diff --git a/apps/web/utils/ai/choose-rule/execute.ts b/apps/web/utils/ai/choose-rule/execute.ts
index 814393a934..83e63cc806 100644
--- a/apps/web/utils/ai/choose-rule/execute.ts
+++ b/apps/web/utils/ai/choose-rule/execute.ts
@@ -9,8 +9,6 @@ import { createScopedLogger } from "@/utils/logger";
 import { markNeedsReply } from "@/utils/reply-tracker/inbound";
 import { internalDateToDate } from "@/utils/date";
 
-const logger = createScopedLogger("ai-execute-act");
-
 type ExecutedRuleWithActionItems = Prisma.ExecutedRuleGetPayload<{
   include: { actionItems: true };
 }>;
@@ -27,11 +25,13 @@ export async function executeAct({
   userEmail: string;
   isReplyTrackingRule: boolean;
 }) {
-  logger.info("Executing rule", {
-    userEmail,
+  const logger = createScopedLogger("ai-execute-act").with({
+    email: userEmail,
     executedRuleId: executedRule.id,
     ruleId: executedRule.ruleId,
     isReplyTrackingRule,
+    threadId: executedRule.threadId,
+    messageId: executedRule.messageId,
   });
 
   async function labelActed() {
@@ -55,10 +55,7 @@ export async function executeAct({
   });
 
   if (pendingRules.count === 0) {
-    logger.info("Executed rule is not pending or does not exist", {
-      userEmail,
-      executedRuleId: executedRule.id,
-    });
+    logger.info("Executed rule is not pending or does not exist");
     return;
   }
 
@@ -88,13 +85,7 @@ export async function executeAct({
         gmail,
       );
     } catch (error) {
-      logger.error("Failed to create reply tracker", {
-        error,
-        userId: executedRule.userId,
-        email: userEmail,
-        threadId: executedRule.threadId,
-        messageId: executedRule.messageId,
-      });
+      logger.error("Failed to create reply tracker", { error });
     }
   }
 
@@ -109,17 +100,12 @@ export async function executeAct({
   if (updateResult.status === "rejected") {
     logger.error("Failed to update executed rule", {
       error: updateResult.reason,
-      userId: executedRule.userId,
-      email: userEmail,
-      ruleId: executedRule.ruleId,
     });
   }
 
   if (labelResult.status === "rejected") {
     logger.error("Failed to label acted", {
       error: labelResult.reason,
-      userId: executedRule.userId,
-      email: userEmail,
     });
   }
 }
diff --git a/apps/web/utils/logger.ts b/apps/web/utils/logger.ts
index 1878b96fa5..8b5eb06d96 100644
--- a/apps/web/utils/logger.ts
+++ b/apps/web/utils/logger.ts
@@ -2,6 +2,8 @@
 import { log } from "next-axiom";
 import { env } from "@/env";
 
+export type Logger = ReturnType<typeof createScopedLogger>;
+
 type LogLevel = "info" | "error" | "warn" | "trace";
 
 const colors = {
@@ -15,50 +17,66 @@ const colors = {
 export function createScopedLogger(scope: string) {
   if (env.NEXT_PUBLIC_AXIOM_TOKEN) return createAxiomLogger(scope);
 
-  const formatMessage = (level: LogLevel, message: string, args: unknown[]) => {
-    const formattedArgs = args
-      .map((arg) =>
-        typeof arg === "object" ? JSON.stringify(arg, null, 2) : String(arg),
-      )
-      .join(" ");
-
-    const msg = `[${scope}]: ${message} ${formattedArgs}`;
-
-    if (process.env.NODE_ENV === "development")
-      return `${colors[level]}${msg}${colors.reset}`;
-    return msg;
-  };
+  const createLogger = (fields: Record<string, unknown> = {}) => {
+    const formatMessage = (
+      level: LogLevel,
+      message: string,
+      args: unknown[],
+    ) => {
+      const allArgs = [...args];
+      if (Object.keys(fields).length > 0) {
+        allArgs.push(fields);
+      }
 
-  return {
-    info: (message: string, ...args: unknown[]) =>
-      console.log(formatMessage("info", message, args)),
+      const formattedArgs = allArgs
+        .map((arg) =>
+          typeof arg === "object" ? JSON.stringify(arg, null, 2) : String(arg),
+        )
+        .join(" ");
 
-    error: (message: string, ...args: unknown[]) =>
-      console.error(formatMessage("error", message, args)),
+      const msg = `[${scope}]: ${message} ${formattedArgs}`;
 
-    warn: (message: string, ...args: unknown[]) =>
-      console.warn(formatMessage("warn", message, args)),
+      if (process.env.NODE_ENV === "development")
+        return `${colors[level]}${msg}${colors.reset}`;
+      return msg;
+    };
 
-    trace: (message: string, ...args: unknown[]) => {
-      if (process.env.NODE_ENV !== "production") {
-        console.log(formatMessage("trace", message, args));
-      }
-    },
+    return {
+      info: (message: string, ...args: unknown[]) =>
+        console.log(formatMessage("info", message, args)),
+      error: (message: string, ...args: unknown[]) =>
+        console.error(formatMessage("error", message, args)),
+      warn: (message: string, ...args: unknown[]) =>
+        console.warn(formatMessage("warn", message, args)),
+      trace: (message: string, ...args: unknown[]) => {
+        if (process.env.NODE_ENV !== "production") {
+          console.log(formatMessage("trace", message, args));
+        }
+      },
+      with: (newFields: Record<string, unknown>) =>
+        createLogger({ ...fields, ...newFields }),
+    };
   };
+
+  return createLogger();
 }
 
 function createAxiomLogger(scope: string) {
-  return {
+  const createLogger = (fields: Record<string, unknown> = {}) => ({
     info: (message: string, args?: Record<string, unknown>) =>
-      log.info(message, { scope, ...args }),
+      log.info(message, { scope, ...fields, ...args }),
     error: (message: string, args?: Record<string, unknown>) =>
-      log.error(message, { scope, ...args }),
+      log.error(message, { scope, ...fields, ...args }),
     warn: (message: string, args?: Record<string, unknown>) =>
-      log.warn(message, { scope, ...args }),
+      log.warn(message, { scope, ...fields, ...args }),
     trace: (message: string, args?: Record<string, unknown>) => {
       if (process.env.NODE_ENV !== "production") {
-        log.debug(message, { scope, ...args });
+        log.debug(message, { scope, ...fields, ...args });
       }
     },
-  };
+    with: (newFields: Record<string, unknown>) =>
+      createLogger({ ...fields, ...newFields }),
+  });
+
+  return createLogger();
 }
diff --git a/apps/web/utils/reply-tracker/inbound.ts b/apps/web/utils/reply-tracker/inbound.ts
index 31f556d428..0ecf4e9be2 100644
--- a/apps/web/utils/reply-tracker/inbound.ts
+++ b/apps/web/utils/reply-tracker/inbound.ts
@@ -15,8 +15,6 @@ import { getEmailForLLM } from "@/utils/get-email-from-message";
 import { aiChooseRule } from "@/utils/ai/choose-rule/ai-choose-rule";
 import { getReplyTrackingRule } from "@/utils/reply-tracker";
 
-const logger = createScopedLogger("reply-tracker/inbound");
-
 export async function markNeedsReply(
   userId: string,
   threadId: string,
@@ -24,6 +22,14 @@ export async function markNeedsReply(
   sentAt: Date,
   gmail: gmail_v1.Gmail,
 ) {
+  const logger = createScopedLogger("reply-tracker/inbound").with({
+    userId,
+    threadId,
+    messageId,
+  });
+
+  logger.info("Marking thread as needs reply");
+
   const { awaitingReplyLabelId, needsReplyLabelId } =
     await getReplyTrackingLabels(gmail);
 
@@ -69,29 +75,20 @@ export async function markNeedsReply(
   const [dbResult, removeLabelResult, newLabelResult] =
     await Promise.allSettled([dbPromise, removeLabelPromise, newLabelPromise]);
 
-  const errorOptions = {
-    userId,
-    threadId,
-    messageId,
-  };
-
   if (dbResult.status === "rejected") {
     logger.error("Failed to mark needs reply", {
-      ...errorOptions,
       error: dbResult.reason,
     });
   }
 
   if (removeLabelResult.status === "rejected") {
     logger.error("Failed to remove awaiting reply label", {
-      ...errorOptions,
       error: removeLabelResult.reason,
     });
   }
 
   if (newLabelResult.status === "rejected") {
     logger.error("Failed to label needs reply", {
-      ...errorOptions,
       error: newLabelResult.reason,
     });
   }
diff --git a/apps/web/utils/reply-tracker/outbound.ts b/apps/web/utils/reply-tracker/outbound.ts
index cd6ef73d1d..1c6b4c9ea4 100644
--- a/apps/web/utils/reply-tracker/outbound.ts
+++ b/apps/web/utils/reply-tracker/outbound.ts
@@ -5,7 +5,7 @@ import { aiCheckIfNeedsReply } from "@/utils/ai/reply/check-if-needs-reply";
 import prisma from "@/utils/prisma";
 import { getThreadMessages } from "@/utils/gmail/thread";
 import { ThreadTrackerType, type User } from "@prisma/client";
-import { createScopedLogger } from "@/utils/logger";
+import { createScopedLogger, type Logger } from "@/utils/logger";
 import { getEmailForLLM } from "@/utils/get-email-from-message";
 import {
   labelAwaitingReply,
@@ -15,8 +15,6 @@ import {
 import { internalDateToDate } from "@/utils/date";
 import { getReplyTrackingRule } from "@/utils/reply-tracker";
 
-const logger = createScopedLogger("outbound-reply");
-
 export async function handleOutboundReply(
   user: Pick<User, "id" | "about"> & UserEmailWithAI,
   message: ParsedMessage,
@@ -42,12 +40,15 @@ export async function handleOutboundReply(
 
   const threadMessages = await getThreadMessages(message.threadId, gmail);
 
+  const logger = createScopedLogger("reply-tracker/outbound").with({
+    email: user.email,
+    userId: user.id,
+    messageId: message.id,
+    threadId: message.threadId,
+  });
+
   if (!threadMessages?.length) {
-    logger.error("No thread messages found", {
-      email: user.email,
-      messageId: message.id,
-      threadId: message.threadId,
-    });
+    logger.error("No thread messages found");
     return;
   }
 
@@ -66,6 +67,7 @@ export async function handleOutboundReply(
 
   // if yes, create a tracker
   if (result.needsReply) {
+    logger.info("Needs reply. Creating reply tracker outbound");
     await createReplyTrackerOutbound({
       gmail,
       userId,
@@ -73,6 +75,7 @@ export async function handleOutboundReply(
       messageId: message.id,
       awaitingReplyLabelId,
       sentAt: internalDateToDate(message.internalDate),
+      logger,
     });
   } else {
     logger.info("No need to reply");
@@ -86,6 +89,7 @@ async function createReplyTrackerOutbound({
   messageId,
   awaitingReplyLabelId,
   sentAt,
+  logger,
 }: {
   gmail: gmail_v1.Gmail;
   userId: string;
@@ -93,6 +97,7 @@ async function createReplyTrackerOutbound({
   messageId: string;
   awaitingReplyLabelId: string;
   sentAt: Date;
+  logger: Logger;
 }) {
   if (!threadId || !messageId) return;
 
@@ -125,22 +130,14 @@ async function createReplyTrackerOutbound({
     labelPromise,
   ]);
 
-  const errorOptions = {
-    userId,
-    threadId,
-    messageId,
-  };
-
   if (upsertResult.status === "rejected") {
     logger.error("Failed to upsert reply tracker", {
-      ...errorOptions,
       error: upsertResult.reason,
     });
   }
 
   if (labelResult.status === "rejected") {
     logger.error("Failed to label reply tracker", {
-      ...errorOptions,
       error: labelResult.reason,
     });
   }