diff --git a/apps/webapp/app/services/logger.server.ts b/apps/webapp/app/services/logger.server.ts
index 15b248f0d94..b03802afefd 100644
--- a/apps/webapp/app/services/logger.server.ts
+++ b/apps/webapp/app/services/logger.server.ts
@@ -50,7 +50,7 @@ function flattenArgs(args: Array<Record<string, unknown> | undefined>) {
 export const logger = new Logger(
   "webapp",
   (process.env.APP_LOG_LEVEL ?? "info") as LogLevel,
-  ["examples", "output", "connectionString", "payload"],
+  ["examples", "output", "connectionString", "payload", "metadata", "seedMetadata"],
   sensitiveDataReplacer,
   () => {
     const fields = currentFieldsStore.getStore();
diff --git a/apps/webapp/app/services/metadata/updateMetadata.server.ts b/apps/webapp/app/services/metadata/updateMetadata.server.ts
index c44dacf65c5..07dc236c976 100644
--- a/apps/webapp/app/services/metadata/updateMetadata.server.ts
+++ b/apps/webapp/app/services/metadata/updateMetadata.server.ts
@@ -6,7 +6,11 @@ import type {
 import { applyMetadataOperations, parsePacket } from "@trigger.dev/core/v3";
 import type { PrismaClientOrTransaction } from "~/db.server";
 import type { AuthenticatedEnvironment } from "~/services/apiAuth.server";
-import { handleMetadataPacket, MetadataTooLargeError } from "~/utils/packets";
+import {
+  handleMetadataPacket,
+  handleMetadataPacketWithByteLength,
+  MetadataTooLargeError,
+} from "~/utils/packets";
 import { ServiceValidationError } from "~/v3/services/common.server";
 import { Effect, Schedule, Duration, Fiber } from "effect";
 import { type RuntimeFiber } from "effect/Fiber";
@@ -91,9 +95,14 @@ export class UpdateMetadataService {
         this._bufferedOperations.clear();
 
         yield* Effect.sync(() => {
-          if (this.flushLoggingEnabled) {
+          if (this.flushLoggingEnabled && currentOperations.size > 0) {
+            const operationCount = Array.from(currentOperations.values()).reduce(
+              (sum, ops) => sum + ops.length,
+              0
+            );
             this.logger.debug(`[UpdateMetadataService] Flushing operations`, {
-              operations: Object.fromEntries(currentOperations),
+              runCount: currentOperations.size,
+              operationCount,
             });
           }
         });
@@ -520,9 +529,9 @@ export class UpdateMetadataService {
 
       if (this.flushLoggingEnabled) {
         this.logger.debug(`[updateRunMetadataWithOperations] Updated metadata for run`, {
-          metadata: applyResults.newMetadata,
-          operations: operations,
           runId,
+          metadataKeyCount: Object.keys(applyResults.newMetadata).length,
+          operationCount: operations.length,
         });
       }
 
@@ -549,16 +558,18 @@ export class UpdateMetadataService {
     body: UpdateMetadataRequestBody,
     existingMetadata: IOPacket
   ): Promise<{ metadata: Record<string, unknown> | undefined; updatedAtMs?: number }> {
-    const metadataPacket = handleMetadataPacket(
+    const metadataPacketWithByteLength = handleMetadataPacketWithByteLength(
       body.metadata,
       "application/json",
       this.maximumSize
     );
 
-    if (!metadataPacket) {
+    if (!metadataPacketWithByteLength) {
       return { metadata: {} };
     }
 
+    const { packet: metadataPacket, byteLength: metadataSizeBytes } = metadataPacketWithByteLength;
+
     let updatedAtMs: number | undefined;
 
     if (
@@ -567,8 +578,8 @@ export class UpdateMetadataService {
     ) {
       if (this.flushLoggingEnabled) {
         this.logger.debug(`[updateRunMetadataDirectly] Updating metadata directly for run`, {
-          metadata: metadataPacket.data,
           runId,
+          metadataSizeBytes,
         });
       }
 
@@ -607,7 +618,7 @@ export class UpdateMetadataService {
     if (this.flushLoggingEnabled) {
       this.logger.debug(`[ingestRunOperations] Ingesting operations for run`, {
         runId,
-        bufferedOperations,
+        operationCount: bufferedOperations.length,
       });
     }
 
diff --git a/apps/webapp/app/utils/packets.ts b/apps/webapp/app/utils/packets.ts
index 7a522d6f7af..27217c7f2ae 100644
--- a/apps/webapp/app/utils/packets.ts
+++ b/apps/webapp/app/utils/packets.ts
@@ -13,6 +13,14 @@ export function handleMetadataPacket(
   metadataType: string,
   maximumSize: number
 ): IOPacket | undefined {
+  return handleMetadataPacketWithByteLength(metadata, metadataType, maximumSize)?.packet;
+}
+
+export function handleMetadataPacketWithByteLength(
+  metadata: any,
+  metadataType: string,
+  maximumSize: number
+): { packet: IOPacket; byteLength: number } | undefined {
   let metadataPacket: IOPacket | undefined = undefined;
 
   if (typeof metadata === "string") {
@@ -33,5 +41,5 @@ export function handleMetadataPacket(
     throw new MetadataTooLargeError(`Metadata exceeds maximum size of ${maximumSize} bytes`);
   }
 
-  return metadataPacket;
+  return { packet: metadataPacket, byteLength };
 }
diff --git a/apps/webapp/app/v3/services/alerts/deliverAlert.server.ts b/apps/webapp/app/v3/services/alerts/deliverAlert.server.ts
index 0905f7c768f..070be65f7ad 100644
--- a/apps/webapp/app/v3/services/alerts/deliverAlert.server.ts
+++ b/apps/webapp/app/v3/services/alerts/deliverAlert.server.ts
@@ -455,7 +455,10 @@ export class DeliverAlertService extends BaseService {
                 error,
               };
 
-              await this.#deliverWebhook(payload, webhookProperties.data);
+              await this.#deliverWebhook(payload, webhookProperties.data, {
+                webhookId: alert.channel.id,
+                runId: alert.taskRun.friendlyId,
+              });
               break;
             }
             case "v2": {
@@ -516,7 +519,10 @@ export class DeliverAlertService extends BaseService {
                 },
               };
 
-              await this.#deliverWebhook(payload, webhookProperties.data);
+              await this.#deliverWebhook(payload, webhookProperties.data, {
+                webhookId: alert.channel.id,
+                runId: alert.taskRun.friendlyId,
+              });
 
               break;
             }
@@ -577,7 +583,9 @@ export class DeliverAlertService extends BaseService {
                 vercel: this.#buildWebhookVercelObject(deploymentMeta.vercelDeploymentUrl),
               };
 
-              await this.#deliverWebhook(payload, webhookProperties.data);
+              await this.#deliverWebhook(payload, webhookProperties.data, {
+                webhookId: alert.channel.id,
+              });
               break;
             }
             case "v2": {
@@ -616,7 +624,9 @@ export class DeliverAlertService extends BaseService {
                 },
               };
 
-              await this.#deliverWebhook(payload, webhookProperties.data);
+              await this.#deliverWebhook(payload, webhookProperties.data, {
+                webhookId: alert.channel.id,
+              });
 
               break;
             }
@@ -671,7 +681,9 @@ export class DeliverAlertService extends BaseService {
                 vercel: this.#buildWebhookVercelObject(deploymentMeta.vercelDeploymentUrl),
               };
 
-              await this.#deliverWebhook(payload, webhookProperties.data);
+              await this.#deliverWebhook(payload, webhookProperties.data, {
+                webhookId: alert.channel.id,
+              });
               break;
             }
             case "v2": {
@@ -716,7 +728,9 @@ export class DeliverAlertService extends BaseService {
                 },
               };
 
-              await this.#deliverWebhook(payload, webhookProperties.data);
+              await this.#deliverWebhook(payload, webhookProperties.data, {
+                webhookId: alert.channel.id,
+              });
 
               break;
             }
@@ -1017,7 +1031,11 @@ export class DeliverAlertService extends BaseService {
     }
   }
 
-  async #deliverWebhook<T>(payload: T, webhook: ProjectAlertWebhookProperties) {
+  async #deliverWebhook<T>(
+    payload: T,
+    webhook: ProjectAlertWebhookProperties,
+    context: { webhookId: string; runId?: string }
+  ) {
     const rawPayload = JSON.stringify(payload);
     const hashPayload = Buffer.from(rawPayload, "utf-8");
 
@@ -1046,15 +1064,17 @@ export class DeliverAlertService extends BaseService {
     });
 
     if (!response.ok) {
+      // Never log the request/response body here: it is customer-controlled alert
+      // content and may include stack traces or other application data.
       logger.info("[DeliverAlert] Failed to send alert webhook", {
         status: response.status,
         statusText: response.statusText,
-        url: webhook.url,
-        body: payload,
-        signature,
+        urlHost: safeUrlHost(webhook.url),
+        webhookId: context.webhookId,
+        runId: context.runId,
       });
 
-      throw new Error(`Failed to send alert webhook to ${webhook.url}`);
+      throw new Error(`Failed to send alert webhook to ${safeUrlHost(webhook.url)}`);
     }
   }
 
@@ -1435,3 +1455,11 @@ function isWebAPIHTTPError(error: unknown): error is WebAPIHTTPError {
 function isWebAPIRateLimitedError(error: unknown): error is WebAPIRateLimitedError {
   return (error as WebAPIRateLimitedError).code === ErrorCode.RateLimitedError;
 }
+
+function safeUrlHost(url: string): string {
+  try {
+    return new URL(url).host;
+  } catch {
+    return "unknown";
+  }
+}
diff --git a/packages/redis-worker/src/worker.ts b/packages/redis-worker/src/worker.ts
index 58988b81896..b9240acaa63 100644
--- a/packages/redis-worker/src/worker.ts
+++ b/packages/redis-worker/src/worker.ts
@@ -140,7 +140,7 @@ class Worker<TCatalog extends WorkerCatalog> {
   > = new Map();
 
   constructor(private options: WorkerOptions<TCatalog>) {
-    this.logger = options.logger ?? new Logger("Worker", "debug");
+    this.logger = options.logger ?? new Logger("Worker", "debug", ["item"]);
     this.tracer = options.tracer ?? trace.getTracer(options.name);
     this.meter = options.meter ?? metrics.getMeter(options.name);
 
@@ -608,7 +608,8 @@ class Worker<TCatalog extends WorkerCatalog> {
                 this.logger.error("Unhandled error in processItem:", {
                   error: err,
                   workerId,
-                  item,
+                  id: queueItem.id,
+                  job: queueItem.job,
                 });
               }
             );
@@ -933,11 +934,12 @@ class Worker<TCatalog extends WorkerCatalog> {
       const errorLogLevel =
         error && typeof error === "object" && "logLevel" in error ? error.logLevel : undefined;
 
+      // Never include the raw item/payload here: it is job data that may be
+      // customer-controlled. It is retrievable via `getJob(id)` if needed for triage.
       const logAttributes = {
         name: this.options.name,
         id,
         job,
-        item,
         visibilityTimeoutMs,
         error,
         errorMessage,
@@ -994,7 +996,6 @@ class Worker<TCatalog extends WorkerCatalog> {
           name: this.options.name,
           id,
           job,
-          item,
           retryDate,
           retryDelay,
           visibilityTimeoutMs,
@@ -1015,7 +1016,6 @@ class Worker<TCatalog extends WorkerCatalog> {
             name: this.options.name,
             id,
             job,
-            item,
             visibilityTimeoutMs,
             error: requeueError,
           }