diff --git a/apps/web/app/api/google/webhook/route.ts b/apps/web/app/api/google/webhook/route.ts
index 99a769e95e..48c6374408 100644
--- a/apps/web/app/api/google/webhook/route.ts
+++ b/apps/web/app/api/google/webhook/route.ts
@@ -53,6 +53,7 @@ async function processWebhookAsync(
   } catch (error) {
     await handleWebhookError(error, {
       email: decodedData.emailAddress,
+      emailAccountId: "unknown", // TODO: add emailAccountId
       url: "/api/google/webhook",
       logger,
     });
diff --git a/apps/web/app/api/outlook/webhook/route.ts b/apps/web/app/api/outlook/webhook/route.ts
index 0017262fab..90a12ff0ef 100644
--- a/apps/web/app/api/outlook/webhook/route.ts
+++ b/apps/web/app/api/outlook/webhook/route.ts
@@ -104,6 +104,7 @@ async function processNotificationsAsync(
       if (emailAccount?.email) {
         await handleWebhookError(error, {
           email: emailAccount.email,
+          emailAccountId: emailAccount.id,
           url: "/api/outlook/webhook",
           logger,
         });
diff --git a/apps/web/utils/actions/middleware.ts b/apps/web/utils/actions/middleware.ts
deleted file mode 100644
index 671ca07c6a..0000000000
--- a/apps/web/utils/actions/middleware.ts
+++ /dev/null
@@ -1,146 +0,0 @@
-import {
-  captureException,
-  withServerActionInstrumentation,
-} from "@sentry/nextjs";
-import {
-  checkCommonErrors,
-  isAICallError,
-  isAWSThrottlingError,
-  type ActionError,
-  type ServerActionResponse,
-} from "@/utils/error";
-import { logErrorToPosthog } from "@/utils/error.server";
-import { isDuplicateError } from "@/utils/prisma-helpers";
-import { createScopedLogger } from "@/utils/logger";
-import { env } from "@/env";
-
-// NOTE: this file is not longer in use but we want to move over functionality to the `actionClient`
-
-const logger = createScopedLogger("action-middleware");
-
-// Utility type to ensure we're dealing with object types only
-type EnsureObject<T> = T extends object ? T : never;
-
-/**
- * Wraps an action in instrumentation to capture errors and send them to Sentry
- * We also make sure to always return an object, so that if the client doesn't get a response,
- * it's because there was an error, and likely it was a timeout because otherwise it would receive the response.
- * We also handle thrown errors and convert them to an object with an error message.
- * Actions are expected to return { error: string } objects when they fail, but if an error is thrown, we handle it here.
- * NOTE: future updates: we can do more when errors are thrown like we do with `withError` middleware for API routes.
- */
-export function withActionInstrumentation<
-  Args extends any[],
-  Result extends object | undefined = undefined,
-  Err extends object = Record<string, unknown>,
->(
-  name: string,
-  action: (...args: Args) => Promise<ServerActionResponse<Result, Err>>,
-  options?: { recordResponse?: boolean },
-) {
-  return async (
-    ...args: Args
-  ): Promise<
-    ServerActionResponse<EnsureObject<Result> & { success: boolean }, Err>
-  > => {
-    try {
-      const result = await withServerActionInstrumentation(
-        name,
-        {
-          recordResponse: options?.recordResponse ?? true,
-        },
-        async () => {
-          try {
-            logger.info(`Action: ${name}`, { action: name });
-            const res = await action(...args);
-
-            if (!res) {
-              return { success: true } as EnsureObject<Result> & {
-                success: boolean;
-              };
-            }
-
-            if ("error" in res) return res;
-
-            return {
-              success: true,
-              ...res,
-            } as unknown as EnsureObject<Result> & {
-              success: true;
-            };
-          } catch (error) {
-            if (isDuplicateError(error)) {
-              captureException(error, { extra: { actionName: name } });
-
-              logger.error("Duplicate item error", { action: name, error });
-
-              return {
-                error: "Duplicate item error",
-                success: false,
-              } as unknown as ActionError<Err>;
-            }
-
-            if (isAWSThrottlingError(error)) {
-              captureException(error, { extra: { actionName: name } });
-
-              logger.error("AWS throttling error", { action: name, error });
-
-              return {
-                error: error.message,
-                success: false,
-              } as unknown as ActionError<Err>;
-            }
-
-            if (isAICallError(error)) {
-              // Quick fix: log full error in development. TODO: handle properly
-              if (env.NODE_ENV === "development") {
-                // biome-ignore lint/suspicious/noConsole: helpful for debugging
-                console.error(error);
-              }
-
-              logger.error("AI call error", {
-                action: name,
-                error: (error.data as any)?.message,
-              });
-              return {
-                error:
-                  (error.data as any)?.error?.message ??
-                  "An error occurred while calling the AI",
-                success: false,
-              } as unknown as ActionError<Err>;
-            }
-
-            // don't throw known errors to Sentry
-            const apiError = checkCommonErrors(error, name);
-            if (apiError) {
-              await logErrorToPosthog("action", name, apiError.type);
-
-              logger.error("API error", { action: name, error: apiError });
-
-              return {
-                error: apiError.message,
-                success: false,
-              } as unknown as ActionError<Err>;
-            }
-
-            throw error;
-          }
-        },
-      );
-
-      return result;
-    } catch (error) {
-      logger.error("Error in action", { action: name, error });
-
-      // Quick fix: log full error in development. TODO: handle properly
-      if (env.NODE_ENV === "development") {
-      }
-
-      // error is already captured by Sentry in `withServerActionInstrumentation`
-      return {
-        error: "An error occurred",
-        success: false,
-      } as ActionError<Err & { success: false }>;
-    }
-  };
-}
diff --git a/apps/web/utils/ai/assistant/process-user-request.ts b/apps/web/utils/ai/assistant/process-user-request.ts
index 9c594c8823..3fd8064d30 100644
--- a/apps/web/utils/ai/assistant/process-user-request.ts
+++ b/apps/web/utils/ai/assistant/process-user-request.ts
@@ -157,7 +157,7 @@ ${stringifyEmailSimple(getEmailForLLM(originalEmail))}
   const modelOptions = getModel(emailAccount.user, "chat");
 
   const generateText = createGenerateText({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "Process user request",
     modelOptions,
   });
diff --git a/apps/web/utils/ai/calendar/availability.ts b/apps/web/utils/ai/calendar/availability.ts
index 5005ebabd1..d2e574b0a5 100644
--- a/apps/web/utils/ai/calendar/availability.ts
+++ b/apps/web/utils/ai/calendar/availability.ts
@@ -90,7 +90,7 @@ ${threadContent}
   const modelOptions = getModel(emailAccount.user);
 
   const generateText = createGenerateText({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "Calendar availability analysis",
     modelOptions,
   });
diff --git a/apps/web/utils/ai/categorize-sender/ai-categorize-senders.ts b/apps/web/utils/ai/categorize-sender/ai-categorize-senders.ts
index dd4fe02ddd..60e819439e 100644
--- a/apps/web/utils/ai/categorize-sender/ai-categorize-senders.ts
+++ b/apps/web/utils/ai/categorize-sender/ai-categorize-senders.ts
@@ -89,7 +89,7 @@ ${formatCategoriesForPrompt(categories)}
   const modelOptions = getModel(emailAccount.user, "economy");
 
   const generateObject = createGenerateObject({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "Categorize senders bulk",
     modelOptions,
   });
diff --git a/apps/web/utils/ai/categorize-sender/ai-categorize-single-sender.ts b/apps/web/utils/ai/categorize-sender/ai-categorize-single-sender.ts
index e5bac0f9e8..7206beea0e 100644
--- a/apps/web/utils/ai/categorize-sender/ai-categorize-single-sender.ts
+++ b/apps/web/utils/ai/categorize-sender/ai-categorize-single-sender.ts
@@ -49,7 +49,7 @@ ${formatCategoriesForPrompt(categories)}
   const modelOptions = getModel(emailAccount.user);
 
   const generateObject = createGenerateObject({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "Categorize sender",
     modelOptions,
   });
diff --git a/apps/web/utils/ai/choose-rule/ai-choose-args.ts b/apps/web/utils/ai/choose-rule/ai-choose-args.ts
index 6fd7791945..c1975d5853 100644
--- a/apps/web/utils/ai/choose-rule/ai-choose-args.ts
+++ b/apps/web/utils/ai/choose-rule/ai-choose-args.ts
@@ -85,7 +85,7 @@ export async function aiGenerateArgs({
 
   const generateObject = createGenerateObject({
     label: "Args for rule",
-    userEmail: emailAccount.email,
+    emailAccount,
     modelOptions,
   });
 
diff --git a/apps/web/utils/ai/choose-rule/ai-choose-rule.ts b/apps/web/utils/ai/choose-rule/ai-choose-rule.ts
index 143989c3b3..28d151e76e 100644
--- a/apps/web/utils/ai/choose-rule/ai-choose-rule.ts
+++ b/apps/web/utils/ai/choose-rule/ai-choose-rule.ts
@@ -73,7 +73,7 @@ async function getAiResponse(options: GetAiResponseOptions): Promise<{
   const modelOptions = getModel(emailAccount.user, modelType);
 
   const generateObject = createGenerateObject({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "Choose rule",
     modelOptions,
   });
diff --git a/apps/web/utils/ai/choose-rule/ai-detect-recurring-pattern.ts b/apps/web/utils/ai/choose-rule/ai-detect-recurring-pattern.ts
index 803f427838..7042184b1a 100644
--- a/apps/web/utils/ai/choose-rule/ai-detect-recurring-pattern.ts
+++ b/apps/web/utils/ai/choose-rule/ai-detect-recurring-pattern.ts
@@ -97,7 +97,7 @@ ${getEmailListPrompt({ messages: emails, messageMaxLength: 500 })}
     const modelOptions = getModel(emailAccount.user, "chat");
 
     const generateObject = createGenerateObject({
-      userEmail: emailAccount.email,
+      emailAccount,
       label: "Detect recurring pattern",
       modelOptions,
     });
diff --git a/apps/web/utils/ai/clean/ai-clean-select-labels.ts b/apps/web/utils/ai/clean/ai-clean-select-labels.ts
index be8739cc11..b091d6a4ad 100644
--- a/apps/web/utils/ai/clean/ai-clean-select-labels.ts
+++ b/apps/web/utils/ai/clean/ai-clean-select-labels.ts
@@ -30,7 +30,7 @@ ${instructions}
   const modelOptions = getModel(emailAccount.user);
 
   const generateObject = createGenerateObject({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "Clean - Select Labels",
     modelOptions,
   });
diff --git a/apps/web/utils/ai/clean/ai-clean.ts b/apps/web/utils/ai/clean/ai-clean.ts
index a9117095d0..5acc3ea4b3 100644
--- a/apps/web/utils/ai/clean/ai-clean.ts
+++ b/apps/web/utils/ai/clean/ai-clean.ts
@@ -93,7 +93,7 @@ The current date is ${currentDate}.
   const modelOptions = getModel(emailAccount.user);
 
   const generateObject = createGenerateObject({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "Clean",
     modelOptions,
   });
diff --git a/apps/web/utils/ai/digest/summarize-email-for-digest.ts b/apps/web/utils/ai/digest/summarize-email-for-digest.ts
index 96292b8dd2..b385bcacdf 100644
--- a/apps/web/utils/ai/digest/summarize-email-for-digest.ts
+++ b/apps/web/utils/ai/digest/summarize-email-for-digest.ts
@@ -81,7 +81,7 @@ ${getUserInfoPrompt({ emailAccount })}`;
     const modelOptions = getModel(emailAccount.user);
 
     const generateObject = createGenerateObject({
-      userEmail: emailAccount.email,
+      emailAccount,
       label: "Summarize email",
       modelOptions,
     });
diff --git a/apps/web/utils/ai/group/create-group.ts b/apps/web/utils/ai/group/create-group.ts
index 92b3b39e0c..bb49878293 100644
--- a/apps/web/utils/ai/group/create-group.ts
+++ b/apps/web/utils/ai/group/create-group.ts
@@ -84,7 +84,7 @@ Key guidelines:
   const modelOptions = getModel(emailAccount.user);
 
   const generateText = createGenerateText({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "Create group",
     modelOptions,
   });
@@ -154,7 +154,7 @@ Guidelines:
   const modelOptions = getModel(emailAccount.user);
 
   const generateText = createGenerateText({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "Verify group criteria",
     modelOptions,
   });
diff --git a/apps/web/utils/ai/knowledge/extract-from-email-history.ts b/apps/web/utils/ai/knowledge/extract-from-email-history.ts
index 3753a164dc..2fef89674c 100644
--- a/apps/web/utils/ai/knowledge/extract-from-email-history.ts
+++ b/apps/web/utils/ai/knowledge/extract-from-email-history.ts
@@ -90,7 +90,7 @@ export async function aiExtractFromEmailHistory({
     const modelOptions = getModel(emailAccount.user, "economy");
 
     const generateObject = createGenerateObject({
-      userEmail: emailAccount.email,
+      emailAccount,
       label: "Email history extraction",
       modelOptions,
     });
diff --git a/apps/web/utils/ai/knowledge/extract.ts b/apps/web/utils/ai/knowledge/extract.ts
index 09b2bb871b..a35d098e96 100644
--- a/apps/web/utils/ai/knowledge/extract.ts
+++ b/apps/web/utils/ai/knowledge/extract.ts
@@ -91,7 +91,7 @@ export async function aiExtractRelevantKnowledge({
     const modelOptions = getModel(emailAccount.user, "economy");
 
     const generateObject = createGenerateObject({
-      userEmail: emailAccount.email,
+      emailAccount,
       label: "Knowledge extraction",
       modelOptions,
     });
diff --git a/apps/web/utils/ai/knowledge/persona.ts b/apps/web/utils/ai/knowledge/persona.ts
index 5050990174..134a5561e3 100644
--- a/apps/web/utils/ai/knowledge/persona.ts
+++ b/apps/web/utils/ai/knowledge/persona.ts
@@ -96,7 +96,7 @@ ${getEmailListPrompt({ messages: emails, messageMaxLength: 1000 })}
   const modelOptions = getModel(emailAccount.user, "economy");
 
   const generateObject = createGenerateObject({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "Persona Analysis",
     modelOptions,
   });
diff --git a/apps/web/utils/ai/knowledge/writing-style.ts b/apps/web/utils/ai/knowledge/writing-style.ts
index 38a83c0d4f..cf240a27c9 100644
--- a/apps/web/utils/ai/knowledge/writing-style.ts
+++ b/apps/web/utils/ai/knowledge/writing-style.ts
@@ -68,7 +68,7 @@ ${getUserInfoPrompt({ emailAccount })}`;
   const modelOptions = getModel(emailAccount.user);
 
   const generateObject = createGenerateObject({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "Writing Style Analysis",
     modelOptions,
   });
diff --git a/apps/web/utils/ai/mcp/mcp-agent.ts b/apps/web/utils/ai/mcp/mcp-agent.ts
index ea8d124f1d..419c5e95c8 100644
--- a/apps/web/utils/ai/mcp/mcp-agent.ts
+++ b/apps/web/utils/ai/mcp/mcp-agent.ts
@@ -58,7 +58,7 @@ ${getEmailListPrompt({ messages, messageMaxLength: 1000, maxMessages: 5 })}
   const modelOptions = getModel(emailAccount.user, "economy");
 
   const generateText = createGenerateText({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "MCP Agent",
     modelOptions,
   });
diff --git a/apps/web/utils/ai/reply/check-if-needs-reply.ts b/apps/web/utils/ai/reply/check-if-needs-reply.ts
index 068aff2bc7..53053854a9 100644
--- a/apps/web/utils/ai/reply/check-if-needs-reply.ts
+++ b/apps/web/utils/ai/reply/check-if-needs-reply.ts
@@ -55,7 +55,7 @@ Decide if the message we are sending needs a reply. Respond with a JSON object w
   const modelOptions = getModel(emailAccount.user);
 
   const generateObject = createGenerateObject({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "Check if needs reply",
     modelOptions,
   });
diff --git a/apps/web/utils/ai/reply/determine-thread-status.ts b/apps/web/utils/ai/reply/determine-thread-status.ts
index 04d8532b3d..acaa63be65 100644
--- a/apps/web/utils/ai/reply/determine-thread-status.ts
+++ b/apps/web/utils/ai/reply/determine-thread-status.ts
@@ -107,7 +107,7 @@ Based on the full thread context above, determine the current status of this thr
   const modelOptions = getModel(emailAccount.user, modelType);
 
   const generateObject = createGenerateObject({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "Determine thread status",
     modelOptions,
   });
diff --git a/apps/web/utils/ai/reply/draft-with-knowledge.ts b/apps/web/utils/ai/reply/draft-with-knowledge.ts
index bf415bfd5f..3fe5cb31b8 100644
--- a/apps/web/utils/ai/reply/draft-with-knowledge.ts
+++ b/apps/web/utils/ai/reply/draft-with-knowledge.ts
@@ -187,7 +187,7 @@ export async function aiDraftWithKnowledge({
     const modelOptions = getModel(emailAccount.user);
 
     const generateObject = createGenerateObject({
-      userEmail: emailAccount.email,
+      emailAccount,
       label: "Email draft with knowledge",
       modelOptions,
     });
diff --git a/apps/web/utils/ai/reply/generate-nudge.ts b/apps/web/utils/ai/reply/generate-nudge.ts
index 69b5f3707e..7002f4478a 100644
--- a/apps/web/utils/ai/reply/generate-nudge.ts
+++ b/apps/web/utils/ai/reply/generate-nudge.ts
@@ -32,7 +32,7 @@ IMPORTANT: The person you're writing an email for is: ${messages.at(-1)?.from}.`
 
   const generateText = createGenerateText({
     label: "Reply",
-    userEmail: emailAccount.email,
+    emailAccount,
     modelOptions,
   });
 
diff --git a/apps/web/utils/ai/reply/reply-context-collector.ts b/apps/web/utils/ai/reply/reply-context-collector.ts
index 996ad9194d..645bd84994 100644
--- a/apps/web/utils/ai/reply/reply-context-collector.ts
+++ b/apps/web/utils/ai/reply/reply-context-collector.ts
@@ -87,7 +87,7 @@ ${getTodayForLLM()}`;
     const modelOptions = getModel(emailAccount.user, "economy");
 
     const generateText = createGenerateText({
-      userEmail: emailAccount.email,
+      emailAccount,
       label: "Reply context collector",
       modelOptions,
     });
diff --git a/apps/web/utils/ai/report/analyze-email-behavior.ts b/apps/web/utils/ai/report/analyze-email-behavior.ts
index ae6d7dd85e..b8aaef5f7b 100644
--- a/apps/web/utils/ai/report/analyze-email-behavior.ts
+++ b/apps/web/utils/ai/report/analyze-email-behavior.ts
@@ -60,7 +60,7 @@ Analyze the email patterns and identify:
   const modelOptions = getModel(emailAccount.user, "economy");
 
   const generateObject = createGenerateObject({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "email-report-email-behavior",
     modelOptions,
   });
diff --git a/apps/web/utils/ai/report/analyze-label-optimization.ts b/apps/web/utils/ai/report/analyze-label-optimization.ts
index 30fb983a06..7e2dd60f11 100644
--- a/apps/web/utils/ai/report/analyze-label-optimization.ts
+++ b/apps/web/utils/ai/report/analyze-label-optimization.ts
@@ -55,7 +55,7 @@ Each suggestion should include the reason and expected impact.`;
   const modelOptions = getModel(emailAccount.user, "economy");
 
   const generateObject = createGenerateObject({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "email-report-label-analysis",
     modelOptions,
   });
diff --git a/apps/web/utils/ai/report/build-user-persona.ts b/apps/web/utils/ai/report/build-user-persona.ts
index 7fff7c5bb2..2383665bd4 100644
--- a/apps/web/utils/ai/report/build-user-persona.ts
+++ b/apps/web/utils/ai/report/build-user-persona.ts
@@ -67,7 +67,7 @@ Analyze the data and identify:
   const modelOptions = getModel(emailAccount.user);
 
   const generateObject = createGenerateObject({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "email-report-user-persona",
     modelOptions,
   });
diff --git a/apps/web/utils/ai/report/generate-actionable-recommendations.ts b/apps/web/utils/ai/report/generate-actionable-recommendations.ts
index 2be62583bb..53add316d9 100644
--- a/apps/web/utils/ai/report/generate-actionable-recommendations.ts
+++ b/apps/web/utils/ai/report/generate-actionable-recommendations.ts
@@ -62,7 +62,7 @@ Focus on practical, implementable solutions that improve email organization and
   const modelOptions = getModel(emailAccount.user);
 
   const generateObject = createGenerateObject({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "email-report-actionable-recommendations",
     modelOptions,
   });
diff --git a/apps/web/utils/ai/report/generate-executive-summary.ts b/apps/web/utils/ai/report/generate-executive-summary.ts
index 5c6e9668a1..89bf6c1d3c 100644
--- a/apps/web/utils/ai/report/generate-executive-summary.ts
+++ b/apps/web/utils/ai/report/generate-executive-summary.ts
@@ -140,7 +140,7 @@ Generate:
   const modelOptions = getModel(emailAccount.user);
 
   const generateObject = createGenerateObject({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "email-report-executive-summary",
     modelOptions,
   });
diff --git a/apps/web/utils/ai/report/response-patterns.ts b/apps/web/utils/ai/report/response-patterns.ts
index c0973d0bd9..3ddc172ac4 100644
--- a/apps/web/utils/ai/report/response-patterns.ts
+++ b/apps/web/utils/ai/report/response-patterns.ts
@@ -91,7 +91,7 @@ Only suggest categories that are meaningful and provide clear organizational val
   const modelOptions = getModel(emailAccount.user);
 
   const generateObject = createGenerateObject({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "email-report-response-patterns",
     modelOptions,
   });
diff --git a/apps/web/utils/ai/report/summarize-emails.ts b/apps/web/utils/ai/report/summarize-emails.ts
index 7b11934bd8..c04e934009 100644
--- a/apps/web/utils/ai/report/summarize-emails.ts
+++ b/apps/web/utils/ai/report/summarize-emails.ts
@@ -83,7 +83,7 @@ Return the analysis as a JSON array of objects.`;
   const modelOptions = getModel(emailAccount.user, "economy");
 
   const generateObject = createGenerateObject({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "email-report-summary-generation",
     modelOptions,
   });
diff --git a/apps/web/utils/ai/rule/create-rule.ts b/apps/web/utils/ai/rule/create-rule.ts
index 1a83d7e609..aa8c25385c 100644
--- a/apps/web/utils/ai/rule/create-rule.ts
+++ b/apps/web/utils/ai/rule/create-rule.ts
@@ -17,7 +17,7 @@ export async function aiCreateRule(
   const modelOptions = getModel(emailAccount.user);
 
   const generateObject = createGenerateObject({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "Categorize rule",
     modelOptions,
   });
diff --git a/apps/web/utils/ai/rule/diff-rules.ts b/apps/web/utils/ai/rule/diff-rules.ts
index d0a8172f6b..50deb3842f 100644
--- a/apps/web/utils/ai/rule/diff-rules.ts
+++ b/apps/web/utils/ai/rule/diff-rules.ts
@@ -60,7 +60,7 @@ Return the result in JSON format. Do not include any other text in your response
   const modelOptions = getModel(emailAccount.user, "chat");
 
   const generateObject = createGenerateObject({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "Diff rules",
     modelOptions,
   });
diff --git a/apps/web/utils/ai/rule/find-existing-rules.ts b/apps/web/utils/ai/rule/find-existing-rules.ts
index 48be8e2159..a29f7a0873 100644
--- a/apps/web/utils/ai/rule/find-existing-rules.ts
+++ b/apps/web/utils/ai/rule/find-existing-rules.ts
@@ -47,7 +47,7 @@ Please return the existing rules that match the prompt rules in JSON format.
   const modelOptions = getModel(emailAccount.user, "chat");
 
   const generateObject = createGenerateObject({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "Find existing rules",
     modelOptions,
   });
diff --git a/apps/web/utils/ai/rule/generate-rules-prompt.ts b/apps/web/utils/ai/rule/generate-rules-prompt.ts
index a1eb4ea54a..624cdd5107 100644
--- a/apps/web/utils/ai/rule/generate-rules-prompt.ts
+++ b/apps/web/utils/ai/rule/generate-rules-prompt.ts
@@ -106,7 +106,7 @@ IMPORTANT: Do not create overly specific rules that only occur on a one off basi
   const modelOptions = getModel(emailAccount.user, "chat");
 
   const generateObject = createGenerateObject({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "Generate rules prompt",
     modelOptions,
   });
diff --git a/apps/web/utils/ai/rule/prompt-to-rules-old.ts b/apps/web/utils/ai/rule/prompt-to-rules-old.ts
index 80b8acf1bf..10d9a5a650 100644
--- a/apps/web/utils/ai/rule/prompt-to-rules-old.ts
+++ b/apps/web/utils/ai/rule/prompt-to-rules-old.ts
@@ -44,7 +44,7 @@ ${cleanedPromptFile}
   const modelOptions = getModel(emailAccount.user, "chat");
 
   const generateObject = createGenerateObject({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "Prompt to rules",
     modelOptions,
   });
diff --git a/apps/web/utils/ai/rule/prompt-to-rules.ts b/apps/web/utils/ai/rule/prompt-to-rules.ts
index b7a69861fa..41f6ad0544 100644
--- a/apps/web/utils/ai/rule/prompt-to-rules.ts
+++ b/apps/web/utils/ai/rule/prompt-to-rules.ts
@@ -31,7 +31,7 @@ ${cleanedPromptFile}
   const modelOptions = getModel(emailAccount.user, "chat");
 
   const generateObject = createGenerateObject({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "Prompt to rules",
     modelOptions,
   });
diff --git a/apps/web/utils/ai/snippets/find-snippets.ts b/apps/web/utils/ai/snippets/find-snippets.ts
index 961a3f44bc..c33dac91bf 100644
--- a/apps/web/utils/ai/snippets/find-snippets.ts
+++ b/apps/web/utils/ai/snippets/find-snippets.ts
@@ -51,7 +51,7 @@ ${getEmailListPrompt({ messages: sentEmails, messageMaxLength: 2000 })}`;
   const modelOptions = getModel(emailAccount.user, "chat");
 
   const generateObject = createGenerateObject({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "ai-find-snippets",
     modelOptions,
   });
diff --git a/apps/web/utils/calendar/client.ts b/apps/web/utils/calendar/client.ts
index 195f963f5b..9cfaa33273 100644
--- a/apps/web/utils/calendar/client.ts
+++ b/apps/web/utils/calendar/client.ts
@@ -47,7 +47,10 @@ export const getCalendarClientWithRefresh = async ({
   expiresAt: number | null;
   emailAccountId: string;
 }): Promise<calendar_v3.Calendar> => {
-  if (!refreshToken) throw new SafeError("No refresh token");
+  if (!refreshToken) {
+    logger.error("No refresh token", { emailAccountId });
+    throw new SafeError("No refresh token");
+  }
 
   // Check if token is still valid
   if (expiresAt && expiresAt > Date.now()) {
diff --git a/apps/web/utils/cold-email/is-cold-email.ts b/apps/web/utils/cold-email/is-cold-email.ts
index 141641d577..ca3f84c2eb 100644
--- a/apps/web/utils/cold-email/is-cold-email.ts
+++ b/apps/web/utils/cold-email/is-cold-email.ts
@@ -142,7 +142,7 @@ ${stringifyEmail(email, 500)}
   const modelOptions = getModel(emailAccount.user, modelType);
 
   const generateObject = createGenerateObject({
-    userEmail: emailAccount.email,
+    emailAccount,
     label: "Cold email check",
     modelOptions,
   });
diff --git a/apps/web/utils/error.server.ts b/apps/web/utils/error.server.ts
index b7aed9a2b4..0510e4b88f 100644
--- a/apps/web/utils/error.server.ts
+++ b/apps/web/utils/error.server.ts
@@ -9,12 +9,19 @@ export async function logErrorToPosthog(
   type: "api" | "action",
   url: string,
   errorType: string,
+  emailAccountId: string,
 ) {
   try {
     const session = await auth();
     if (session?.user.email) {
       setUser({ email: session.user.email });
-      await trackError({ email: session.user.email, errorType, type, url });
+      await trackError({
+        email: session.user.email,
+        emailAccountId,
+        errorType,
+        type,
+        url,
+      });
     }
   } catch (error) {
     logger.error("Error logging to PostHog:", { error });
diff --git a/apps/web/utils/gmail/client.ts b/apps/web/utils/gmail/client.ts
index 42449e1a0c..6af17ff9e5 100644
--- a/apps/web/utils/gmail/client.ts
+++ b/apps/web/utils/gmail/client.ts
@@ -57,7 +57,10 @@ export const getGmailClientWithRefresh = async ({
   expiresAt: number | null;
   emailAccountId: string;
 }): Promise<gmail_v1.Gmail> => {
-  if (!refreshToken) throw new SafeError("No refresh token");
+  if (!refreshToken) {
+    logger.error("No refresh token", { emailAccountId });
+    throw new SafeError("No refresh token");
+  }
 
   // we handle refresh ourselves so not passing in expiresAt
   const auth = getAuth({ accessToken, refreshToken });
diff --git a/apps/web/utils/llms/index.ts b/apps/web/utils/llms/index.ts
index 13fd7fc0b1..a24ea7a7bd 100644
--- a/apps/web/utils/llms/index.ts
+++ b/apps/web/utils/llms/index.ts
@@ -15,7 +15,7 @@ import {
 import { jsonrepair } from "jsonrepair";
 import type { LanguageModelV2 } from "@ai-sdk/provider";
 import { saveAiUsage } from "@/utils/usage";
-import type { UserAIFields } from "@/utils/llms/types";
+import type { EmailAccountWithAI, UserAIFields } from "@/utils/llms/types";
 import { addUserErrorMessage, ErrorType } from "@/utils/error-messages";
 import {
   captureException,
@@ -42,11 +42,11 @@ const commonOptions: {
 } = { experimental_telemetry: { isEnabled: true } };
 
 export function createGenerateText({
-  userEmail,
+  emailAccount,
   label,
   modelOptions,
 }: {
-  userEmail: string;
+  emailAccount: Pick<EmailAccountWithAI, "email" | "id">;
   label: string;
   modelOptions: ReturnType<typeof getModel>;
 }): typeof generateText {
@@ -71,7 +71,7 @@ export function createGenerateText({
 
       if (result.usage) {
         await saveAiUsage({
-          email: userEmail,
+          email: emailAccount.email,
           usage: result.usage,
           provider: modelOptions.provider,
           model: modelOptions.modelName,
@@ -105,23 +105,35 @@ export function createGenerateText({
         try {
           return await generate(modelOptions.backupModel);
         } catch (error) {
-          await handleError(error, userEmail, label, modelOptions.modelName);
+          await handleError(
+            error,
+            emailAccount.email,
+            emailAccount.id,
+            label,
+            modelOptions.modelName,
+          );
           throw error;
         }
       }
 
-      await handleError(error, userEmail, label, modelOptions.modelName);
+      await handleError(
+        error,
+        emailAccount.email,
+        emailAccount.id,
+        label,
+        modelOptions.modelName,
+      );
       throw error;
     }
   };
 }
 
 export function createGenerateObject({
-  userEmail,
+  emailAccount,
   label,
   modelOptions,
 }: {
-  userEmail: string;
+  emailAccount: Pick<EmailAccountWithAI, "email" | "id">;
   label: string;
   modelOptions: ReturnType<typeof getModel>;
 }): typeof generateObject {
@@ -158,7 +170,7 @@ export function createGenerateObject({
 
       if (result.usage) {
         await saveAiUsage({
-          email: userEmail,
+          email: emailAccount.email,
           usage: result.usage,
           provider: modelOptions.provider,
           model: modelOptions.modelName,
@@ -173,7 +185,13 @@ export function createGenerateObject({
 
       return result;
     } catch (error) {
-      await handleError(error, userEmail, label, modelOptions.modelName);
+      await handleError(
+        error,
+        emailAccount.email,
+        emailAccount.id,
+        label,
+        modelOptions.modelName,
+      );
       throw error;
     }
   };
@@ -265,10 +283,17 @@ export async function chatCompletionStream({
 async function handleError(
   error: unknown,
   userEmail: string,
+  emailAccountId: string,
   label: string,
   modelName: string,
 ) {
-  logger.error("Error in LLM call", { error, userEmail, label, modelName });
+  logger.error("Error in LLM call", {
+    error,
+    userEmail,
+    emailAccountId,
+    label,
+    modelName,
+  });
 
   if (APICallError.isInstance(error)) {
     if (isIncorrectOpenAIAPIKeyError(error)) {
diff --git a/apps/web/utils/logger.ts b/apps/web/utils/logger.ts
index 4cc912e1fa..2a523c308a 100644
--- a/apps/web/utils/logger.ts
+++ b/apps/web/utils/logger.ts
@@ -120,13 +120,44 @@ function createNullLogger() {
 
 function formatError(args?: Record<string, unknown>) {
   if (env.NODE_ENV !== "production") return args;
-  const error = args?.error;
-  if (error) args.error = cleanError(error);
-  return args;
+  if (!args?.error) return args;
+
+  const error = args.error;
+  const errorMessage =
+    error instanceof Error
+      ? error.message
+      : typeof error === "object" && error !== null && "message" in error
+        ? (error as { message: unknown }).message
+        : error;
+
+  const errorFull = serializeError(error);
+
+  return {
+    ...args,
+    error: errorMessage,
+    errorFull,
+  };
 }
 
-function cleanError(error: unknown) {
-  if (error instanceof Error) return error.message;
+function serializeError(error: unknown): unknown {
+  if (error instanceof Error) {
+    // Convert Error instance to plain object so hashSensitiveFields can process it
+    const serialized: Record<string, unknown> = {
+      name: error.name,
+      message: error.message,
+      stack: error.stack,
+    };
+
+    // Copy all enumerable properties
+    for (const key in error) {
+      if (Object.hasOwn(error, key)) {
+        serialized[key] = (error as any)[key];
+      }
+    }
+
+    return serialized;
+  }
+
   return error;
 }
 
@@ -167,6 +198,8 @@ const REDACTED_FIELD_NAMES = new Set([
   "refresh_token",
   "idToken",
   "id_token",
+  "headers",
+  "authorization",
 ]);
 
 /**
diff --git a/apps/web/utils/middleware.ts b/apps/web/utils/middleware.ts
index 83c34625ea..3b242d2fe9 100644
--- a/apps/web/utils/middleware.ts
+++ b/apps/web/utils/middleware.ts
@@ -102,7 +102,7 @@ function withMiddleware<T extends NextRequest>(
 
       const apiError = checkCommonErrors(error, req.url);
       if (apiError) {
-        await logErrorToPosthog("api", req.url, apiError.type);
+        await logErrorToPosthog("api", req.url, apiError.type, "unknown"); // TODO: add emailAccountId
 
         return NextResponse.json(
           { error: apiError.message, isKnownError: true },
diff --git a/apps/web/utils/outlook/client.ts b/apps/web/utils/outlook/client.ts
index 9c252d0520..ac14c79808 100644
--- a/apps/web/utils/outlook/client.ts
+++ b/apps/web/utils/outlook/client.ts
@@ -101,7 +101,10 @@ export const getOutlookClientWithRefresh = async ({
   expiresAt: number | null;
   emailAccountId: string;
 }): Promise<OutlookClient> => {
-  if (!refreshToken) throw new SafeError("No refresh token");
+  if (!refreshToken) {
+    logger.error("No refresh token", { emailAccountId });
+    throw new SafeError("No refresh token");
+  }
 
   // Check if token needs refresh
   const expiryDate = expiresAt ? expiresAt : null;
diff --git a/apps/web/utils/outlook/thread.ts b/apps/web/utils/outlook/thread.ts
index 7c85127beb..755f672227 100644
--- a/apps/web/utils/outlook/thread.ts
+++ b/apps/web/utils/outlook/thread.ts
@@ -113,7 +113,7 @@ export async function getThreadsWithNextPageToken({
   }
 
   const response: { value: Message[]; "@odata.nextLink"?: string } =
-    await request.get();
+    await withOutlookRetry(() => request.get());
 
   // Group messages by conversationId to create thread-like structure
   const threadMap = new Map<string, { id: string; snippet: string }>();
@@ -137,13 +137,15 @@ export async function getThreadsFromSender(
   sender: string,
   limit: number,
 ): Promise<Array<{ id: string; snippet: string }>> {
-  const response: { value: Message[] } = await client
-    .getClient()
-    .api("/me/messages")
-    .filter(`from/emailAddress/address eq '${escapeODataString(sender)}'`)
-    .top(limit)
-    .select("id,conversationId,bodyPreview")
-    .get();
+  const response: { value: Message[] } = await withOutlookRetry(() =>
+    client
+      .getClient()
+      .api("/me/messages")
+      .filter(`from/emailAddress/address eq '${escapeODataString(sender)}'`)
+      .top(limit)
+      .select("id,conversationId,bodyPreview")
+      .get(),
+  );
 
   // Group messages by conversationId
   const threadMap = new Map<string, { id: string; snippet: string }>();
@@ -164,13 +166,15 @@ export async function getThreadsFromSenderWithSubject(
   sender: string,
   limit: number,
 ): Promise<Array<{ id: string; snippet: string; subject: string }>> {
-  const response: { value: Message[] } = await client
-    .getClient()
-    .api("/me/messages")
-    .filter(`from/emailAddress/address eq '${escapeODataString(sender)}'`)
-    .top(limit)
-    .select("id,conversationId,subject,bodyPreview")
-    .get();
+  const response: { value: Message[] } = await withOutlookRetry(() =>
+    client
+      .getClient()
+      .api("/me/messages")
+      .filter(`from/emailAddress/address eq '${escapeODataString(sender)}'`)
+      .top(limit)
+      .select("id,conversationId,subject,bodyPreview")
+      .get(),
+  );
 
   // Group messages by conversationId
   const threadMap = new Map<
diff --git a/apps/web/utils/posthog.ts b/apps/web/utils/posthog.ts
index 9b4a41b58c..05b344e37c 100644
--- a/apps/web/utils/posthog.ts
+++ b/apps/web/utils/posthog.ts
@@ -1,6 +1,7 @@
 import { PostHog } from "posthog-node";
 import { env } from "@/env";
 import { createScopedLogger } from "@/utils/logger";
+import { hash } from "@/utils/hash";
 
 const logger = createScopedLogger("posthog");
 
@@ -70,6 +71,33 @@ export async function deletePosthogUser(options: { email: string }) {
   }
 }
 
+export async function aliasPosthogUser({
+  oldEmail,
+  newEmail,
+}: {
+  oldEmail: string;
+  newEmail: string;
+}) {
+  if (!env.NEXT_PUBLIC_POSTHOG_KEY) {
+    logger.warn("NEXT_PUBLIC_POSTHOG_KEY not set");
+    return;
+  }
+
+  try {
+    const client = new PostHog(env.NEXT_PUBLIC_POSTHOG_KEY);
+    // Alias links the old distinct ID to the new distinct ID
+    // This ensures all historical events remain connected
+    client.alias({ distinctId: newEmail, alias: oldEmail });
+    await client.shutdown();
+    logger.info("PostHog user aliased", {
+      oldEmail: hash(oldEmail),
+      newEmail: hash(newEmail),
+    });
+  } catch (error) {
+    logger.error("Error aliasing PostHog user", { error });
+  }
+}
+
 export async function posthogCaptureEvent(
   email: string,
   event: string,
@@ -130,17 +158,19 @@ export async function trackStripeCheckoutCompleted(email: string) {
 
 export async function trackError({
   email,
+  emailAccountId,
   errorType,
   type,
   url,
 }: {
   email: string;
+  emailAccountId: string;
   errorType: string;
   type: "api" | "action";
   url: string;
 }) {
   return posthogCaptureEvent(email, errorType, {
-    $set: { isError: true, type, url },
+    $set: { isError: true, type, url, emailAccountId },
   });
 }
 
diff --git a/apps/web/utils/webhook/error-handler.ts b/apps/web/utils/webhook/error-handler.ts
index 0de406d6e4..3ff0510da9 100644
--- a/apps/web/utils/webhook/error-handler.ts
+++ b/apps/web/utils/webhook/error-handler.ts
@@ -10,16 +10,18 @@ export async function handleWebhookError(
   error: unknown,
   options: {
     email: string;
+    emailAccountId: string;
     url: string;
     logger: Logger;
   },
 ) {
-  const { email, url, logger } = options;
+  const { email, emailAccountId, url, logger } = options;
 
   const apiError = checkCommonErrors(error, url);
   if (apiError) {
     await trackError({
       email,
+      emailAccountId,
       errorType: apiError.type,
       type: "api",
       url,
diff --git a/version.txt b/version.txt
index 1099837570..3cc122cbc0 100644
--- a/version.txt
+++ b/version.txt
@@ -1 +1 @@
-v2.18.5
+v2.18.6