diff --git a/app/app.py b/app/app.py
index 3c66a05..709e48f 100644
--- a/app/app.py
+++ b/app/app.py
@@ -7,14 +7,15 @@ the Flask application instance with comprehensive security hardening.
 import os
 import secrets
 
-from flask import Flask, g, request, redirect, jsonify, render_template, url_for
-from flask_cors import CORS
-from app.extensions import db, login_manager, csrf, limiter, babel
-from sqlalchemy import text
-from werkzeug.exceptions import HTTPException
 import markupsafe
 from dotenv import load_dotenv
+from flask import Flask, g, jsonify, redirect, render_template, request, url_for
+from flask_cors import CORS
+from sqlalchemy import text
+from werkzeug.exceptions import HTTPException
+
 from app import i18n
+from app.extensions import babel, csrf, db, limiter, login_manager
 
 load_dotenv()
 
@@ -265,13 +266,13 @@ def create_app(config=None):
     configure_logging(app)
 
     from app.routes.auth import auth_bp
-    from app.routes.tryouts import tryouts_bp
     from app.routes.evaluations import evaluations_bp
-    from app.routes.users import users_bp
     from app.routes.main import main_bp
-    from app.routes.teams import teams_bp
     from app.routes.matches import matches_bp
     from app.routes.team_matches import team_matches_bp
+    from app.routes.teams import teams_bp
+    from app.routes.tryouts import tryouts_bp
+    from app.routes.users import users_bp
 
     app.register_blueprint(auth_bp)
     app.register_blueprint(tryouts_bp)
diff --git a/app/discord_bot.py b/app/discord_bot.py
index 3e10e6a..12604a0 100644
--- a/app/discord_bot.py
+++ b/app/discord_bot.py
@@ -6,21 +6,22 @@ This module provides a persistent bot that handles:
 - Daily reminders at 18:00 EDT for upcoming events
 """
 
-import os
+import asyncio
 import json
 import logging
+import os
 import tempfile
-import time
-import asyncio
 import threading
+import time
 import traceback
 from datetime import datetime, timedelta
+from queue import Empty, Queue
 from zoneinfo import ZoneInfo
-from queue import Queue, Empty
-from discord import Intents
-from discord.ext import commands
+
 from apscheduler.schedulers.asyncio import AsyncIOScheduler
 from apscheduler.triggers.cron import CronTrigger
+from discord import Intents
+from discord.ext import commands
 from dotenv import load_dotenv
 
 load_dotenv()
@@ -453,8 +454,8 @@ class TeamTryoutsBot(commands.Bot):
     async def handle_one_on_one_approve(self, coach, message_id, request_id, channel):
         """Handle coach approving a One on One request."""
         try:
-            from app.models import OneOnOneRequest
             from app.extensions import db
+            from app.models import OneOnOneRequest
 
             request = OneOnOneRequest.query.get(request_id)
             if not request:
@@ -498,8 +499,8 @@ class TeamTryoutsBot(commands.Bot):
     async def handle_one_on_one_reject(self, coach, message_id, request_id, channel):
         """Handle coach rejecting a One on One request."""
         try:
-            from app.models import OneOnOneRequest
             from app.extensions import db
+            from app.models import OneOnOneRequest
 
             request = OneOnOneRequest.query.get(request_id)
             if not request:
@@ -743,14 +744,15 @@ class TeamTryoutsBot(commands.Bot):
     async def _send_daily_reminders_impl(self):
         """Internal implementation of daily reminders with proper app context."""
         try:
+            from sqlalchemy.orm import joinedload
+
             from app.models import (
                 Match,
-                Tryout,
                 MatchParticipant,
-                TryoutRegistration,
                 OneOnOneRequest,
+                Tryout,
+                TryoutRegistration,
             )
-            from sqlalchemy.orm import joinedload
 
             now = datetime.now(self.timezone)
             tomorrow = now.date() + timedelta(days=1)
diff --git a/app/extensions.py b/app/extensions.py
index d262e4b..c6ad0e1 100644
--- a/app/extensions.py
+++ b/app/extensions.py
@@ -1,10 +1,10 @@
-from flask_sqlalchemy import SQLAlchemy
-from flask_login import LoginManager
-from flask_wtf.csrf import CSRFProtect
-from werkzeug.security import generate_password_hash, check_password_hash
+from flask_babel import Babel
 from flask_limiter import Limiter
 from flask_limiter.util import get_remote_address
-from flask_babel import Babel
+from flask_login import LoginManager
+from flask_sqlalchemy import SQLAlchemy
+from flask_wtf.csrf import CSRFProtect
+from werkzeug.security import check_password_hash, generate_password_hash
 
 # Database and extension initialization
 db = SQLAlchemy()
diff --git a/app/logging_config.py b/app/logging_config.py
index 003365c..2dd0616 100644
--- a/app/logging_config.py
+++ b/app/logging_config.py
@@ -11,8 +11,8 @@ Usage:
 
 import logging
 import os
-from logging.handlers import RotatingFileHandler
 import re
+from logging.handlers import RotatingFileHandler
 
 
 class SensitiveDataFilter(logging.Filter):
diff --git a/app/models/_associations.py b/app/models/_associations.py
index 207fa54..d41cc8b 100644
--- a/app/models/_associations.py
+++ b/app/models/_associations.py
@@ -2,7 +2,6 @@
 
 from app.extensions import db
 
-
 org_team_coaches = db.Table(
     'org_team_coaches',
     db.Column(
diff --git a/app/models/availability/__init__.py b/app/models/availability/__init__.py
index b60623d..ae053f8 100644
--- a/app/models/availability/__init__.py
+++ b/app/models/availability/__init__.py
@@ -1,7 +1,7 @@
 """Availability models — BaseAvailability and its concrete subclasses."""
 
 from app.models.availability.base import BaseAvailability
-from app.models.availability.player_disponibility import PlayerDisponibility
 from app.models.availability.coach_availability import CoachAvailability
+from app.models.availability.player_disponibility import PlayerDisponibility
 
 __all__ = ['BaseAvailability', 'PlayerDisponibility', 'CoachAvailability']
diff --git a/app/models/availability/base.py b/app/models/availability/base.py
index 6fc6c4e..4aee7ce 100644
--- a/app/models/availability/base.py
+++ b/app/models/availability/base.py
@@ -1,8 +1,9 @@
 """Abstract base class for availability models (PlayerDisponibility + CoachAvailability)."""
 
-from app.extensions import db
 from datetime import datetime
 
+from app.extensions import db
+
 
 class BaseAvailability(db.Model):
     """Shared schema for player disponibilities and coach availabilities."""
diff --git a/app/models/contract.py b/app/models/contract.py
index e1a97ca..889a9ac 100644
--- a/app/models/contract.py
+++ b/app/models/contract.py
@@ -1,8 +1,9 @@
 """Contract documents for players to sign."""
 
-from app.extensions import db
 from datetime import datetime
 
+from app.extensions import db
+
 
 class Contract(db.Model):
     """Contract documents for players to sign."""
@@ -48,8 +49,8 @@ class Contract(db.Model):
             return True
 
         from app.models.user_model.admin import Admin
-        from app.models.user_model.manager import Manager
         from app.models.user_model.coach import Coach
+        from app.models.user_model.manager import Manager
         from app.models.user_model.user import User
         from app.permissions import coach_can_access_player
 
diff --git a/app/models/evaluation.py b/app/models/evaluation.py
index 8127d6e..0492eb9 100644
--- a/app/models/evaluation.py
+++ b/app/models/evaluation.py
@@ -1,8 +1,9 @@
 """Player evaluation record."""
 
-from app.extensions import db
 from datetime import datetime
 
+from app.extensions import db
+
 
 class Evaluation(db.Model):
     """Player evaluation record."""
diff --git a/app/models/match_model/base.py b/app/models/match_model/base.py
index ca63991..f95232c 100644
--- a/app/models/match_model/base.py
+++ b/app/models/match_model/base.py
@@ -1,8 +1,9 @@
 """Abstract base class for match models (Match + TeamMatch)."""
 
-from app.extensions import db
 from datetime import datetime
 
+from app.extensions import db
+
 
 class BaseMatch(db.Model):
     """Shared schema for tryout-scoped matches and regular-season team matches."""
diff --git a/app/models/one_on_one_request.py b/app/models/one_on_one_request.py
index 2a726ca..1b1e94f 100644
--- a/app/models/one_on_one_request.py
+++ b/app/models/one_on_one_request.py
@@ -1,8 +1,9 @@
 """Request from player to coach for a One on One session."""
 
-from app.extensions import db
 from datetime import datetime
 
+from app.extensions import db
+
 
 class OneOnOneRequest(db.Model):
     """Request from player to coach for a One on One session."""
diff --git a/app/models/org_team/org_team.py b/app/models/org_team/org_team.py
index 86e9007..ae0a0b1 100644
--- a/app/models/org_team/org_team.py
+++ b/app/models/org_team/org_team.py
@@ -1,8 +1,9 @@
 """Persistent organisation team (e.g. Varsity, JV)."""
 
+from datetime import datetime
+
 from app.extensions import db
 from app.models._associations import org_team_coaches, org_team_managers
-from datetime import datetime
 
 
 class OrgTeam(db.Model):
diff --git a/app/models/org_team/team_player.py b/app/models/org_team/team_player.py
index c36fe7b..d07865c 100644
--- a/app/models/org_team/team_player.py
+++ b/app/models/org_team/team_player.py
@@ -1,8 +1,9 @@
 """Many-to-many junction: player to org-team."""
 
-from app.extensions import db
 from datetime import datetime
 
+from app.extensions import db
+
 
 class TeamPlayer(db.Model):
     """Many-to-many: player to org-team."""
diff --git a/app/models/participant/base.py b/app/models/participant/base.py
index 6d5d99c..7293699 100644
--- a/app/models/participant/base.py
+++ b/app/models/participant/base.py
@@ -1,8 +1,9 @@
 """Abstract base class for match participant models."""
 
-from app.extensions import db
 from datetime import datetime
 
+from app.extensions import db
+
 
 class BaseParticipant(db.Model):
     """Shared schema for match participants."""
diff --git a/app/models/personal_note.py b/app/models/personal_note.py
index b8c3bc8..4745202 100644
--- a/app/models/personal_note.py
+++ b/app/models/personal_note.py
@@ -1,8 +1,9 @@
 """Personal notes from coach to individual player."""
 
-from app.extensions import db
 from datetime import datetime
 
+from app.extensions import db
+
 
 class PersonalNote(db.Model):
     """Personal notes from coach to individual player."""
diff --git a/app/models/team/team.py b/app/models/team/team.py
index d243fdc..4611fe1 100644
--- a/app/models/team/team.py
+++ b/app/models/team/team.py
@@ -1,8 +1,9 @@
 """Tryout-specific team (e.g. Alpha, Bravo within a single tryout)."""
 
-from app.extensions import db
 from datetime import datetime
 
+from app.extensions import db
+
 
 class Team(db.Model):
     """Tryout-specific team (e.g. Alpha, Bravo within a single tryout)."""
diff --git a/app/models/team/team_member.py b/app/models/team/team_member.py
index 8861298..391048f 100644
--- a/app/models/team/team_member.py
+++ b/app/models/team/team_member.py
@@ -1,8 +1,9 @@
 """Link between a player and a tryout-specific team."""
 
-from app.extensions import db
 from datetime import datetime
 
+from app.extensions import db
+
 
 class TeamMember(db.Model):
     """Link between a player and a tryout-specific team."""
diff --git a/app/models/team_note.py b/app/models/team_note.py
index 46ebbfb..76c8c21 100644
--- a/app/models/team_note.py
+++ b/app/models/team_note.py
@@ -1,8 +1,9 @@
 """Team improvement notes from coach."""
 
-from app.extensions import db
 from datetime import datetime
 
+from app.extensions import db
+
 
 class TeamNote(db.Model):
     """Team improvement notes from coach."""
diff --git a/app/models/tryout/tryout.py b/app/models/tryout/tryout.py
index 3d34a49..e9f4a74 100644
--- a/app/models/tryout/tryout.py
+++ b/app/models/tryout/tryout.py
@@ -1,8 +1,9 @@
 """Tryout event for player evaluations and team formation."""
 
+from datetime import datetime
+
 from app.extensions import db
 from app.models._associations import tryout_coaches
-from datetime import datetime
 
 
 class Tryout(db.Model):
diff --git a/app/models/tryout/tryout_registration.py b/app/models/tryout/tryout_registration.py
index 162f7d8..007e77b 100644
--- a/app/models/tryout/tryout_registration.py
+++ b/app/models/tryout/tryout_registration.py
@@ -1,8 +1,9 @@
 """Registration linking a player to a tryout."""
 
-from app.extensions import db
 from datetime import datetime
 
+from app.extensions import db
+
 
 class TryoutRegistration(db.Model):
     """Registration linking a player to a tryout."""
diff --git a/app/models/user_gamertag.py b/app/models/user_gamertag.py
index 8c2c591..589d32d 100644
--- a/app/models/user_gamertag.py
+++ b/app/models/user_gamertag.py
@@ -1,9 +1,10 @@
 """Store gamertag per game for each user."""
 
-from app.extensions import db
-from app.models._constants import TRN_URLS, PLATFORM_CODES, PLATFORM_DEFAULTS
 from urllib.parse import quote
 
+from app.extensions import db
+from app.models._constants import PLATFORM_CODES, PLATFORM_DEFAULTS, TRN_URLS
+
 
 class UserGamertag(db.Model):
     """Store gamertag per game for each user."""
diff --git a/app/models/user_model/__init__.py b/app/models/user_model/__init__.py
index 2a81dbb..a1e2670 100644
--- a/app/models/user_model/__init__.py
+++ b/app/models/user_model/__init__.py
@@ -1,10 +1,10 @@
 """User hierarchy — single-table polymorphic inheritance (User → Admin, Manager, Coach, Player, Scout)."""
 
-from app.models.user_model.user import User
 from app.models.user_model.admin import Admin
-from app.models.user_model.manager import Manager
 from app.models.user_model.coach import Coach
+from app.models.user_model.manager import Manager
 from app.models.user_model.player import Player
 from app.models.user_model.scout import Scout
+from app.models.user_model.user import User
 
 __all__ = ['User', 'Admin', 'Manager', 'Coach', 'Player', 'Scout']
diff --git a/app/models/user_model/manager.py b/app/models/user_model/manager.py
index 10a7b94..aa95fb3 100644
--- a/app/models/user_model/manager.py
+++ b/app/models/user_model/manager.py
@@ -27,9 +27,10 @@ class Manager(User):
         return True
 
     def get_visible_tryouts(self):
-        from app.models.tryout.tryout import Tryout
         from sqlalchemy import or_
 
+        from app.models.tryout.tryout import Tryout
+
         return (
             Tryout.query.filter(or_(Tryout.created_by == self.id, Tryout.manager_id == self.id))
             .order_by(Tryout.date)
diff --git a/app/models/user_model/player.py b/app/models/user_model/player.py
index 30229c0..a3ceeea 100644
--- a/app/models/user_model/player.py
+++ b/app/models/user_model/player.py
@@ -9,9 +9,9 @@ class Player(User):
     __mapper_args__ = {'polymorphic_identity': 'player'}
 
     def get_visible_tryouts(self):
-        from app.models.tryout.tryout import Tryout
         from app.models.match_model.match import Match
         from app.models.participant.match_participant import MatchParticipant
+        from app.models.tryout.tryout import Tryout
 
         # tryouts they registered for
         player_tryout_ids = [r.tryout_id for r in self.tryout_registrations.all()]
diff --git a/app/models/user_model/user.py b/app/models/user_model/user.py
index 3a27544..231a726 100644
--- a/app/models/user_model/user.py
+++ b/app/models/user_model/user.py
@@ -1,9 +1,11 @@
 """Base User model — shared fields and polymorphic configuration."""
 
-from app.extensions import db
-from flask_login import UserMixin
 from datetime import datetime
 
+from flask_login import UserMixin
+
+from app.extensions import db
+
 
 class User(UserMixin, db.Model):
     """Base user model — shared fields for every role.
diff --git a/app/permissions.py b/app/permissions.py
index 00bfe7f..b0d39ae 100644
--- a/app/permissions.py
+++ b/app/permissions.py
@@ -28,7 +28,6 @@ and from tests without a request context.
 
 from app.extensions import db
 
-
 # ---------------------------------------------------------------------------
 # Team attachment
 # ---------------------------------------------------------------------------
diff --git a/app/routes/auth.py b/app/routes/auth.py
index 0ad9015..ff0d383 100644
--- a/app/routes/auth.py
+++ b/app/routes/auth.py
@@ -5,21 +5,23 @@ protection, logout with session clearing, and new user registration with
 password policy enforcement and CAPTCHA verification.
 """
 
-import uuid
 import os
 import secrets
+import uuid
 from datetime import datetime, timedelta
-from flask import Blueprint, render_template, redirect, url_for, flash, request, session
-from flask_login import login_user, logout_user, login_required, current_user
-from app.extensions import db, hash_password, check_password, limiter
-from app.models import User, Player, ESPORT_GAMES
-from app.validators import RegisterSchema, LoginSchema
+from urllib.parse import urlencode, urlparse
+
+import requests
+from flask import Blueprint, flash, redirect, render_template, request, session, url_for
+from flask_babel import gettext as _
+from flask_login import current_user, login_required, login_user, logout_user
+from marshmallow import ValidationError
+
+from app.extensions import check_password, db, hash_password, limiter
 from app.i18n import LOCALE_SESSION_KEY
 from app.logging_config import log_auth_event
-from flask_babel import gettext as _
-from marshmallow import ValidationError
-from urllib.parse import urlparse, urlencode
-import requests
+from app.models import ESPORT_GAMES, Player, User
+from app.validators import LoginSchema, RegisterSchema
 
 #: Session key holding the pending OAuth2 anti-forgery token.
 DISCORD_STATE_KEY = 'discord_oauth_state'
diff --git a/app/routes/evaluations.py b/app/routes/evaluations.py
index ba696c8..2f57a4b 100644
--- a/app/routes/evaluations.py
+++ b/app/routes/evaluations.py
@@ -3,22 +3,23 @@
 Uses polymorphic isinstance checks instead of role-string comparisons.
 """
 
-from flask import Blueprint, render_template, redirect, url_for, flash, request
-from flask_login import login_required, current_user
+from flask import Blueprint, flash, redirect, render_template, request, url_for
 from flask_babel import gettext as _
-from app.extensions import db
-from app.models import (
-    Admin,
-    Player,
-    User,
-    Tryout,
-    Evaluation,
-    TryoutRegistration,
-    GAME_POSITIONS,
-)
+from flask_login import current_user, login_required
 from sqlalchemy import func
 from sqlalchemy.orm import aliased
 
+from app.extensions import db
+from app.models import (
+    GAME_POSITIONS,
+    Admin,
+    Evaluation,
+    Player,
+    Tryout,
+    TryoutRegistration,
+    User,
+)
+
 evaluations_bp = Blueprint('evaluations', __name__, url_prefix='/evaluations')
 
 
diff --git a/app/routes/main.py b/app/routes/main.py
index 8b85347..2691b3d 100644
--- a/app/routes/main.py
+++ b/app/routes/main.py
@@ -3,27 +3,29 @@
 Uses polymorphic isinstance checks instead of role-string comparisons.
 """
 
-from flask import Blueprint, render_template, redirect, url_for, flash, request
-from flask_login import login_required, current_user
+from datetime import date
+
+from flask import Blueprint, flash, redirect, render_template, request, url_for
 from flask_babel import gettext as _
+from flask_login import current_user, login_required
+from sqlalchemy import func
+
 from app.extensions import db
 from app.models import (
     Admin,
-    Manager,
     Coach,
-    Player,
-    Scout,
-    User,
-    Tryout,
     Evaluation,
-    TryoutRegistration,
-    TeamMember,
+    Manager,
     Match,
     MatchParticipant,
+    Player,
+    Scout,
+    TeamMember,
+    Tryout,
+    TryoutRegistration,
+    User,
 )
 from app.permissions import coach_tryout_ids
-from sqlalchemy import func
-from datetime import date
 
 main_bp = Blueprint('main', __name__)
 
diff --git a/app/routes/matches.py b/app/routes/matches.py
index 1488f5a..8101bc0 100644
--- a/app/routes/matches.py
+++ b/app/routes/matches.py
@@ -3,30 +3,31 @@
 Uses polymorphic isinstance checks instead of role-string comparisons.
 """
 
-from flask import Blueprint, render_template, redirect, url_for, flash, request, jsonify
-from flask_login import login_required, current_user
+from datetime import datetime, timedelta
+
+from flask import Blueprint, flash, jsonify, redirect, render_template, request, url_for
 from flask_babel import gettext as _
+from flask_login import current_user, login_required
+from sqlalchemy.orm import joinedload
+
 from app.extensions import db
 from app.models import (
     Admin,
-    Manager,
     Coach,
-    Player,
-    Scout,
-    User,
-    Tryout,
+    Manager,
     Match,
     MatchParticipant,
-    Team,
-    TeamMember,
-    TryoutRegistration,
-    PlayerDisponibility,
     OneOnOneRequest,
     PersonalNote,
+    Player,
+    PlayerDisponibility,
+    Scout,
+    Team,
+    TeamMember,
+    Tryout,
+    TryoutRegistration,
+    User,
 )
-from datetime import datetime, timedelta
-
-from sqlalchemy.orm import joinedload
 from app.services.scheduling import notify_participants, zip_participants
 
 matches_bp = Blueprint('matches', __name__, url_prefix='/matches')
diff --git a/app/routes/team_matches.py b/app/routes/team_matches.py
index 584a473..1d28c0f 100644
--- a/app/routes/team_matches.py
+++ b/app/routes/team_matches.py
@@ -3,22 +3,24 @@
 Uses polymorphic isinstance checks instead of role-string comparisons.
 """
 
-from flask import Blueprint, render_template, redirect, url_for, flash, request, jsonify
-from flask_login import login_required, current_user
+from datetime import datetime, timedelta
+
+from flask import Blueprint, flash, jsonify, redirect, render_template, request, url_for
 from flask_babel import gettext as _
+from flask_login import current_user, login_required
+
 from app.extensions import db
 from app.models import (
     Admin,
-    Manager,
     Coach,
-    Player,
+    Manager,
     OrgTeam,
+    Player,
     TeamMatch,
     TeamMatchParticipant,
     TeamPlayer,
 )
 from app.permissions import can_manage_org_team, coach_org_teams, visible_org_teams
-from datetime import datetime, timedelta
 from app.services.scheduling import notify_participants, zip_participants
 
 team_matches_bp = Blueprint('team_matches', __name__, url_prefix='/team-matches')
diff --git a/app/routes/teams.py b/app/routes/teams.py
index d038437..62011f5 100644
--- a/app/routes/teams.py
+++ b/app/routes/teams.py
@@ -3,27 +3,29 @@
 Uses polymorphic isinstance checks instead of role-string comparisons.
 """
 
-from flask import Blueprint, render_template, redirect, url_for, flash, request, jsonify
-from flask_login import login_required, current_user
+from datetime import datetime
+
+from flask import Blueprint, flash, jsonify, redirect, render_template, request, url_for
 from flask_babel import gettext as _
+from flask_login import current_user, login_required
+
 from app.extensions import db
 from app.models import (
     Admin,
-    Manager,
     Coach,
-    Player,
-    OrgTeam,
-    User,
-    PersonalNote,
-    TeamNote,
-    Tryout,
-    TeamPlayer,
-    TeamMatch,
     Contract,
+    Manager,
     OneOnOneRequest,
+    OrgTeam,
+    PersonalNote,
+    Player,
+    TeamMatch,
+    TeamNote,
+    TeamPlayer,
+    Tryout,
+    User,
 )
 from app.permissions import visible_org_teams
-from datetime import datetime
 
 teams_bp = Blueprint('teams', __name__, url_prefix='/teams')
 
diff --git a/app/routes/tryouts.py b/app/routes/tryouts.py
index 84b6e7b..d304bb2 100644
--- a/app/routes/tryouts.py
+++ b/app/routes/tryouts.py
@@ -4,30 +4,32 @@ This module handles CRUD operations for tryouts and player registrations.
 Uses polymorphic isinstance checks instead of role-string comparisons.
 """
 
-from flask import Blueprint, render_template, redirect, url_for, flash, request, abort
-from flask_login import login_required, current_user
+from datetime import datetime
+
+from flask import Blueprint, abort, flash, redirect, render_template, request, url_for
 from flask_babel import gettext as _
+from flask_login import current_user, login_required
+
 from app.extensions import db
 from app.models import (
-    Admin,
-    Manager,
-    Coach,
-    Player,
-    Scout,
-    User,
-    Tryout,
-    TryoutRegistration,
-    Evaluation,
-    Team,
-    TeamMember,
-    OrgTeam,
-    Match,
-    MatchParticipant,
-    PersonalNote,
     ESPORT_GAMES,
     GAME_POSITIONS,
+    Admin,
+    Coach,
+    Evaluation,
+    Manager,
+    Match,
+    MatchParticipant,
+    OrgTeam,
+    PersonalNote,
+    Player,
+    Scout,
+    Team,
+    TeamMember,
+    Tryout,
+    TryoutRegistration,
+    User,
 )
-from datetime import datetime
 
 tryouts_bp = Blueprint('tryouts', __name__, url_prefix='/tryouts')
 
diff --git a/app/routes/users/__init__.py b/app/routes/users/__init__.py
index 9af3bf6..7fb7bbd 100644
--- a/app/routes/users/__init__.py
+++ b/app/routes/users/__init__.py
@@ -9,16 +9,16 @@ keeps its single `from app.routes.users import users_bp`. The blueprint
 itself lives in blueprint.py to keep that import one-directional.
 """
 
-from app.routes.users.blueprint import users_bp
-
 # Imported for their side effect: each module attaches its routes to
 # users_bp. Order does not matter; none of them import each other.
-from app.routes.users import accounts  # noqa: F401,E402
-from app.routes.users import availability  # noqa: F401,E402
-from app.routes.users import contracts  # noqa: F401,E402
-from app.routes.users import notes  # noqa: F401,E402
-from app.routes.users import one_on_one  # noqa: F401,E402
-from app.routes.users import profile  # noqa: F401,E402
+from app.routes.users import (
+    accounts,  # noqa: F401,E402
+    availability,  # noqa: F401,E402
+    contracts,  # noqa: F401,E402
+    notes,  # noqa: F401,E402
+    one_on_one,  # noqa: F401,E402
+    profile,  # noqa: F401,E402
+)
 
 # Re-exported because tests and other modules reach for them by name.
 from app.routes.users._shared import (  # noqa: F401,E402
@@ -26,6 +26,7 @@ from app.routes.users._shared import (  # noqa: F401,E402
     ALLOWED_SIGNED_EXTENSIONS,
     pdf_upload_error,
 )
+from app.routes.users.blueprint import users_bp
 
 __all__ = [
     'ALLOWED_CONTRACT_EXTENSIONS',
diff --git a/app/routes/users/_shared.py b/app/routes/users/_shared.py
index 7951ea1..72a851e 100644
--- a/app/routes/users/_shared.py
+++ b/app/routes/users/_shared.py
@@ -8,7 +8,7 @@ from flask import flash, request
 from flask_babel import gettext as _
 
 from app.extensions import db
-from app.models import Admin, Coach, Manager, Player, Scout, GAME_PLATFORMS, UserGamertag
+from app.models import GAME_PLATFORMS, Admin, Coach, Manager, Player, Scout, UserGamertag
 
 ALLOWED_CONTRACT_EXTENSIONS = {'pdf'}
 ALLOWED_SIGNED_EXTENSIONS = {'pdf'}
diff --git a/app/routes/users/accounts.py b/app/routes/users/accounts.py
index 5bb4caa..1d431f8 100644
--- a/app/routes/users/accounts.py
+++ b/app/routes/users/accounts.py
@@ -12,12 +12,13 @@ from marshmallow import ValidationError
 from app.extensions import db, hash_password
 from app.logging_config import log_auth_event
 from app.models import (
+    ESPORT_GAMES,
+    GAME_PLATFORMS,
+    USER_TYPES,
     Admin,
     CoachAvailability,
     Contract,
-    ESPORT_GAMES,
     Evaluation,
-    GAME_PLATFORMS,
     Match,
     MatchParticipant,
     OneOnOneRequest,
@@ -31,7 +32,6 @@ from app.models import (
     TeamPlayer,
     Tryout,
     TryoutRegistration,
-    USER_TYPES,
     User,
     UserGamertag,
 )
diff --git a/app/routes/users/availability.py b/app/routes/users/availability.py
index 9ec1aa4..de594a2 100644
--- a/app/routes/users/availability.py
+++ b/app/routes/users/availability.py
@@ -15,7 +15,6 @@ from app.extensions import db
 from app.models import Coach, CoachAvailability, PlayerDisponibility, User
 from app.routes.users.blueprint import users_bp
 
-
 DAY_NAMES = ['Monday', 'Tuesday', 'Wednesday', 'Thursday', 'Friday', 'Saturday', 'Sunday']
 
 
diff --git a/app/routes/users/one_on_one.py b/app/routes/users/one_on_one.py
index 1f76024..6ff2829 100644
--- a/app/routes/users/one_on_one.py
+++ b/app/routes/users/one_on_one.py
@@ -119,7 +119,8 @@ def one_on_one():
         return redirect(url_for('users.one_on_one'))
 
     # Build list of upcoming dates that have coach availability
-    from datetime import date as date_cls, timedelta as td
+    from datetime import date as date_cls
+    from datetime import timedelta as td
 
     today = date_cls.today()
     available_days = {av['day_of_week'] for av in coach_availability}
diff --git a/app/routes/users/profile.py b/app/routes/users/profile.py
index 69c4f33..2898431 100644
--- a/app/routes/users/profile.py
+++ b/app/routes/users/profile.py
@@ -8,11 +8,11 @@ from marshmallow import ValidationError
 from app.extensions import db, hash_password
 from app.logging_config import log_auth_event
 from app.models import (
-    CoachAvailability,
-    Coach,
-    Contract,
     ESPORT_GAMES,
     GAME_PLATFORMS,
+    Coach,
+    CoachAvailability,
+    Contract,
     Player,
     User,
 )
diff --git a/app/supporting_scripts/run_https.py b/app/supporting_scripts/run_https.py
index 788ca91..4ea3e8e 100644
--- a/app/supporting_scripts/run_https.py
+++ b/app/supporting_scripts/run_https.py
@@ -13,10 +13,12 @@ Accept the self-signed certificate warning in your browser to proceed.
 
 import os
 import socket
-import subprocess
 import ssl
+import subprocess
 import sys
+
 from waitress.server import create_server
+
 from app.app import create_app
 
 CERT_FILE = 'certs/localhost.pem'
diff --git a/app/supporting_scripts/security_scan.py b/app/supporting_scripts/security_scan.py
index e783462..dc8afa9 100644
--- a/app/supporting_scripts/security_scan.py
+++ b/app/supporting_scripts/security_scan.py
@@ -12,12 +12,12 @@ Usage:
     python security_scan.py [--url http://localhost:5000]
 """
 
-import os
-import sys
 import json
-import subprocess
-import urllib.request
+import os
 import ssl
+import subprocess
+import sys
+import urllib.request
 from datetime import datetime
 
 
diff --git a/app/validators.py b/app/validators.py
index a22c886..1c6e981 100644
--- a/app/validators.py
+++ b/app/validators.py
@@ -11,18 +11,19 @@ Usage:
 """
 
 import re
+
 from flask_babel import lazy_gettext as _l
 from marshmallow import (
-    Schema,
-    fields,
-    validate,
-    ValidationError,
-    pre_load,
-    validates_schema,
     EXCLUDE,
+    Schema,
+    ValidationError,
+    fields,
+    pre_load,
+    validate,
+    validates_schema,
 )
-from app.models import USER_TYPES
 
+from app.models import USER_TYPES
 
 # =============================================================================
 # Custom Validators
diff --git a/pyproject.toml b/pyproject.toml
index a29f5f6..a954859 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -42,11 +42,10 @@ exclude = [".venv", "venv", "migrations", "docs"]
 #   RET          return-flow tidiness
 #   SIM          obvious simplifications
 #   UP           syntax available on the 3.12 this targets
-#
-# isort (I) is not enabled yet: it would reorder imports in 48 files, i.e. a
-# second sweep of pure churn right after the formatting commit. Worth doing,
-# worth doing on its own.
-select = ["E4", "E7", "E9", "F", "B", "C4", "RET", "SIM", "UP"]
+#   I            isort; enabled in its own commit, for the same reason the
+#                formatting got one — the diff is churn and must not hide
+#                behind a behavioural change
+select = ["E4", "E7", "E9", "F", "B", "C4", "RET", "SIM", "UP", "I"]
 
 # Forcing a ternary reads worse than the if/else it replaces in the one place
 # it fires (evaluations.py, choosing a sort direction).
@@ -56,7 +55,14 @@ ignore = ["SIM108"]
 # Intentional re-export facade: `from app.models import User, Tryout, ...`
 # is the documented entry point, and importing the modules is what
 # registers every model with SQLAlchemy.
-"app/models/__init__.py" = ["F401"]
+#
+# I001 is off here too. The imports are grouped into eleven commented
+# layers that spell out the dependency graph (constants → users → teams →
+# tryouts → matches → participants). Alphabetising them leaves every
+# heading above an import it does not describe, and the file's one job is
+# to be read. The order is documentation, not a requirement: the suite
+# passes either way.
+"app/models/__init__.py" = ["F401", "I001"]
 "app/models/user_model/__init__.py" = ["F401"]
 "tests/conftest.py" = ["E402"]
 
diff --git a/tests/test_authorization.py b/tests/test_authorization.py
index 1e16df4..a865114 100644
--- a/tests/test_authorization.py
+++ b/tests/test_authorization.py
@@ -98,9 +98,10 @@ class TestHorizontalAccess:
     def test_player_cannot_delete_another_players_availability(
         self, app, client, as_role, make_user
     ):
-        from app.models import PlayerDisponibility
         from datetime import time
 
+        from app.models import PlayerDisponibility
+
         owner_id = make_user('player')
         with app.app_context():
             slot = PlayerDisponibility(
diff --git a/wsgi.py b/wsgi.py
index d9d6dfe..791a5dd 100644
--- a/wsgi.py
+++ b/wsgi.py
@@ -12,8 +12,9 @@ Configuration via environment variables:
     WAITRESS_THREADS: Number of worker threads (default: CPU*2+1)
 """
 
-import os
 import multiprocessing
+import os
+
 from app.app import create_app
 
 app = create_app()