diff --git a/apps/web/app/(app)/automation/RuleForm.tsx b/apps/web/app/(app)/automation/RuleForm.tsx
index 60aa557aaa..16ac616406 100644
--- a/apps/web/app/(app)/automation/RuleForm.tsx
+++ b/apps/web/app/(app)/automation/RuleForm.tsx
@@ -31,8 +31,9 @@ import {
   ActionType,
   CategoryFilterType,
   LogicalOperator,
+  SystemType,
 } from "@prisma/client";
-import { ConditionType } from "@/utils/config";
+import { ConditionType, type CoreConditionType } from "@/utils/config";
 import { createRuleAction, updateRuleAction } from "@/utils/actions/rule";
 import {
   type CreateRuleBody,
@@ -195,7 +196,7 @@ export function RuleForm({
       ConditionType.STATIC,
       ConditionType.CATEGORY,
     ].find((type) => !usedConditions.has(type)) as
-      | Exclude<ConditionType, "GROUP">
+      | CoreConditionType
       | undefined;
   }, [conditions]);
 
@@ -265,8 +266,17 @@ export function RuleForm({
         />
       </div>
 
+      {showSystemTypeBadge(rule.systemType) && (
+        <div className="mt-2 flex items-center gap-2">
+          <Badge color="green">
+            This rule has special preset logic that may impact your conditions
+          </Badge>
+        </div>
+      )}
+
       <div className="mt-6 flex items-end justify-between">
         <TypographyH3>Conditions</TypographyH3>
+
         <div className="flex items-center gap-1.5">
           <DropdownMenu>
             <DropdownMenuTrigger asChild>
@@ -801,9 +811,10 @@ function ReplyTrackerAction() {
   return (
     <div className="h-full flex items-center justify-center">
       <div className="text-center text-sm text-muted-foreground max-w-sm">
-        Tracks conversations this rule applies to.{" "}
-        <Badge color="green">{NEEDS_REPLY_LABEL_NAME}</Badge> will be
-        automatically removed after you reply.
+        Used for reply tracking (Reply Zero). This action tracks emails this
+        rule is applied to and removes the{" "}
+        <Badge color="green">{NEEDS_REPLY_LABEL_NAME}</Badge> label after you
+        reply to the email.
       </div>
     </div>
   );
@@ -963,3 +974,9 @@ function ActionField({
     </div>
   );
 }
+
+function showSystemTypeBadge(systemType?: SystemType | null): boolean {
+  if (systemType === SystemType.TO_REPLY) return true;
+  if (systemType === SystemType.CALENDAR) return true;
+  return false;
+}
diff --git a/apps/web/app/(app)/automation/examples.ts b/apps/web/app/(app)/automation/examples.ts
index c049d19b3e..42ab3b95b2 100644
--- a/apps/web/app/(app)/automation/examples.ts
+++ b/apps/web/app/(app)/automation/examples.ts
@@ -19,10 +19,7 @@ export function hasExampleParams(rule: {
 
 const commonPrompts = [
   "Label urgent emails as 'Urgent'",
-  "Label newsletters as 'Newsletter' and archive them",
-  "Label marketing emails as 'Marketing' and archive them",
   "Label emails from @mycompany.com addresses as 'Team'",
-  "Label receipts as 'Receipt' and archive them",
 ];
 
 const common = `${commonPrompts.map((prompt) => `* ${prompt}`).join(".\n")}.`;
@@ -53,9 +50,7 @@ const founderPrompt = `* If someone asks to set up a call, draft a reply with my
 * Label emails from investors as "Investor".
 * Label legal documents as "Legal".
 * Label emails about travel as "Travel".
-* Label recruitment related emails as "Hiring".
-* Label marketing and newsletter emails as "Marketing" and archive them.
-* Label receipts as 'Receipt' and archive them.`;
+* Label recruitment related emails as "Hiring".`;
 
 export const personas = {
   founder: {
@@ -76,8 +71,7 @@ I've attached my media kit and pricing.
 * Label emails about affiliate programs as "Affiliate" and archive them.
 * Label collaboration requests as "Collab" and draft a reply asking about their audience size and engagement rates.
 * Label brand partnership emails as "Brand Deal" and forward to manager@example.com
-* Label media inquiries as "Press" and draft a reply a polite reply.
-* Label marketing and newsletter emails as "Marketing" and archive them.`,
+* Label media inquiries as "Press" and draft a reply a polite reply.`,
   },
   investor: {
     label: "💰 Investor",
@@ -94,8 +88,7 @@ I've attached my media kit and pricing.
 * Forward emails about industry research reports to research@vc.com
 * If someone asks for a warm intro to a portfolio company, draft a reply asking for more context about why they want to connect.
 * Label emails about fund administration as "Fund Admin".
-* Label emails about speaking at investment conferences as "Speaking Opportunity".
-* Label marketing and newsletter emails as "Marketing" and archive them.`,
+* Label emails about speaking at investment conferences as "Speaking Opportunity".`,
   },
   assistant: {
     label: "📋 Assistant",
@@ -197,10 +190,7 @@ I've attached my media kit and pricing.
 * Label emails about exam schedules as "Exam".
 * Label emails about campus events as "Event" and archive them.
 * If someone asks for class notes, draft a reply with our shared Google Drive folder link: https://drive.google.com/drive/u/0/folders/1234567890.
-* Label emails about tutoring opportunities as "Tutoring" and draft a reply with that my rate is $70/hour or $40/hour for group tutoring.
-
-* Label newsletters as 'Newsletter' and archive them
-* Label marketing emails as 'Marketing' and archive them`,
+* Label emails about tutoring opportunities as "Tutoring" and draft a reply with that my rate is $70/hour or $40/hour for group tutoring.`,
   },
   reachout: {
     label: "💬 Reachout",
diff --git a/apps/web/app/(app)/automation/onboarding/CategoriesSetup.tsx b/apps/web/app/(app)/automation/onboarding/CategoriesSetup.tsx
index 2dd99c34a5..b42662bcc5 100644
--- a/apps/web/app/(app)/automation/onboarding/CategoriesSetup.tsx
+++ b/apps/web/app/(app)/automation/onboarding/CategoriesSetup.tsx
@@ -32,8 +32,10 @@ import {
   type CreateRulesOnboardingBody,
 } from "@/utils/actions/rule.validation";
 import { TooltipExplanation } from "@/components/TooltipExplanation";
-import { ASSISTANT_ONBOARDING_COOKIE } from "@/utils/cookies";
-import { markOnboardingAsCompleted } from "@/utils/cookies";
+import {
+  ASSISTANT_ONBOARDING_COOKIE,
+  markOnboardingAsCompleted,
+} from "@/utils/cookies";
 
 const NEXT_URL = "/automation/onboarding/draft-replies";
 
diff --git a/apps/web/app/(app)/automation/onboarding/page.tsx b/apps/web/app/(app)/automation/onboarding/page.tsx
index 59b1bb5c45..9278b2bddc 100644
--- a/apps/web/app/(app)/automation/onboarding/page.tsx
+++ b/apps/web/app/(app)/automation/onboarding/page.tsx
@@ -2,9 +2,13 @@ import { Card } from "@/components/ui/card";
 import { CategoriesSetup } from "./CategoriesSetup";
 import { auth } from "@/app/api/auth/[...nextauth]/auth";
 import prisma from "@/utils/prisma";
-import { ActionType, ColdEmailSetting, type Prisma } from "@prisma/client";
+import {
+  ActionType,
+  ColdEmailSetting,
+  SystemType,
+  type Prisma,
+} from "@prisma/client";
 import type { CategoryAction } from "@/utils/actions/rule.validation";
-import { RuleName } from "@/utils/rule/consts";
 
 export default async function OnboardingPage() {
   const session = await auth();
@@ -23,7 +27,7 @@ type UserPreferences = Prisma.UserGetPayload<{
   select: {
     rules: {
       select: {
-        name: true;
+        systemType: true;
         actions: {
           select: { type: true };
         };
@@ -39,7 +43,7 @@ async function getUserPreferences(userId: string) {
     select: {
       rules: {
         select: {
-          name: true,
+          systemType: true,
           actions: {
             select: {
               type: true,
@@ -55,11 +59,11 @@ async function getUserPreferences(userId: string) {
   return {
     toReply: getToReplySetting(user.rules),
     coldEmails: getColdEmailSetting(user.coldEmailBlocker),
-    newsletter: getRuleSetting(RuleName.Newsletter, user.rules),
-    marketing: getRuleSetting(RuleName.Marketing, user.rules),
-    calendar: getRuleSetting(RuleName.Calendar, user.rules),
-    receipt: getRuleSetting(RuleName.Receipt, user.rules),
-    notification: getRuleSetting(RuleName.Notification, user.rules),
+    newsletter: getRuleSetting(SystemType.NEWSLETTER, user.rules),
+    marketing: getRuleSetting(SystemType.MARKETING, user.rules),
+    calendar: getRuleSetting(SystemType.CALENDAR, user.rules),
+    receipt: getRuleSetting(SystemType.RECEIPT, user.rules),
+    notification: getRuleSetting(SystemType.NOTIFICATION, user.rules),
   };
 }
 
@@ -75,10 +79,10 @@ function getToReplySetting(
 }
 
 function getRuleSetting(
-  name: string,
+  systemType: SystemType,
   rules?: UserPreferences["rules"],
 ): CategoryAction | undefined {
-  const rule = rules?.find((rule) => rule.name === name);
+  const rule = rules?.find((rule) => rule.systemType === systemType);
   if (!rule) return undefined;
 
   if (rule.actions.some((action) => action.type === ActionType.ARCHIVE))
diff --git a/apps/web/app/(app)/automation/rule/create/page.tsx b/apps/web/app/(app)/automation/rule/create/page.tsx
index a202fb4a4e..85d38d79f2 100644
--- a/apps/web/app/(app)/automation/rule/create/page.tsx
+++ b/apps/web/app/(app)/automation/rule/create/page.tsx
@@ -2,13 +2,13 @@ import { RuleForm } from "@/app/(app)/automation/RuleForm";
 import { examples } from "@/app/(app)/automation/create/examples";
 import { getEmptyCondition } from "@/utils/condition";
 import { ActionType } from "@prisma/client";
-import type { ConditionType } from "@/utils/config";
+import type { CoreConditionType } from "@/utils/config";
 
 export default async function CreateRulePage(props: {
   searchParams: Promise<{
     example?: string;
     groupId?: string;
-    type?: Exclude<ConditionType, "GROUP">;
+    type?: CoreConditionType;
     categoryId?: string;
     label?: string;
   }>;
diff --git a/apps/web/app/api/user/rules/route.ts b/apps/web/app/api/user/rules/route.ts
index ef24b77c34..20475d9ae2 100644
--- a/apps/web/app/api/user/rules/route.ts
+++ b/apps/web/app/api/user/rules/route.ts
@@ -5,9 +5,9 @@ import prisma from "@/utils/prisma";
 
 export type RulesResponse = Awaited<ReturnType<typeof getRules>>;
 
-async function getRules(options: { userId: string }) {
+async function getRules({ userId }: { userId: string }) {
   return await prisma.rule.findMany({
-    where: { userId: options.userId },
+    where: { userId },
     include: {
       actions: true,
       group: { select: { name: true } },
diff --git a/apps/web/prisma/migrations/20250414091625_rule_system_type/migration.sql b/apps/web/prisma/migrations/20250414091625_rule_system_type/migration.sql
new file mode 100644
index 0000000000..8fe665c503
--- /dev/null
+++ b/apps/web/prisma/migrations/20250414091625_rule_system_type/migration.sql
@@ -0,0 +1,14 @@
+/*
+  Warnings:
+
+  - A unique constraint covering the columns `[userId,systemType]` on the table `Rule` will be added. If there are existing duplicate values, this will fail.
+
+*/
+-- CreateEnum
+CREATE TYPE "SystemType" AS ENUM ('TO_REPLY', 'NEWSLETTER', 'MARKETING', 'CALENDAR', 'RECEIPT', 'NOTIFICATION');
+
+-- AlterTable
+ALTER TABLE "Rule" ADD COLUMN     "systemType" "SystemType";
+
+-- CreateIndex
+CREATE UNIQUE INDEX "Rule_userId_systemType_key" ON "Rule"("userId", "systemType");
diff --git a/apps/web/prisma/migrations/20250414103126_migrate_system_rule_types/migration.sql b/apps/web/prisma/migrations/20250414103126_migrate_system_rule_types/migration.sql
new file mode 100644
index 0000000000..3e6736bc93
--- /dev/null
+++ b/apps/web/prisma/migrations/20250414103126_migrate_system_rule_types/migration.sql
@@ -0,0 +1,6 @@
+UPDATE "Rule" SET "systemType" = 'TO_REPLY' WHERE "name" = 'To Reply';
+UPDATE "Rule" SET "systemType" = 'NEWSLETTER' WHERE "name" = 'Newsletter';
+UPDATE "Rule" SET "systemType" = 'MARKETING' WHERE "name" = 'Marketing';
+UPDATE "Rule" SET "systemType" = 'CALENDAR' WHERE "name" = 'Calendar';
+UPDATE "Rule" SET "systemType" = 'RECEIPT' WHERE "name" = 'Receipt';
+UPDATE "Rule" SET "systemType" = 'NOTIFICATION' WHERE "name" = 'Notification';
\ No newline at end of file
diff --git a/apps/web/prisma/schema.prisma b/apps/web/prisma/schema.prisma
index 2a7dd5589c..fd1b5d69dc 100644
--- a/apps/web/prisma/schema.prisma
+++ b/apps/web/prisma/schema.prisma
@@ -206,7 +206,10 @@ model Rule {
   categoryFilterType CategoryFilterType?
   categoryFilters    Category[]
 
+  systemType SystemType?
+
   @@unique([name, userId])
+  @@unique([userId, systemType])
 }
 
 model Action {
@@ -601,3 +604,13 @@ enum CleanAction {
   ARCHIVE
   MARK_READ
 }
+
+enum SystemType {
+  TO_REPLY
+  NEWSLETTER
+  MARKETING
+  CALENDAR
+  RECEIPT
+  NOTIFICATION
+  // COLD_EMAIL // handled separately. we may unify in the future
+}
diff --git a/apps/web/utils/actions/rule.ts b/apps/web/utils/actions/rule.ts
index c5e7f387ed..accca81185 100644
--- a/apps/web/utils/actions/rule.ts
+++ b/apps/web/utils/actions/rule.ts
@@ -23,7 +23,12 @@ import { getGmailAccessToken, getGmailClient } from "@/utils/gmail/client";
 import { aiFindExampleMatches } from "@/utils/ai/example-matches/find-example-matches";
 import { withActionInstrumentation } from "@/utils/actions/middleware";
 import { flattenConditions } from "@/utils/condition";
-import { ActionType, ColdEmailSetting, LogicalOperator } from "@prisma/client";
+import {
+  ActionType,
+  ColdEmailSetting,
+  LogicalOperator,
+  SystemType,
+} from "@prisma/client";
 import {
   updatePromptFileOnRuleUpdated,
   updateRuleInstructionsAndPromptFile,
@@ -85,6 +90,7 @@ export const createRuleAction = withActionInstrumentation(
             : undefined,
           userId: session.user.id,
           conditionalOperator: body.conditionalOperator || LogicalOperator.AND,
+          systemType: body.systemType || undefined,
           // conditions
           instructions: conditions.instructions || null,
           from: conditions.from || null,
@@ -159,6 +165,7 @@ export const updateRuleAction = withActionInstrumentation(
             name: body.name || undefined,
             conditionalOperator:
               body.conditionalOperator || LogicalOperator.AND,
+            systemType: body.systemType || undefined,
             // conditions
             instructions: conditions.instructions || null,
             from: conditions.from || null,
@@ -419,13 +426,14 @@ export const createRulesOnboardingAction = withActionInstrumentation(
   "createRulesOnboarding",
   async (options: CreateRulesOnboardingBody) => {
     const session = await auth();
-    if (!session?.user.id) return { error: "Not logged in" };
+    const userId = session?.user.id;
+    if (!userId) return { error: "Not logged in" };
 
     const { data, error } = createRulesOnboardingBody.safeParse(options);
     if (error) return { error: error.message };
 
     const user = await prisma.user.findUnique({
-      where: { id: session.user.id },
+      where: { id: userId },
       select: { rulesPrompt: true },
     });
     if (!user) return { error: "User not found" };
@@ -438,7 +446,7 @@ export const createRulesOnboardingAction = withActionInstrumentation(
     // cold email blocker
     if (isSet(data.coldEmail)) {
       const promise = prisma.user.update({
-        where: { id: session.user.id },
+        where: { id: userId },
         data: {
           coldEmailBlocker:
             data.coldEmail === "label"
@@ -483,9 +491,11 @@ export const createRulesOnboardingAction = withActionInstrumentation(
       runOnThreads: boolean,
       categoryAction: "label" | "label_archive",
       label: string,
+      systemType: SystemType,
+      userId: string,
     ) {
       const existingRule = await prisma.rule.findUnique({
-        where: { name_userId: { name, userId: session?.user.id! } },
+        where: { userId_systemType: { userId, systemType } },
       });
 
       if (existingRule) {
@@ -520,9 +530,10 @@ export const createRulesOnboardingAction = withActionInstrumentation(
         const promise = prisma.rule
           .create({
             data: {
-              userId: session?.user.id!,
+              userId,
               name,
               instructions,
+              systemType,
               automate: true,
               runOnThreads,
               actions: {
@@ -553,10 +564,10 @@ export const createRulesOnboardingAction = withActionInstrumentation(
       }
     }
 
-    async function deleteRule(name: string) {
+    async function deleteRule(systemType: SystemType, userId: string) {
       const promise = async () => {
         const rule = await prisma.rule.findUnique({
-          where: { name_userId: { name, userId: session?.user.id! } },
+          where: { userId_systemType: { userId, systemType } },
         });
         if (!rule) return;
         await prisma.rule.delete({ where: { id: rule.id } });
@@ -573,9 +584,11 @@ export const createRulesOnboardingAction = withActionInstrumentation(
         false,
         data.newsletter,
         "Newsletter",
+        SystemType.NEWSLETTER,
+        userId,
       );
     } else {
-      deleteRule(RuleName.Newsletter);
+      deleteRule(SystemType.NEWSLETTER, userId);
     }
 
     // marketing
@@ -587,9 +600,11 @@ export const createRulesOnboardingAction = withActionInstrumentation(
         false,
         data.marketing,
         "Marketing",
+        SystemType.MARKETING,
+        userId,
       );
     } else {
-      deleteRule(RuleName.Marketing);
+      deleteRule(SystemType.MARKETING, userId);
     }
 
     // calendar
@@ -601,9 +616,11 @@ export const createRulesOnboardingAction = withActionInstrumentation(
         false,
         data.calendar,
         "Calendar",
+        SystemType.CALENDAR,
+        userId,
       );
     } else {
-      deleteRule(RuleName.Calendar);
+      deleteRule(SystemType.CALENDAR, userId);
     }
 
     // receipt
@@ -615,9 +632,11 @@ export const createRulesOnboardingAction = withActionInstrumentation(
         false,
         data.receipt,
         "Receipt",
+        SystemType.RECEIPT,
+        userId,
       );
     } else {
-      deleteRule(RuleName.Receipt);
+      deleteRule(SystemType.RECEIPT, userId);
     }
 
     // notification
@@ -629,9 +648,11 @@ export const createRulesOnboardingAction = withActionInstrumentation(
         false,
         data.notification,
         "Notification",
+        SystemType.NOTIFICATION,
+        userId,
       );
     } else {
-      deleteRule(RuleName.Notification);
+      deleteRule(SystemType.NOTIFICATION, userId);
     }
 
     await Promise.allSettled(promises);
diff --git a/apps/web/utils/actions/rule.validation.ts b/apps/web/utils/actions/rule.validation.ts
index d271466de5..75282a42a9 100644
--- a/apps/web/utils/actions/rule.validation.ts
+++ b/apps/web/utils/actions/rule.validation.ts
@@ -3,6 +3,7 @@ import {
   ActionType,
   CategoryFilterType,
   LogicalOperator,
+  SystemType,
 } from "@prisma/client";
 import { ConditionType } from "@/utils/config";
 
@@ -120,6 +121,16 @@ export const createRuleBody = z.object({
     .enum([LogicalOperator.AND, LogicalOperator.OR])
     .default(LogicalOperator.AND)
     .optional(),
+  systemType: z
+    .enum([
+      SystemType.TO_REPLY,
+      SystemType.NEWSLETTER,
+      SystemType.MARKETING,
+      SystemType.CALENDAR,
+      SystemType.RECEIPT,
+      SystemType.NOTIFICATION,
+    ])
+    .nullish(),
 });
 export type CreateRuleBody = z.infer<typeof createRuleBody>;
 
diff --git a/apps/web/utils/ai/choose-rule/match-rules.test.ts b/apps/web/utils/ai/choose-rule/match-rules.test.ts
index 248ec1c1f5..f358a5eb3b 100644
--- a/apps/web/utils/ai/choose-rule/match-rules.test.ts
+++ b/apps/web/utils/ai/choose-rule/match-rules.test.ts
@@ -1,4 +1,5 @@
 import { describe, it, expect, vi, beforeEach } from "vitest";
+import type { gmail_v1 } from "@googleapis/gmail";
 import { findMatchingRule, matchesStaticRule } from "./match-rules";
 import {
   type Category,
@@ -20,6 +21,8 @@ import { aiChooseRule } from "@/utils/ai/choose-rule/ai-choose-rule";
 // Run with:
 // pnpm test match-rules.test.ts
 
+const gmail = {} as gmail_v1.Gmail;
+
 vi.mock("server-only", () => ({}));
 vi.mock("@/utils/prisma");
 vi.mock("@/utils/ai/choose-rule/ai-choose-rule", () => ({
@@ -104,8 +107,7 @@ describe("findMatchingRule", () => {
       headers: getHeaders({ from: "test@example.com" }),
     });
     const user = getUser();
-
-    const result = await findMatchingRule(rules, message, user);
+    const result = await findMatchingRule(rules, message, user, gmail);
 
     expect(result.rule?.id).toBe(rule.id);
     expect(result.reason).toBe("Matched static conditions");
@@ -119,7 +121,7 @@ describe("findMatchingRule", () => {
     });
     const user = getUser();
 
-    const result = await findMatchingRule(rules, message, user);
+    const result = await findMatchingRule(rules, message, user, gmail);
 
     expect(result.rule?.id).toBe(rule.id);
     expect(result.reason).toBe("Matched static conditions");
@@ -133,7 +135,7 @@ describe("findMatchingRule", () => {
     });
     const user = getUser();
 
-    const result = await findMatchingRule(rules, message, user);
+    const result = await findMatchingRule(rules, message, user, gmail);
 
     expect(result.rule?.id).toBeUndefined();
     expect(result.reason).toBeUndefined();
@@ -158,7 +160,7 @@ describe("findMatchingRule", () => {
     });
     const user = getUser();
 
-    const result = await findMatchingRule(rules, message, user);
+    const result = await findMatchingRule(rules, message, user, gmail);
 
     expect(result.rule?.id).toBe(rule.id);
     expect(result.reason).toBe(`Matched group item: "FROM: test@example.com"`);
@@ -177,7 +179,7 @@ describe("findMatchingRule", () => {
     const message = getMessage();
     const user = getUser();
 
-    const result = await findMatchingRule(rules, message, user);
+    const result = await findMatchingRule(rules, message, user, gmail);
 
     expect(result.rule?.id).toBe(rule.id);
     expect(result.reason).toBe('Matched category: "category"');
@@ -196,7 +198,7 @@ describe("findMatchingRule", () => {
     const message = getMessage();
     const user = getUser();
 
-    const result = await findMatchingRule(rules, message, user);
+    const result = await findMatchingRule(rules, message, user, gmail);
 
     expect(result.rule?.id).toBeUndefined();
     expect(result.reason).toBeUndefined();
@@ -232,7 +234,7 @@ describe("findMatchingRule", () => {
     });
     const user = getUser();
 
-    const result = await findMatchingRule(rules, message, user);
+    const result = await findMatchingRule(rules, message, user, gmail);
 
     expect(result.rule?.id).toBe(rule.id);
     expect(result.reason).toBe(`Matched group item: "FROM: test@example.com"`);
@@ -262,7 +264,7 @@ describe("findMatchingRule", () => {
     });
     const user = getUser();
 
-    const result = await findMatchingRule(rules, message, user);
+    const result = await findMatchingRule(rules, message, user, gmail);
 
     expect(result.rule?.id).toBe(rule.id);
     expect(result.reason).toBeDefined();
@@ -293,7 +295,7 @@ describe("findMatchingRule", () => {
     });
     const user = getUser();
 
-    const result = await findMatchingRule(rules, message, user);
+    const result = await findMatchingRule(rules, message, user, gmail);
 
     expect(result.rule).toBeUndefined();
     expect(result.reason).toBeDefined();
@@ -315,7 +317,7 @@ describe("findMatchingRule", () => {
     const message = getMessage();
     const user = getUser();
 
-    const result = await findMatchingRule(rules, message, user);
+    const result = await findMatchingRule(rules, message, user, gmail);
 
     expect(result.rule?.id).toBe(rule.id);
     expect(result.reason).toBe('Matched category: "category"');
@@ -336,7 +338,7 @@ describe("findMatchingRule", () => {
     const message = getMessage();
     const user = getUser();
 
-    const result = await findMatchingRule(rules, message, user);
+    const result = await findMatchingRule(rules, message, user, gmail);
 
     expect(result.rule?.id).toBe(rule.id);
     expect(result.reason).toBe('Matched category: "category"');
@@ -378,7 +380,7 @@ describe("findMatchingRule", () => {
     });
     const user = getUser();
 
-    const result = await findMatchingRule(rules, message, user);
+    const result = await findMatchingRule(rules, message, user, gmail);
 
     expect(result.rule).toBeUndefined();
     expect(result.reason).toBeUndefined();
@@ -418,7 +420,7 @@ describe("findMatchingRule", () => {
     });
     const user = getUser();
 
-    const result = await findMatchingRule(rules, message, user);
+    const result = await findMatchingRule(rules, message, user, gmail);
 
     expect(result.rule?.id).toBe(rule.id);
     expect(result.reason).toContain("test@example.com");
@@ -459,7 +461,7 @@ describe("findMatchingRule", () => {
     });
     const user = getUser();
 
-    const result = await findMatchingRule(rules, message, user);
+    const result = await findMatchingRule(rules, message, user, gmail);
 
     // Should match the first rule only
     expect(result.rule?.id).toBe("rule1");
diff --git a/apps/web/utils/ai/choose-rule/match-rules.ts b/apps/web/utils/ai/choose-rule/match-rules.ts
index 9180426bb9..004ebe9f01 100644
--- a/apps/web/utils/ai/choose-rule/match-rules.ts
+++ b/apps/web/utils/ai/choose-rule/match-rules.ts
@@ -1,3 +1,4 @@
+import type { gmail_v1 } from "@googleapis/gmail";
 import { getConditionTypes, isAIRule } from "@/utils/condition";
 import {
   findMatchingGroup,
@@ -8,7 +9,12 @@ import type {
   RuleWithActions,
   RuleWithActionsAndCategories,
 } from "@/utils/types";
-import { CategoryFilterType, LogicalOperator, type User } from "@prisma/client";
+import {
+  CategoryFilterType,
+  LogicalOperator,
+  type User,
+  SystemType,
+} from "@prisma/client";
 import { ConditionType } from "@/utils/config";
 import prisma from "@/utils/prisma";
 import { aiChooseRule } from "@/utils/ai/choose-rule/ai-choose-rule";
@@ -21,9 +27,13 @@ import type {
   MatchingRuleResult,
 } from "@/utils/ai/choose-rule/types";
 import { extractEmailAddress } from "@/utils/email";
+import { hasIcsAttachment } from "@/utils/parse/calender-event";
+import { checkSenderReplyHistory } from "@/utils/reply-tracker/check-sender-reply-history";
 
 const logger = createScopedLogger("match-rules");
 
+const TO_REPLY_RECEIVED_THRESHOLD = 10;
+
 // if we find a match, return it
 // if we don't find a match, return the potential matches
 // ai rules need further processing to determine if they match
@@ -32,15 +42,37 @@ async function findPotentialMatchingRules({
   rules,
   message,
   isThread,
+  gmail,
 }: {
   rules: RuleWithActionsAndCategories[];
   message: ParsedMessage;
   isThread: boolean;
+  gmail: gmail_v1.Gmail;
 }): Promise<MatchingRuleResult> {
   const potentialMatches: (RuleWithActionsAndCategories & {
     instructions: string;
   })[] = [];
 
+  // Check for calendar preset match
+  const isCalendarEvent = hasIcsAttachment(message);
+  if (isCalendarEvent) {
+    const calendarRule = rules.find(
+      (r) => r.systemType === SystemType.CALENDAR,
+    );
+    if (calendarRule) {
+      logger.info("Found matching calendar rule", {
+        ruleId: calendarRule.id,
+        messageId: message.id,
+      });
+      return {
+        match: calendarRule,
+        matchReasons: [
+          { type: ConditionType.PRESET, systemType: SystemType.CALENDAR },
+        ],
+      };
+    }
+  }
+
   // groups singleton
   let groups: Awaited<ReturnType<typeof getGroupsWithRules>>;
   // only load once and only when needed
@@ -143,7 +175,14 @@ async function findPotentialMatchingRules({
     }
   }
 
-  return { potentialMatches };
+  // Apply TO_REPLY preset filter before returning potential matches
+  const filteredPotentialMatches = await filterToReplyPreset(
+    potentialMatches,
+    message,
+    gmail,
+  );
+
+  return { potentialMatches: filteredPotentialMatches };
 }
 
 function getMatchReason(matchReasons?: MatchReason[]): string | undefined {
@@ -158,6 +197,8 @@ function getMatchReason(matchReasons?: MatchReason[]): string | undefined {
           return `Matched group item: "${reason.groupItem.type}: ${reason.groupItem.value}"`;
         case ConditionType.CATEGORY:
           return `Matched category: "${reason.category.name}"`;
+        case ConditionType.PRESET:
+          return "Matched a system preset";
       }
     })
     .join(", ");
@@ -167,8 +208,9 @@ export async function findMatchingRule(
   rules: RuleWithActionsAndCategories[],
   message: ParsedMessage,
   user: Pick<User, "id" | "email" | "about"> & UserAIFields,
+  gmail: gmail_v1.Gmail,
 ) {
-  const result = await findMatchingRuleWithReasons(rules, message, user);
+  const result = await findMatchingRuleWithReasons(rules, message, user, gmail);
   return {
     ...result,
     reason: result.reason || getMatchReason(result.matchReasons || []),
@@ -179,6 +221,7 @@ async function findMatchingRuleWithReasons(
   rules: RuleWithActionsAndCategories[],
   message: ParsedMessage,
   user: Pick<User, "id" | "email" | "about"> & UserAIFields,
+  gmail: gmail_v1.Gmail,
 ): Promise<{
   rule?: RuleWithActionsAndCategories;
   matchReasons?: MatchReason[];
@@ -190,6 +233,7 @@ async function findMatchingRuleWithReasons(
       rules,
       message,
       isThread,
+      gmail,
     });
 
   if (match) return { rule: match, matchReasons };
@@ -272,3 +316,52 @@ async function matchesCategoryRule(
 
   return matchedFilter;
 }
+
+// Helper function to filter out TO_REPLY preset if conditions met
+async function filterToReplyPreset(
+  potentialMatches: (RuleWithActionsAndCategories & { instructions: string })[],
+  message: ParsedMessage,
+  gmail: gmail_v1.Gmail,
+): Promise<(RuleWithActionsAndCategories & { instructions: string })[]> {
+  const toReplyRuleIndex = potentialMatches.findIndex(
+    (r) => r.systemType === SystemType.TO_REPLY,
+  );
+
+  if (toReplyRuleIndex === -1) {
+    return potentialMatches; // No TO_REPLY rule found
+  }
+
+  const senderEmail = message.headers.from;
+  if (!senderEmail) {
+    return potentialMatches; // Cannot check history without sender email
+  }
+
+  try {
+    const { hasReplied, receivedCount } = await checkSenderReplyHistory(
+      gmail,
+      senderEmail,
+      TO_REPLY_RECEIVED_THRESHOLD,
+    );
+
+    // If user hasn't replied and received count meets/exceeds the threshold, filter out the rule.
+    if (!hasReplied && receivedCount >= TO_REPLY_RECEIVED_THRESHOLD) {
+      logger.info(
+        "Filtering out TO_REPLY rule due to no prior reply and high received count",
+        {
+          ruleId: potentialMatches[toReplyRuleIndex].id,
+          senderEmail,
+          receivedCount,
+        },
+      );
+      return potentialMatches.filter((_, index) => index !== toReplyRuleIndex);
+    }
+  } catch (error) {
+    // Log the error but proceed without filtering in case of failure
+    logger.error("Error checking reply history for TO_REPLY filter", {
+      senderEmail,
+      error,
+    });
+  }
+
+  return potentialMatches;
+}
diff --git a/apps/web/utils/ai/choose-rule/run-rules.ts b/apps/web/utils/ai/choose-rule/run-rules.ts
index d31183d2e7..d5035c7d03 100644
--- a/apps/web/utils/ai/choose-rule/run-rules.ts
+++ b/apps/web/utils/ai/choose-rule/run-rules.ts
@@ -45,7 +45,7 @@ export async function runRules({
   user: Pick<User, "id" | "email" | "about"> & UserAIFields;
   isTest: boolean;
 }): Promise<RunRulesResult> {
-  const result = await findMatchingRule(rules, message, user);
+  const result = await findMatchingRule(rules, message, user, gmail);
 
   analyzeSenderPatternIfAiMatch(isTest, result, message, user);
 
diff --git a/apps/web/utils/ai/choose-rule/types.ts b/apps/web/utils/ai/choose-rule/types.ts
index adbb97e001..3cbd7fb80c 100644
--- a/apps/web/utils/ai/choose-rule/types.ts
+++ b/apps/web/utils/ai/choose-rule/types.ts
@@ -1,6 +1,6 @@
-import type { RuleWithActionsAndCategories } from "@/utils/types";
-import type { Category, Group, GroupItem } from "@prisma/client";
+import type { Category, Group, GroupItem, SystemType } from "@prisma/client";
 import type { ConditionType } from "@/utils/config";
+import type { RuleWithActionsAndCategories } from "@/utils/types";
 
 export type StaticMatch = {
   type: Extract<ConditionType, "STATIC">;
@@ -21,7 +21,17 @@ export type AiMatch = {
   type: Extract<ConditionType, "AI">;
 };
 
-export type MatchReason = StaticMatch | GroupMatch | CategoryMatch | AiMatch;
+export type PresetMatch = {
+  type: Extract<ConditionType, "PRESET">;
+  systemType: SystemType;
+};
+
+export type MatchReason =
+  | StaticMatch
+  | GroupMatch
+  | CategoryMatch
+  | AiMatch
+  | PresetMatch;
 
 export type MatchingRuleResult = {
   match?: RuleWithActionsAndCategories;
diff --git a/apps/web/utils/ai/reply/check-reply-tracking.ts b/apps/web/utils/ai/reply/check-reply-tracking.ts
deleted file mode 100644
index ff9b100141..0000000000
--- a/apps/web/utils/ai/reply/check-reply-tracking.ts
+++ /dev/null
@@ -1,49 +0,0 @@
-import { z } from "zod";
-import type { Rule } from "@prisma/client";
-import { chatCompletionObject } from "@/utils/llms";
-import type { UserEmailWithAI } from "@/utils/llms/types";
-import { createScopedLogger } from "@/utils/logger";
-
-const logger = createScopedLogger("check-reply-tracking");
-
-const schema = z.object({
-  replyTrackingRuleId: z.string().nullable(),
-});
-
-export async function aiFindReplyTrackingRule({
-  rules,
-  user,
-}: {
-  rules: Pick<Rule, "id" | "instructions">[];
-  user: UserEmailWithAI;
-}) {
-  const system = `You are an AI assistant that finds a rule that is designed to track email replies.
-If no such rule is found, return null.`;
-
-  const prompt = `<rules>
-${rules
-  .map(
-    (rule) =>
-      `<rule>
-  <id>${rule.id}</id>
-  <instructions>${rule.instructions}</instructions>
-</rule>`,
-  )
-  .join("\n")}
-</rules>`;
-
-  logger.trace("Input", { system, prompt });
-
-  const aiResponse = await chatCompletionObject({
-    userAi: user,
-    system,
-    prompt,
-    schema,
-    userEmail: user.email || "",
-    usageLabel: "Check reply tracking",
-  });
-
-  logger.trace("Result", { response: aiResponse.object });
-
-  return aiResponse.object;
-}
diff --git a/apps/web/utils/condition.ts b/apps/web/utils/condition.ts
index 90ec42d84b..fed871ee14 100644
--- a/apps/web/utils/condition.ts
+++ b/apps/web/utils/condition.ts
@@ -4,7 +4,7 @@ import {
   type Category,
   type Rule,
 } from "@prisma/client";
-import { ConditionType } from "@/utils/config";
+import { ConditionType, type CoreConditionType } from "@/utils/config";
 import type {
   CreateRuleBody,
   ZodCondition,
@@ -91,7 +91,7 @@ export function getConditionTypes(
 }
 
 export function getEmptyCondition(
-  type: Exclude<ConditionType, "GROUP">,
+  type: CoreConditionType,
   category?: string,
 ): ZodCondition {
   switch (type) {
@@ -179,6 +179,8 @@ function conditionTypeToString(conditionType: ConditionType): string {
       return "Group";
     case ConditionType.CATEGORY:
       return "Category";
+    case ConditionType.PRESET:
+      return "Preset";
     default:
       // biome-ignore lint/correctness/noSwitchDeclarations: intentional exhaustive check
       const exhaustiveCheck: never = conditionType;
diff --git a/apps/web/utils/config.ts b/apps/web/utils/config.ts
index 928a81cdb2..311f1dd8f5 100644
--- a/apps/web/utils/config.ts
+++ b/apps/web/utils/config.ts
@@ -7,6 +7,8 @@ export const ConditionType = {
   STATIC: "STATIC",
   GROUP: "GROUP",
   CATEGORY: "CATEGORY",
+  PRESET: "PRESET",
 } as const;
 
 export type ConditionType = (typeof ConditionType)[keyof typeof ConditionType];
+export type CoreConditionType = Exclude<ConditionType, "GROUP" | "PRESET">;
diff --git a/apps/web/utils/parse/calender-event.ts b/apps/web/utils/parse/calender-event.ts
index 9ecbbc9c33..1c3b3214ef 100644
--- a/apps/web/utils/parse/calender-event.ts
+++ b/apps/web/utils/parse/calender-event.ts
@@ -48,14 +48,8 @@ export function analyzeCalendarEvent(email: ParsedMessage): CalendarEventInfo {
   // Check body for calendar event indicators
   const body = email.textHtml || "";
 
-  // Check for iCalendar data
-  const hasiCalData =
-    body.includes("BEGIN:VCALENDAR") ||
-    body.includes("BEGIN:VEVENT") ||
-    body.includes("method=REQUEST");
-
   // Determine if it's a calendar event based on checks
-  result.isCalendarEvent = hasCalendarSubject || hasiCalData;
+  result.isCalendarEvent = hasCalendarSubject || hasIcsAttachment(email);
 
   if (result.isCalendarEvent) {
     // Extract event title
@@ -239,6 +233,22 @@ export function analyzeCalendarEvent(email: ParsedMessage): CalendarEventInfo {
   return result;
 }
 
+/**
+ * Checks if an email has a .ics file attachment.
+ * @param email The email to check.
+ * @returns True if a .ics attachment is found, false otherwise.
+ */
+export function hasIcsAttachment(email: ParsedMessage): boolean {
+  if (!email.attachments || email.attachments.length === 0) {
+    return false;
+  }
+
+  return email.attachments.some(
+    (attachment) =>
+      attachment.filename?.toLowerCase().endsWith(".ics"),
+  );
+}
+
 export function isCalendarEventInPast(email: ParsedMessage) {
   const calendarEvent = analyzeCalendarEvent(email);
 
diff --git a/apps/web/utils/reply-tracker/check-sender-reply-history.ts b/apps/web/utils/reply-tracker/check-sender-reply-history.ts
new file mode 100644
index 0000000000..d5bbce83ec
--- /dev/null
+++ b/apps/web/utils/reply-tracker/check-sender-reply-history.ts
@@ -0,0 +1,113 @@
+import type { gmail_v1 } from "@googleapis/gmail";
+import { extractEmailAddress } from "@/utils/email";
+import { createScopedLogger } from "@/utils/logger";
+import { getMessages } from "@/utils/gmail/message";
+
+const logger = createScopedLogger("reply-tracker/query");
+
+/**
+ * Checks if a user has ever sent a reply to a specific sender and counts received emails
+ * using the Gmail API.
+ * @param gmail The authenticated Gmail API client instance.
+ * @param senderEmail The email address of the sender.
+ * @param receivedThreshold The number of received emails to check against.
+ * @returns An object containing `hasReplied` (boolean) and `receivedCount` (number, capped at receivedThreshold).
+ */
+export async function checkSenderReplyHistory(
+  gmail: gmail_v1.Gmail,
+  senderEmail: string,
+  receivedThreshold: number,
+): Promise<{ hasReplied: boolean; receivedCount: number }> {
+  const cleanSenderEmail = extractEmailAddress(senderEmail);
+  if (!cleanSenderEmail) {
+    logger.warn("Could not extract email from sender", { senderEmail });
+    // Default to assuming a reply might be needed if email is invalid
+    return { hasReplied: true, receivedCount: 0 };
+  }
+
+  try {
+    // Run checks in parallel for efficiency
+    const [hasReplied, receivedCount] = await Promise.all([
+      checkIfReplySent(gmail, cleanSenderEmail),
+      countReceivedMessages(gmail, cleanSenderEmail, receivedThreshold),
+    ]).catch((error) => {
+      logger.error("Timeout or error in parallel operations", {
+        error,
+        cleanSenderEmail,
+      });
+      return [true, 0] as const; // Safe defaults
+    });
+
+    logger.info("Sender reply history check final result", {
+      senderEmail,
+      cleanSenderEmail,
+      hasReplied,
+      receivedCount,
+    });
+
+    return { hasReplied, receivedCount };
+  } catch (error) {
+    // Catch potential errors from Promise.all or other unexpected issues
+    logger.error("Overall error checking sender reply history", {
+      error,
+      senderEmail,
+      cleanSenderEmail,
+    });
+    // Default to assuming a reply might be needed on error
+    return { hasReplied: true, receivedCount: 0 };
+  }
+}
+
+// Helper to check if a reply was sent to the sender
+async function checkIfReplySent(
+  gmail: gmail_v1.Gmail,
+  cleanSenderEmail: string,
+): Promise<boolean> {
+  try {
+    const query = `from:me to:${cleanSenderEmail} label:sent`;
+    const response = await getMessages(gmail, { query, maxResults: 1 });
+    const sent = (response.messages?.length ?? 0) > 0;
+    logger.info("Checked for sent reply", { cleanSenderEmail, sent });
+    return sent;
+  } catch (error) {
+    logger.error("Error checking if reply was sent", {
+      error,
+      cleanSenderEmail,
+    });
+    return true; // Default to true on error (safer for TO_REPLY filtering)
+  }
+}
+
+// Helper to count messages received from the sender up to a threshold
+async function countReceivedMessages(
+  gmail: gmail_v1.Gmail,
+  cleanSenderEmail: string,
+  threshold: number,
+): Promise<number> {
+  try {
+    const query = `from:${cleanSenderEmail}`;
+    logger.info(`Checking received message count (up to ${threshold})`, {
+      cleanSenderEmail,
+      threshold,
+    });
+
+    // Fetch up to the threshold number of message IDs.
+    const response = await getMessages(gmail, {
+      query,
+      maxResults: threshold,
+    });
+    const count = response.messages?.length ?? 0;
+
+    logger.info("Received message count check result", {
+      cleanSenderEmail,
+      count,
+    });
+    return count;
+  } catch (error) {
+    logger.error("Error counting received messages", {
+      error,
+      cleanSenderEmail,
+    });
+    return 0; // Default to 0 on error
+  }
+}
diff --git a/apps/web/utils/reply-tracker/enable.ts b/apps/web/utils/reply-tracker/enable.ts
index 804311fab3..8ac97e1f34 100644
--- a/apps/web/utils/reply-tracker/enable.ts
+++ b/apps/web/utils/reply-tracker/enable.ts
@@ -1,7 +1,6 @@
 import prisma from "@/utils/prisma";
-import { aiFindReplyTrackingRule } from "@/utils/ai/reply/check-reply-tracking";
 import { safeCreateRule } from "@/utils/rule/rule";
-import { ActionType, type Prisma } from "@prisma/client";
+import { ActionType, SystemType, type Prisma } from "@prisma/client";
 import {
   defaultReplyTrackerInstructions,
   NEEDS_REPLY_LABEL_NAME,
@@ -31,9 +30,12 @@ export async function enableReplyTracker(userId: string) {
       about: true,
       rulesPrompt: true,
       rules: {
+        where: {
+          systemType: SystemType.TO_REPLY,
+        },
         select: {
           id: true,
-          instructions: true,
+          systemType: true,
           actions: {
             select: {
               id: true,
@@ -48,14 +50,7 @@ export async function enableReplyTracker(userId: string) {
 
   if (!user) return { error: "User not found" };
 
-  const result = user.rules.length
-    ? await aiFindReplyTrackingRule({
-        rules: user.rules,
-        user,
-      })
-    : null;
-
-  const rule = user.rules.find((r) => r.id === result?.replyTrackingRuleId);
+  const rule = user.rules.find((r) => r.systemType === SystemType.TO_REPLY);
 
   let ruleId: string | null = rule?.id || null;
 
@@ -103,6 +98,8 @@ export async function enableReplyTracker(userId: string) {
         ],
       },
       userId,
+      null,
+      SystemType.TO_REPLY,
     );
 
     if ("error" in newRule) {
diff --git a/apps/web/utils/rule/rule.ts b/apps/web/utils/rule/rule.ts
index ba6b64a552..4c97f54c94 100644
--- a/apps/web/utils/rule/rule.ts
+++ b/apps/web/utils/rule/rule.ts
@@ -1,7 +1,12 @@
 import type { CreateOrUpdateRuleSchemaWithCategories } from "@/utils/ai/rule/create-rule-schema";
 import prisma, { isDuplicateError } from "@/utils/prisma";
 import { createScopedLogger } from "@/utils/logger";
-import { ActionType, type Prisma, type Rule } from "@prisma/client";
+import {
+  ActionType,
+  type SystemType,
+  type Prisma,
+  type Rule,
+} from "@prisma/client";
 import { getUserCategoriesForNames } from "@/utils/category.server";
 import { getActionRiskLevel, type RiskAction } from "@/utils/risk";
 import { hasExampleParams } from "@/app/(app)/automation/examples";
@@ -26,6 +31,7 @@ export async function safeCreateRule(
   result: CreateOrUpdateRuleSchemaWithCategories,
   userId: string,
   categoryNames?: string[] | null,
+  systemType?: SystemType | null,
 ) {
   const categoryIds = await getUserCategoriesForNames(
     userId,
@@ -37,6 +43,7 @@ export async function safeCreateRule(
       result,
       userId,
       categoryIds,
+      systemType,
     });
     return rule;
   } catch (error) {
@@ -98,10 +105,12 @@ export async function createRule({
   result,
   userId,
   categoryIds,
+  systemType,
 }: {
   result: CreateOrUpdateRuleSchemaWithCategories;
   userId: string;
   categoryIds?: string[] | null;
+  systemType?: SystemType | null;
 }) {
   const mappedActions = mapActionFields(result.actions);
 
@@ -109,6 +118,7 @@ export async function createRule({
     data: {
       name: result.name,
       userId,
+      systemType,
       actions: { createMany: { data: mappedActions } },
       automate: shouldAutomate(
         result,