diff --git a/apps/webapp/app/v3/scheduleEngine.server.ts b/apps/webapp/app/v3/scheduleEngine.server.ts
index cc7bb3bd0e..ef3cabe64d 100644
--- a/apps/webapp/app/v3/scheduleEngine.server.ts
+++ b/apps/webapp/app/v3/scheduleEngine.server.ts
@@ -7,6 +7,7 @@ import { logger } from "~/services/logger.server";
 import { singleton } from "~/utils/singleton";
 import { TriggerTaskService } from "./services/triggerTask.server";
 import { meter, tracer } from "./tracer.server";
+import { workerQueue } from "~/services/worker.server";
 
 export const scheduleEngine = singleton("ScheduleEngine", createScheduleEngine);
 
@@ -117,7 +118,24 @@ function createScheduleEngine() {
       }
     },
     isDevEnvironmentConnectedHandler: isDevEnvironmentConnectedHandler,
+    onRegisterScheduleInstance: removeDeprecatedWorkerQueueItem,
   });
 
   return engine;
 }
+
+async function removeDeprecatedWorkerQueueItem(instanceId: string) {
+  // We need to dequeue the instance from the existing workerQueue
+  try {
+    await workerQueue.dequeue(`scheduled-task-instance:${instanceId}`);
+
+    logger.debug("Removed deprecated worker queue item", {
+      instanceId,
+    });
+  } catch (error) {
+    logger.error("Error dequeuing scheduled task instance from deprecated queue", {
+      instanceId,
+      error: error instanceof Error ? error.message : String(error),
+    });
+  }
+}
diff --git a/internal-packages/schedule-engine/src/engine/index.ts b/internal-packages/schedule-engine/src/engine/index.ts
index 3efafe73ca..47dc1e31e1 100644
--- a/internal-packages/schedule-engine/src/engine/index.ts
+++ b/internal-packages/schedule-engine/src/engine/index.ts
@@ -8,7 +8,7 @@ import {
   Tracer,
 } from "@internal/tracing";
 import { Logger } from "@trigger.dev/core/logger";
-import { PrismaClient, TaskSchedule, TaskScheduleInstance } from "@trigger.dev/database";
+import { PrismaClient } from "@trigger.dev/database";
 import { Worker, type JobHandlerParams } from "@trigger.dev/redis-worker";
 import { calculateDistributedExecutionTime } from "./distributedScheduling.js";
 import { calculateNextScheduledTimestamp, nextScheduledTimestamps } from "./scheduleCalculation.js";
@@ -122,6 +122,19 @@ export class ScheduleEngine {
     return startSpan(this.tracer, "registerNextTaskScheduleInstance", async (span) => {
       const startTime = Date.now();
 
+      if (this.options.onRegisterScheduleInstance) {
+        const [registerError] = await tryCatch(
+          this.options.onRegisterScheduleInstance(params.instanceId)
+        );
+
+        if (registerError) {
+          this.logger.error("Error calling the onRegisterScheduleInstance callback", {
+            instanceId: params.instanceId,
+            error: registerError,
+          });
+        }
+      }
+
       span.setAttribute("instanceId", params.instanceId);
 
       this.logger.debug("Starting schedule registration", {
@@ -382,10 +395,11 @@ export class ScheduleEngine {
           span.setAttribute("skip_reason", skipReason);
         }
 
-        if (shouldTrigger) {
-          const scheduleTimestamp =
-            params.exactScheduleTime ?? instance.nextScheduledTimestamp ?? new Date();
+        // Calculate the schedule timestamp that will be used (regardless of whether we trigger or not)
+        const scheduleTimestamp =
+          params.exactScheduleTime ?? instance.nextScheduledTimestamp ?? new Date();
 
+        if (shouldTrigger) {
           const payload = {
             scheduleId: instance.taskSchedule.friendlyId,
             type: instance.taskSchedule.type as "DECLARATIVE" | "IMPERATIVE",
@@ -427,7 +441,7 @@ export class ScheduleEngine {
               payload,
               scheduleInstanceId: instance.id,
               scheduleId: instance.taskSchedule.id,
-              exactScheduleTime: params.exactScheduleTime,
+              exactScheduleTime: scheduleTimestamp,
             })
           );
 
@@ -523,7 +537,7 @@ export class ScheduleEngine {
             id: params.instanceId,
           },
           data: {
-            lastScheduledTimestamp: instance.nextScheduledTimestamp,
+            lastScheduledTimestamp: scheduleTimestamp,
           },
         });
 
diff --git a/internal-packages/schedule-engine/src/engine/types.ts b/internal-packages/schedule-engine/src/engine/types.ts
index 6b62fd4175..8cad80c303 100644
--- a/internal-packages/schedule-engine/src/engine/types.ts
+++ b/internal-packages/schedule-engine/src/engine/types.ts
@@ -48,6 +48,7 @@ export interface ScheduleEngineOptions {
   meter?: Meter;
   onTriggerScheduledTask: TriggerScheduledTaskCallback;
   isDevEnvironmentConnectedHandler: (environmentId: string) => Promise<boolean>;
+  onRegisterScheduleInstance?: (instanceId: string) => Promise<void>;
 }
 
 export interface UpsertScheduleParams {