diff --git a/CHANGELOG.md b/CHANGELOG.md
index 8a1647d3b58..93a11b77510 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -28,6 +28,7 @@ Docs: https://docs.openclaw.ai
 
 - Agents/compaction safeguard pre-check: skip embedded compaction before entering the Pi SDK when a session has no real conversation messages, avoiding unnecessary LLM API calls on idle sessions. (#36451) thanks @Sid-Qin.
 - iMessage/cron completion announces: strip leaked inline reply tags (for example `[[reply_to:6100]]`) from user-visible completion text so announcement deliveries do not expose threading metadata. (#24600) Thanks @vincentkoc.
+- Sessions/daily reset transcript archival: archive prior transcript files during stale-session scheduled/daily resets by capturing the previous session entry before rollover, preventing orphaned transcript files on disk. (#35493) Thanks @byungsker.
 - Feishu/group slash command detection: normalize group mention wrappers before command-authorization probing so mention-prefixed commands (for example `@Bot/model` and `@Bot /reset`) are recognized as gateway commands instead of being forwarded to the agent. (#35994) Thanks @liuxiaopai-ai.
 - Agents/context pruning: guard assistant thinking/text char estimation against malformed blocks (missing `thinking`/`text` strings or null entries) so pruning no longer crashes with malformed provider content. (openclaw#35146) thanks @Sid-Qin.
 - Agents/schema cleaning: detect Venice + Grok model IDs as xAI-proxied targets so unsupported JSON Schema keywords are stripped before requests, preventing Venice/Grok `Invalid arguments` failures. (openclaw#35355) thanks @Sid-Qin.
diff --git a/src/auto-reply/reply/session.test.ts b/src/auto-reply/reply/session.test.ts
index 8cfb6b5e7d9..b0feaca4a23 100644
--- a/src/auto-reply/reply/session.test.ts
+++ b/src/auto-reply/reply/session.test.ts
@@ -1457,6 +1457,61 @@ describe("initSessionState preserves behavior overrides across /new and /reset",
     archiveSpy.mockRestore();
   });
 
+  it("archives the old session transcript on daily/scheduled reset (stale session)", async () => {
+    // Daily resets occur when the session becomes stale (not via /new or /reset command).
+    // Previously, previousSessionEntry was only set when resetTriggered=true, leaving
+    // old transcript files orphaned on disk. Refs #35481.
+    vi.useFakeTimers();
+    try {
+      // Simulate: it is 5am, session was last active at 3am (before 4am daily boundary)
+      vi.setSystemTime(new Date(2026, 0, 18, 5, 0, 0));
+      const storePath = await createStorePath("openclaw-stale-archive-");
+      const sessionKey = "agent:main:telegram:dm:archive-stale-user";
+      const existingSessionId = "stale-session-to-be-archived";
+
+      await writeSessionStoreFast(storePath, {
+        [sessionKey]: {
+          sessionId: existingSessionId,
+          updatedAt: new Date(2026, 0, 18, 3, 0, 0).getTime(),
+        },
+      });
+
+      const sessionUtils = await import("../../gateway/session-utils.fs.js");
+      const archiveSpy = vi.spyOn(sessionUtils, "archiveSessionTranscripts");
+
+      const cfg = { session: { store: storePath } } as OpenClawConfig;
+      const result = await initSessionState({
+        ctx: {
+          Body: "hello",
+          RawBody: "hello",
+          CommandBody: "hello",
+          From: "user-stale",
+          To: "bot",
+          ChatType: "direct",
+          SessionKey: sessionKey,
+          Provider: "telegram",
+          Surface: "telegram",
+        },
+        cfg,
+        commandAuthorized: true,
+      });
+
+      expect(result.isNewSession).toBe(true);
+      expect(result.resetTriggered).toBe(false);
+      expect(result.sessionId).not.toBe(existingSessionId);
+      expect(archiveSpy).toHaveBeenCalledWith(
+        expect.objectContaining({
+          sessionId: existingSessionId,
+          storePath,
+          reason: "reset",
+        }),
+      );
+      archiveSpy.mockRestore();
+    } finally {
+      vi.useRealTimers();
+    }
+  });
+
   it("idle-based new session does NOT preserve overrides (no entry to read)", async () => {
     const storePath = await createStorePath("openclaw-idle-no-preserve-");
     const sessionKey = "agent:main:telegram:dm:new-user";
diff --git a/src/auto-reply/reply/session.ts b/src/auto-reply/reply/session.ts
index 60bcc78135b..a0e730334e2 100644
--- a/src/auto-reply/reply/session.ts
+++ b/src/auto-reply/reply/session.ts
@@ -328,7 +328,6 @@ export async function initSessionState(params: {
     sessionStore[retiredLegacyMainDelivery.key] = retiredLegacyMainDelivery.entry;
   }
   const entry = sessionStore[sessionKey];
-  const previousSessionEntry = resetTriggered && entry ? { ...entry } : undefined;
   const now = Date.now();
   const isThread = resolveThreadFlag({
     sessionKey,
@@ -354,6 +353,11 @@ export async function initSessionState(params: {
   const freshEntry = entry
     ? evaluateSessionFreshness({ updatedAt: entry.updatedAt, now, policy: resetPolicy }).fresh
     : false;
+  // Capture the current session entry before any reset so its transcript can be
+  // archived afterward.  We need to do this for both explicit resets (/new, /reset)
+  // and for scheduled/daily resets where the session has become stale (!freshEntry).
+  // Without this, daily-reset transcripts are left as orphaned files on disk (#35481).
+  const previousSessionEntry = (resetTriggered || !freshEntry) && entry ? { ...entry } : undefined;
 
   if (!isNewSession && freshEntry) {
     sessionId = entry.sessionId;