diff --git a/dojo_plugin/pages/discord.py b/dojo_plugin/pages/discord.py
index a98fccbc7..77b8389f2 100644
--- a/dojo_plugin/pages/discord.py
+++ b/dojo_plugin/pages/discord.py
@@ -69,4 +69,12 @@ def discord_redirect():
         db.session.rollback()
         return {"success": False, "error": "Discord user already in use"}, 400
 
+    # DM the user the flag for white belt
+    discord_dojo = Dojos.from_id("discord-dojo").first()
+    if discord_dojo:
+        discord_challenge == discord_dojo.modules[0].challenges[0]
+        flag = serialize_user_flag(user_id, discord_challenge.challenge_id)
+        send_dm("""You have linked your pwn.college account with this discord account! You may now submit the flag: {flag}.""", discord_id)
+        send_dm("""**NOTE:** This is the ONLY communication from pwn.college that you will receive over discord DMs. Assume any other communication is a phishing attempt!""", discord_id)
+
     return redirect("/settings#discord")
diff --git a/dojo_plugin/utils/discord.py b/dojo_plugin/utils/discord.py
index b2d314258..63a3b93fc 100644
--- a/dojo_plugin/utils/discord.py
+++ b/dojo_plugin/utils/discord.py
@@ -24,6 +24,9 @@ def discord_request(endpoint, method="GET", **json):
 def guild_request(endpoint, method="GET", **json):
     return discord_request(f"/guilds/{DISCORD_GUILD_ID}{endpoint}", method=method, **json)
 
+def bot_request(endpoint, method="GET", **json):
+    return discord_request(f"/users/@me{endpoint}", method=method, **json)
+
 
 def get_bot_join_server_url():
     # "Server Members Intent" also required
@@ -94,6 +97,11 @@ def send_message(message, channel_name):
     discord_request(f"/channels/{channel_id}/messages", method="POST", content=message)
 
 
+def send_dm(message, recipient_id):
+    channel_id = bot_request("/channels", method="POST", recipient_id=recipient_id)["id"]
+    discord_request(f"/channels/{channel_id}/messages", method="POST", content=message)
+
+
 def add_role(discord_id, role_name):
     role_id = get_discord_roles()[role_name]
     guild_request(f"/members/{discord_id}/roles/{role_id}", method="PUT")