diff --git a/packages/cli/src/__tests__/kill-with-timeout.test.ts b/packages/cli/src/__tests__/kill-with-timeout.test.ts
new file mode 100644
index 00000000..39824df9
--- /dev/null
+++ b/packages/cli/src/__tests__/kill-with-timeout.test.ts
@@ -0,0 +1,54 @@
+import { describe, expect, it } from "bun:test";
+import { killWithTimeout } from "../shared/ssh";
+
+describe("killWithTimeout", () => {
+  it("sends SIGKILL after grace period if process ignores SIGTERM", async () => {
+    const signals: (number | undefined)[] = [];
+    const proc = {
+      kill(signal?: number) {
+        signals.push(signal);
+      },
+    };
+
+    killWithTimeout(proc, 100);
+    await new Promise((r) => setTimeout(r, 200));
+
+    expect(signals).toEqual([
+      undefined,
+      9,
+    ]);
+  });
+
+  it("does not throw if process is already dead when SIGKILL fires", async () => {
+    let callCount = 0;
+    const proc = {
+      kill(signal?: number) {
+        callCount++;
+        if (callCount > 1) {
+          throw new Error("No such process");
+        }
+      },
+    };
+
+    killWithTimeout(proc, 50);
+    await new Promise((r) => setTimeout(r, 150));
+
+    // Should not throw — the error is caught internally
+    expect(callCount).toBe(2);
+  });
+
+  it("does not send SIGKILL if initial SIGTERM throws", async () => {
+    const signals: (number | undefined)[] = [];
+    const proc = {
+      kill(_signal?: number) {
+        throw new Error("No such process");
+      },
+    };
+
+    killWithTimeout(proc, 50);
+    await new Promise((r) => setTimeout(r, 150));
+
+    // No signals recorded because the first kill() threw
+    expect(signals).toEqual([]);
+  });
+});
diff --git a/packages/cli/src/shared/ssh.ts b/packages/cli/src/shared/ssh.ts
index bf1538fa..26e639e1 100644
--- a/packages/cli/src/shared/ssh.ts
+++ b/packages/cli/src/shared/ssh.ts
@@ -112,7 +112,6 @@ export function sleep(ms: number): Promise<void> {
 export function killWithTimeout(
   proc: {
     kill(signal?: number): void;
-    readonly killed: boolean;
   },
   gracePeriodMs = 5000,
 ): void {
@@ -121,11 +120,7 @@ export function killWithTimeout(
     return;
   }
   const sigkillTimer = setTimeout(() => {
-    tryCatch(() => {
-      if (!proc.killed) {
-        proc.kill(9);
-      }
-    });
+    tryCatch(() => proc.kill(9));
   }, gracePeriodMs);
   // Don't let this timer keep the event loop alive — the process may already
   // be dead from SIGTERM, so there's no reason to block exit for 5 seconds.