py
index 1376c6cfee..e48cb50276 100644
--- a/src/scancode/cli.py
+++ b/src/scancode/cli.py
@@ -1390,7 +1390,7 @@ def terminate_pool(pool):
 
 def terminate_pool_with_backoff(pool, number_of_trials=3):
     # try a few times to terminate,
-    for trial in range(number_of_trials, 1):
+    for trial in range(number_of_trials):
         try:
             pool.terminate()
             break
diff --git a/tests/scancode/test_cli.py b/tests/scancode/test_cli.py
index 858baf68ca..50bf5e504b 100644
--- a/tests/scancode/test_cli.py
+++ b/tests/scancode/test_cli.py
@@ -1036,3 +1036,48 @@ def test_scan_does_validate_input_and_fails_on_faulty_json_input(test_file, expe
 def test_scan_does_validate_input_and_does_not_fail_on_valid_json_input():
     test_file = test_env.get_test_loc('various-inputs/true-scan-json.json')
     run_scan_click(['--from-json', test_file, '--json-pp', '-'], retry=False)
+    
+
+def test_terminate_pool_with_backoff_retries_on_windows_error():
+    """
+    Regression test: ensure terminate_pool_with_backoff actually executes
+    its retry loop. The old range(number_of_trials, 1) was always empty
+    so pool.terminate() was never called.
+    """
+    import builtins
+    from unittest.mock import MagicMock
+    import scancode.cli as _cli_mod
+    from scancode.cli import terminate_pool_with_backoff
+
+    _WindowsError = _cli_mod.__dict__.get(
+        'WindowsError',
+        getattr(builtins, 'WindowsError', Exception),
+    )
+
+    pool = MagicMock()
+    call_count = [0]
+
+    def flaky_terminate():
+        call_count[0] += 1
+        if call_count[0] < 2:
+            raise _WindowsError("fake windows error")
+
+    pool.terminate.side_effect = flaky_terminate
+
+    terminate_pool_with_backoff(pool, number_of_trials=3)
+
+    assert pool.terminate.call_count == 2
+
+
+def test_terminate_pool_with_backoff_succeeds_on_first_try():
+    """
+    Ensure terminate_pool_with_backoff breaks out of loop immediately
+    on success without unnecessary retries.
+    """
+    from unittest.mock import MagicMock
+    from scancode.cli import terminate_pool_with_backoff
+
+    pool = MagicMock()
+    terminate_pool_with_backoff(pool, number_of_trials=3)
+
+    assert pool.terminate.call_count == 1
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