diff --git a/apps/sim/app/api/cron/cleanup-stale-executions/route.ts b/apps/sim/app/api/cron/cleanup-stale-executions/route.ts
index c8b74944dbe..0f5f62074d4 100644
--- a/apps/sim/app/api/cron/cleanup-stale-executions/route.ts
+++ b/apps/sim/app/api/cron/cleanup-stale-executions/route.ts
@@ -245,10 +245,14 @@ export const GET = withRouteHandler(async (request: NextRequest) => {
               = (${asyncJobs.metadata}->>'maxDurationSeconds')::numeric
         ELSE FALSE
       END`
+      // A bare `Date` in a raw template reaches the driver unserialized; `sql.param`
+      // binds it through the column encoder, as `lt(column, date)` does elsewhere here.
+      const staleProcessingCutoff = sql.param(now, asyncJobs.startedAt)
+      const staleProcessingFallbackCutoff = sql.param(staleThreshold, asyncJobs.startedAt)
       const staleProcessingDurationPredicate = sql<boolean>`CASE
         WHEN ${hasPositiveMaxDuration}
-          THEN ${asyncJobs.startedAt} + ((${asyncJobs.metadata}->>'maxDurationSeconds')::double precision * interval '1 second') < ${now}
-        ELSE ${asyncJobs.startedAt} < ${staleThreshold}
+          THEN ${asyncJobs.startedAt} + ((${asyncJobs.metadata}->>'maxDurationSeconds')::double precision * interval '1 second') < ${staleProcessingCutoff}
+        ELSE ${asyncJobs.startedAt} < ${staleProcessingFallbackCutoff}
       END`
       const staleProcessingPredicate = and(
         eq(asyncJobs.status, JOB_STATUS.PROCESSING),
diff --git a/packages/testing/src/mocks/database.mock.ts b/packages/testing/src/mocks/database.mock.ts
index 455c90f66c8..d246ba9d603 100644
--- a/packages/testing/src/mocks/database.mock.ts
+++ b/packages/testing/src/mocks/database.mock.ts
@@ -6,6 +6,16 @@ import { vi } from 'vitest'
  */
 export function createMockSql() {
   const sqlFn = (strings: TemplateStringsArray, ...values: any[]) => {
+    // Same hazard as `sql.param(date)` below, and the form that actually shipped:
+    // an interpolated `Date` carries no column context, so drizzle skips
+    // `PgTimestamp.mapToDriverValue` and postgres-js receives a Date it cannot serialize.
+    if (values.some((value) => value instanceof Date)) {
+      throw new Error(
+        'sql`…${date}` interpolates a Date without an encoder, which reaches ' +
+          'postgres-js as a Date object its unsafe path cannot serialize. Bind ' +
+          'through the matching column: sql.param(date, table.timestampColumn).'
+      )
+    }
     const fragment = {
       strings,
       values,