diff --git a/CHANGELOG.md b/CHANGELOG.md
index a584998c7..8e948628a 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -29,6 +29,7 @@
 - UI: show gateway auth guidance + doc link on unauthorized Control UI connections.
 - Security: warn on weak model tiers (Haiku, below GPT-5, below Claude 4.5) in `clawdbot security audit`.
 - Apps: store node auth tokens encrypted (Keychain/SecurePrefs).
+- Cron: isolated cron jobs now start a fresh session id on every run to prevent context buildup.
 - Daemon: share profile/state-dir resolution across service helpers and honor `CLAWDBOT_STATE_DIR` for Windows task scripts.
 - Docs: clarify multi-gateway rescue bot guidance. (#969) — thanks @bjesuiter.
 - Agents: add Current Date & Time system prompt section with configurable time format (auto/12/24).
diff --git a/docs/automation/cron-jobs.md b/docs/automation/cron-jobs.md
index a7c006c7d..3fc3fedde 100644
--- a/docs/automation/cron-jobs.md
+++ b/docs/automation/cron-jobs.md
@@ -78,6 +78,7 @@ Isolated jobs run a dedicated agent turn in session `cron:<jobId>`.
 
 Key behaviors:
 - Prompt is prefixed with `[cron:<jobId> <job name>]` for traceability.
+- Each run starts a **fresh session id** (no prior conversation carry-over).
 - A summary is posted to the main session (prefix `Cron`, configurable).
 - `wakeMode: "now"` triggers an immediate heartbeat after posting the summary.
 - If `payload.deliver: true`, output is delivered to a channel; otherwise it stays internal.
diff --git a/docs/concepts/session.md b/docs/concepts/session.md
index 94995b633..b90493267 100644
--- a/docs/concepts/session.md
+++ b/docs/concepts/session.md
@@ -57,6 +57,7 @@ the workspace is writable. See [Memory](/concepts/memory) and
 - Idle expiry: `session.idleMinutes` (default 60). After the timeout a new `sessionId` is minted on the next message.
 - Reset triggers: exact `/new` or `/reset` (plus any extras in `resetTriggers`) start a fresh session id and pass the remainder of the message through. If `/new` or `/reset` is sent alone, Clawdbot runs a short “hello” greeting turn to confirm the reset.
 - Manual reset: delete specific keys from the store or remove the JSONL transcript; the next message recreates them.
+- Isolated cron jobs always mint a fresh `sessionId` per run (no idle reuse).
 
 ## Send policy (optional)
 Block delivery for specific session types without listing individual ids.
diff --git a/src/cron/isolated-agent.uses-last-non-empty-agent-text-as.test.ts b/src/cron/isolated-agent.uses-last-non-empty-agent-text-as.test.ts
index 5e3223410..c796580be 100644
--- a/src/cron/isolated-agent.uses-last-non-empty-agent-text-as.test.ts
+++ b/src/cron/isolated-agent.uses-last-non-empty-agent-text-as.test.ts
@@ -48,6 +48,12 @@ async function writeSessionStore(home: string) {
   return storePath;
 }
 
+async function readSessionEntry(storePath: string, key: string) {
+  const raw = await fs.readFile(storePath, "utf-8");
+  const store = JSON.parse(raw) as Record<string, { sessionId?: string }>;
+  return store[key];
+}
+
 function makeCfg(
   home: string,
   storePath: string,
@@ -466,4 +472,51 @@ describe("runCronIsolatedAgentTurn", () => {
       expect(deps.sendMessageWhatsApp).not.toHaveBeenCalled();
     });
   });
+
+  it("starts a fresh session id for each cron run", async () => {
+    await withTempHome(async (home) => {
+      const storePath = await writeSessionStore(home);
+      const deps: CliDeps = {
+        sendMessageWhatsApp: vi.fn(),
+        sendMessageTelegram: vi.fn(),
+        sendMessageDiscord: vi.fn(),
+        sendMessageSignal: vi.fn(),
+        sendMessageIMessage: vi.fn(),
+      };
+      vi.mocked(runEmbeddedPiAgent).mockResolvedValue({
+        payloads: [{ text: "ok" }],
+        meta: {
+          durationMs: 5,
+          agentMeta: { sessionId: "s", provider: "p", model: "m" },
+        },
+      });
+
+      const cfg = makeCfg(home, storePath);
+      const job = makeJob({ kind: "agentTurn", message: "ping", deliver: false });
+
+      await runCronIsolatedAgentTurn({
+        cfg,
+        deps,
+        job,
+        message: "ping",
+        sessionKey: "cron:job-1",
+        lane: "cron",
+      });
+      const first = await readSessionEntry(storePath, "agent:main:cron:job-1");
+
+      await runCronIsolatedAgentTurn({
+        cfg,
+        deps,
+        job,
+        message: "ping",
+        sessionKey: "cron:job-1",
+        lane: "cron",
+      });
+      const second = await readSessionEntry(storePath, "agent:main:cron:job-1");
+
+      expect(first?.sessionId).toBeDefined();
+      expect(second?.sessionId).toBeDefined();
+      expect(second?.sessionId).not.toBe(first?.sessionId);
+    });
+  });
 });
diff --git a/src/cron/isolated-agent/run.ts b/src/cron/isolated-agent/run.ts
index 65e8ccde7..99db389a2 100644
--- a/src/cron/isolated-agent/run.ts
+++ b/src/cron/isolated-agent/run.ts
@@ -206,8 +206,10 @@ export async function runCronIsolatedAgentTurn(params: {
   const base = `[cron:${params.job.id} ${params.job.name}] ${params.message}`.trim();
   const commandBody = base;
 
-  const needsSkillsSnapshot = cronSession.isNewSession || !cronSession.sessionEntry.skillsSnapshot;
+  const existingSnapshot = cronSession.sessionEntry.skillsSnapshot;
   const skillsSnapshotVersion = getSkillsSnapshotVersion(workspaceDir);
+  const needsSkillsSnapshot =
+    !existingSnapshot || existingSnapshot.version !== skillsSnapshotVersion;
   const skillsSnapshot = needsSkillsSnapshot
     ? buildWorkspaceSkillSnapshot(workspaceDir, {
         config: cfgWithAgentDefaults,
diff --git a/src/cron/isolated-agent/session.ts b/src/cron/isolated-agent/session.ts
index 555396d3d..e6eb81d14 100644
--- a/src/cron/isolated-agent/session.ts
+++ b/src/cron/isolated-agent/session.ts
@@ -1,12 +1,7 @@
 import crypto from "node:crypto";
 
 import type { ClawdbotConfig } from "../../config/config.js";
-import {
-  DEFAULT_IDLE_MINUTES,
-  loadSessionStore,
-  resolveStorePath,
-  type SessionEntry,
-} from "../../config/sessions.js";
+import { loadSessionStore, resolveStorePath, type SessionEntry } from "../../config/sessions.js";
 
 export function resolveCronSession(params: {
   cfg: ClawdbotConfig;
@@ -15,16 +10,13 @@ export function resolveCronSession(params: {
   agentId: string;
 }) {
   const sessionCfg = params.cfg.session;
-  const idleMinutes = Math.max(sessionCfg?.idleMinutes ?? DEFAULT_IDLE_MINUTES, 1);
-  const idleMs = idleMinutes * 60_000;
   const storePath = resolveStorePath(sessionCfg?.store, {
     agentId: params.agentId,
   });
   const store = loadSessionStore(storePath);
   const entry = store[params.sessionKey];
-  const fresh = entry && params.nowMs - entry.updatedAt <= idleMs;
-  const sessionId = fresh ? entry.sessionId : crypto.randomUUID();
-  const systemSent = fresh ? Boolean(entry.systemSent) : false;
+  const sessionId = crypto.randomUUID();
+  const systemSent = false;
   const sessionEntry: SessionEntry = {
     sessionId,
     updatedAt: params.nowMs,
@@ -36,6 +28,8 @@ export function resolveCronSession(params: {
     sendPolicy: entry?.sendPolicy,
     lastChannel: entry?.lastChannel,
     lastTo: entry?.lastTo,
+    lastAccountId: entry?.lastAccountId,
+    skillsSnapshot: entry?.skillsSnapshot,
   };
-  return { storePath, store, sessionEntry, systemSent, isNewSession: !fresh };
+  return { storePath, store, sessionEntry, systemSent, isNewSession: true };
 }