diff --git a/apps/web/app/(app)/layout.tsx b/apps/web/app/(app)/layout.tsx
index a26d2d77ef..08c1c7bc8c 100644
--- a/apps/web/app/(app)/layout.tsx
+++ b/apps/web/app/(app)/layout.tsx
@@ -62,7 +62,7 @@ export default async function AppLayout({
       });
     } catch (error) {
       logger.error("Failed to update last login", { email, error });
-      captureException(error, {}, email);
+      captureException(error, { userEmail: email });
     }
   });
 
diff --git a/apps/web/app/(app)/sentry-identify.tsx b/apps/web/app/(app)/sentry-identify.tsx
index 1962eb20b3..24480aa539 100644
--- a/apps/web/app/(app)/sentry-identify.tsx
+++ b/apps/web/app/(app)/sentry-identify.tsx
@@ -2,11 +2,22 @@
 
 import { useEffect } from "react";
 import * as Sentry from "@sentry/nextjs";
+import { useAccount } from "@/providers/EmailAccountProvider";
 
 export function SentryIdentify({ email }: { email: string }) {
+  const { emailAccountId } = useAccount();
+
   useEffect(() => {
     Sentry.setUser({ email });
   }, [email]);
 
+  useEffect(() => {
+    if (emailAccountId) {
+      Sentry.setTag("emailAccountId", emailAccountId);
+    } else {
+      Sentry.setTag("emailAccountId", undefined);
+    }
+  }, [emailAccountId]);
+
   return null;
 }
diff --git a/apps/web/app/api/google/webhook/process-history.ts b/apps/web/app/api/google/webhook/process-history.ts
index abc7eb2a3d..cbcd4d9042 100644
--- a/apps/web/app/api/google/webhook/process-history.ts
+++ b/apps/web/app/api/google/webhook/process-history.ts
@@ -1,5 +1,6 @@
 import uniqBy from "lodash/uniqBy";
 import { NextResponse } from "next/server";
+import * as Sentry from "@sentry/nextjs";
 import { getGmailClientWithRefresh } from "@/utils/gmail/client";
 import { GmailLabel } from "@/utils/gmail/label";
 import { captureException } from "@/utils/error";
@@ -48,6 +49,12 @@ export async function processHistoryForUser(
     hasAiAccess: userHasAiAccess,
   } = validation.data;
 
+  Sentry.setTag("emailAccountId", validatedEmailAccount.id);
+  Sentry.setUser({
+    id: validatedEmailAccount.userId,
+    email: validatedEmailAccount.email,
+  });
+
   if (
     !validatedEmailAccount.account?.access_token ||
     !validatedEmailAccount.account?.refresh_token
@@ -130,7 +137,7 @@ export async function processHistoryForUser(
       return NextResponse.json({ ok: true });
     }
 
-    captureException(error, { extra: { decodedData } }, email);
+    captureException(error, { userEmail: email, extra: { decodedData } });
     logger.error("Error processing webhook", {
       error:
         error instanceof Error
@@ -198,11 +205,10 @@ async function processHistory(options: ProcessHistoryOptions, logger: Logger) {
       try {
         await processHistoryItem(event, options, log);
       } catch (error) {
-        captureException(
-          error,
-          { extra: { userEmail, messageId: event.item.message?.id } },
+        captureException(error, {
           userEmail,
-        );
+          extra: { messageId: event.item.message?.id },
+        });
         logger.error("Error processing history item", { error });
       }
     }
diff --git a/apps/web/app/api/outlook/webhook/process-history.ts b/apps/web/app/api/outlook/webhook/process-history.ts
index 366110ffc9..f66164e7af 100644
--- a/apps/web/app/api/outlook/webhook/process-history.ts
+++ b/apps/web/app/api/outlook/webhook/process-history.ts
@@ -1,4 +1,5 @@
 import { NextResponse } from "next/server";
+import * as Sentry from "@sentry/nextjs";
 import { captureException } from "@/utils/error";
 import { createEmailProvider } from "@/utils/email/provider";
 import type { OutlookResourceData } from "@/app/api/outlook/webhook/types";
@@ -43,6 +44,12 @@ export async function processHistoryForUser({
     hasAiAccess: userHasAiAccess,
   } = validation.data;
 
+  Sentry.setTag("emailAccountId", validatedEmailAccount.id);
+  Sentry.setUser({
+    id: validatedEmailAccount.userId,
+    email: validatedEmailAccount.email,
+  });
+
   const accountProvider =
     validatedEmailAccount.account?.provider || "microsoft";
 
@@ -75,11 +82,11 @@ export async function processHistoryForUser({
       return NextResponse.json({ ok: true });
     }
 
-    captureException(
-      error,
-      { extra: { subscriptionId, resourceData } },
-      validatedEmailAccount.email,
-    );
+    captureException(error, {
+      emailAccountId: validatedEmailAccount.id,
+      userEmail: validatedEmailAccount.email,
+      extra: { subscriptionId, resourceData },
+    });
     logger.error("Error processing webhook", {
       resourceData,
       email: validatedEmailAccount.email,
diff --git a/apps/web/app/api/resend/digest/route.ts b/apps/web/app/api/resend/digest/route.ts
index 114cb05cb1..1e6883ad4e 100644
--- a/apps/web/app/api/resend/digest/route.ts
+++ b/apps/web/app/api/resend/digest/route.ts
@@ -66,7 +66,7 @@ export const POST = verifySignatureAppRouter(
       return NextResponse.json(result);
     } catch (error) {
       logger.error("Error sending digest email", { error });
-      captureException(error);
+      captureException(error, { emailAccountId });
       return NextResponse.json(
         { success: false, error: "Error sending digest email" },
         { status: 500 },
diff --git a/apps/web/next.config.ts b/apps/web/next.config.ts
index 82fe3ca5fb..460582d6f9 100644
--- a/apps/web/next.config.ts
+++ b/apps/web/next.config.ts
@@ -326,7 +326,7 @@ if (env.MICROSOFT_CLIENT_ID && !env.MICROSOFT_WEBHOOK_CLIENT_STATE) {
 const withSerwist = withSerwistInit({
   swSrc: "app/sw.ts",
   swDest: "public/sw.js",
-  disable: env.NODE_ENV !== "production",
+  disable: process.env.NODE_ENV !== "production",
   maximumFileSizeToCacheInBytes: 3 * 1024 * 1024, // 3MB
 });
 
diff --git a/apps/web/providers/ChatProvider.tsx b/apps/web/providers/ChatProvider.tsx
index c69c872223..41cb9a9c3e 100644
--- a/apps/web/providers/ChatProvider.tsx
+++ b/apps/web/providers/ChatProvider.tsx
@@ -76,7 +76,7 @@ export function ChatProvider({ children }: { children: React.ReactNode }) {
     },
     onError: (error) => {
       console.error(error);
-      captureException(error, { extra: { emailAccountId } });
+      captureException(error);
       toastError({
         title: "An error occured!",
         description: error.message || "",
diff --git a/apps/web/utils/actions/safe-action.ts b/apps/web/utils/actions/safe-action.ts
index a30a958fdc..edaf64f675 100644
--- a/apps/web/utils/actions/safe-action.ts
+++ b/apps/web/utils/actions/safe-action.ts
@@ -1,4 +1,5 @@
 import { createSafeActionClient } from "next-safe-action";
+import * as Sentry from "@sentry/nextjs";
 import { withServerActionInstrumentation } from "@sentry/nextjs";
 import { randomUUID } from "node:crypto";
 import { z } from "zod";
@@ -35,20 +36,16 @@ const baseClient = createSafeActionClient({
     }
     if (error instanceof SafeError) return error.message;
 
-    captureException(
-      error,
-      {
-        extra: {
-          metadata,
-          userId: context?.userId,
-          userEmail: context?.userEmail,
-          emailAccountId: context?.emailAccountId,
-          bindArgsClientInputs,
-          error: error.message,
-        },
+    captureException(error, {
+      userId: context?.userId,
+      userEmail: context?.userEmail,
+      emailAccountId: context?.emailAccountId,
+      extra: {
+        metadata,
+        bindArgsClientInputs,
+        error: error.message,
       },
-      context?.userEmail,
-    );
+    });
 
     return "An unknown error occurred.";
   },
@@ -104,6 +101,10 @@ export const actionClient = baseClient
       throw new SafeError("Unauthorized");
     }
 
+    // Set Sentry context for this action
+    Sentry.setTag("emailAccountId", emailAccountId);
+    Sentry.setUser({ id: userId, email: userEmail });
+
     const logger = ctx.logger.with({
       userId,
       userEmail,
diff --git a/apps/web/utils/ai/actions.ts b/apps/web/utils/ai/actions.ts
index edd766545a..3f460dad9d 100644
--- a/apps/web/utils/ai/actions.ts
+++ b/apps/web/utils/ai/actions.ts
@@ -328,6 +328,7 @@ const move_folder: ActionFunction<{ folderId?: string | null }> = async ({
 
 const notify_sender: ActionFunction<Record<string, unknown>> = async ({
   email,
+  emailAccountId,
   userEmail,
   logger,
 }) => {
@@ -355,10 +356,10 @@ const notify_sender: ActionFunction<Record<string, unknown>> = async ({
     captureException(
       new Error(result.error ?? "Cold email notification failed"),
       {
-        extra: { actionType: ActionType.NOTIFY_SENDER, senderEmail },
+        emailAccountId,
+        extra: { actionType: ActionType.NOTIFY_SENDER },
         sampleRate: 0.01,
       },
-      userEmail,
     );
     return;
   }
diff --git a/apps/web/utils/auth.ts b/apps/web/utils/auth.ts
index e5e79b8acc..8295e6b544 100644
--- a/apps/web/utils/auth.ts
+++ b/apps/web/utils/auth.ts
@@ -173,7 +173,7 @@ async function postSignUp({
           userId,
           error,
         });
-        captureException(error, undefined, email);
+        captureException(error, { userEmail: email });
       });
 
     await createLoopsContact(
@@ -188,7 +188,7 @@ async function postSignUp({
           email,
           error,
         });
-        captureException(error, undefined, email);
+        captureException(error, { userEmail: email });
       }
     });
   };
@@ -198,7 +198,7 @@ async function postSignUp({
       email,
       error,
     });
-    captureException(error, undefined, email);
+    captureException(error, { userEmail: email });
   });
 
   const dub = trackDubSignUp({ id: userId, email, name, image }, logger).catch(
@@ -207,7 +207,7 @@ async function postSignUp({
         email,
         error,
       });
-      captureException(error, undefined, email);
+      captureException(error, { userEmail: email });
     },
   );
 
diff --git a/apps/web/utils/email/watch-manager.ts b/apps/web/utils/email/watch-manager.ts
index e82544a805..606772b350 100644
--- a/apps/web/utils/email/watch-manager.ts
+++ b/apps/web/utils/email/watch-manager.ts
@@ -252,7 +252,7 @@ async function watchEmails({
       });
     } else {
       logger.error("Error watching inbox", { error });
-      captureException(error);
+      captureException(error, { emailAccountId });
     }
 
     return { success: false, error };
@@ -279,7 +279,7 @@ export async function unwatchEmails({
       logger.warn("Error unwatching emails, invalid grant");
     } else {
       logger.error("Error unwatching emails", { error });
-      captureException(error);
+      captureException(error, { emailAccountId });
     }
   }
 
diff --git a/apps/web/utils/error.ts b/apps/web/utils/error.ts
index fadc551d75..d2c40cb84d 100644
--- a/apps/web/utils/error.ts
+++ b/apps/web/utils/error.ts
@@ -30,18 +30,30 @@ export function isGmailError(
   );
 }
 
+export type CaptureExceptionContext = {
+  // emailAccountId is set automatically via:
+  // - Frontend: SentryIdentify component
+  // - API routes: emailAccountMiddleware
+  // - Server actions: actionClient
+  // Only pass explicitly for code outside these contexts (e.g., cron jobs).
+  emailAccountId?: string | null;
+  userId?: string | null;
+  userEmail?: string;
+  extra?: Record<string, any>;
+  sampleRate?: number;
+};
+
 export function captureException(
   error: unknown,
-  additionalInfo?: { extra?: Record<string, any>; sampleRate?: number },
-  userEmail?: string,
+  context: CaptureExceptionContext = {},
 ) {
   if (isKnownApiError(error)) {
     const logger = createScopedLogger("captureException");
-    logger.warn("Known API error", { error, additionalInfo });
+    logger.warn("Known API error", { error, context });
     return;
   }
 
-  const sampleRate = additionalInfo?.sampleRate;
+  const { sampleRate, userEmail, emailAccountId, userId, extra } = context;
   if (
     Number.isFinite(sampleRate) &&
     process.env.NODE_ENV === "production" &&
@@ -51,7 +63,16 @@ export function captureException(
   }
 
   if (userEmail) setUser({ email: userEmail });
-  sentryCaptureException(error, additionalInfo);
+
+  const sentryExtra = {
+    ...extra,
+    ...(emailAccountId && { emailAccountId }),
+    ...(userId && { userId }),
+  };
+
+  sentryCaptureException(error, {
+    extra: Object.keys(sentryExtra).length > 0 ? sentryExtra : undefined,
+  });
 }
 
 export type ActionError<E extends object = Record<string, unknown>> = {
diff --git a/apps/web/utils/llms/index.ts b/apps/web/utils/llms/index.ts
index 2cdbda307e..4bd1f765ed 100644
--- a/apps/web/utils/llms/index.ts
+++ b/apps/web/utils/llms/index.ts
@@ -271,13 +271,10 @@ export async function chatCompletionStream({
           error,
         });
         logger.trace("Result", { result });
-        captureException(
-          error,
-          {
-            extra: { label },
-          },
+        captureException(error, {
           userEmail,
-        );
+          extra: { label },
+        });
       }
     },
     onError: (error) => {
@@ -286,13 +283,10 @@ export async function chatCompletionStream({
         userEmail,
         error,
       });
-      captureException(
-        error,
-        {
-          extra: { label },
-        },
+      captureException(error, {
         userEmail,
-      );
+        extra: { label },
+      });
     },
   });
 
diff --git a/apps/web/utils/middleware.ts b/apps/web/utils/middleware.ts
index 4cb5d85c83..0e33edcf40 100644
--- a/apps/web/utils/middleware.ts
+++ b/apps/web/utils/middleware.ts
@@ -1,6 +1,7 @@
 import { ZodError } from "zod";
 import { type NextRequest, NextResponse, after } from "next/server";
 import { randomUUID } from "node:crypto";
+import * as Sentry from "@sentry/nextjs";
 import { captureException, checkCommonErrors, SafeError } from "@/utils/error";
 import { env } from "@/env";
 import { logErrorToPosthog } from "@/utils/error.server";
@@ -273,6 +274,9 @@ async function emailAccountMiddleware(
     );
   }
 
+  Sentry.setTag("emailAccountId", emailAccountId);
+  Sentry.setUser({ id: userId, email });
+
   // Create a new request with email account info
   const emailAccountReq = req.clone() as RequestWithEmailAccount;
   emailAccountReq.auth = { userId, emailAccountId, email };
diff --git a/apps/web/utils/outlook/subscription-manager.ts b/apps/web/utils/outlook/subscription-manager.ts
index d046efdd1e..c77a1d3acf 100644
--- a/apps/web/utils/outlook/subscription-manager.ts
+++ b/apps/web/utils/outlook/subscription-manager.ts
@@ -78,7 +78,7 @@ export class OutlookSubscriptionManager {
         : null;
     } catch (error) {
       this.logger.error("Failed to create subscription", { error });
-      captureException(error);
+      captureException(error, { emailAccountId: this.emailAccountId });
       return null;
     }
   }
@@ -115,7 +115,7 @@ export class OutlookSubscriptionManager {
           });
         }
 
-        captureException(error);
+        captureException(error, { emailAccountId: this.emailAccountId });
         return null;
       }
     }
diff --git a/apps/web/utils/user/delete.ts b/apps/web/utils/user/delete.ts
index 176f4a7651..f4b5ea3c8c 100644
--- a/apps/web/utils/user/delete.ts
+++ b/apps/web/utils/user/delete.ts
@@ -65,12 +65,12 @@ export async function deleteUser({
         error,
         userId,
       });
-      captureException(error, { extra: { userId } }, userId);
+      captureException(error);
     });
 
     clearCachedPerplexityResearchForUser(userId).catch((error) => {
       logger.error("Error clearing cached Perplexity research", { error });
-      captureException(error, { extra: { userId } }, userId);
+      captureException(error);
     });
 
     // Then proceed with the regular deletion process
@@ -89,13 +89,13 @@ export async function deleteUser({
       const customError = new Error("User deletion error");
       customError.cause = originalError;
 
-      captureException(customError, { extra: { failures, userId } });
+      captureException(customError, { extra: { failures } });
     }
   } catch (error) {
     logger.error("Error during user resources deletion process", {
       error,
     });
-    captureException(error, { extra: { userId } }, userId);
+    captureException(error);
   }
 }
 
@@ -143,7 +143,7 @@ async function deleteResources({
     logger.error("Error during database user deletion process", {
       error,
     });
-    captureException(error, { extra: { emailAccountId } }, email);
+    captureException(error, { emailAccountId, userEmail: email });
     throw error;
   }
 
diff --git a/version.txt b/version.txt
index 5f712777e6..f45c3ceb33 100644
--- a/version.txt
+++ b/version.txt
@@ -1 +1 @@
-v2.25.5
+v2.25.6