diff --git a/src/plugin/command-execute-before.test.ts b/src/plugin/command-execute-before.test.ts
new file mode 100644
index 000000000..5bcf19888
--- /dev/null
+++ b/src/plugin/command-execute-before.test.ts
@@ -0,0 +1,114 @@
+import { describe, expect, mock, test } from "bun:test"
+
+import { createCommandExecuteBeforeHandler } from "./command-execute-before"
+
+describe("createCommandExecuteBeforeHandler", () => {
+  test("#given stopped session and /ulw-loop #when command.execute.before runs #then clear is called", async () => {
+    // given
+    const clear = mock(() => {})
+    const isStopped = mock(() => true)
+    const startLoop = mock(() => true)
+    const handler = createCommandExecuteBeforeHandler({
+      hooks: {
+        ralphLoop: {
+          startLoop,
+          cancelLoop: mock(() => true),
+        },
+        stopContinuationGuard: {
+          isStopped,
+          clear,
+        },
+      },
+    })
+
+    // when
+    await handler(
+      {
+        command: "ulw-loop",
+        sessionID: "ses-stopped",
+        arguments: "Ship feature",
+      },
+      {
+        parts: [],
+      },
+    )
+
+    // then
+    expect(startLoop).toHaveBeenCalledTimes(1)
+    expect(isStopped).toHaveBeenCalledWith("ses-stopped")
+    expect(clear).toHaveBeenCalledTimes(1)
+    expect(clear).toHaveBeenCalledWith("ses-stopped")
+  })
+
+  test("#given stopped session and /start-work #when command.execute.before runs #then clear is called", async () => {
+    // given
+    const clear = mock(() => {})
+    const isStopped = mock(() => true)
+    const startWorkHook = mock(async () => {})
+    const handler = createCommandExecuteBeforeHandler({
+      hooks: {
+        startWork: {
+          "command.execute.before": startWorkHook,
+        },
+        stopContinuationGuard: {
+          isStopped,
+          clear,
+        },
+      },
+    })
+
+    // when
+    await handler(
+      {
+        command: "start-work",
+        sessionID: "ses-stopped",
+        arguments: "",
+      },
+      {
+        parts: [],
+      },
+    )
+
+    // then
+    expect(startWorkHook).toHaveBeenCalledTimes(1)
+    expect(isStopped).toHaveBeenCalledWith("ses-stopped")
+    expect(clear).toHaveBeenCalledTimes(1)
+    expect(clear).toHaveBeenCalledWith("ses-stopped")
+  })
+
+  test("#given non-stopped session and /ulw-loop #when command.execute.before runs #then clear is not called", async () => {
+    // given
+    const clear = mock(() => {})
+    const isStopped = mock(() => false)
+    const startLoop = mock(() => true)
+    const handler = createCommandExecuteBeforeHandler({
+      hooks: {
+        ralphLoop: {
+          startLoop,
+          cancelLoop: mock(() => true),
+        },
+        stopContinuationGuard: {
+          isStopped,
+          clear,
+        },
+      },
+    })
+
+    // when
+    await handler(
+      {
+        command: "ulw-loop",
+        sessionID: "ses-running",
+        arguments: "Ship feature",
+      },
+      {
+        parts: [],
+      },
+    )
+
+    // then
+    expect(startLoop).toHaveBeenCalledTimes(1)
+    expect(isStopped).toHaveBeenCalledWith("ses-running")
+    expect(clear).not.toHaveBeenCalled()
+  })
+})
diff --git a/src/plugin/command-execute-before.ts b/src/plugin/command-execute-before.ts
index f480bbc8b..f1663b832 100644
--- a/src/plugin/command-execute-before.ts
+++ b/src/plugin/command-execute-before.ts
@@ -1,5 +1,6 @@
 import type { CreatedHooks } from "../create-hooks"
 import { parseRalphLoopArguments } from "../hooks/ralph-loop/command-arguments"
+import { log } from "../shared/logger"
 
 type CommandExecuteBeforeInput = {
   command: string
@@ -45,6 +46,13 @@ export function createCommandExecuteBeforeHandler(args: {
         })
         output.message ??= {}
         output.message[NATIVE_LOOP_TRIGGERED_FLAG] = true
+        if (hooks.stopContinuationGuard?.isStopped(sessionID)) {
+          hooks.stopContinuationGuard.clear(sessionID)
+          log("[stop-continuation] Stop state cleared by native command", {
+            sessionID,
+            command: normalizedCommand,
+          })
+        }
       } else if (normalizedCommand === "cancel-ralph") {
         hooks.ralphLoop.cancelLoop(sessionID)
         output.message ??= {}
@@ -58,6 +66,13 @@ export function createCommandExecuteBeforeHandler(args: {
       && hasPartsOutput(output)
     ) {
       await hooks.startWork["command.execute.before"]?.(input, output)
+      if (hooks.stopContinuationGuard?.isStopped(sessionID)) {
+        hooks.stopContinuationGuard.clear(sessionID)
+        log("[stop-continuation] Stop state cleared by native command", {
+          sessionID,
+          command: normalizedCommand,
+        })
+      }
     }
   }
 }