diff --git a/db/migrations/20250810031908_init/migration.sql b/db/migrations/20250810031908_init/migration.sql
index e1c14bd..f01eaeb 100644
--- a/db/migrations/20250810031908_init/migration.sql
+++ b/db/migrations/20250810031908_init/migration.sql
@@ -13,6 +13,7 @@ CREATE TABLE "public"."CheckinStreak" (
     "first_date" TIMESTAMP(3) NOT NULL DEFAULT CURRENT_TIMESTAMP,
     "last_date" TIMESTAMP(3),
     "streak" INTEGER NOT NULL DEFAULT 0,
+    "streak_broken_at" TIMESTAMP(3) DEFAULT NULL,
     "updated_at" TIMESTAMP(3),
 
     CONSTRAINT "CheckinStreak_pkey" PRIMARY KEY ("id")
diff --git a/db/schema.prisma b/db/schema.prisma
index d51a486..b63aff1 100644
--- a/db/schema.prisma
+++ b/db/schema.prisma
@@ -23,6 +23,7 @@ model CheckinStreak {
   first_date DateTime @default(now())
   last_date DateTime?
   streak Int @default(0)
+  streak_broken_at DateTime?
   updated_at DateTime?
 
   user User @relation(fields: [user_id], references: [id])
diff --git a/docker-compose.yml b/docker-compose.yml
index a433552..09711c4 100644
--- a/docker-compose.yml
+++ b/docker-compose.yml
@@ -14,7 +14,7 @@ services:
         condition: service_healthy
     volumes:
       - ./src:/usr/src/app/src
-      - ./db:/usr/src/app/db
+      - ./db/schema.prisma:/usr/src/app/db/schema.prisma
       - ./prisma.config.ts:/usr/src/app/prisma.config.ts
       - ./package.json:/usr/src/app/package.json
       - ./tsconfig.json:/usr/src/app/tsconfig.json
diff --git a/src/bot/events/client-ready/jobs/handlers/reset-grinder-roles.ts b/src/bot/events/client-ready/jobs/handlers/reset-grinder-roles.ts
index 5d7e831..e8a6940 100644
--- a/src/bot/events/client-ready/jobs/handlers/reset-grinder-roles.ts
+++ b/src/bot/events/client-ready/jobs/handlers/reset-grinder-roles.ts
@@ -27,9 +27,9 @@ export default {
                 const guild = await client.guilds.fetch(process.env.GUILD_ID!)
                 const channel = await getChannel(guild, GRIND_ASHES_CHANNEL)
                 ResetGrinderRoles.assertChannel(channel)
-                const users = await ResetGrinderRoles.getUsersWithLatestCheckin(client.prisma)
+                const users = await ResetGrinderRoles.getUsersWithLatestStreak(client.prisma)
 
-                await ResetGrinderRoles.validateUsers(guild, channel, users)
+                await ResetGrinderRoles.validateUsers(client.prisma, guild, channel, users)
 
                 log.success(ResetGrinderRoles.MSG.JobSuccess)
             })
diff --git a/src/bot/events/client-ready/jobs/validators/reset-grinder-roles.ts b/src/bot/events/client-ready/jobs/validators/reset-grinder-roles.ts
index b462bf2..287406c 100644
--- a/src/bot/events/client-ready/jobs/validators/reset-grinder-roles.ts
+++ b/src/bot/events/client-ready/jobs/validators/reset-grinder-roles.ts
@@ -1,4 +1,6 @@
 import type { PrismaClient } from '@generatedDB/client'
+import type { CheckinStreak } from '@type/checkin-streak'
+import type { User } from '@type/user'
 import type { Guild, GuildMember, TextChannel } from 'discord.js'
 import { getGrindRoles, GRINDER_ROLE } from '@config/discord'
 import { isDateToday, isDateYesterday } from '@utils/date'
@@ -6,14 +8,6 @@ import { sendAsBot } from '@utils/discord'
 import { log } from '@utils/logger'
 import { ResetGrinderRolesMessage } from '../messages/reset-grinder-roles'
 
-interface UserWithLatestCheckin {
-    discord_id: string
-    checkins: {
-        status: string
-        created_at: Date
-    }[]
-}
-
 export class ResetGrinderRoles extends ResetGrinderRolesMessage {
     static hasValidCheckin(checkin?: { created_at: Date, status: string }): boolean {
         if (!checkin)
@@ -39,14 +33,19 @@ export class ResetGrinderRoles extends ResetGrinderRolesMessage {
         }
     }
 
-    static async validateUsers(guild: Guild, channel: TextChannel, users: UserWithLatestCheckin[]) {
+    static async validateUsers(prisma: PrismaClient, guild: Guild, channel: TextChannel, users: User[]) {
         for (const user of users) {
             const lastCheckin = user.checkins?.[0]
             if (this.hasValidCheckin(lastCheckin))
                 continue
 
+            const checkinStreak = user.checkin_streaks?.[0]
+            if (!checkinStreak)
+                continue
+
             const member = await guild.members.fetch(user.discord_id)
             await this.removeGrinderRoles(member)
+            await this.breakCheckinStreakAt(prisma, checkinStreak)
 
             await sendAsBot(
                 null,
@@ -58,7 +57,7 @@ export class ResetGrinderRoles extends ResetGrinderRolesMessage {
         }
     }
 
-    static async getUsersWithLatestCheckin(prisma: PrismaClient): Promise<UserWithLatestCheckin[]> {
+    static async getUsersWithLatestStreak(prisma: PrismaClient): Promise<User[]> {
         const users = await prisma.user.findMany({
             select: {
                 discord_id: true,
@@ -70,9 +69,32 @@ export class ResetGrinderRoles extends ResetGrinderRolesMessage {
                     orderBy: { created_at: 'desc' },
                     take: 1,
                 },
+                checkin_streaks: {
+                    orderBy: { first_date: 'desc' },
+                    take: 1,
+                    where: {
+                        streak_broken_at: null,
+                    },
+                    include: {
+                        checkins: {
+                            orderBy: { created_at: 'desc' },
+                            take: 1,
+                        },
+                    },
+                },
             },
-        }) as UserWithLatestCheckin[]
+        }) as User[]
 
         return users
     }
+
+    static async breakCheckinStreakAt(prisma: PrismaClient, checkinStreak: CheckinStreak) {
+        await prisma.checkinStreak.update({
+            where: { id: checkinStreak.id },
+            data: {
+                streak_broken_at: new Date(),
+                updated_at: new Date(),
+            },
+        })
+    }
 }
diff --git a/src/types/checkin-streak.d.ts b/src/types/checkin-streak.d.ts
index 301006b..bb06cd4 100644
--- a/src/types/checkin-streak.d.ts
+++ b/src/types/checkin-streak.d.ts
@@ -7,6 +7,7 @@ export interface CheckinStreak {
     first_date: Date
     last_date?: Date | null
     streak: number
+    streak_broken_at?: Date | null
     updated_at?: Date | null
 
     user?: User