diff --git a/apps/webapp/app/runEngine/concerns/idempotencyKeys.server.ts b/apps/webapp/app/runEngine/concerns/idempotencyKeys.server.ts
index 689e7a5736..ac7099357d 100644
--- a/apps/webapp/app/runEngine/concerns/idempotencyKeys.server.ts
+++ b/apps/webapp/app/runEngine/concerns/idempotencyKeys.server.ts
@@ -3,6 +3,7 @@ import type { PrismaClientOrTransaction, TaskRun } from "@trigger.dev/database";
 import { logger } from "~/services/logger.server";
 import { resolveIdempotencyKeyTTL } from "~/utils/idempotencyKeys.server";
 import type { RunEngine } from "~/v3/runEngine.server";
+import { shouldIdempotencyKeyBeCleared } from "~/v3/taskStatus";
 import type { TraceEventConcern, TriggerTaskRequest } from "../types";
 
 export type IdempotencyKeyConcernResult =
@@ -41,6 +42,7 @@ export class IdempotencyKeyConcern {
       : undefined;
 
     if (existingRun) {
+      // The idempotency key has expired
       if (existingRun.idempotencyKeyExpiresAt && existingRun.idempotencyKeyExpiresAt < new Date()) {
         logger.debug("[TriggerTaskService][call] Idempotency key has expired", {
           idempotencyKey: request.options?.idempotencyKey,
@@ -52,42 +54,62 @@ export class IdempotencyKeyConcern {
           where: { id: existingRun.id, idempotencyKey },
           data: { idempotencyKey: null, idempotencyKeyExpiresAt: null },
         });
-      } else {
-        const associatedWaitpoint = existingRun.associatedWaitpoint;
-        const parentRunId = request.body.options?.parentRunId;
-        const resumeParentOnCompletion = request.body.options?.resumeParentOnCompletion;
-        //We're using `andWait` so we need to block the parent run with a waitpoint
-        if (associatedWaitpoint && resumeParentOnCompletion && parentRunId) {
-          await this.traceEventConcern.traceIdempotentRun(
-            request,
-            {
-              existingRun,
-              idempotencyKey,
-              incomplete: associatedWaitpoint.status === "PENDING",
-              isError: associatedWaitpoint.outputIsError,
-            },
-            async (event) => {
-              //block run with waitpoint
-              await this.engine.blockRunWithWaitpoint({
-                runId: RunId.fromFriendlyId(parentRunId),
-                waitpoints: associatedWaitpoint.id,
-                spanIdToComplete: event.spanId,
-                batch: request.options?.batchId
-                  ? {
-                      id: request.options.batchId,
-                      index: request.options.batchIndex ?? 0,
-                    }
-                  : undefined,
-                projectId: request.environment.projectId,
-                organizationId: request.environment.organizationId,
-                tx: this.prisma,
-              });
-            }
-          );
-        }
 
-        return { isCached: true, run: existingRun };
+        return { isCached: false, idempotencyKey, idempotencyKeyExpiresAt };
       }
+
+      // If the existing run failed or was expired, we clear the key and do a new run
+      if (shouldIdempotencyKeyBeCleared(existingRun.status)) {
+        logger.debug("[TriggerTaskService][call] Idempotency key should be cleared", {
+          idempotencyKey: request.options?.idempotencyKey,
+          runStatus: existingRun.status,
+          runId: existingRun.id,
+        });
+
+        // Update the existing run to remove the idempotency key
+        await this.prisma.taskRun.updateMany({
+          where: { id: existingRun.id, idempotencyKey },
+          data: { idempotencyKey: null, idempotencyKeyExpiresAt: null },
+        });
+
+        return { isCached: false, idempotencyKey, idempotencyKeyExpiresAt };
+      }
+
+      // We have an idempotent run, so we return it
+      const associatedWaitpoint = existingRun.associatedWaitpoint;
+      const parentRunId = request.body.options?.parentRunId;
+      const resumeParentOnCompletion = request.body.options?.resumeParentOnCompletion;
+      //We're using `andWait` so we need to block the parent run with a waitpoint
+      if (associatedWaitpoint && resumeParentOnCompletion && parentRunId) {
+        await this.traceEventConcern.traceIdempotentRun(
+          request,
+          {
+            existingRun,
+            idempotencyKey,
+            incomplete: associatedWaitpoint.status === "PENDING",
+            isError: associatedWaitpoint.outputIsError,
+          },
+          async (event) => {
+            //block run with waitpoint
+            await this.engine.blockRunWithWaitpoint({
+              runId: RunId.fromFriendlyId(parentRunId),
+              waitpoints: associatedWaitpoint.id,
+              spanIdToComplete: event.spanId,
+              batch: request.options?.batchId
+                ? {
+                    id: request.options.batchId,
+                    index: request.options.batchIndex ?? 0,
+                  }
+                : undefined,
+              projectId: request.environment.projectId,
+              organizationId: request.environment.organizationId,
+              tx: this.prisma,
+            });
+          }
+        );
+      }
+
+      return { isCached: true, run: existingRun };
     }
 
     return { isCached: false, idempotencyKey, idempotencyKeyExpiresAt };
diff --git a/apps/webapp/app/v3/eventRepository.server.ts b/apps/webapp/app/v3/eventRepository.server.ts
index d70deb3ef4..687fbe9e76 100644
--- a/apps/webapp/app/v3/eventRepository.server.ts
+++ b/apps/webapp/app/v3/eventRepository.server.ts
@@ -1097,7 +1097,7 @@ export class EventRepository {
       tracestate: typeof tracestate === "string" ? tracestate : undefined,
       duration: options.incomplete ? 0 : duration,
       isPartial: failedWithError ? false : options.incomplete,
-      isError: !!failedWithError,
+      isError: options.isError === true || !!failedWithError,
       message: message,
       serviceName: "api server",
       serviceNamespace: "trigger.dev",
diff --git a/apps/webapp/app/v3/taskStatus.ts b/apps/webapp/app/v3/taskStatus.ts
index 6b276bfc00..b5e1d915cf 100644
--- a/apps/webapp/app/v3/taskStatus.ts
+++ b/apps/webapp/app/v3/taskStatus.ts
@@ -128,3 +128,7 @@ export function isRestorableRunStatus(status: TaskRunStatus): boolean {
 export function isRestorableAttemptStatus(status: TaskRunAttemptStatus): boolean {
   return RESTORABLE_ATTEMPT_STATUSES.includes(status);
 }
+
+export function shouldIdempotencyKeyBeCleared(status: TaskRunStatus): boolean {
+  return isFailedRunStatus(status) || status === "EXPIRED";
+}