diff --git a/experimental/ssh/internal/client/ssh-server-bootstrap.py b/experimental/ssh/internal/client/ssh-server-bootstrap.py
index b881268838..bef6b809fe 100644
--- a/experimental/ssh/internal/client/ssh-server-bootstrap.py
+++ b/experimental/ssh/internal/client/ssh-server-bootstrap.py
@@ -137,6 +137,15 @@ def detached_descendants(server_pgid):
     return sorted(survivors, key=int)
 
 
+def has_children():
+    """Probe without reaping; WNOHANG returning None still means children exist."""
+    try:
+        os.waitid(os.P_ALL, 0, os.WEXITED | os.WNOHANG | os.WNOWAIT)
+    except ChildProcessError:
+        return False
+    return True
+
+
 def wait_for_detached_descendants(server_pgid):
     """Hold the notebook open while detached work is still running.
 
@@ -154,7 +163,7 @@ def wait_for_detached_descendants(server_pgid):
     reported_at = 0.0
     while True:
         survivors = detached_descendants(server_pgid)
-        if not survivors:
+        if not survivors and not has_children():
             print("No detached processes left, releasing the run", flush=True)
             return
         now = time.monotonic()
diff --git a/experimental/ssh/internal/client/ssh_server_bootstrap_test.go b/experimental/ssh/internal/client/ssh_server_bootstrap_test.go
new file mode 100644
index 0000000000..fe29b12aff
--- /dev/null
+++ b/experimental/ssh/internal/client/ssh_server_bootstrap_test.go
@@ -0,0 +1,17 @@
+package client_test
+
+import (
+	"os/exec"
+	"testing"
+
+	"github.com/databricks/cli/libs/python"
+	"github.com/stretchr/testify/require"
+)
+
+func TestSSHServerBootstrap(test *testing.T) {
+	test.Parallel()
+
+	cmd := exec.CommandContext(test.Context(), python.GetExecutable(), "testdata/ssh_server_bootstrap_test.py")
+	output, err := cmd.CombinedOutput()
+	require.NoError(test, err, "%s", output)
+}
diff --git a/experimental/ssh/internal/client/testdata/ssh_server_bootstrap_test.py b/experimental/ssh/internal/client/testdata/ssh_server_bootstrap_test.py
new file mode 100644
index 0000000000..c3ebf8f728
--- /dev/null
+++ b/experimental/ssh/internal/client/testdata/ssh_server_bootstrap_test.py
@@ -0,0 +1,63 @@
+#!/usr/bin/env python3
+"""Test notebook linger helpers without importing Databricks runtime dependencies."""
+
+import ast
+import unittest
+from pathlib import Path
+from types import SimpleNamespace
+from unittest.mock import Mock, call
+
+
+class LingerTest(unittest.TestCase):
+    def test_wait_for_detached_descendants(self):
+        source = Path(__file__).resolve().parents[1] / "ssh-server-bootstrap.py"
+        module = ast.parse(source.read_text())
+        module.body = [
+            node
+            for node in module.body
+            if isinstance(node, ast.FunctionDef) and node.name in {"has_children", "wait_for_detached_descendants"}
+        ]
+        code = compile(module, str(source), "exec")
+
+        cases = {
+            "no children": ([[]], [ChildProcessError()], [], 0),
+            "child awaiting adoption": ([[], ["42"], []], [None, ChildProcessError()], [0, 1], 2),
+            "exited child awaiting reaping": ([[], []], [object(), ChildProcessError()], [0], 1),
+            "adopted child": ([["42"], []], [ChildProcessError()], [0], 1),
+            "pending adoption spans multiple polls": (
+                [[], [], ["42"], []],
+                [None, None, ChildProcessError()],
+                [0, 1, 2],
+                2,
+            ),
+            "pending adoption report interval": ([[], [], []], [None, None, ChildProcessError()], [0, 300], 2),
+        }
+        for name, (survivors, children, timestamps, report_count) in cases.items():
+            with self.subTest(name=name):
+                mock_os = SimpleNamespace(P_ALL=0, WEXITED=1, WNOHANG=2, WNOWAIT=4, waitid=Mock(side_effect=children))
+                mock_time = SimpleNamespace(monotonic=Mock(side_effect=timestamps), sleep=Mock())
+                namespace = {
+                    "os": mock_os,
+                    "time": mock_time,
+                    "detached_descendants": Mock(side_effect=survivors),
+                    "LINGER_POLL_SECONDS": 1,
+                    "LINGER_REPORT_SECONDS": 300,
+                    "print": Mock(),
+                }
+                exec(code, namespace)
+
+                namespace["wait_for_detached_descendants"](123)
+
+                self.assertEqual(namespace["detached_descendants"].call_args_list, [call(123)] * len(survivors))
+                self.assertEqual(
+                    mock_os.waitid.call_args_list,
+                    [call(mock_os.P_ALL, 0, mock_os.WEXITED | mock_os.WNOHANG | mock_os.WNOWAIT)] * len(children),
+                )
+                self.assertEqual(mock_time.sleep.call_args_list, [call(1)] * (len(survivors) - 1))
+                self.assertEqual(mock_time.monotonic.call_count, len(timestamps))
+                self.assertEqual(namespace["print"].call_count, report_count + 1)
+                self.assertIn("No detached processes left", namespace["print"].call_args[0][0])
+
+
+if __name__ == "__main__":
+    unittest.main()