diff --git a/src/discord/commands/global/d.setup.ts b/src/discord/commands/global/d.setup.ts
index eb9d0444..ef70716e 100644
--- a/src/discord/commands/global/d.setup.ts
+++ b/src/discord/commands/global/d.setup.ts
@@ -652,8 +652,22 @@ export async function helperButton(
   }
 
   // Do everything else
+
   const role = await interaction.guild?.roles.fetch(guildData.role_helper);
 
+  const user = await db.users.findUnique({
+    where: {
+      discord_id: target.user.id,
+    },
+  });
+
+  const userHasBeenAHelper = user?.last_was_helper !== null;
+
+  if (!user) {
+    log.error(F, `No user found for discord_id: ${target.user.id}`);
+    return;
+  }
+
   if (!role) {
     await interaction.reply({
       content: stripIndents`It looks like the guilds helper role was deleted, talk to the server admin about this! They may need to re-run \`/setup tripsit\``,
@@ -662,17 +676,32 @@ export async function helperButton(
     return;
   }
 
+  // If the role being requested is the Helper or Contributor role, check if they have been banned first
+  if (role.id === guildData.role_helper && userData.helper_role_ban) {
+    await interaction.editReply({ content: 'Unable to add this role. If you feel this is an error, please talk to the team!' });
+    return;
+  }
+
   if (target.roles.cache.has(role.id)) {
+    await target.roles.remove(role);
     await interaction.reply({
-      content: stripIndents`You already have the helper role!`,
+      content: stripIndents`Your helper role has been removed. If you ever want to re-apply it, just click the button again!`,
       ephemeral: true,
     });
     return;
   }
 
-  // If the role being requested is the Helper or Contributor role, check if they have been banned first
-  if (role.id === guildData.role_helper && userData.helper_role_ban) {
-    await interaction.editReply({ content: 'Unable to add this role. If you feel this is an error, please talk to the team!' });
+  if (userHasBeenAHelper && !target.roles.cache.has(role.id)) {
+    await target.roles.add(role);
+    if (interaction.guild.id === env.DISCORD_GUILD_ID) {
+      const channelTripsitters = await interaction.guild?.channels.fetch(env.CHANNEL_TRIPSITTERS) as TextChannel;
+      await channelTripsitters.send(stripIndents`${target.displayName} has re-joined as a ${role.name}.`);
+    }
+    const metaChannel = await interaction.guild?.channels.fetch(guildData.channel_tripsitmeta) as TextChannel;
+    await interaction.reply({
+      content: stripIndents`Welcome back, go check out ${metaChannel}!`,
+      ephemeral: true,
+    });
     return;
   }
 
@@ -746,8 +775,22 @@ export async function helperButton(
       // log.debug(F, `introMessage: ${introMessage}`);
 
       await target.roles.add(role);
+
+      // Update the last date when they were given the helper role
+      await db.users.upsert({
+        where: {
+          discord_id: interaction.user.id,
+        },
+        create: {
+          discord_id: interaction.user.id,
+        },
+        update: {
+          last_was_helper: new Date(),
+        },
+      });
+
       const metaChannel = await i.guild?.channels.fetch(guildData.channel_tripsitmeta) as TextChannel;
-      await i.editReply({ content: `Added role ${role.name}, go check out ${metaChannel}!` });
+      await i.editReply({ content: `Added role ${role.name}, go check out ${metaChannel}! If you ever want to remove it, just click the button again.` });
 
       if (metaChannel.id === guildData.channel_tripsitmeta) {
         const introString = `
@@ -801,7 +844,6 @@ export async function helperButton(
           **If you have any questions, please reach out!**
         `);
       }
-
       if (i.guild.id === env.DISCORD_GUILD_ID) {
         const channelTripsitters = await i.guild?.channels.fetch(env.CHANNEL_TRIPSITTERS) as TextChannel;
         const roleTripsitter = await i.guild?.roles.fetch(guildData.role_tripsitter) as Role;
diff --git a/src/prisma/tripbot/migrations/20240929004151_add_last_was_helper/migration.sql b/src/prisma/tripbot/migrations/20240929004151_add_last_was_helper/migration.sql
new file mode 100644
index 00000000..cb0d1a5d
--- /dev/null
+++ b/src/prisma/tripbot/migrations/20240929004151_add_last_was_helper/migration.sql
@@ -0,0 +1,2 @@
+-- AlterTable
+ALTER TABLE "users" ADD COLUMN     "last_was_helper" TIMESTAMP(3);
diff --git a/src/prisma/tripbot/schema.prisma b/src/prisma/tripbot/schema.prisma
index a815453d..02764e69 100644
--- a/src/prisma/tripbot/schema.prisma
+++ b/src/prisma/tripbot/schema.prisma
@@ -174,6 +174,7 @@ model users {
   wordle_scores                                             wordle_scores[]
   connections_scores                                        connections_scores[]
   mini_scores                                               mini_scores[]
+  last_was_helper                                           DateTime?
 }
 
 model wordle_scores {