diff --git a/packages/opencode/src/session/message-v2.ts b/packages/opencode/src/session/message-v2.ts
index 1bea9f52c3ec..afa42b67bb57 100644
--- a/packages/opencode/src/session/message-v2.ts
+++ b/packages/opencode/src/session/message-v2.ts
@@ -575,25 +575,33 @@ export const filterCompactedEffect = Effect.fnUntraced(function* (sessionID: Ses
   return filterCompacted(yield* stream(sessionID))
 })
 
+// Message IDs contain a truncated 48-bit timestamp prefix, so lexical order
+// wraps every 2^36 milliseconds. Storage already orders by (time.created, id);
+// use the same migration-safe ordering here, with id only breaking ties inside
+// one millisecond.
+export function compareChronological(a: Info, b: Info) {
+  return a.time.created - b.time.created || a.id.localeCompare(b.id)
+}
+
 // 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. Derive each binding by persisted creation
+// time rather than lexical id order. tasks are compaction/subtask parts
+// attached to user messages newer than the latest finished assistant — i.e.
+// unprocessed work.
 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" && (!user || compareChronological(info, user) > 0)) user = info
+    if (info.role === "assistant" && (!assistant || compareChronological(info, assistant) > 0)) assistant = info
+    if (info.role === "assistant" && info.finish && (!finished || compareChronological(info, finished) > 0))
+      finished = info
   }
   const tasks = msgs.flatMap((m) =>
-    finished && m.info.id <= finished.id
+    finished && compareChronological(m.info, finished) <= 0
       ? []
       : m.parts.filter((p): p is CompactionPart | SubtaskPart => p.type === "compaction" || p.type === "subtask"),
   )
diff --git a/packages/opencode/src/session/prompt.ts b/packages/opencode/src/session/prompt.ts
index eb116f6b960f..6f79eda00a37 100644
--- a/packages/opencode/src/session/prompt.ts
+++ b/packages/opencode/src/session/prompt.ts
@@ -1112,7 +1112,7 @@ const layer = Layer.effect(
             lastAssistant?.finish &&
             !["tool-calls"].includes(lastAssistant.finish) &&
             !hasToolCalls &&
-            lastUser.id < lastAssistant.id
+            MessageV2.compareChronological(lastUser, lastAssistant) < 0
           ) {
             const orphan = lastAssistantMsg?.parts.find(
               (part): part is SessionV1.ToolPart => part.type === "tool" && isOrphanedInterruptedTool(part),
diff --git a/packages/opencode/test/session/message-v2.test.ts b/packages/opencode/test/session/message-v2.test.ts
index 9bb688aeddb0..5bf2b9fbb82c 100644
--- a/packages/opencode/test/session/message-v2.test.ts
+++ b/packages/opencode/test/session/message-v2.test.ts
@@ -61,12 +61,12 @@ const model: Provider.Model = {
   release_date: "2026-01-01",
 }
 
-function userInfo(id: string): SessionV1.User {
+function userInfo(id: string, created = 0): SessionV1.User {
   return {
     id,
     sessionID,
     role: "user",
-    time: { created: 0 },
+    time: { created },
     agent: "user",
     model: { providerID, modelID: ModelV2.ID.make("test") },
     tools: {},
@@ -79,13 +79,14 @@ function assistantInfo(
   parentID: string,
   error?: SessionV1.Assistant["error"],
   meta?: { providerID: string; modelID: string },
+  created = 0,
 ): SessionV1.Assistant {
   const infoModel = meta ?? { providerID: model.providerID, modelID: model.api.id }
   return {
     id,
     sessionID,
     role: "assistant",
-    time: { created: 0 },
+    time: { created },
     error,
     parentID,
     modelID: infoModel.modelID,
@@ -1633,6 +1634,28 @@ describe("session.message-v2.latest", () => {
     expect(state.tasks).toEqual([])
   })
 
+  test("uses creation time across the 48-bit ascending-id rollover", () => {
+    const boundary = 2 ** 36
+    const beforeID = "msg_fffffffff001AAAAAAAAAAAAAA"
+    const afterID = "msg_000000000001BBBBBBBBBBBBBB"
+    expect(afterID < beforeID).toBe(true)
+
+    const before: SessionV1.WithParts = {
+      info: userInfo(beforeID, boundary - 1),
+      parts: [],
+    }
+    const after: SessionV1.WithParts = {
+      info: { ...assistantInfo(afterID, beforeID, undefined, undefined, boundary), finish: "stop" },
+      parts: [],
+    }
+
+    const state = MessageV2.latest([after, before])
+    expect(String(state.user?.id)).toBe(beforeID)
+    expect(String(state.assistant?.id)).toBe(afterID)
+    expect(String(state.finished?.id)).toBe(afterID)
+    expect(MessageV2.compareChronological(before.info, after.info)).toBeLessThan(0)
+  })
+
   test("a fresh compaction-user newer than the latest summary surfaces in tasks", () => {
     const newCompactionUser: SessionV1.WithParts = {
       info: userInfo(NEW_COMPACTION_USER),
diff --git a/packages/opencode/test/session/messages-pagination.test.ts b/packages/opencode/test/session/messages-pagination.test.ts
index b67c982ebcd3..ed5cbe240d03 100644
--- a/packages/opencode/test/session/messages-pagination.test.ts
+++ b/packages/opencode/test/session/messages-pagination.test.ts
@@ -271,6 +271,33 @@ describe("MessageV2.page", () => {
     ),
   )
 
+  it.instance("keeps storage order chronological across the 48-bit id rollover", () =>
+    withSession(({ session }) =>
+      Effect.gen(function* () {
+        const created = yield* session.create({})
+        const boundary = 2 ** 36
+        const ids = [MessageID.make("msg_fffffffff001AAAAAAAAAAAAAA"), MessageID.make("msg_000000000001BBBBBBBBBBBBBB")]
+        for (const [index, id] of ids.entries()) {
+          yield* session.updateMessage({
+            id,
+            sessionID: created.id,
+            role: "user",
+            time: { created: boundary - 1 + index },
+            agent: "test",
+            model: { providerID: "test", modelID: "test" },
+            tools: {},
+            mode: "",
+          } as unknown as SessionV1.Info)
+        }
+
+        const result = yield* MessageV2.page({ sessionID: created.id, limit: 10 })
+        expect(ids[1]! < ids[0]!).toBe(true)
+        expect(result.items.map((item) => item.info.id)).toEqual(ids)
+        yield* session.remove(created.id)
+      }),
+    ),
+  )
+
   it.instance("does not return messages from other sessions", () =>
     Effect.gen(function* () {
       const session = yield* SessionNs.Service