diff --git a/CTFd/api/v1/tokens.py b/CTFd/api/v1/tokens.py
index 2c2011a4..975b8708 100644
--- a/CTFd/api/v1/tokens.py
+++ b/CTFd/api/v1/tokens.py
@@ -85,11 +85,14 @@ class TokenList(Resource):
     def post(self):
         req = request.get_json()
         expiration = req.get("expiration")
+        description = req.get("description")
         if expiration:
             expiration = datetime.datetime.strptime(expiration, "%Y-%m-%d")
 
         user = get_current_user()
-        token = generate_user_token(user, expiration=expiration)
+        token = generate_user_token(
+            user, expiration=expiration, description=description
+        )
 
         # Explicitly use admin view so that user's can see the value of their token
         schema = TokenSchema(view="admin")
diff --git a/CTFd/forms/self.py b/CTFd/forms/self.py
index c527138b..d325bc5d 100644
--- a/CTFd/forms/self.py
+++ b/CTFd/forms/self.py
@@ -1,6 +1,6 @@
 from flask import session
 from flask_babel import lazy_gettext as _l
-from wtforms import PasswordField, SelectField, StringField
+from wtforms import PasswordField, SelectField, StringField, TextAreaField
 from wtforms.fields.html5 import DateField, URLField
 
 from CTFd.constants.languages import SELECT_LANGUAGE_LIST
@@ -50,4 +50,5 @@ def SettingsForm(*args, **kwargs):
 
 class TokensForm(BaseForm):
     expiration = DateField(_l("Expiration"))
+    description = TextAreaField("Usage Description")
     submit = SubmitField(_l("Generate"))
diff --git a/CTFd/models/__init__.py b/CTFd/models/__init__.py
index 45f9d21b..a09bbc66 100644
--- a/CTFd/models/__init__.py
+++ b/CTFd/models/__init__.py
@@ -916,6 +916,7 @@ class Tokens(db.Model):
         db.DateTime,
         default=lambda: datetime.datetime.utcnow() + datetime.timedelta(days=30),
     )
+    description = db.Column(db.Text)
     value = db.Column(db.String(128), unique=True)
 
     user = db.relationship("Users", foreign_keys="Tokens.user_id", lazy="select")
diff --git a/CTFd/schemas/tokens.py b/CTFd/schemas/tokens.py
index d6ae4d36..094a01db 100644
--- a/CTFd/schemas/tokens.py
+++ b/CTFd/schemas/tokens.py
@@ -9,8 +9,16 @@ class TokenSchema(ma.ModelSchema):
         dump_only = ("id", "expiration", "type")
 
     views = {
-        "admin": ["id", "type", "user_id", "created", "expiration", "value"],
-        "user": ["id", "type", "created", "expiration"],
+        "admin": [
+            "id",
+            "type",
+            "user_id",
+            "created",
+            "expiration",
+            "description",
+            "value",
+        ],
+        "user": ["id", "type", "created", "expiration", "description"],
     }
 
     def __init__(self, view=None, *args, **kwargs):
diff --git a/CTFd/themes/core/templates/settings.html b/CTFd/themes/core/templates/settings.html
index 74b29cc4..1095786e 100644
--- a/CTFd/themes/core/templates/settings.html
+++ b/CTFd/themes/core/templates/settings.html
@@ -81,7 +81,10 @@
 							<b>{{ form.expiration.label }}</b>
 							{{ form.expiration(class="form-control") }}
 						</div>
-
+						<div class="form-group">
+							<b>{{ form.description.label }}</b>
+							{{ form.description(class="form-control", rows="3") }}
+						</div>
 						<div class="form-group text-right">
 							{{ form.submit(class="btn btn-md btn-primary btn-outlined") }}
 						</div>
@@ -96,6 +99,7 @@
 							<tr>
 								<td class="text-center"><b>Created</b></td>
 								<td class="text-center"><b>Expiration</b></td>
+								<td class="text-center"><b>Description</b></td>
 								<td class="text-center"><b>Delete</b></td>
 							</tr>
 						</thead>
@@ -104,6 +108,7 @@
 							<tr>
 								<td><span data-time="{{ token.created | isoformat }}"></span></td>
 								<td><span data-time="{{ token.expiration | isoformat }}"></span></td>
+								<td><span>{{ token.description | default('', true) }}</span></td>
 								<td class="text-center">
 									<span class="delete-token" role="button" data-token-id="{{ token.id }}">
 										<i class="btn-fa fas fa-times"></i>
diff --git a/CTFd/utils/security/auth.py b/CTFd/utils/security/auth.py
index d098c4a3..6d62b5da 100644
--- a/CTFd/utils/security/auth.py
+++ b/CTFd/utils/security/auth.py
@@ -34,13 +34,15 @@ def logout_user():
     session.clear()
 
 
-def generate_user_token(user, expiration=None):
+def generate_user_token(user, expiration=None, description=None):
     temp_token = True
     while temp_token is not None:
-        value = hexencode(os.urandom(32))
+        value = "ctfd_" + hexencode(os.urandom(32))
         temp_token = UserTokens.query.filter_by(value=value).first()
 
-    token = UserTokens(user_id=user.id, expiration=expiration, value=value)
+    token = UserTokens(
+        user_id=user.id, expiration=expiration, description=description, value=value
+    )
     db.session.add(token)
     db.session.commit()
     return token
diff --git a/migrations/versions/9e6f6578ca84_add_description_column_to_tokens_table.py b/migrations/versions/9e6f6578ca84_add_description_column_to_tokens_table.py
new file mode 100644
index 00000000..da2dbedf
--- /dev/null
+++ b/migrations/versions/9e6f6578ca84_add_description_column_to_tokens_table.py
@@ -0,0 +1,23 @@
+"""Add description column to tokens table
+
+Revision ID: 9e6f6578ca84
+Revises: 0def790057c1
+Create Date: 2023-06-21 23:22:34.179636
+
+"""
+import sqlalchemy as sa
+from alembic import op
+
+# revision identifiers, used by Alembic.
+revision = "9e6f6578ca84"
+down_revision = "0def790057c1"
+branch_labels = None
+depends_on = None
+
+
+def upgrade():
+    op.add_column("tokens", sa.Column("description", sa.Text(), nullable=True))
+
+
+def downgrade():
+    op.drop_column("tokens", "description")