@@ -577,29 +577,32 @@ export const filterCompactedEffect = Effect.fnUntraced(function* (sessionID: Ses
 
 // filterCompacted reorders messages for model consumption
 // ([compaction-user, summary, ...retained tail..., continue-user]), so array
-// position is not chronological. Derive each binding by max id (MessageID
-// is monotonic via MessageID.ascending) so a pre-compaction overflowing tail
-// assistant doesn't get mistaken for the most recent turn. tasks are
-// compaction/subtask parts attached to user messages newer than the latest
-// finished assistant — i.e. unprocessed work.
+// position is not chronological. IDs are only a deterministic tie-breaker
+// because imported messages do not necessarily have monotonic IDs.
 export function latest(msgs: WithParts[]) {
   let user: User | undefined
   let assistant: Assistant | undefined
   let finished: Assistant | undefined
   for (const msg of msgs) {
     const info = msg.info
-    if (info.role === "user" && (!user || info.id > user.id)) user = info
-    if (info.role === "assistant" && (!assistant || info.id > assistant.id)) assistant = info
-    if (info.role === "assistant" && info.finish && (!finished || info.id > finished.id)) finished = info
+    if (info.role === "user" && isAfter(info, user)) user = info
+    if (info.role === "assistant" && isAfter(info, assistant)) assistant = info
+    if (info.role === "assistant" && info.finish && isAfter(info, finished)) finished = info
   }
   const tasks = msgs.flatMap((m) =>
-    finished && m.info.id <= finished.id
+    finished && !isAfter(m.info, finished)
       ? []
       : m.parts.filter((p): p is CompactionPart | SubtaskPart => p.type === "compaction" || p.type === "subtask"),
   )
   return { user, assistant, finished, tasks }
 }
 
+function isAfter(info: Info, other?: Info) {
+  if (!other) return true
+  if (info.time.created !== other.time.created) return info.time.created > other.time.created
+  return info.id > other.id
+}
+
 export function fromError(
   e: unknown,
   ctx: { providerID: ProviderV2.ID; aborted?: boolean },
 
@@ -1112,7 +1112,7 @@ const layer = Layer.effect(
             lastAssistant?.finish &&
             !["tool-calls"].includes(lastAssistant.finish) &&
             !hasToolCalls &&
-            lastUser.id < lastAssistant.id
+            lastAssistant.parentID === lastUser.id
           ) {
             const orphan = lastAssistantMsg?.parts.find(
               (part): part is SessionV1.ToolPart => part.type === "tool" && isOrphanedInterruptedTool(part),
 
@@ -1611,6 +1611,44 @@ describe("session.message-v2.latest", () => {
     ] as SessionV1.Part[],
   }
 
+  test("selects latest messages by creation time when IDs are nonmonotonic", () => {
+    const oldUser = { ...userInfo("msg_z_user"), time: { created: 100 } }
+    const newUser = { ...userInfo("msg_a_user"), time: { created: 200 } }
+    const oldAssistant = {
+      ...assistantInfo("msg_z_assistant", oldUser.id),
+      time: { created: 300 },
+      finish: "stop",
+    } as SessionV1.Assistant
+    const newAssistant = {
+      ...assistantInfo("msg_a_assistant", newUser.id),
+      time: { created: 400 },
+      finish: "stop",
+    } as SessionV1.Assistant
+
+    const state = MessageV2.latest([
+      { info: newAssistant, parts: [] },
+      { info: oldUser, parts: [] },
+      { info: oldAssistant, parts: [] },
+      { info: newUser, parts: [] },
+    ])
+
+    expect(state.user?.id).toBe(newUser.id)
+    expect(state.assistant?.id).toBe(newAssistant.id)
+    expect(state.finished?.id).toBe(newAssistant.id)
+  })
+
+  test("uses ID as a deterministic tie-breaker for equal creation times", () => {
+    const lower = { ...userInfo("msg_a_user"), time: { created: 100 } }
+    const higher = { ...userInfo("msg_z_user"), time: { created: 100 } }
+
+    const state = MessageV2.latest([
+      { info: higher, parts: [] },
+      { info: lower, parts: [] },
+    ])
+
+    expect(state.user?.id).toBe(higher.id)
+  })
+
   // Regression for double auto-compaction. The reorder in filterCompacted
   // (#27145) returns [compaction-user, summary, ...tail..., continue-user],
   // so picking lastFinished by array position landed on the pre-compaction
@@ -1659,4 +1697,33 @@ describe("session.message-v2.latest", () => {
     expect(state.tasks).toHaveLength(1)
     expect(state.tasks[0]).toMatchObject({ type: "compaction", auto: true })
   })
+
+  test("selects compaction and subtask work after the finished boundary by creation time", () => {
+    const finished = {
+      ...assistantInfo("msg_z_finished", "msg_parent"),
+      time: { created: 200 },
+      finish: "stop",
+    } as SessionV1.Assistant
+    const oldTask: SessionV1.WithParts = {
+      info: { ...userInfo("msg_z_old"), time: { created: 100 } },
+      parts: [{ ...basePart("msg_z_old", "old"), type: "compaction", auto: true }] as SessionV1.Part[],
+    }
+    const newTask: SessionV1.WithParts = {
+      info: { ...userInfo("msg_a_new"), time: { created: 300 } },
+      parts: [
+        {
+          ...basePart("msg_a_new", "new"),
+          type: "subtask",
+          prompt: "inspect",
+          description: "inspect ordering",
+          agent: "general",
+        },
+      ] as SessionV1.Part[],
+    }
+
+    const state = MessageV2.latest([newTask, { info: finished, parts: [] }, oldTask])
+
+    expect(state.tasks).toHaveLength(1)
+    expect(state.tasks[0]).toMatchObject({ type: "subtask", prompt: "inspect" })
+  })
 })
@@ -460,6 +460,46 @@ noLLMServer.instance(
   { config: cfg },
 )
 
+noLLMServer.instance(
+  "loop exits for a completed parent turn with nonmonotonic message IDs",
+  () =>
+    Effect.gen(function* () {
+      const prompt = yield* SessionPrompt.Service
+      const sessions = yield* Session.Service
+      const chat = yield* sessions.create({ title: "Pinned" })
+      const userID = MessageID.make("msg_z_user")
+      const assistantID = MessageID.make("msg_a_assistant")
+      yield* sessions.updateMessage({
+        id: userID,
+        role: "user",
+        sessionID: chat.id,
+        agent: "build",
+        model: ref,
+        time: { created: 100 },
+      })
+      yield* sessions.updateMessage({
+        id: assistantID,
+        role: "assistant",
+        parentID: userID,
+        sessionID: chat.id,
+        mode: "build",
+        agent: "build",
+        cost: 0,
+        path: { cwd: "/tmp", root: "/tmp" },
+        tokens: { input: 0, output: 0, reasoning: 0, cache: { read: 0, write: 0 } },
+        modelID: ref.modelID,
+        providerID: ref.providerID,
+        time: { created: 200, completed: 201 },
+        finish: "stop",
+      })
+
+      const result = yield* prompt.loop({ sessionID: chat.id })
+
+      expect(result.info.id).toBe(assistantID)
+    }),
+  { config: cfg },
+)
+
 it.instance("loop exits without an LLM request for interrupted orphan tool calls", () =>
   Effect.gen(function* () {
     const { llm } = yield* useServerConfig(providerCfg)