From b3d0e0cb458265fa234176cddc8af136733a4d15 Mon Sep 17 00:00:00 2001
From: Peter Steinberger <steipete@gmail.com>
Date: Mon, 16 Feb 2026 23:31:26 +0000
Subject: [PATCH] fix(cron): preserve overrides and harden next-run calculation

---
 src/cron/isolated-agent/session.test.ts | 6 +-----
 src/cron/isolated-agent/session.ts      | 5 ++---
 src/cron/schedule.ts                    | 5 ++---
 3 files changed, 5 insertions(+), 11 deletions(-)

diff --git a/src/cron/isolated-agent/session.test.ts b/src/cron/isolated-agent/session.test.ts
index 519b2744c..270628e81 100644
--- a/src/cron/isolated-agent/session.test.ts
+++ b/src/cron/isolated-agent/session.test.ts
@@ -150,12 +150,8 @@ describe("resolveCronSession", () => {
         "webhook:stable-key": {
           updatedAt: Date.now() - 1000,
           modelOverride: "some-model",
-        } as unknown as {
-          sessionId: string;
-          updatedAt: number;
-          modelOverride?: string;
         },
-      });
+      } as ReturnType<typeof loadSessionStore>);
       vi.mocked(evaluateSessionFreshness).mockReturnValue({ fresh: true });
 
       const result = resolveCronSession({
diff --git a/src/cron/isolated-agent/session.ts b/src/cron/isolated-agent/session.ts
index fcc2579cb..0f23c836c 100644
--- a/src/cron/isolated-agent/session.ts
+++ b/src/cron/isolated-agent/session.ts
@@ -59,9 +59,8 @@ export function resolveCronSession(params: {
   }
 
   const sessionEntry: SessionEntry = {
-    // Spread existing entry to preserve conversation context when reusing
-    // (the spread already copies all fields when !isNewSession, no need to re-assign)
-    ...(isNewSession ? undefined : entry),
+    // Preserve existing per-session overrides even when rolling to a new sessionId.
+    ...entry,
     // Always update these core fields
     sessionId,
     updatedAt: params.nowMs,
diff --git a/src/cron/schedule.ts b/src/cron/schedule.ts
index a459bc5be..669aae32b 100644
--- a/src/cron/schedule.ts
+++ b/src/cron/schedule.ts
@@ -62,13 +62,12 @@ export function computeNextRunAtMs(schedule: CronSchedule, nowMs: number): numbe
   }
 
   // Guard against same-second rescheduling loops: if croner returns
-  // "now" (or an earlier instant) when the job completed mid-second,
-  // retry from the next whole second.
+  // "now" (or an earlier instant), retry from the next whole second.
   const nextSecondMs = Math.floor(nowMs / 1000) * 1000 + 1000;
   const retry = cron.nextRun(new Date(nextSecondMs));
   if (!retry) {
     return undefined;
   }
   const retryMs = retry.getTime();
-  return Number.isFinite(retryMs) ? retryMs : undefined;
+  return Number.isFinite(retryMs) && retryMs > nowMs ? retryMs : undefined;
 }