diff --git a/src/hooks/stop-continuation-guard/hook.ts b/src/hooks/stop-continuation-guard/hook.ts
index 747b7a9b6..ce3ba7c0b 100644
--- a/src/hooks/stop-continuation-guard/hook.ts
+++ b/src/hooks/stop-continuation-guard/hook.ts
@@ -100,10 +100,16 @@ export function createStopContinuationGuardHook(
   }: {
     sessionID?: string
   }): Promise<void> => {
-    if (sessionID && stoppedSessions.has(sessionID)) {
-      clear(sessionID)
-      log(`[${HOOK_NAME}] Cleared stop state on new user message`, { sessionID })
-    }
+    // Intentionally no-op: stop state should persist across user messages.
+    // Previously this cleared the stop on any new user message, but that caused
+    // /stop-continuation to be ineffective — the user's very next message
+    // (including normal chat) would re-enable continuation.
+    //
+    // Stop state is now only cleared by:
+    // 1. /start-work (or /ulw-loop, /ralph-loop) via explicit clear() call
+    // 2. session.deleted event
+    // 3. Future /resume-continuation command
+    void sessionID
   }
 
   return {
diff --git a/src/hooks/stop-continuation-guard/index.test.ts b/src/hooks/stop-continuation-guard/index.test.ts
index a0d08f217..65d1a17b8 100644
--- a/src/hooks/stop-continuation-guard/index.test.ts
+++ b/src/hooks/stop-continuation-guard/index.test.ts
@@ -162,7 +162,7 @@ describe("stop-continuation-guard", () => {
     expect(guard.isStopped(session2)).toBe(false)
   })
 
-  test("should clear stopped state on new user message (chat.message)", async () => {
+  test("should NOT clear stopped state on new user message (chat.message)", async () => {
     // given - a session that was stopped
     const guard = createStopContinuationGuardHook(createMockPluginInput())
     const sessionID = "test-session-4"
@@ -172,7 +172,38 @@ describe("stop-continuation-guard", () => {
     // when - user sends a new message
     await guard["chat.message"]({ sessionID })
 
-    // then - stop state should be cleared (one-time only)
+    // then - stop state should persist (not cleared by user messages)
+    // Stop is only cleared by explicit work-starting commands (/start-work, /ralph-loop, /ulw-loop)
+    // or session deletion. This prevents /stop-continuation from being ineffective.
+    expect(guard.isStopped(sessionID)).toBe(true)
+  })
+
+  test("should persist stop state across multiple user messages", async () => {
+    // given - a session that was stopped
+    const guard = createStopContinuationGuardHook(createMockPluginInput())
+    const sessionID = "test-session-persist"
+    guard.stop(sessionID)
+
+    // when - user sends multiple messages
+    await guard["chat.message"]({ sessionID })
+    await guard["chat.message"]({ sessionID })
+    await guard["chat.message"]({ sessionID })
+
+    // then - stop state remains active
+    expect(guard.isStopped(sessionID)).toBe(true)
+  })
+
+  test("should clear stop state only via explicit clear() call", () => {
+    // given - a session that was stopped
+    const guard = createStopContinuationGuardHook(createMockPluginInput())
+    const sessionID = "test-session-explicit-clear"
+    guard.stop(sessionID)
+    expect(guard.isStopped(sessionID)).toBe(true)
+
+    // when - clear is called (simulating /start-work or /ralph-loop)
+    guard.clear(sessionID)
+
+    // then - stop state is cleared
     expect(guard.isStopped(sessionID)).toBe(false)
   })
 
diff --git a/src/plugin/tool-execute-before.ts b/src/plugin/tool-execute-before.ts
index e7585b7b3..3649720b9 100644
--- a/src/plugin/tool-execute-before.ts
+++ b/src/plugin/tool-execute-before.ts
@@ -184,6 +184,19 @@ export function createToolExecuteBeforeHandler(args: {
           sessionID,
         })
       }
+
+      // Clear stop state when user explicitly resumes work via work-starting commands.
+      // This ensures /stop-continuation persists until the user intentionally restarts.
+      const workStartingCommands = ["start-work", "ralph-loop", "ulw-loop"]
+      if (workStartingCommands.includes(command ?? "") && sessionID) {
+        if (hooks.stopContinuationGuard?.isStopped(sessionID)) {
+          hooks.stopContinuationGuard.clear(sessionID)
+          log("[stop-continuation] Stop state cleared by work-starting command", {
+            sessionID,
+            command,
+          })
+        }
+      }
     }
   }
 }