diff --git a/apps/webapp/app/v3/services/completeAttempt.server.ts b/apps/webapp/app/v3/services/completeAttempt.server.ts
index 13d120aba6..cc4472f1e7 100644
--- a/apps/webapp/app/v3/services/completeAttempt.server.ts
+++ b/apps/webapp/app/v3/services/completeAttempt.server.ts
@@ -1,5 +1,6 @@
 import { Attributes } from "@opentelemetry/api";
 import {
+  MachinePresetName,
   TaskRunContext,
   TaskRunError,
   TaskRunErrorCodes,
@@ -8,9 +9,7 @@ import {
   TaskRunExecutionRetry,
   TaskRunFailedExecutionResult,
   TaskRunSuccessfulExecutionResult,
-  exceptionEventEnhancer,
   flattenAttributes,
-  internalErrorFromUnexpectedExit,
   isManualOutOfMemoryError,
   sanitizeError,
   shouldRetryError,
@@ -32,8 +31,8 @@ import { CancelAttemptService } from "./cancelAttempt.server";
 import { CreateCheckpointService } from "./createCheckpoint.server";
 import { FinalizeTaskRunService } from "./finalizeTaskRun.server";
 import { RetryAttemptService } from "./retryAttempt.server";
-import { updateMetadataService } from "~/services/metadata/updateMetadata.server";
 import { getTaskEventStoreTableForRun } from "../taskEventStore.server";
+import { socketIo } from "../handleSocketIo.server";
 
 type FoundAttempt = Awaited<ReturnType<typeof findAttempt>>;
 
@@ -256,9 +255,12 @@ export class CompleteAttemptService extends BaseService {
 
     let retriableError = shouldRetryError(taskRunErrorEnhancer(completion.error));
     let isOOMRetry = false;
+    let isOOMAttempt = isOOMError(completion.error);
+    let isOnMaxOOMMachine = false;
+    let oomMachine: MachinePresetName | undefined;
 
-    //OOM errors should retry (if an OOM machine is specified)
-    if (isOOMError(completion.error)) {
+    //OOM errors should retry (if an OOM machine is specified, and we're not already on it)
+    if (isOOMAttempt) {
       const retryConfig = FailedTaskRunRetryHelper.getRetryConfig({
         run: {
           ...taskRunAttempt.taskRun,
@@ -268,10 +270,10 @@ export class CompleteAttemptService extends BaseService {
         execution,
       });
 
-      if (
-        retryConfig?.outOfMemory?.machine &&
-        retryConfig.outOfMemory.machine !== taskRunAttempt.taskRun.machinePreset
-      ) {
+      oomMachine = retryConfig?.outOfMemory?.machine;
+      isOnMaxOOMMachine = oomMachine === taskRunAttempt.taskRun.machinePreset;
+
+      if (oomMachine && !isOnMaxOOMMachine) {
         //we will retry
         isOOMRetry = true;
         retriableError = true;
@@ -290,7 +292,7 @@ export class CompleteAttemptService extends BaseService {
             id: taskRunAttempt.taskRunId,
           },
           data: {
-            machinePreset: retryConfig.outOfMemory.machine,
+            machinePreset: oomMachine,
           },
         });
       }
@@ -309,11 +311,17 @@ export class CompleteAttemptService extends BaseService {
         environment,
         checkpoint,
         forceRequeue: isOOMRetry,
+        oomMachine,
       });
     }
 
     // The attempt has failed and we won't retry
 
+    if (isOOMAttempt && isOnMaxOOMMachine && environment.type !== "DEVELOPMENT") {
+      // The attempt failed due to an OOM error but we're already on the machine we should retry on
+      exitRun(taskRunAttempt.taskRunId);
+    }
+
     // Now we need to "complete" the task run event/span
     await eventRepository.completeEvent(
       getTaskEventStoreTableForRun(taskRunAttempt.taskRun),
@@ -507,6 +515,11 @@ export class CompleteAttemptService extends BaseService {
 
     if (forceRequeue) {
       logger.debug("[CompleteAttemptService] Forcing retry via queue", { runId: run.id });
+
+      // The run won't know it should shut down as we make the decision to force requeue here
+      // This also ensures that this change is backwards compatible with older workers
+      exitRun(run.id);
+
       await retryViaQueue();
       return;
     }
@@ -544,6 +557,7 @@ export class CompleteAttemptService extends BaseService {
     environment,
     checkpoint,
     forceRequeue = false,
+    oomMachine,
   }: {
     execution: TaskRunExecution;
     executionRetry: TaskRunExecutionRetry;
@@ -552,29 +566,38 @@ export class CompleteAttemptService extends BaseService {
     environment: AuthenticatedEnvironment;
     checkpoint?: CheckpointData;
     forceRequeue?: boolean;
+    /** Setting this will also alter the retry span message */
+    oomMachine?: MachinePresetName;
   }) {
     const retryAt = new Date(executionRetry.timestamp);
 
     // Retry the task run
-    await eventRepository.recordEvent(`Retry #${execution.attempt.number} delay`, {
-      taskSlug: taskRunAttempt.taskRun.taskIdentifier,
-      environment,
-      attributes: {
-        metadata: this.#generateMetadataAttributesForNextAttempt(execution),
-        properties: {
-          retryAt: retryAt.toISOString(),
-        },
-        runId: taskRunAttempt.taskRun.friendlyId,
-        style: {
-          icon: "schedule-attempt",
+    await eventRepository.recordEvent(
+      `Retry #${execution.attempt.number} delay${oomMachine ? " after OOM" : ""}`,
+      {
+        taskSlug: taskRunAttempt.taskRun.taskIdentifier,
+        environment,
+        attributes: {
+          metadata: this.#generateMetadataAttributesForNextAttempt(execution),
+          properties: {
+            retryAt: retryAt.toISOString(),
+            previousMachine: oomMachine
+              ? taskRunAttempt.taskRun.machinePreset ?? undefined
+              : undefined,
+            nextMachine: oomMachine,
+          },
+          runId: taskRunAttempt.taskRun.friendlyId,
+          style: {
+            icon: "schedule-attempt",
+          },
+          queueId: taskRunAttempt.queueId,
+          queueName: taskRunAttempt.taskRun.queue,
         },
-        queueId: taskRunAttempt.queueId,
-        queueName: taskRunAttempt.taskRun.queue,
-      },
-      context: taskRunAttempt.taskRun.traceContext as Record<string, string | undefined>,
-      spanIdSeed: `retry-${taskRunAttempt.number + 1}`,
-      endTime: retryAt,
-    });
+        context: taskRunAttempt.taskRun.traceContext as Record<string, string | undefined>,
+        spanIdSeed: `retry-${taskRunAttempt.number + 1}`,
+        endTime: retryAt,
+      }
+    );
 
     logger.debug("[CompleteAttemptService] Retrying", {
       taskRun: taskRunAttempt.taskRun.friendlyId,
@@ -753,3 +776,10 @@ function isOOMError(error: TaskRunError) {
 
   return false;
 }
+
+function exitRun(runId: string) {
+  socketIo.coordinatorNamespace.emit("REQUEST_RUN_CANCELLATION", {
+    version: "v1",
+    runId,
+  });
+}