diff --git a/prisma/schema.prisma b/prisma/schema.prisma
index 559da2f..17cef68 100644
--- a/prisma/schema.prisma
+++ b/prisma/schema.prisma
@@ -11,6 +11,7 @@ enum OptionKey {
   TAG_PREFIX
   MAX_TAGS_PER_MESSAGE
   DAYS_TO_KEEP_TAGS
+  DAYS_TO_KEEP_USER_BOT_MESSAGES
 }
 
 // Options for the bot, stored in the database.
diff --git a/src/common/events/index.ts b/src/common/events/index.ts
index d3f25bd..390008c 100644
--- a/src/common/events/index.ts
+++ b/src/common/events/index.ts
@@ -5,6 +5,7 @@ import { readyEvent } from '@/features/ready/index.js';
 import type { DiscordEvent } from './types.js';
 import archiveChannels from '@/features/archive-channels/index.js';
 import { tagReceivedEvent } from '@/features/tags/tag-received.js';
+import { reactionAddEvent } from '@/features/reactions/index.js';
 
 export const events: DiscordEvent[] = [
   readyEvent,
@@ -13,4 +14,5 @@ export const events: DiscordEvent[] = [
   interactionCreateEvent,
   archiveChannels,
   tagReceivedEvent,
+  reactionAddEvent,
 ].flat();
diff --git a/src/features/reactions/index.ts b/src/features/reactions/index.ts
new file mode 100644
index 0000000..1742c9e
--- /dev/null
+++ b/src/features/reactions/index.ts
@@ -0,0 +1,38 @@
+import { createEvent } from '@/common/events/create-event.js';
+import {
+  Events,
+  MessageReaction,
+  PartialMessageReaction,
+  PartialUser,
+  User,
+} from 'discord.js';
+import { removeUserBotMessage } from './remove-user-bot-message.js';
+
+export type ReactionAddEvent = {
+  reaction: MessageReaction | PartialMessageReaction;
+  user: User | PartialUser;
+};
+
+const handlers = [removeUserBotMessage];
+
+export const reactionAddEvent = createEvent(
+  {
+    name: Events.MessageReactionAdd,
+  },
+  async (reaction, user, details) => {
+    if (user.bot) {
+      return;
+    }
+    try {
+      if (reaction.partial) {
+        await reaction.fetch();
+      }
+    } catch {
+      return;
+    }
+
+    for (const handler of handlers) {
+      await handler(reaction, user, details);
+    }
+  }
+);
diff --git a/src/features/reactions/remove-user-bot-message.ts b/src/features/reactions/remove-user-bot-message.ts
new file mode 100644
index 0000000..ccab885
--- /dev/null
+++ b/src/features/reactions/remove-user-bot-message.ts
@@ -0,0 +1,45 @@
+import type { ClientEvents, Events, GuildMember } from 'discord.js';
+import { UserBotMessagesService } from '@/services/user-bot-messages/user-bot-messages-service.js';
+
+const DELETE_EMOJIS = ['🗑️', '❌'];
+
+export const removeUserBotMessage: (
+  ...args: ClientEvents[Events.MessageReactionAdd]
+) => Promise<void> | void = async (reaction, user) => {
+  if (
+    reaction.emoji.name === null ||
+    !DELETE_EMOJIS.includes(reaction.emoji.name)
+  ) {
+    return;
+  }
+
+  if (reaction.message.author?.id !== user.client.user.id) {
+    return;
+  }
+
+  const guild = reaction.message.guild;
+  if (guild === null) {
+    return;
+  }
+
+  let member: GuildMember;
+  try {
+    member =
+      guild.members.cache.get(user.id) ?? (await guild.members.fetch(user.id));
+  } catch {
+    return;
+  }
+
+  try {
+    const deleted = await UserBotMessagesService.deleteUserBotMessage({
+      messageId: reaction.message.id,
+      user: member,
+    });
+
+    if (deleted) {
+      await reaction.message.delete();
+    }
+  } catch {
+    return;
+  }
+};
diff --git a/src/features/ready/index.ts b/src/features/ready/index.ts
index 95c365c..93ac662 100644
--- a/src/features/ready/index.ts
+++ b/src/features/ready/index.ts
@@ -6,6 +6,7 @@ import { fetchAndCachePublicChannelsMessages } from '@/util/cache.js';
 import { syncGuidesToChannel } from '@/util/post-guides.js';
 import { leaveIfNotAllowedServer } from '@/util/server-guard.js';
 import { syncArchiveCategoryChannels } from '../archive-channels/util.js';
+import { UserBotMessagesService } from '@/services/user-bot-messages/user-bot-messages-service.js';
 
 export const readyEvent = createEvent(
   {
@@ -71,5 +72,7 @@ export const readyEvent = createEvent(
         error
       );
     }
+
+    void UserBotMessagesService.startExpiredMessageCleanup();
   }
 );
diff --git a/src/options.ts b/src/options.ts
index e3adc1e..001f629 100644
--- a/src/options.ts
+++ b/src/options.ts
@@ -23,6 +23,11 @@ const OptionsDefaults = {
     type: 'number',
     displayName: 'Days to Keep Tags',
   },
+  [OptionKey.DAYS_TO_KEEP_USER_BOT_MESSAGES]: {
+    value: '7',
+    type: 'number',
+    displayName: 'Days to Keep User Bot Messages',
+  },
 } as const satisfies Record<OptionKey, OptionValue>;
 
 export type OptionTypeOf<K extends OptionKey> =
diff --git a/src/services/user-bot-messages/user-bot-messages-service.ts b/src/services/user-bot-messages/user-bot-messages-service.ts
index dcca54a..3a6bb60 100644
--- a/src/services/user-bot-messages/user-bot-messages-service.ts
+++ b/src/services/user-bot-messages/user-bot-messages-service.ts
@@ -2,8 +2,8 @@ import type { GuildMember } from 'discord.js';
 import { prisma } from '@/db/prisma.js';
 import { isStaff } from '@/util/permissions.js';
 import { DAY } from '@/constants/time.js';
-
-const CLEANUP_INTERVAL_MS = 60 * 60 * 1000; // every hour
+import { getBotOption } from '@/options.js';
+import { OptionKey } from '@/generated/prisma/enums.js';
 
 export const UserBotMessagesService = {
   async deleteUserBotMessage({
@@ -65,6 +65,9 @@ export const UserBotMessagesService = {
     };
 
     void cleanup();
-    setInterval(cleanup, CLEANUP_INTERVAL_MS);
+    const daysToKeep = getBotOption(
+      OptionKey.DAYS_TO_KEEP_USER_BOT_MESSAGES
+    ).value;
+    setInterval(cleanup, daysToKeep * DAY);
   },
 };