diff --git a/scripts/e2e/lib/upgrade-survivor/assertions.mjs b/scripts/e2e/lib/upgrade-survivor/assertions.mjs
index d46235fa327a..4a04e9fb9133 100644
--- a/scripts/e2e/lib/upgrade-survivor/assertions.mjs
+++ b/scripts/e2e/lib/upgrade-survivor/assertions.mjs
@@ -96,13 +96,14 @@ function assert(condition, message) {
 
 function seedLegacySessionMetadata(stateDir) {
   const legacySessionsDir = path.join(stateDir, "sessions");
+  const baseUpdatedAt = Date.now() - 24 * 60 * 60 * 1000;
   writeJson(path.join(legacySessionsDir, "sessions.json"), {
     main: {
       sessionId: LEGACY_SESSION_MAIN_ID,
       sessionFile: path.join(legacySessionsDir, `${LEGACY_SESSION_MAIN_ID}.jsonl`),
       provider: "openai",
       model: "gpt-5.5",
-      updatedAt: 1710000000000,
+      updatedAt: baseUpdatedAt,
       skillsSnapshot: {
         prompt: "legacy prompt survives as metadata",
         resolvedSkills: [
@@ -118,14 +119,14 @@ function seedLegacySessionMetadata(stateDir) {
       sessionFile: path.join(legacySessionsDir, `${LEGACY_SESSION_DIRECT_ID}.jsonl`),
       provider: "openai",
       model: "gpt-5.5",
-      updatedAt: 1710000000100,
+      updatedAt: baseUpdatedAt + 100,
     },
     "slack:channel:CUPGRADE": {
       sessionId: LEGACY_SESSION_GROUP_ID,
       sessionFile: path.join(legacySessionsDir, `${LEGACY_SESSION_GROUP_ID}.jsonl`),
       provider: "openai",
       model: "gpt-5.5",
-      updatedAt: 1710000000200,
+      updatedAt: baseUpdatedAt + 200,
       lastChannel: "slack",
       lastTo: "CUPGRADE",
     },
diff --git a/test/scripts/upgrade-survivor-assertions.test.ts b/test/scripts/upgrade-survivor-assertions.test.ts
index 50793214c9e9..1c94397944e2 100644
--- a/test/scripts/upgrade-survivor-assertions.test.ts
+++ b/test/scripts/upgrade-survivor-assertions.test.ts
@@ -1,6 +1,6 @@
 // Upgrade Survivor Assertions tests cover upgrade survivor assertions script behavior.
 import { execFileSync } from "node:child_process";
-import { mkdtempSync, mkdirSync, rmSync, writeFileSync } from "node:fs";
+import { mkdtempSync, mkdirSync, readFileSync, rmSync, writeFileSync } from "node:fs";
 import { tmpdir } from "node:os";
 import { join } from "node:path";
 import { DatabaseSync } from "node:sqlite";
@@ -248,6 +248,71 @@ describe("upgrade survivor assertions", () => {
     expect(new Set(scenarios).size).toBe(scenarios.length);
   });
 
+  it("seeds recent ordered legacy session timestamps", () => {
+    const root = mkdtempSync(join(tmpdir(), "openclaw-upgrade-survivor-seed-"));
+    try {
+      const stateDir = join(root, "state");
+      const workspace = join(root, "workspace");
+      mkdirSync(stateDir, { recursive: true });
+      mkdirSync(workspace, { recursive: true });
+
+      const beforeSeed = Date.now();
+      execFileSync(process.execPath, [ASSERTIONS_PATH, "seed"], {
+        env: {
+          ...process.env,
+          OPENCLAW_STATE_DIR: stateDir,
+          OPENCLAW_TEST_WORKSPACE_DIR: workspace,
+          OPENCLAW_UPGRADE_SURVIVOR_SCENARIO: "base",
+        },
+        stdio: "pipe",
+      });
+      const afterSeed = Date.now();
+
+      const sessions = JSON.parse(
+        readFileSync(join(stateDir, "sessions", "sessions.json"), "utf8"),
+      ) as Record<string, { sessionId?: unknown; updatedAt?: unknown }>;
+      const seededRows = [
+        sessions.main,
+        sessions["+15551234567"],
+        sessions["slack:channel:CUPGRADE"],
+      ];
+      expect(seededRows.map((row) => row?.sessionId)).toEqual([
+        "upgrade-main-session",
+        "upgrade-direct-session",
+        "upgrade-group-session",
+      ]);
+
+      const timestamps = seededRows.map((row) => row?.updatedAt);
+      for (const timestamp of timestamps) {
+        expect(typeof timestamp).toBe("number");
+      }
+      const [mainUpdatedAt, directUpdatedAt, groupUpdatedAt] = timestamps as [
+        number,
+        number,
+        number,
+      ];
+      expect(directUpdatedAt - mainUpdatedAt).toBe(100);
+      expect(groupUpdatedAt - mainUpdatedAt).toBe(200);
+      expect(mainUpdatedAt).toBeLessThan(directUpdatedAt);
+      expect(directUpdatedAt).toBeLessThan(groupUpdatedAt);
+
+      const dayMs = 24 * 60 * 60 * 1000;
+      const thirtyDaysMs = 30 * dayMs;
+      for (const [timestamp, offset] of [
+        [mainUpdatedAt, 0],
+        [directUpdatedAt, 100],
+        [groupUpdatedAt, 200],
+      ] as const) {
+        expect(timestamp).toBeGreaterThanOrEqual(beforeSeed - dayMs + offset);
+        expect(timestamp).toBeLessThanOrEqual(afterSeed - dayMs + offset);
+        expect(timestamp).toBeGreaterThan(afterSeed - thirtyDaysMs);
+        expect(timestamp).toBeLessThanOrEqual(afterSeed);
+      }
+    } finally {
+      rmSync(root, { force: true, recursive: true });
+    }
+  });
+
   it("accepts the ACPX OpenClaw tools bridge scenario during seed", () => {
     const root = mkdtempSync(join(tmpdir(), "openclaw-upgrade-survivor-acpx-"));
     try {