diff --git a/apps/webapp/app/models/jobRunExecution.server.ts b/apps/webapp/app/models/jobRunExecution.server.ts
index 41076ae644..1b40d6526a 100644
--- a/apps/webapp/app/models/jobRunExecution.server.ts
+++ b/apps/webapp/app/models/jobRunExecution.server.ts
@@ -27,6 +27,7 @@ export type EnqueueRunExecutionV2Options = {
   runAt?: Date;
   resumeTaskId?: string;
   isRetry?: boolean;
+  skipRetrying?: boolean;
 };
 
 export async function enqueueRunExecutionV2(
@@ -47,6 +48,7 @@ export async function enqueueRunExecutionV2(
       tx,
       runAt: options.runAt,
       jobKey: `job_run:${run.id}`,
+      maxAttempts: options.skipRetrying ? 1 : undefined,
     }
   );
 }
diff --git a/apps/webapp/app/platform/zodWorker.server.ts b/apps/webapp/app/platform/zodWorker.server.ts
index 327ab6c38c..ea3cafe4b9 100644
--- a/apps/webapp/app/platform/zodWorker.server.ts
+++ b/apps/webapp/app/platform/zodWorker.server.ts
@@ -195,12 +195,13 @@ export class ZodWorker<TMessageCatalog extends MessageCatalogSchema> {
   ): Promise<GraphileJob> {
     const task = this.#tasks[identifier];
 
-    const optionsWithoutTx = omit(options ?? {}, ["tx"]);
+    const optionsWithoutTx = removeUndefinedKeys(omit(options ?? {}, ["tx"]));
     const taskWithoutJobKey = omit(task, ["jobKey"]);
 
+    // Make sure options passed in to enqueue take precedence over task options
     const spec = {
-      ...optionsWithoutTx,
       ...taskWithoutJobKey,
+      ...optionsWithoutTx,
     };
 
     if (typeof task.queueName === "function") {
@@ -437,3 +438,12 @@ export class ZodWorker<TMessageCatalog extends MessageCatalogSchema> {
     logger.debug(`[worker][${this.#name}] ${message}`, args);
   }
 }
+
+function removeUndefinedKeys<T extends object>(obj: T): T {
+  for (let key in obj) {
+    if (Object.prototype.hasOwnProperty.call(obj, key) && obj[key] === undefined) {
+      delete obj[key];
+    }
+  }
+  return obj;
+}
diff --git a/apps/webapp/app/routes/api.v1.endpoints.$environmentId.$endpointSlug.index.$indexHookIdentifier.ts b/apps/webapp/app/routes/api.v1.endpoints.$environmentId.$endpointSlug.index.$indexHookIdentifier.ts
index ce54de2329..5429b9b21e 100644
--- a/apps/webapp/app/routes/api.v1.endpoints.$environmentId.$endpointSlug.index.$indexHookIdentifier.ts
+++ b/apps/webapp/app/routes/api.v1.endpoints.$environmentId.$endpointSlug.index.$indexHookIdentifier.ts
@@ -1,4 +1,5 @@
 import { ActionArgs, LoaderArgs, json } from "@remix-run/server-runtime";
+import { RuntimeEnvironmentType } from "@trigger.dev/database";
 import { z } from "zod";
 import { PrismaClient, prisma } from "~/db.server";
 import { logger } from "~/services/logger.server";
@@ -99,6 +100,9 @@ export class TriggerEndpointIndexHookService {
           slug: endpointSlug,
         },
       },
+      include: {
+        environment: true,
+      },
     });
 
     if (!endpoint) {
@@ -122,6 +126,8 @@ export class TriggerEndpointIndexHookService {
       },
       {
         runAt: new Date(Date.now() + 5000),
+        maxAttempts:
+          endpoint.environment.type === RuntimeEnvironmentType.DEVELOPMENT ? 1 : undefined,
       }
     );
   }
diff --git a/apps/webapp/app/services/endpointApi.server.ts b/apps/webapp/app/services/endpointApi.server.ts
index e7cba31e3d..6804b63948 100644
--- a/apps/webapp/app/services/endpointApi.server.ts
+++ b/apps/webapp/app/services/endpointApi.server.ts
@@ -28,7 +28,10 @@ export class EndpointApiError extends Error {
 }
 
 export class EndpointApi {
-  constructor(private apiKey: string, private url: string) {}
+  constructor(
+    private apiKey: string,
+    private url: string
+  ) {}
 
   async ping(endpointId: string): Promise<PongResponse> {
     const response = await safeFetch(this.url, {
diff --git a/apps/webapp/app/services/endpoints/createEndpoint.server.ts b/apps/webapp/app/services/endpoints/createEndpoint.server.ts
index 3b2fbe9788..bd1839222f 100644
--- a/apps/webapp/app/services/endpoints/createEndpoint.server.ts
+++ b/apps/webapp/app/services/endpoints/createEndpoint.server.ts
@@ -4,6 +4,7 @@ import { AuthenticatedEnvironment } from "../apiAuth.server";
 import { EndpointApi } from "../endpointApi.server";
 import { workerQueue } from "../worker.server";
 import { env } from "~/env.server";
+import { RuntimeEnvironmentType } from "@trigger.dev/database";
 
 const indexingHookIdentifier = customAlphabet("0123456789abcdefghijklmnopqrstuvxyz", 10);
 
@@ -51,6 +52,9 @@ export class CreateEndpointService {
               slug: id,
             },
           },
+          include: {
+            environment: true,
+          },
           create: {
             environment: {
               connect: {
@@ -83,7 +87,11 @@ export class CreateEndpointService {
             id: endpoint.id,
             source: "INTERNAL",
           },
-          { tx }
+          {
+            tx,
+            maxAttempts:
+              endpoint.environment.type === RuntimeEnvironmentType.DEVELOPMENT ? 1 : undefined,
+          }
         );
 
         return endpoint;
diff --git a/apps/webapp/app/services/endpoints/validateCreateEndpoint.server.ts b/apps/webapp/app/services/endpoints/validateCreateEndpoint.server.ts
index fca8e4d6ea..d578a26d9d 100644
--- a/apps/webapp/app/services/endpoints/validateCreateEndpoint.server.ts
+++ b/apps/webapp/app/services/endpoints/validateCreateEndpoint.server.ts
@@ -5,6 +5,7 @@ import { AuthenticatedEnvironment } from "../apiAuth.server";
 import { workerQueue } from "../worker.server";
 import { CreateEndpointError } from "./createEndpoint.server";
 import { EndpointApi } from "../endpointApi.server";
+import { RuntimeEnvironmentType } from "@trigger.dev/database";
 
 const indexingHookIdentifier = customAlphabet("0123456789abcdefghijklmnopqrstuvxyz", 10);
 
@@ -35,6 +36,9 @@ export class ValidateCreateEndpointService {
               slug: validationResult.endpointId,
             },
           },
+          include: {
+            environment: true,
+          },
           create: {
             environment: {
               connect: {
@@ -67,7 +71,11 @@ export class ValidateCreateEndpointService {
             id: endpoint.id,
             source: "INTERNAL",
           },
-          { tx }
+          {
+            tx,
+            maxAttempts:
+              endpoint.environment.type === RuntimeEnvironmentType.DEVELOPMENT ? 1 : undefined,
+          }
         );
 
         return endpoint;
diff --git a/apps/webapp/app/services/events/ingestSendEvent.server.ts b/apps/webapp/app/services/events/ingestSendEvent.server.ts
index 41fffed53d..a4130bfdbc 100644
--- a/apps/webapp/app/services/events/ingestSendEvent.server.ts
+++ b/apps/webapp/app/services/events/ingestSendEvent.server.ts
@@ -7,7 +7,10 @@ import { logger } from "../logger.server";
 export class IngestSendEvent {
   #prismaClient: PrismaClientOrTransaction;
 
-  constructor(prismaClient: PrismaClientOrTransaction = prisma, private deliverEvents = true) {
+  constructor(
+    prismaClient: PrismaClientOrTransaction = prisma,
+    private deliverEvents = true
+  ) {
     this.#prismaClient = prismaClient;
   }
 
diff --git a/apps/webapp/app/services/runs/continueRun.server.ts b/apps/webapp/app/services/runs/continueRun.server.ts
index 97f0ae4f30..00dad4ad22 100644
--- a/apps/webapp/app/services/runs/continueRun.server.ts
+++ b/apps/webapp/app/services/runs/continueRun.server.ts
@@ -1,3 +1,4 @@
+import { RuntimeEnvironmentType } from "@trigger.dev/database";
 import { $transaction, Prisma, PrismaClient, prisma } from "~/db.server";
 import { enqueueRunExecutionV2 } from "~/models/jobRunExecution.server";
 
@@ -16,6 +17,9 @@ export class ContinueRunService {
       async (tx) => {
         const run = await tx.jobRun.findUniqueOrThrow({
           where: { id: runId },
+          include: {
+            environment: true,
+          },
         });
 
         if (!RESUMABLE_STATUSES.includes(run.status)) {
@@ -35,7 +39,9 @@ export class ContinueRunService {
           },
         });
 
-        await enqueueRunExecutionV2(run, tx);
+        await enqueueRunExecutionV2(run, tx, {
+          skipRetrying: run.environment.type === RuntimeEnvironmentType.DEVELOPMENT,
+        });
       },
       { timeout: 10000 }
     );
diff --git a/apps/webapp/app/services/runs/performRunExecutionV2.server.ts b/apps/webapp/app/services/runs/performRunExecutionV2.server.ts
index 95d2bce6bb..01c8f9f4d2 100644
--- a/apps/webapp/app/services/runs/performRunExecutionV2.server.ts
+++ b/apps/webapp/app/services/runs/performRunExecutionV2.server.ts
@@ -6,7 +6,7 @@ import {
   RunJobSuccess,
   RunSourceContextSchema,
 } from "@trigger.dev/core";
-import type { Task } from "@trigger.dev/database";
+import { RuntimeEnvironmentType, type Task } from "@trigger.dev/database";
 import { generateErrorMessage } from "zod-error";
 import { eventRecordToApiJson } from "~/api.server";
 import { $transaction, PrismaClient, PrismaClientOrTransaction, prisma } from "~/db.server";
@@ -135,7 +135,9 @@ export class PerformRunExecutionV2Service {
           },
         });
 
-        await enqueueRunExecutionV2(run, tx);
+        await enqueueRunExecutionV2(run, tx, {
+          skipRetrying: run.environment.type === RuntimeEnvironmentType.DEVELOPMENT,
+        });
       });
     }
   }
@@ -337,6 +339,7 @@ export class PerformRunExecutionV2Service {
           runAt: data.task.delayUntil ?? undefined,
           resumeTaskId: data.task.id,
           isRetry,
+          skipRetrying: run.environment.type === RuntimeEnvironmentType.DEVELOPMENT,
         });
       }
     });
@@ -409,6 +412,7 @@ export class PerformRunExecutionV2Service {
         runAt: data.retryAt,
         resumeTaskId: data.task.id,
         isRetry,
+        skipRetrying: run.environment.type === RuntimeEnvironmentType.DEVELOPMENT,
       });
     });
   }
@@ -464,7 +468,9 @@ export class PerformRunExecutionV2Service {
             },
           });
 
-          await enqueueRunExecutionV2(run, tx);
+          await enqueueRunExecutionV2(run, tx, {
+            skipRetrying: run.environment.type === RuntimeEnvironmentType.DEVELOPMENT,
+          });
 
           break;
         }
diff --git a/apps/webapp/app/services/runs/startRun.server.ts b/apps/webapp/app/services/runs/startRun.server.ts
index b9b647534b..818e310c54 100644
--- a/apps/webapp/app/services/runs/startRun.server.ts
+++ b/apps/webapp/app/services/runs/startRun.server.ts
@@ -1,4 +1,9 @@
-import type { ConnectionType, Integration, IntegrationConnection } from "@trigger.dev/database";
+import {
+  RuntimeEnvironmentType,
+  type ConnectionType,
+  type Integration,
+  type IntegrationConnection,
+} from "@trigger.dev/database";
 import type { PrismaClient, PrismaClientOrTransaction } from "~/db.server";
 import { prisma } from "~/db.server";
 import { enqueueRunExecutionV2 } from "~/models/jobRunExecution.server";
@@ -83,7 +88,9 @@ export class StartRunService {
 
     const updatedRun = await updateRun();
 
-    await enqueueRunExecutionV2(updatedRun, this.#prismaClient);
+    await enqueueRunExecutionV2(updatedRun, this.#prismaClient, {
+      skipRetrying: run.environment.type === RuntimeEnvironmentType.DEVELOPMENT,
+    });
   }
 
   async #handleMissingConnections(id: string, runConnectionsByKey: RunConnectionsByKey) {
@@ -140,6 +147,7 @@ async function findRun(tx: PrismaClientOrTransaction, id: string) {
     where: { id },
     include: {
       queue: true,
+      environment: true,
       version: {
         include: {
           integrations: {
diff --git a/apps/webapp/app/services/sources/handleHttpSource.server.ts b/apps/webapp/app/services/sources/handleHttpSource.server.ts
index 019a562206..1abd7da57e 100644
--- a/apps/webapp/app/services/sources/handleHttpSource.server.ts
+++ b/apps/webapp/app/services/sources/handleHttpSource.server.ts
@@ -2,6 +2,7 @@ import type { PrismaClient } from "~/db.server";
 import { prisma } from "~/db.server";
 import { workerQueue } from "../worker.server";
 import { requestUrl } from "~/utils/requestUrl.server";
+import { RuntimeEnvironmentType } from "@trigger.dev/database";
 
 export class HandleHttpSourceService {
   #prismaClient: PrismaClient;
@@ -55,6 +56,8 @@ export class HandleHttpSourceService {
           {
             queueName: `endpoint-${triggerSource.endpointId}`,
             tx,
+            maxAttempts:
+              triggerSource.environment.type === RuntimeEnvironmentType.DEVELOPMENT ? 1 : undefined,
           }
         );
       });
diff --git a/apps/webapp/app/services/tasks/performTaskOperation.server.ts b/apps/webapp/app/services/tasks/performTaskOperation.server.ts
index eb425bbf57..fb5a6304ad 100644
--- a/apps/webapp/app/services/tasks/performTaskOperation.server.ts
+++ b/apps/webapp/app/services/tasks/performTaskOperation.server.ts
@@ -1,3 +1,5 @@
+import { env } from "process";
+import { Run } from "~/presenters/RunPresenter.server";
 import {
   FetchOperationSchema,
   FetchRequestInit,
@@ -6,7 +8,7 @@ import {
   RedactString,
   calculateRetryAt,
 } from "@trigger.dev/core";
-import type { Task } from "@trigger.dev/database";
+import { RuntimeEnvironmentType, type Task } from "@trigger.dev/database";
 import { $transaction, PrismaClient, PrismaClientOrTransaction, prisma } from "~/db.server";
 import { enqueueRunExecutionV2 } from "~/models/jobRunExecution.server";
 import { formatUnknownError } from "~/utils/formatErrors.server";
@@ -244,7 +246,9 @@ export class PerformTaskOperationService {
   }
 
   async #resumeRunExecution(task: NonNullable<FoundTask>, prisma: PrismaClientOrTransaction) {
-    await enqueueRunExecutionV2(task.run, prisma);
+    await enqueueRunExecutionV2(task.run, prisma, {
+      skipRetrying: task.run.environment.type === RuntimeEnvironmentType.DEVELOPMENT,
+    });
   }
 }
 
@@ -281,6 +285,7 @@ async function findTask(prisma: PrismaClient, id: string) {
       attempts: true,
       run: {
         include: {
+          environment: true,
           queue: true,
         },
       },