diff --git a/files/classes/__init__.py b/files/classes/__init__.py
index 88f8ab9fc..94a356ec4 100644
--- a/files/classes/__init__.py
+++ b/files/classes/__init__.py
@@ -1,6 +1,7 @@
 # load sqlalchemy's declarative base...
-from sqlalchemy.ext.declarative import declarative_base
-Base = declarative_base()
+from sqlalchemy.orm import DeclarativeBase
+class Base(DeclarativeBase):
+	pass
 
 # then load all of our classes :)
 from .alts import *
diff --git a/files/classes/alts.py b/files/classes/alts.py
index 2cff4b7c2..d70f76193 100644
--- a/files/classes/alts.py
+++ b/files/classes/alts.py
@@ -1,17 +1,19 @@
 import time
+from typing import Optional
 
-from sqlalchemy import Column, ForeignKey
+from sqlalchemy.orm import Mapped, mapped_column
 from sqlalchemy.sql.sqltypes import *
 
 from files.classes import Base
+from files.helpers.types import user_id_fk_pk
 
 class Alt(Base):
 	__tablename__ = "alts"
 
-	user1 = Column(Integer, ForeignKey("users.id"), primary_key=True)
-	user2 = Column(Integer, ForeignKey("users.id"), primary_key=True)
-	is_manual = Column(Boolean, default=False)
-	created_utc = Column(Integer)
+	user1: Mapped[user_id_fk_pk]
+	user2: Mapped[user_id_fk_pk]
+	is_manual: Mapped[bool] = mapped_column(default=False)
+	created_utc: Mapped[Optional[int]]
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
diff --git a/files/classes/award.py b/files/classes/award.py
index c7538fadd..440c3a3b9 100644
--- a/files/classes/award.py
+++ b/files/classes/award.py
@@ -1,30 +1,34 @@
 import time
+from typing import Optional, TYPE_CHECKING
 
-from sqlalchemy import Column, ForeignKey
-from sqlalchemy.orm import relationship
+from sqlalchemy.orm import Mapped, mapped_column, relationship
 from sqlalchemy.sql.sqltypes import *
 
 from files.classes import Base
 from files.helpers.config.awards import AWARDS, HOUSE_AWARDS
 from files.helpers.lazy import lazy
+from files.helpers.types import comment_id_fk, int_pk, post_id_fk, user_id_fk
+
+if TYPE_CHECKING:
+	from files.classes import Comment, Post, User
 
 
 class AwardRelationship(Base):
 	__tablename__ = "award_relationships"
 
-	id = Column(Integer, primary_key=True)
-	user_id = Column(Integer, ForeignKey("users.id"))
-	post_id = Column(Integer, ForeignKey("posts.id"))
-	comment_id = Column(Integer, ForeignKey("comments.id"))
-	kind = Column(String)
-	awarded_utc = Column(Integer)
-	created_utc = Column(Integer)
-	price_paid = Column(Integer, default = 0)
-	note = Column(String)
+	id: Mapped[int_pk]
+	user_id: Mapped[user_id_fk]
+	post_id: Mapped[Optional[post_id_fk]]
+	comment_id: Mapped[Optional[comment_id_fk]]
+	kind: Mapped[str]
+	awarded_utc: Mapped[Optional[int]]
+	created_utc: Mapped[Optional[int]]
+	price_paid: Mapped[int] = mapped_column(default = 0)
+	note: Mapped[Optional[str]]
 
-	user = relationship("User", primaryjoin="AwardRelationship.user_id==User.id", back_populates="awards")
-	post = relationship("Post", primaryjoin="AwardRelationship.post_id==Post.id", back_populates="awards")
-	comment = relationship("Comment", primaryjoin="AwardRelationship.comment_id==Comment.id", back_populates="awards")
+	user: Mapped["User"] = relationship(primaryjoin="AwardRelationship.user_id==User.id", back_populates="awards")
+	post: Mapped["Post"] = relationship(primaryjoin="AwardRelationship.post_id==Post.id", back_populates="awards")
+	comment: Mapped["Comment"] = relationship(primaryjoin="AwardRelationship.comment_id==Comment.id", back_populates="awards")
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
diff --git a/files/classes/badges.py b/files/classes/badges.py
index c6230c645..a755421a3 100644
--- a/files/classes/badges.py
+++ b/files/classes/badges.py
@@ -1,20 +1,26 @@
 import time
+from typing import Optional, TYPE_CHECKING
 
-from sqlalchemy import Column, ForeignKey
-from sqlalchemy.orm import relationship
+from sqlalchemy import ForeignKey
+from sqlalchemy.orm import Mapped, mapped_column, relationship
 from sqlalchemy.sql.sqltypes import *
 
 from files.classes import Base
 from files.helpers.config.const import *
 from files.helpers.lazy import lazy
+from files.helpers.types import int_pk, user_id_fk_pk
+
+if TYPE_CHECKING:
+	from files.classes import User
+
 
 class BadgeDef(Base):
 	__tablename__ = "badge_defs"
 
-	id = Column(Integer, primary_key=True, autoincrement=True)
-	name = Column(String)
-	description = Column(String)
-	created_utc = Column(Integer)
+	id: Mapped[int_pk] = mapped_column(autoincrement=True)
+	name: Mapped[str]
+	description: Mapped[Optional[str]]
+	created_utc: Mapped[int]
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
@@ -32,14 +38,14 @@ class Badge(Base):
 
 	__tablename__ = "badges"
 
-	user_id = Column(Integer, ForeignKey('users.id'), primary_key=True)
-	badge_id = Column(Integer, ForeignKey('badge_defs.id'), primary_key=True)
-	description = Column(String)
-	url = Column(String)
-	created_utc = Column(Integer)
+	user_id: Mapped[user_id_fk_pk]
+	badge_id: Mapped[int] = mapped_column(ForeignKey('badge_defs.id'), primary_key=True)
+	description: Mapped[Optional[str]]
+	url: Mapped[Optional[str]]
+	created_utc: Mapped[int]
 
-	user = relationship("User", back_populates="badges")
-	badge = relationship("BadgeDef", primaryjoin="Badge.badge_id == BadgeDef.id", lazy="joined", innerjoin=True)
+	user: Mapped["User"] = relationship(back_populates="badges")
+	badge: Mapped["BadgeDef"] = relationship(primaryjoin="Badge.badge_id == BadgeDef.id", lazy="joined", innerjoin=True)
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs:
diff --git a/files/classes/casino_game.py b/files/classes/casino_game.py
index 8864204ea..9d5233619 100644
--- a/files/classes/casino_game.py
+++ b/files/classes/casino_game.py
@@ -1,29 +1,33 @@
 import json
 import time
+from typing import TYPE_CHECKING
 
-from sqlalchemy import Column, ForeignKey
-from sqlalchemy.orm import relationship
+from sqlalchemy.orm import Mapped, mapped_column, relationship
 from sqlalchemy.sql.sqltypes import *
 
 from files.classes import Base
 from files.helpers.lazy import lazy
+from files.helpers.types import int_pk, user_id_fk
+
+if TYPE_CHECKING:
+	from files.classes import User
 
 CASINO_GAME_KINDS = ['blackjack', 'slots', 'roulette']
 
 class CasinoGame(Base):
 	__tablename__ = "casino_games"
 
-	id = Column(Integer, primary_key=True)
-	user_id = Column(Integer, ForeignKey("users.id"))
-	created_utc = Column(Integer)
-	active = Column(Boolean, default=True)
-	currency = Column(String)
-	wager = Column(Integer)
-	winnings = Column(Integer)
-	kind = Column(String)
-	game_state = Column(JSON)
+	id: Mapped[int_pk]
+	user_id: Mapped[user_id_fk]
+	created_utc: Mapped[int]
+	active: Mapped[bool] = mapped_column(default=True)
+	currency: Mapped[str]
+	wager: Mapped[int]
+	winnings: Mapped[int]
+	kind: Mapped[str]
+	game_state: Mapped[str] = mapped_column(JSON)
 
-	user = relationship("User")
+	user: Mapped["User"] = relationship()
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs:
diff --git a/files/classes/clients.py b/files/classes/clients.py
index f4bebecfb..a7ccac0f7 100644
--- a/files/classes/clients.py
+++ b/files/classes/clients.py
@@ -1,29 +1,35 @@
 import time
+from typing import Annotated, Optional, TYPE_CHECKING
 
 from flask import g
-from sqlalchemy import Column, ForeignKey
-from sqlalchemy.orm import relationship, load_only
+from sqlalchemy import ForeignKey
+from sqlalchemy.orm import Mapped, load_only, mapped_column, relationship
 from sqlalchemy.sql.sqltypes import *
 
 from files.classes import Base
 from files.helpers.config.const import *
 from files.helpers.lazy import lazy
+from files.helpers.types import int_pk, user_id_fk, user_id_fk_pk
 
 from .comment import Comment
 from .post import Post
 
+if TYPE_CHECKING:
+	from files.classes import User
+
+
 class OauthApp(Base):
 	__tablename__ = "oauth_apps"
 
-	id = Column(Integer, primary_key=True)
-	client_id = Column(String)
-	app_name = Column(String)
-	redirect_uri = Column(String)
-	description = Column(String)
-	author_id = Column(Integer, ForeignKey("users.id"))
-	created_utc = Column(Integer)
+	id: Mapped[int_pk]
+	client_id: Mapped[Optional[Annotated[str, 64]]]
+	app_name: Mapped[str]
+	redirect_uri: Mapped[str]
+	description: Mapped[str]
+	author_id: Mapped[user_id_fk]
+	created_utc: Mapped[Optional[int]]
 
-	author = relationship("User", back_populates="apps")
+	author: Mapped["User"] = relationship(back_populates="apps")
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
@@ -51,13 +57,13 @@ class OauthApp(Base):
 
 class ClientAuth(Base):
 	__tablename__ = "client_auths"
-	user_id = Column(Integer, ForeignKey("users.id"), primary_key=True)
-	oauth_client = Column(Integer, ForeignKey("oauth_apps.id"), primary_key=True)
-	access_token = Column(String)
-	created_utc = Column(Integer)
+	user_id: Mapped[user_id_fk_pk]
+	oauth_client: Mapped[int] = mapped_column(ForeignKey("oauth_apps.id"), primary_key=True)
+	access_token: Mapped[str]
+	created_utc: Mapped[Optional[int]]
 
-	user = relationship("User")
-	application = relationship("OauthApp")
+	user: Mapped["User"] = relationship()
+	application: Mapped["OauthApp"] = relationship()
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
diff --git a/files/classes/comment.py b/files/classes/comment.py
index 18b775815..ac2a7e785 100644
--- a/files/classes/comment.py
+++ b/files/classes/comment.py
@@ -1,12 +1,13 @@
 import time
 from math import floor
 from random import randint
+from typing import Optional, TYPE_CHECKING
 from urllib.parse import parse_qs, urlencode, urlparse
 from flask import g
 
-from sqlalchemy import Column, ForeignKey
+from sqlalchemy import ForeignKey
 from sqlalchemy.dialects.postgresql import TSVECTOR
-from sqlalchemy.orm import relationship
+from sqlalchemy.orm import Mapped, mapped_column, relationship
 from sqlalchemy.schema import FetchedValue
 from sqlalchemy.sql.sqltypes import *
 
@@ -17,10 +18,14 @@ from files.helpers.slurs_and_profanities import *
 from files.helpers.lazy import lazy
 from files.helpers.regex import *
 from files.helpers.sorting_and_time import *
+from files.helpers.types import comment_id_fk, int_pk, post_id_fk, user_id_fk
 from files.helpers.bleach_body import *
 
 from .saves import CommentSaveRelationship
 
+if TYPE_CHECKING:
+	from files.classes import AwardRelationship, CasinoGame, CommentOption, CommentReport, OauthApp, Post, User
+
 def get_emoji_awards_emojis(obj, v, kind, NSFW_EMOJIS):
 	if g.show_nsfw:
 		emojis = [x.note for x in obj.awards if x.kind == kind]
@@ -172,60 +177,60 @@ def add_options(self, body, v):
 class Comment(Base):
 	__tablename__ = "comments"
 
-	id = Column(Integer, primary_key=True)
-	author_id = Column(Integer, ForeignKey("users.id"))
-	parent_post = Column(Integer, ForeignKey("posts.id"))
-	wall_user_id = Column(Integer, ForeignKey("users.id"))
-	created_utc = Column(Integer)
-	edited_utc = Column(Integer, default=0)
-	is_banned = Column(Boolean, default=False)
-	ghost = Column(Boolean, default=False)
-	bannedfor = Column(String)
-	chuddedfor = Column(String)
-	distinguished = Column(Boolean, default=False)
-	deleted_utc = Column(Integer, default=0)
-	is_approved = Column(Integer, ForeignKey("users.id"))
-	level = Column(Integer, default=1)
-	parent_comment_id = Column(Integer, ForeignKey("comments.id"))
-	top_comment_id = Column(Integer)
-	is_bot = Column(Boolean, default=False)
-	stickied = Column(String)
-	stickied_utc = Column(Integer)
-	num_of_pinned_children = Column(Integer, default=0)
-	sentto = Column(Integer, ForeignKey("users.id"))
-	app_id = Column(Integer, ForeignKey("oauth_apps.id"))
-	upvotes = Column(Integer, default=1)
-	downvotes = Column(Integer, default=0)
-	realupvotes = Column(Integer, default=1)
-	body = Column(String)
-	body_html = Column(String)
-	body_ts = Column(TSVECTOR(), server_default=FetchedValue())
-	ban_reason = Column(String)
-	treasure_amount = Column(String)
-	slots_result = Column(String)
-	ping_cost = Column(Integer, default=0)
-	blackjack_result = Column(String)
-	casino_game_id = Column(Integer, ForeignKey("casino_games.id"))
-	chudded = Column(Boolean, default=False)
-	rainbowed = Column(Boolean, default=False)
-	queened = Column(Boolean, default=False)
-	sharpened = Column(Boolean, default=False)
+	id: Mapped[int_pk]
+	author_id: Mapped[user_id_fk]
+	parent_post: Mapped[Optional[post_id_fk]]
+	wall_user_id: Mapped[Optional[user_id_fk]]
+	created_utc: Mapped[int]
+	edited_utc: Mapped[int] = mapped_column(default=0)
+	is_banned: Mapped[bool] = mapped_column(default=False)
+	ghost: Mapped[bool] = mapped_column(default=False)
+	bannedfor: Mapped[Optional[str]]
+	chuddedfor: Mapped[Optional[str]]
+	distinguished: Mapped[bool] = mapped_column(default=False)
+	deleted_utc: Mapped[int] = mapped_column(default=0)
+	is_approved: Mapped[Optional[user_id_fk]]
+	level: Mapped[int] = mapped_column(default=1)
+	parent_comment_id: Mapped[Optional[comment_id_fk]]
+	top_comment_id: Mapped[Optional[int]]
+	is_bot: Mapped[bool] = mapped_column(default=False)
+	stickied: Mapped[Optional[str]]
+	stickied_utc: Mapped[Optional[int]]
+	num_of_pinned_children: Mapped[int] = mapped_column(default=0)
+	sentto: Mapped[Optional[user_id_fk]]
+	app_id: Mapped[Optional[int]] = mapped_column(ForeignKey("oauth_apps.id"))
+	upvotes: Mapped[int] = mapped_column(default=1)
+	downvotes: Mapped[int] = mapped_column(default=0)
+	realupvotes: Mapped[int] = mapped_column(default=1)
+	body: Mapped[Optional[str]]
+	body_html: Mapped[Optional[str]]
+	body_ts: Mapped[str] = mapped_column(TSVECTOR(), server_default=FetchedValue())
+	ban_reason: Mapped[Optional[str]]
+	treasure_amount: Mapped[Optional[str]]
+	slots_result: Mapped[Optional[str]]
+	ping_cost: Mapped[int] = mapped_column(default=0)
+	blackjack_result: Mapped[Optional[str]]
+	casino_game_id: Mapped[Optional[int]] = mapped_column(ForeignKey("casino_games.id"))
+	chudded: Mapped[bool] = mapped_column(default=False)
+	rainbowed: Mapped[bool] = mapped_column(default=False)
+	queened: Mapped[bool] = mapped_column(default=False)
+	sharpened: Mapped[bool] = mapped_column(default=False)
 
 	if FEATURES['NSFW_MARKING']:
-		nsfw = Column(Boolean, default=False)
+		nsfw: Mapped[bool] = mapped_column(default=False)
 	else:
 		nsfw = False
 
-	oauth_app = relationship("OauthApp")
-	post = relationship("Post", back_populates="comments")
-	author = relationship("User", primaryjoin="User.id==Comment.author_id")
-	senttouser = relationship("User", primaryjoin="User.id==Comment.sentto")
-	parent_comment = relationship("Comment", remote_side=[id])
-	awards = relationship("AwardRelationship", order_by="AwardRelationship.awarded_utc.desc()", back_populates="comment")
-	reports = relationship("CommentReport", order_by="CommentReport.created_utc")
-	options = relationship("CommentOption", order_by="CommentOption.id")
-	casino_game = relationship("CasinoGame")
-	wall_user = relationship("User", primaryjoin="User.id==Comment.wall_user_id")
+	oauth_app: Mapped["OauthApp"] = relationship()
+	post: Mapped["Post"] = relationship(back_populates="comments")
+	author: Mapped["User"] = relationship(primaryjoin="User.id==Comment.author_id")
+	senttouser: Mapped["User"] = relationship(primaryjoin="User.id==Comment.sentto")
+	parent_comment: Mapped["Comment"] = relationship(remote_side="Comment.id")
+	awards: Mapped[list["AwardRelationship"]] = relationship(order_by="AwardRelationship.awarded_utc.desc()", back_populates="comment")
+	reports: Mapped[list["CommentReport"]] = relationship(order_by="CommentReport.created_utc")
+	options: Mapped[list["CommentOption"]] = relationship(order_by="CommentOption.id")
+	casino_game: Mapped["CasinoGame"] = relationship()
+	wall_user: Mapped["User"] = relationship(primaryjoin="User.id==Comment.wall_user_id")
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs:
diff --git a/files/classes/domains.py b/files/classes/domains.py
index 4c6bf820c..af586a55d 100644
--- a/files/classes/domains.py
+++ b/files/classes/domains.py
@@ -1,15 +1,17 @@
 import time
+from typing import Optional
 
-from sqlalchemy import Column
+from sqlalchemy.orm import Mapped, mapped_column
 from sqlalchemy.sql.sqltypes import *
 
 from files.classes import Base
+from files.helpers.types import str_pk
 
 class BannedDomain(Base):
 	__tablename__ = "banneddomains"
-	domain = Column(String, primary_key=True)
-	reason = Column(String)
-	created_utc = Column(Integer)
+	domain: Mapped[str_pk]
+	reason: Mapped[str]
+	created_utc: Mapped[Optional[int]]
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
diff --git a/files/classes/emoji.py b/files/classes/emoji.py
index 1b43d5719..04f95e40c 100644
--- a/files/classes/emoji.py
+++ b/files/classes/emoji.py
@@ -1,21 +1,23 @@
 import time
+from typing import Optional
 
-from sqlalchemy import Column, ForeignKey
+from sqlalchemy.orm import Mapped, mapped_column
 from sqlalchemy.sql.sqltypes import *
 
 from files.classes import Base
+from files.helpers.types import str_pk, user_id_fk
 
 class Emoji(Base):
 	__tablename__ = "emojis"
 
-	name = Column(String, primary_key=True)
-	kind = Column(String)
-	author_id = Column(Integer, ForeignKey("users.id"))
-	tags = Column(String)
-	count = Column(Integer, default=0)
-	submitter_id = Column(Integer, ForeignKey("users.id"))
-	created_utc = Column(Integer)
-	nsfw = Column(Boolean, default=False)
+	name: Mapped[str_pk]
+	kind: Mapped[str]
+	author_id: Mapped[user_id_fk]
+	tags: Mapped[str]
+	count: Mapped[int] = mapped_column(default=0)
+	submitter_id: Mapped[Optional[user_id_fk]]
+	created_utc: Mapped[int]
+	nsfw: Mapped[bool] = mapped_column(default=False)
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
diff --git a/files/classes/follows.py b/files/classes/follows.py
index 67e253eec..ba9b6169d 100644
--- a/files/classes/follows.py
+++ b/files/classes/follows.py
@@ -1,19 +1,24 @@
 import time
+from typing import TYPE_CHECKING
 
-from sqlalchemy import Column, ForeignKey
-from sqlalchemy.orm import relationship
+from sqlalchemy.orm import Mapped, mapped_column, relationship
 from sqlalchemy.sql.sqltypes import *
 
 from files.classes import Base
+from files.helpers.types import user_id_fk_pk
+
+if TYPE_CHECKING:
+	from files.classes import User
+
 
 class Follow(Base):
 	__tablename__ = "follows"
-	target_id = Column(Integer, ForeignKey("users.id"), primary_key=True)
-	user_id = Column(Integer, ForeignKey("users.id"), primary_key=True)
-	created_utc = Column(Integer)
+	target_id: Mapped[user_id_fk_pk]
+	user_id: Mapped[user_id_fk_pk]
+	created_utc: Mapped[int]
 
-	user = relationship("User", uselist=False, primaryjoin="User.id==Follow.user_id", back_populates="following")
-	target = relationship("User", uselist=False, primaryjoin="User.id==Follow.target_id", back_populates="followers")
+	user: Mapped["User"] = relationship(uselist=False, primaryjoin="User.id==Follow.user_id", back_populates="following")
+	target: Mapped["User"] = relationship(uselist=False, primaryjoin="User.id==Follow.target_id", back_populates="followers")
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
diff --git a/files/classes/group.py b/files/classes/group.py
index 525e607f2..a7ea4f3c3 100644
--- a/files/classes/group.py
+++ b/files/classes/group.py
@@ -1,25 +1,29 @@
 import time
+from typing import Optional, TYPE_CHECKING
 
-from sqlalchemy import Column
-from sqlalchemy.orm import relationship
-from sqlalchemy.types import Integer
+from sqlalchemy.orm import Mapped, relationship
 
 from files.classes import Base
 from files.helpers.lazy import lazy
 from files.helpers.config.const import *
+from files.helpers.types import str_pk, user_id_fk
 
 from .group_membership import *
 
+if TYPE_CHECKING:
+	from files.classes import User
+
+
 class Group(Base):
 	__tablename__ = "groups"
-	name = Column(String, primary_key=True)
-	created_utc = Column(Integer)
-	owner_id = Column(Integer, ForeignKey("users.id"))
-	description = Column(String)
-	description_html = Column(String)
+	name: Mapped[str_pk]
+	created_utc: Mapped[int]
+	owner_id: Mapped[Optional[user_id_fk]]
+	description: Mapped[Optional[str]]
+	description_html: Mapped[Optional[str]]
 
-	memberships = relationship("GroupMembership", primaryjoin="GroupMembership.group_name==Group.name", order_by="GroupMembership.approved_utc")
-	owner = relationship("User", primaryjoin="Group.owner_id==User.id")
+	memberships: Mapped[list["GroupMembership"]] = relationship(primaryjoin="GroupMembership.group_name==Group.name", order_by="GroupMembership.approved_utc")
+	owner: Mapped["User"] = relationship(primaryjoin="Group.owner_id==User.id")
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
diff --git a/files/classes/group_membership.py b/files/classes/group_membership.py
index e0adf493d..c50b74eae 100644
--- a/files/classes/group_membership.py
+++ b/files/classes/group_membership.py
@@ -1,20 +1,25 @@
 import time
+from typing import Optional, TYPE_CHECKING
 
-from sqlalchemy import Column, ForeignKey
-from sqlalchemy.orm import relationship
-from sqlalchemy.types import Integer, String, Boolean
+from sqlalchemy import ForeignKey
+from sqlalchemy.orm import Mapped, mapped_column, relationship
 
 from files.classes import Base
+from files.helpers.types import user_id_fk_pk
+
+if TYPE_CHECKING:
+	from files.classes.user import User
+
 
 class GroupMembership(Base):
 	__tablename__ = "group_memberships"
-	user_id = Column(Integer, ForeignKey("users.id"), primary_key=True)
-	group_name = Column(String, ForeignKey("groups.name"), primary_key=True)
-	created_utc = Column(Integer)
-	approved_utc = Column(Integer)
-	is_mod = Column(Boolean, default=False)
+	user_id: Mapped[user_id_fk_pk]
+	group_name: Mapped[str] = mapped_column(ForeignKey("groups.name"), primary_key=True)
+	created_utc: Mapped[int]
+	approved_utc: Mapped[Optional[int]]
+	is_mod: Mapped[bool] = mapped_column(default=False)
 
-	user = relationship("User", uselist=False)
+	user: Mapped["User"] = relationship(uselist=False)
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
diff --git a/files/classes/hats.py b/files/classes/hats.py
index 746ffc73f..a24e3c556 100644
--- a/files/classes/hats.py
+++ b/files/classes/hats.py
@@ -1,27 +1,33 @@
 import time
+from typing import Optional, TYPE_CHECKING
 
-from sqlalchemy import Column, ForeignKey
-from sqlalchemy.orm import relationship
+from sqlalchemy import ForeignKey
+from sqlalchemy.orm import Mapped, mapped_column, relationship
 from sqlalchemy.sql.sqltypes import *
 from flask import g
 
 from files.classes import Base
 from files.helpers.lazy import lazy
 from files.helpers.slurs_and_profanities import censor_slurs_profanities
+from files.helpers.types import int_pk, user_id_fk
+
+if TYPE_CHECKING:
+	from files.classes import User
+
 
 class HatDef(Base):
 	__tablename__ = "hat_defs"
 
-	id = Column(Integer, primary_key=True)
-	name = Column(String)
-	description = Column(String)
-	author_id = Column(Integer, ForeignKey('users.id'))
-	price = Column(Integer)
-	submitter_id = Column(Integer, ForeignKey("users.id"))
-	created_utc = Column(Integer)
+	id: Mapped[int_pk]
+	name: Mapped[str]
+	description: Mapped[str]
+	author_id: Mapped[int] = mapped_column(ForeignKey('users.id'))
+	price: Mapped[int]
+	submitter_id: Mapped[Optional[user_id_fk]]
+	created_utc: Mapped[int]
 
-	author = relationship("User", primaryjoin="HatDef.author_id == User.id", back_populates="designed_hats")
-	submitter = relationship("User", primaryjoin="HatDef.submitter_id == User.id")
+	author: Mapped["User"] = relationship(primaryjoin="HatDef.author_id == User.id", back_populates="designed_hats")
+	submitter: Mapped["User"] = relationship(primaryjoin="HatDef.submitter_id == User.id")
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
@@ -48,13 +54,13 @@ class HatDef(Base):
 class Hat(Base):
 	__tablename__ = "hats"
 
-	user_id = Column(Integer, ForeignKey('users.id'), primary_key=True)
-	hat_id = Column(Integer, ForeignKey('hat_defs.id'), primary_key=True)
-	equipped = Column(Boolean, default=False)
-	created_utc = Column(Integer)
+	user_id: Mapped[int] = mapped_column(ForeignKey('users.id'), primary_key=True)
+	hat_id: Mapped[int] = mapped_column(ForeignKey('hat_defs.id'), primary_key=True)
+	equipped: Mapped[Optional[bool]] = mapped_column(default=False)
+	created_utc: Mapped[Optional[int]]
 
-	hat_def = relationship("HatDef")
-	owners = relationship("User", back_populates="owned_hats")
+	hat_def: Mapped["HatDef"] = relationship()
+	owners: Mapped[list["User"]] = relationship(back_populates="owned_hats")
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
diff --git a/files/classes/hole.py b/files/classes/hole.py
index b4cc4200c..aade37b6b 100644
--- a/files/classes/hole.py
+++ b/files/classes/hole.py
@@ -1,10 +1,9 @@
 import random
 import time
+from typing import Annotated, Optional
 
-from sqlalchemy import Column
 from sqlalchemy.ext.mutable import MutableList
-from sqlalchemy.orm import relationship, deferred
-from sqlalchemy.types import *
+from sqlalchemy.orm import DynamicMapped, Mapped, mapped_column, relationship
 from sqlalchemy.dialects.postgresql import ARRAY
 
 from files.classes import Base
@@ -15,24 +14,24 @@ from .hole_relationship import *
 
 class Hole(Base):
 	__tablename__ = "holes"
-	name = Column(String, primary_key=True)
-	sidebar = Column(String)
-	sidebar_html = Column(String)
-	sidebarurls = Column(MutableList.as_mutable(ARRAY(String)), default=MutableList([]))
-	bannerurls = Column(MutableList.as_mutable(ARRAY(String)), default=MutableList([]))
-	marseyurl = Column(String)
-	css = deferred(Column(String))
-	stealth = Column(Boolean, default=False)
-	public_use = Column(Boolean, default=False)
-	created_utc = Column(Integer)
+	name: Mapped[str] = mapped_column(primary_key=True)
+	sidebar: Mapped[Optional[str]]
+	sidebar_html: Mapped[Optional[str]]
+	sidebarurls: Mapped[list[str]] = mapped_column(MutableList.as_mutable(ARRAY(String)), default=MutableList([]))
+	bannerurls: Mapped[list[str]] = mapped_column(MutableList.as_mutable(ARRAY(String)), default=MutableList([]))
+	marseyurl: Mapped[Optional[str]]
+	css: Mapped[Optional[str]] = mapped_column(deferred=True)
+	stealth: Mapped[Optional[bool]] = mapped_column(default=False)
+	public_use: Mapped[bool] = mapped_column(default=False)
+	created_utc: Mapped[Optional[int]]
 	if SITE_NAME == 'WPD':
 		snappy_quotes = None
 	else:
-		snappy_quotes = deferred(Column(String))
+		snappy_quotes: Mapped[Optional[Annotated[str, HOLE_SNAPPY_QUOTES_LENGTH]]] = mapped_column(deferred=True)
 
-	blocks = relationship("HoleBlock", primaryjoin="HoleBlock.hole==Hole.name")
-	followers = relationship("HoleFollow", primaryjoin="HoleFollow.hole==Hole.name")
-	stealth_hole_unblocks = relationship("StealthHoleUnblock", lazy="dynamic", primaryjoin="StealthHoleUnblock.hole==Hole.name")
+	blocks: Mapped[list["HoleBlock"]] = relationship(primaryjoin="HoleBlock.hole==Hole.name")
+	followers: Mapped[list["HoleFollow"]] = relationship(primaryjoin="HoleFollow.hole==Hole.name")
+	stealth_hole_unblocks: DynamicMapped["StealthHoleUnblock"] = relationship(primaryjoin="StealthHoleUnblock.hole==Hole.name")
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
diff --git a/files/classes/hole_logs.py b/files/classes/hole_logs.py
index aa45dc484..a2e6957ac 100644
--- a/files/classes/hole_logs.py
+++ b/files/classes/hole_logs.py
@@ -1,7 +1,8 @@
 import time
+from typing import Optional, TYPE_CHECKING
 
-from sqlalchemy import Column, ForeignKey
-from sqlalchemy.orm import relationship
+from sqlalchemy import ForeignKey
+from sqlalchemy.orm import Mapped, mapped_column, relationship
 from sqlalchemy.sql.sqltypes import *
 from flask import g
 
@@ -10,23 +11,28 @@ from files.helpers.config.const import *
 from files.helpers.lazy import lazy
 from files.helpers.slurs_and_profanities import censor_slurs_profanities
 from files.helpers.sorting_and_time import make_age_string
+from files.helpers.types import comment_id_fk, int_pk, post_id_fk, user_id_fk
+
+if TYPE_CHECKING:
+	from files.classes import Comment, Post, User
+
 
 class HoleAction(Base):
 	__tablename__ = "hole_actions"
-	id = Column(Integer, primary_key=True)
-	hole = Column(String, ForeignKey("holes.name"))
-	user_id = Column(Integer, ForeignKey("users.id"))
-	kind = Column(String)
-	target_user_id = Column(Integer, ForeignKey("users.id"))
-	target_post_id = Column(Integer, ForeignKey("posts.id"))
-	target_comment_id = Column(Integer, ForeignKey("comments.id"))
-	_note = Column(String)
-	created_utc = Column(Integer)
+	id: Mapped[int_pk]
+	hole: Mapped[str] = mapped_column(ForeignKey("holes.name"))
+	user_id: Mapped[Optional[user_id_fk]]
+	kind: Mapped[Optional[str]]
+	target_user_id: Mapped[Optional[user_id_fk]]
+	target_post_id: Mapped[Optional[post_id_fk]]
+	target_comment_id: Mapped[Optional[comment_id_fk]]
+	_note: Mapped[Optional[str]]
+	created_utc: Mapped[int]
 
-	user = relationship("User", primaryjoin="User.id==HoleAction.user_id")
-	target_user = relationship("User", primaryjoin="User.id==HoleAction.target_user_id")
-	target_post = relationship("Post")
-	target_comment = relationship("Comment")
+	user: Mapped["User"] = relationship(primaryjoin="User.id==HoleAction.user_id")
+	target_user: Mapped["User"] = relationship(primaryjoin="User.id==HoleAction.target_user_id")
+	target_post: Mapped["Post"] = relationship()
+	target_comment: Mapped["Comment"] = relationship()
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
diff --git a/files/classes/hole_relationship.py b/files/classes/hole_relationship.py
index a231ad862..89a9b6971 100644
--- a/files/classes/hole_relationship.py
+++ b/files/classes/hole_relationship.py
@@ -1,18 +1,23 @@
 import time
+from typing import Optional, TYPE_CHECKING
 
-from sqlalchemy import Column, ForeignKey
-from sqlalchemy.orm import relationship
+from sqlalchemy import ForeignKey
+from sqlalchemy.orm import Mapped, relationship, mapped_column
 from sqlalchemy.sql.sqltypes import *
 
 from files.classes import Base
 
+if TYPE_CHECKING:
+	from files.classes import User
+
+
 class HoleRelationship(Base):
 	__tablename__ = NotImplemented
 	__abstract__ = True
 
-	user_id = Column(Integer, ForeignKey("users.id"), primary_key=True)
-	hole = Column(String, ForeignKey("holes.name"), primary_key=True)
-	created_utc = Column(Integer)
+	user_id: Mapped[int] = mapped_column(ForeignKey("users.id"), primary_key=True)
+	hole: Mapped[str] = mapped_column(ForeignKey("holes.name"), primary_key=True)
+	created_utc: Mapped[Optional[int]]
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
@@ -35,5 +40,5 @@ class Mod(HoleRelationship):
 
 class Exile(HoleRelationship):
 	__tablename__ = "exiles"
-	exiler_id = Column(Integer, ForeignKey("users.id"))
-	exiler = relationship("User", primaryjoin="User.id==Exile.exiler_id")
+	exiler_id: Mapped[int] = mapped_column(ForeignKey("users.id"))
+	exiler: Mapped["User"] = relationship(primaryjoin="User.id==Exile.exiler_id")
diff --git a/files/classes/ip_logs.py b/files/classes/ip_logs.py
index 3d6d3db37..a37af0018 100644
--- a/files/classes/ip_logs.py
+++ b/files/classes/ip_logs.py
@@ -1,19 +1,24 @@
 import time
+from typing import TYPE_CHECKING
 
-from sqlalchemy import Column, ForeignKey
-from sqlalchemy.orm import relationship
+from sqlalchemy.orm import Mapped, relationship
 from sqlalchemy.sql.sqltypes import *
 
 from files.classes import Base
+from files.helpers.types import str_pk, user_id_fk_pk
+
+if TYPE_CHECKING:
+	from files.classes import User
+
 
 class IPLog(Base):
 	__tablename__ = "ip_logs"
-	user_id = Column(Integer, ForeignKey("users.id"), primary_key=True)
-	ip = Column(String, primary_key=True)
-	created_utc = Column(Integer)
-	last_used = Column(Integer)
+	user_id: Mapped[user_id_fk_pk]
+	ip: Mapped[str_pk]
+	created_utc: Mapped[int]
+	last_used: Mapped[int]
 
-	user = relationship("User")
+	user: Mapped["User"] = relationship()
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs:
diff --git a/files/classes/lottery.py b/files/classes/lottery.py
index abde47b0b..0e1850f9d 100644
--- a/files/classes/lottery.py
+++ b/files/classes/lottery.py
@@ -1,22 +1,24 @@
 import time
+from typing import Optional
 
-from sqlalchemy import Column, ForeignKey
+from sqlalchemy.orm import Mapped, mapped_column
 from sqlalchemy.sql.sqltypes import *
 
 from files.classes import Base
 from files.helpers.config.const import *
 from files.helpers.lazy import lazy
+from files.helpers.types import int_pk, user_id_fk
 
 class Lottery(Base):
 	__tablename__ = "lotteries"
 
-	id = Column(Integer, primary_key=True)
-	is_active = Column(Boolean, default=False)
-	ends_at = Column(Integer)
-	prize = Column(Integer, default=0)
-	tickets_sold = Column(Integer, default=0)
-	winner_id = Column(Integer, ForeignKey("users.id"))
-	created_utc = Column(Integer)
+	id: Mapped[int_pk]
+	is_active: Mapped[bool] = mapped_column(default=False)
+	ends_at: Mapped[int]
+	prize: Mapped[int] = mapped_column(default=0)
+	tickets_sold: Mapped[int] = mapped_column(default=0)
+	winner_id: Mapped[Optional[user_id_fk]]
+	created_utc: Mapped[Optional[int]]
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
diff --git a/files/classes/media.py b/files/classes/media.py
index 574c0a3c4..939a4a3b4 100644
--- a/files/classes/media.py
+++ b/files/classes/media.py
@@ -1,16 +1,17 @@
 import time
 
-from sqlalchemy import Column, ForeignKey
+from sqlalchemy.orm import Mapped
 from sqlalchemy.sql.sqltypes import *
 from files.classes import Base
+from files.helpers.types import str_pk, user_id_fk
 
 class Media(Base):
 	__tablename__ = "media"
-	kind = Column(String, primary_key=True)
-	filename = Column(String, primary_key=True)
-	user_id = Column(Integer, ForeignKey("users.id"))
-	created_utc = Column(Integer)
-	size = Column(Integer)
+	kind: Mapped[str_pk]
+	filename: Mapped[str_pk]
+	user_id: Mapped[user_id_fk]
+	created_utc: Mapped[int]
+	size: Mapped[int]
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
diff --git a/files/classes/mod_logs.py b/files/classes/mod_logs.py
index 94a009ad3..fefe904c3 100644
--- a/files/classes/mod_logs.py
+++ b/files/classes/mod_logs.py
@@ -1,7 +1,7 @@
 import time
+from typing import Optional, TYPE_CHECKING
 
-from sqlalchemy import Column, ForeignKey
-from sqlalchemy.orm import relationship
+from sqlalchemy.orm import Mapped, relationship
 from sqlalchemy.sql.sqltypes import *
 from flask import g
 
@@ -10,22 +10,27 @@ from files.helpers.config.const import *
 from files.helpers.lazy import lazy
 from files.helpers.slurs_and_profanities import censor_slurs_profanities
 from files.helpers.sorting_and_time import make_age_string
+from files.helpers.types import comment_id_fk, int_pk, post_id_fk, user_id_fk
+
+if TYPE_CHECKING:
+	from files.classes import Comment, Post, User
+
 
 class ModAction(Base):
 	__tablename__ = "modactions"
-	id = Column(Integer, primary_key=True)
-	user_id = Column(Integer, ForeignKey("users.id"))
-	kind = Column(String)
-	target_user_id = Column(Integer, ForeignKey("users.id"))
-	target_post_id = Column(Integer, ForeignKey("posts.id"))
-	target_comment_id = Column(Integer, ForeignKey("comments.id"))
-	_note = Column(String)
-	created_utc = Column(Integer)
+	id: Mapped[int_pk]
+	user_id: Mapped[Optional[user_id_fk]]
+	kind: Mapped[Optional[str]]
+	target_user_id: Mapped[Optional[user_id_fk]]
+	target_post_id: Mapped[Optional[post_id_fk]]
+	target_comment_id: Mapped[Optional[comment_id_fk]]
+	_note: Mapped[Optional[str]]
+	created_utc: Mapped[int]
 
-	user = relationship("User", primaryjoin="User.id==ModAction.user_id")
-	target_user = relationship("User", primaryjoin="User.id==ModAction.target_user_id")
-	target_post = relationship("Post")
-	target_comment = relationship("Comment")
+	user: Mapped["User"] = relationship(primaryjoin="User.id==ModAction.user_id")
+	target_user: Mapped["User"] = relationship(primaryjoin="User.id==ModAction.target_user_id")
+	target_post: Mapped["Post"] = relationship()
+	target_comment: Mapped["Comment"] = relationship()
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
diff --git a/files/classes/notifications.py b/files/classes/notifications.py
index 5ad09c049..5986b106a 100644
--- a/files/classes/notifications.py
+++ b/files/classes/notifications.py
@@ -1,21 +1,26 @@
 import time
+from typing import TYPE_CHECKING
 
-from sqlalchemy import Column, ForeignKey
-from sqlalchemy.orm import relationship
+from sqlalchemy.orm import Mapped, mapped_column, relationship
 from sqlalchemy.sql.sqltypes import *
 
 from files.classes import Base
+from files.helpers.types import comment_id_fk_pk, user_id_fk_pk
+
+if TYPE_CHECKING:
+	from files.classes import Comment, User
+
 
 class Notification(Base):
 	__tablename__ = "notifications"
 
-	user_id = Column(Integer, ForeignKey("users.id"), primary_key=True)
-	comment_id = Column(Integer, ForeignKey("comments.id"), primary_key=True)
-	read = Column(Boolean, default=False)
-	created_utc = Column(Integer)
+	user_id: Mapped[user_id_fk_pk]
+	comment_id: Mapped[comment_id_fk_pk]
+	read: Mapped[bool] = mapped_column(default=False)
+	created_utc: Mapped[int]
 
-	comment = relationship("Comment")
-	user = relationship("User")
+	comment: Mapped["Comment"] = relationship()
+	user: Mapped["User"] = relationship()
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
diff --git a/files/classes/orgy.py b/files/classes/orgy.py
index 80bee5d2f..6f6b795c5 100644
--- a/files/classes/orgy.py
+++ b/files/classes/orgy.py
@@ -1,11 +1,13 @@
 import time
 from flask import g, abort
 import requests
+from typing import Optional
 
-from sqlalchemy import Column, or_
+from sqlalchemy.orm import Mapped, mapped_column
 from sqlalchemy.sql.sqltypes import *
 
 from files.classes import Base
+from files.helpers.types import int_pk
 
 from files.helpers.lazy import lazy
 from files.helpers.config.const import *
@@ -13,13 +15,13 @@ from files.helpers.config.const import *
 class Orgy(Base):
 	__tablename__ = "orgies"
 
-	created_utc = Column(Integer, primary_key=True)
-	type = Column(String)
-	data = Column(String)
-	title = Column(String)
-	start_utc = Column(Integer)
-	end_utc = Column(Integer)
-	started = Column(Boolean, default=False)
+	created_utc: Mapped[int_pk]
+	type: Mapped[str]
+	data: Mapped[str]
+	title: Mapped[str]
+	start_utc: Mapped[int]
+	end_utc: Mapped[Optional[int]]
+	started: Mapped[bool] = mapped_column(default=False)
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
diff --git a/files/classes/polls.py b/files/classes/polls.py
index 3b7923e1e..a5636f3c5 100644
--- a/files/classes/polls.py
+++ b/files/classes/polls.py
@@ -1,23 +1,29 @@
 import time
+from typing import Optional, TYPE_CHECKING
 
-from sqlalchemy import Column, ForeignKey
-from sqlalchemy.orm import relationship
+from sqlalchemy import ForeignKey
+from sqlalchemy.orm import Mapped, mapped_column, relationship
 from sqlalchemy.sql.sqltypes import *
 
 from files.classes import Base
 from files.helpers.lazy import lazy
+from files.helpers.types import comment_id_fk, int_pk, post_id_fk, user_id_fk_pk
+
+if TYPE_CHECKING:
+	from files.classes import Comment, Post, User
+
 
 class PostOption(Base):
 	__tablename__ = "post_options"
 
-	id = Column(Integer, primary_key=True)
-	parent_id = Column(Integer, ForeignKey("posts.id"))
-	body_html = Column(Text)
-	exclusive = Column(Integer)
-	created_utc = Column(Integer)
+	id: Mapped[int_pk]
+	parent_id: Mapped[post_id_fk]
+	body_html: Mapped[str] = mapped_column(Text)
+	exclusive: Mapped[int]
+	created_utc: Mapped[Optional[int]]
 
-	votes = relationship("PostOptionVote")
-	parent = relationship("Post", back_populates="options")
+	votes: Mapped[list["PostOptionVote"]] = relationship()
+	parent: Mapped["Post"] = relationship(back_populates="options")
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
@@ -40,12 +46,12 @@ class PostOptionVote(Base):
 
 	__tablename__ = "post_option_votes"
 
-	option_id = Column(Integer, ForeignKey("post_options.id"), primary_key=True)
-	user_id = Column(Integer, ForeignKey("users.id"), primary_key=True)
-	created_utc = Column(Integer)
-	post_id = Column(Integer, ForeignKey("posts.id"))
+	option_id: Mapped[int] = mapped_column(ForeignKey("post_options.id"), primary_key=True)
+	user_id: Mapped[user_id_fk_pk]
+	created_utc: Mapped[int]
+	post_id: Mapped[Optional[post_id_fk]]
 
-	user = relationship("User")
+	user: Mapped["User"] = relationship()
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
@@ -59,14 +65,14 @@ class CommentOption(Base):
 
 	__tablename__ = "comment_options"
 
-	id = Column(Integer, primary_key=True)
-	parent_id = Column(Integer, ForeignKey("comments.id"))
-	body_html = Column(Text)
-	exclusive = Column(Integer)
-	created_utc = Column(Integer)
+	id: Mapped[int_pk]
+	parent_id: Mapped[comment_id_fk]
+	body_html: Mapped[str] = mapped_column(Text)
+	exclusive: Mapped[int]
+	created_utc: Mapped[Optional[int]]
 
-	votes = relationship("CommentOptionVote")
-	parent = relationship("Comment", back_populates="options")
+	votes: Mapped[list["CommentOptionVote"]] = relationship()
+	parent: Mapped["Comment"] = relationship(back_populates="options")
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
@@ -89,12 +95,12 @@ class CommentOptionVote(Base):
 
 	__tablename__ = "comment_option_votes"
 
-	option_id = Column(Integer, ForeignKey("comment_options.id"), primary_key=True)
-	user_id = Column(Integer, ForeignKey("users.id"), primary_key=True)
-	created_utc = Column(Integer)
-	comment_id = Column(Integer, ForeignKey("comments.id"))
+	option_id: Mapped[int] = mapped_column(ForeignKey("comment_options.id"), primary_key=True)
+	user_id: Mapped[user_id_fk_pk]
+	created_utc: Mapped[int]
+	comment_id: Mapped[Optional[comment_id_fk]]
 
-	user = relationship("User")
+	user: Mapped["User"] = relationship()
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
diff --git a/files/classes/post.py b/files/classes/post.py
index 5fc1b5a6d..dd09ed11b 100644
--- a/files/classes/post.py
+++ b/files/classes/post.py
@@ -1,10 +1,11 @@
 import random
 import time
+from typing import Optional, TYPE_CHECKING
 from urllib.parse import urlparse
 from flask import g
 
-from sqlalchemy import Column, FetchedValue, ForeignKey
-from sqlalchemy.orm import deferred, relationship
+from sqlalchemy import ForeignKey
+from sqlalchemy.orm import Mapped, mapped_column, relationship
 from sqlalchemy.sql.sqltypes import *
 
 from files.classes import Base
@@ -14,6 +15,7 @@ from files.helpers.slurs_and_profanities import *
 from files.helpers.lazy import lazy
 from files.helpers.regex import *
 from files.helpers.sorting_and_time import make_age_string
+from files.helpers.types import int_pk, user_id_fk
 from files.helpers.bleach_body import *
 
 from .comment import *
@@ -22,69 +24,73 @@ from .hole import *
 from .subscriptions import *
 from .saves import SaveRelationship
 
+if TYPE_CHECKING:
+	from files.classes import OauthApp, Report
+
+
 class Post(Base):
 	__tablename__ = "posts"
 
-	id = Column(Integer, primary_key=True)
-	author_id = Column(Integer, ForeignKey("users.id"))
-	edited_utc = Column(Integer, default=0)
-	created_utc = Column(Integer)
-	thumburl = Column(String)
-	posterurl = Column(String)
-	is_banned = Column(Boolean, default=False)
-	bannedfor = Column(String)
-	chuddedfor = Column(String)
-	ghost = Column(Boolean, default=False)
-	effortpost = Column(Boolean, default=False)
-	views = Column(Integer, default=0)
-	deleted_utc = Column(Integer, default=0)
-	distinguished = Column(Boolean, default=False)
-	stickied = Column(String)
-	stickied_utc = Column(Integer)
-	hole_pinned = Column(String)
-	hole = Column(String, ForeignKey("holes.name"))
-	is_pinned = Column(Boolean, default=False)
-	private = Column(Boolean, default=False)
-	comment_count = Column(Integer, default=0)
-	is_approved = Column(Integer, ForeignKey("users.id"))
-	is_bot = Column(Boolean, default=False)
-	upvotes = Column(Integer, default=1)
-	downvotes = Column(Integer, default=0)
-	realupvotes = Column(Integer, default=1)
-	app_id = Column(Integer, ForeignKey("oauth_apps.id"))
-	title = Column(String)
-	title_html = Column(String)
-	url = Column(String)
-	body = Column(String)
-	body_html = Column(String)
-	flair = Column(String)
-	ban_reason = Column(String)
-	embed = Column(String)
-	new = Column(Boolean)
-	notify = Column(Boolean)
-	chudded = Column(Boolean, default=False)
-	rainbowed = Column(Boolean, default=False)
-	queened = Column(Boolean, default=False)
-	sharpened = Column(Boolean, default=False)
-	ping_cost = Column(Integer, default=0)
-	bump_utc = Column(Integer)
+	id: Mapped[int_pk]
+	author_id: Mapped[user_id_fk]
+	edited_utc: Mapped[int] = mapped_column(default=0)
+	created_utc: Mapped[int]
+	thumburl: Mapped[Optional[str]]
+	posterurl: Mapped[Optional[str]]
+	is_banned: Mapped[bool] = mapped_column(default=False)
+	bannedfor: Mapped[Optional[str]]
+	chuddedfor: Mapped[Optional[str]]
+	ghost: Mapped[bool] = mapped_column(default=False)
+	effortpost: Mapped[bool] = mapped_column(default=False)
+	views: Mapped[int] = mapped_column(default=0)
+	deleted_utc: Mapped[int] = mapped_column(default=0)
+	distinguished: Mapped[bool] = mapped_column(default=False)
+	stickied: Mapped[Optional[str]]
+	stickied_utc: Mapped[Optional[int]]
+	hole_pinned: Mapped[Optional[str]]
+	hole: Mapped[Optional[str]] = mapped_column(ForeignKey("holes.name"))
+	is_pinned: Mapped[bool] = mapped_column(default=False)
+	private: Mapped[bool] = mapped_column(default=False)
+	comment_count: Mapped[int] = mapped_column(default=0)
+	is_approved: Mapped[Optional[user_id_fk]]
+	is_bot: Mapped[bool] = mapped_column(default=False)
+	upvotes: Mapped[int] = mapped_column(default=1)
+	downvotes: Mapped[int] = mapped_column(default=0)
+	realupvotes: Mapped[Optional[int]] = mapped_column(default=1)
+	app_id: Mapped[Optional[int]] = mapped_column(ForeignKey("oauth_apps.id"))
+	title: Mapped[str]
+	title_html: Mapped[str]
+	url: Mapped[Optional[str]]
+	body: Mapped[Optional[str]]
+	body_html: Mapped[Optional[str]]
+	flair: Mapped[Optional[str]]
+	ban_reason: Mapped[Optional[str]]
+	embed: Mapped[Optional[str]]
+	new: Mapped[Optional[bool]]
+	notify: Mapped[bool]
+	chudded: Mapped[bool] = mapped_column(default=False)
+	rainbowed: Mapped[bool] = mapped_column(default=False)
+	queened: Mapped[bool] = mapped_column(default=False)
+	sharpened: Mapped[bool] = mapped_column(default=False)
+	ping_cost: Mapped[int] = mapped_column(default=0)
+	bump_utc: Mapped[int]
 
 	if FEATURES['NSFW_MARKING']:
-		nsfw = Column(Boolean, default=False)
+		nsfw: Mapped[bool] = mapped_column(default=False)
 	else:
 		nsfw = False
 
 	if SITE_NAME == 'WPD':
-		cw = Column(Boolean, default=False)
+		cw: Mapped[bool] = mapped_column(default=False)
 
-	author = relationship("User", primaryjoin="Post.author_id==User.id")
-	oauth_app = relationship("OauthApp")
-	approved_by = relationship("User", uselist=False, primaryjoin="Post.is_approved==User.id")
-	awards = relationship("AwardRelationship", order_by="AwardRelationship.awarded_utc.desc()", back_populates="post")
-	reports = relationship("Report", order_by="Report.created_utc")
-	comments = relationship("Comment", primaryjoin="Comment.parent_post==Post.id", back_populates="post")
-	hole_obj = relationship("Hole", primaryjoin="foreign(Post.hole)==remote(Hole.name)")
-	options = relationship("PostOption", order_by="PostOption.id")
+	author: Mapped["User"] = relationship(primaryjoin="Post.author_id==User.id")
+	oauth_app: Mapped["OauthApp"] = relationship()
+	approved_by: Mapped["User"] = relationship(uselist=False, primaryjoin="Post.is_approved==User.id")
+	awards: Mapped[list["AwardRelationship"]] = relationship(order_by="AwardRelationship.awarded_utc.desc()", back_populates="post")
+	reports: Mapped[list["Report"]] = relationship(order_by="Report.created_utc")
+	comments: Mapped[list["Comment"]] = relationship(primaryjoin="Comment.parent_post==Post.id", back_populates="post")
+	hole_obj: Mapped["Hole"] = relationship(primaryjoin="foreign(Post.hole)==remote(Hole.name)")
+	options: Mapped[list["PostOption"]] = relationship(order_by="PostOption.id")
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs:
diff --git a/files/classes/push_subscriptions.py b/files/classes/push_subscriptions.py
index 0a34763a9..24eda989f 100644
--- a/files/classes/push_subscriptions.py
+++ b/files/classes/push_subscriptions.py
@@ -1,15 +1,16 @@
 import time
 
-from sqlalchemy import Column, ForeignKey
+from sqlalchemy.orm import Mapped
 from sqlalchemy.sql.sqltypes import *
 
 from files.classes import Base
+from files.helpers.types import str_pk, user_id_fk_pk
 
 class PushSubscription(Base):
 	__tablename__ = "push_subscriptions"
-	user_id = Column(Integer, ForeignKey("users.id"), primary_key=True)
-	subscription_json = Column(String, primary_key=True)
-	created_utc = Column(Integer)
+	user_id: Mapped[user_id_fk_pk]
+	subscription_json: Mapped[str_pk]
+	created_utc: Mapped[int]
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
diff --git a/files/classes/reports.py b/files/classes/reports.py
index f05e391f2..b99e8d5b1 100644
--- a/files/classes/reports.py
+++ b/files/classes/reports.py
@@ -1,22 +1,27 @@
 import time
+from typing import Optional, TYPE_CHECKING
 
-from sqlalchemy import Column, ForeignKey
-from sqlalchemy.orm import relationship
+from sqlalchemy.orm import Mapped, relationship
 from sqlalchemy.sql.sqltypes import *
 
 from files.classes import Base
 from files.helpers.lazy import lazy
 from files.helpers.slurs_and_profanities import censor_slurs_profanities
+from files.helpers.types import comment_id_fk_pk, post_id_fk_pk, user_id_fk_pk
+
+if TYPE_CHECKING:
+	from files.classes import User
+
 
 class Report(Base):
 	__tablename__ = "reports"
 
-	post_id = Column(Integer, ForeignKey("posts.id"), primary_key=True)
-	user_id = Column(Integer, ForeignKey("users.id"), primary_key=True)
-	reason = Column(String)
-	created_utc = Column(Integer)
+	post_id: Mapped[post_id_fk_pk]
+	user_id: Mapped[user_id_fk_pk]
+	reason: Mapped[Optional[str]]
+	created_utc: Mapped[int]
 
-	user = relationship("User", primaryjoin = "Report.user_id == User.id", uselist = False)
+	user: Mapped["User"] = relationship(primaryjoin = "Report.user_id == User.id", uselist = False)
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
@@ -39,12 +44,12 @@ class Report(Base):
 class CommentReport(Base):
 	__tablename__ = "commentreports"
 
-	comment_id = Column(Integer, ForeignKey("comments.id"), primary_key=True)
-	user_id = Column(Integer, ForeignKey("users.id"), primary_key=True)
-	reason = Column(String)
-	created_utc = Column(Integer)
+	comment_id: Mapped[comment_id_fk_pk]
+	user_id: Mapped[user_id_fk_pk]
+	reason: Mapped[Optional[str]]
+	created_utc: Mapped[int]
 
-	user = relationship("User", primaryjoin = "CommentReport.user_id == User.id", uselist = False)
+	user: Mapped["User"] = relationship(primaryjoin = "CommentReport.user_id == User.id", uselist = False)
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
diff --git a/files/classes/saves.py b/files/classes/saves.py
index 0eeef40d7..186f8bf4a 100644
--- a/files/classes/saves.py
+++ b/files/classes/saves.py
@@ -1,19 +1,25 @@
 import time
+from typing import Optional, TYPE_CHECKING
 
-from sqlalchemy import Column, ForeignKey
-from sqlalchemy.orm import relationship
+from sqlalchemy.orm import Mapped, relationship
 from sqlalchemy.sql.sqltypes import *
 
 from files.classes import Base
+from files.helpers.types import comment_id_fk_pk, post_id_fk_pk, user_id_fk_pk
+
+if TYPE_CHECKING:
+	from files.classes.comment import Comment
+	from files.classes.post import Post
+
 
 class SaveRelationship(Base):
 	__tablename__ = "save_relationship"
 
-	user_id = Column(Integer, ForeignKey("users.id"), primary_key=True)
-	post_id = Column(Integer, ForeignKey("posts.id"), primary_key=True)
-	created_utc = Column(Integer)
+	user_id: Mapped[user_id_fk_pk]
+	post_id: Mapped[post_id_fk_pk]
+	created_utc: Mapped[Optional[int]]
 
-	post = relationship("Post", uselist=False)
+	post: Mapped["Post"] = relationship(uselist=False)
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
@@ -27,11 +33,11 @@ class CommentSaveRelationship(Base):
 
 	__tablename__ = "comment_save_relationship"
 
-	user_id = Column(Integer, ForeignKey("users.id"), primary_key=True)
-	comment_id = Column(Integer, ForeignKey("comments.id"), primary_key=True)
-	created_utc = Column(Integer)
+	user_id: Mapped[user_id_fk_pk]
+	comment_id: Mapped[comment_id_fk_pk]
+	created_utc: Mapped[Optional[int]]
 
-	comment = relationship("Comment", uselist=False)
+	comment: Mapped["Comment"] = relationship(uselist=False)
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
diff --git a/files/classes/subscriptions.py b/files/classes/subscriptions.py
index 46d746fed..f1d581567 100644
--- a/files/classes/subscriptions.py
+++ b/files/classes/subscriptions.py
@@ -1,19 +1,24 @@
 import time
+from typing import Optional, TYPE_CHECKING
 
-from sqlalchemy import Column, ForeignKey
-from sqlalchemy.orm import relationship
+from sqlalchemy.orm import Mapped, relationship
 from sqlalchemy.sql.sqltypes import *
 
 from files.classes import Base
+from files.helpers.types import post_id_fk_pk, user_id_fk_pk
+
+if TYPE_CHECKING:
+	from files.classes import Post, User
+
 
 class Subscription(Base):
 	__tablename__ = "subscriptions"
-	user_id = Column(Integer, ForeignKey("users.id"), primary_key=True)
-	post_id = Column(Integer, ForeignKey("posts.id"), primary_key=True)
-	created_utc = Column(Integer)
+	user_id: Mapped[user_id_fk_pk]
+	post_id: Mapped[post_id_fk_pk]
+	created_utc: Mapped[Optional[int]]
 
-	user = relationship("User", uselist=False)
-	post = relationship("Post", uselist=False)
+	user: Mapped["User"] = relationship(uselist=False)
+	post: Mapped["Post"] = relationship(uselist=False)
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
diff --git a/files/classes/transactions.py b/files/classes/transactions.py
index 4b5457537..1cbed3108 100644
--- a/files/classes/transactions.py
+++ b/files/classes/transactions.py
@@ -1,16 +1,19 @@
-from sqlalchemy import Column
+from typing import Optional
+
+from sqlalchemy.orm import Mapped
 from sqlalchemy.sql.sqltypes import *
 
 from files.classes import Base
+from files.helpers.types import str_pk
 
 class Transaction(Base):
 	__tablename__ = "transactions"
-	id = Column(String, primary_key=True)
-	created_utc = Column(Integer)
-	type = Column(String)
-	amount = Column(Integer)
-	email = Column(String)
-	claimed = Column(Boolean)
+	id: Mapped[str_pk]
+	created_utc: Mapped[int]
+	type: Mapped[str]
+	amount: Mapped[int]
+	email: Mapped[str]
+	claimed: Mapped[Optional[bool]]
 
 	def __repr__(self):
 		return f"<{self.__class__.__name__}(id={self.id})>"
diff --git a/files/classes/user.py b/files/classes/user.py
index a419110c7..e651f5723 100644
--- a/files/classes/user.py
+++ b/files/classes/user.py
@@ -1,9 +1,9 @@
 import random
 from operator import *
+from typing import Optional
 
 import pyotp
-from sqlalchemy import Column, ForeignKey, FetchedValue
-from sqlalchemy.orm import aliased, deferred, Query
+from sqlalchemy.orm import DynamicMapped, Mapped, aliased, mapped_column
 from sqlalchemy.sql import case, func, literal
 from sqlalchemy.sql.expression import not_, and_, or_
 from sqlalchemy.sql.sqltypes import *
@@ -20,6 +20,7 @@ from files.helpers.config.awards import AWARDS_ENABLED, HOUSE_AWARDS
 from files.helpers.media import *
 from files.helpers.security import *
 from files.helpers.sorting_and_time import *
+from files.helpers.types import int_pk, user_id_fk
 from files.helpers.can_see import *
 
 from .alts import Alt
@@ -49,106 +50,106 @@ else:
 class User(Base):
 	__tablename__ = "users"
 
-	id = Column(Integer, primary_key=True)
-	username = Column(String)
-	namecolor = Column(String, default=DEFAULT_COLOR)
-	background = Column(String)
-	profile_background = Column(String)
-	flair = deferred(Column(String))
-	flair_html = Column(String)
-	flaircolor = Column(String, default=DEFAULT_COLOR)
-	theme = Column(String, default=DEFAULT_THEME)
-	themecolor = Column(String, default=DEFAULT_COLOR)
-	song = Column(String)
-	highres = Column(String)
-	profileurl = Column(String)
-	bannerurl = Column(String)
-	house = Column(String, default='')
-	old_house = Column(String, default='')
-	patron = Column(Integer, default=0)
-	patron_utc = Column(Integer, default=0)
-	verified = Column(String)
-	verifiedcolor = Column(String)
-	hieroglyphs = Column(Integer, default=0)
-	rehab = Column(Integer, default=0)
-	longpost = Column(Integer, default=0)
-	bird = Column(Integer, default=0)
-	email = deferred(Column(String))
-	css = Column(String)
-	profilecss = deferred(Column(String))
-	passhash = deferred(Column(String))
-	post_count = Column(Integer, default=0)
-	comment_count = Column(Integer, default=0)
-	received_award_count = Column(Integer, default=0)
-	created_utc = Column(Integer)
-	admin_level = Column(Integer, default=DEFAULT_ADMIN_LEVEL)
-	last_active = Column(Integer)
-	coins_spent = Column(Integer, default=0)
-	coins_spent_on_hats = Column(Integer, default=0)
-	lootboxes_bought = Column(Integer, default=0)
-	chud = Column(Integer, default=0)
-	queen = Column(Integer, default=0)
-	chud_phrase = Column(String)
-	email_verified = Column(Boolean, default=False)
-	shadowbanned = Column(Integer, ForeignKey("users.id"))
-	chudded_by = Column(Integer, ForeignKey("users.id"))
-	slurreplacer = Column(Integer, default=1)
-	profanityreplacer = Column(Integer, default=1)
-	flairchanged = Column(Integer, default=0)
-	namechanged = Column(Integer, default=0)
-	newtab = Column(Boolean, default=False)
-	newtabexternal = Column(Boolean, default=True)
-	frontsize = Column(Integer, default=25)
-	bio = deferred(Column(String))
-	bio_html = Column(String)
-	sig = deferred(Column(String))
-	sig_html = Column(String)
-	show_sigs = Column(Boolean, default=True)
-	progressivestack = Column(Integer, default=0)
-	deflector = Column(Integer, default=0)
-	friends = deferred(Column(String))
-	friends_html = deferred(Column(String))
-	enemies = deferred(Column(String))
-	enemies_html = deferred(Column(String))
-	is_banned = Column(Integer, ForeignKey("users.id"))
-	unban_utc = Column(Integer)
-	ban_reason = deferred(Column(String))
-	shadowban_reason = deferred(Column(String))
-	is_muted = Column(Boolean, default=False)
-	login_nonce = Column(Integer, default=0)
-	coins = Column(Integer, default=DEFAULT_COINS)
-	truescore = Column(Integer, default=0)
-	marseybux = Column(Integer, default=DEFAULT_MARSEYBUX)
-	mfa_secret = deferred(Column(String))
-	is_private = Column(Boolean, default=False)
-	stored_subscriber_count = Column(Integer, default=0)
-	defaultsortingcomments = Column(String, default="hot")
-	defaultsorting = Column(String, default="hot")
-	defaulttime = Column(String, default=DEFAULT_TIME_FILTER)
-	custom_filter_list = Column(String)
-	original_username = Column(String)
-	extra_username = Column(String)
-	prelock_username = Column(String)
-	referred_by = Column(Integer, ForeignKey("users.id"))
-	currently_held_lottery_tickets = Column(Integer, default=0)
-	total_held_lottery_tickets = Column(Integer, default=0)
-	total_lottery_winnings = Column(Integer, default=0)
-	last_viewed_modmail_notifs = Column(Integer, default=0)
-	last_viewed_post_notifs = Column(Integer, default=0)
-	last_viewed_log_notifs = Column(Integer, default=0)
-	last_viewed_offsite_notifs = Column(Integer, default=0)
-	bite = Column(Integer, default=0)
-	owoify = Column(Integer, default=0)
-	sharpen = Column(Integer, default=0)
-	marsify = Column(Integer, default=0)
-	rainbow = Column(Integer, default=0)
-	spider = Column(Integer, default=0)
-	lifetimedonated = Column(Integer, default=0)
-	lifetimedonated_visible = Column(Boolean, default=False)
-	blacklisted_by = Column(Integer, ForeignKey("users.id"))
-	grinch = Column(Boolean, default=SITE_NAME != 'rDrama') #don't put in an if condition, it will cause an error bc it has a not-null constraint
-	group_creation_notifs = Column(Boolean, default=False)
-	effortpost_notifs = Column(Boolean, default=False)
+	id: Mapped[int_pk]
+	username: Mapped[str]
+	namecolor: Mapped[str] = mapped_column(default=DEFAULT_COLOR)
+	background: Mapped[Optional[str]]
+	profile_background: Mapped[Optional[str]]
+	flair: Mapped[Optional[str]] = mapped_column(deferred=True)
+	flair_html: Mapped[Optional[str]]
+	flaircolor: Mapped[str] = mapped_column(default=DEFAULT_COLOR)
+	theme: Mapped[str] = mapped_column(default=DEFAULT_THEME)
+	themecolor: Mapped[str] = mapped_column(default=DEFAULT_COLOR)
+	song: Mapped[Optional[str]]
+	highres: Mapped[Optional[str]]
+	profileurl: Mapped[Optional[str]]
+	bannerurl: Mapped[Optional[str]]
+	house: Mapped[Optional[str]] = mapped_column(default='')
+	old_house: Mapped[Optional[str]] = mapped_column(default='')
+	patron: Mapped[int] = mapped_column(default=0)
+	patron_utc: Mapped[int] = mapped_column(default=0)
+	verified: Mapped[Optional[str]]
+	verifiedcolor: Mapped[Optional[str]]
+	hieroglyphs: Mapped[Optional[int]] = mapped_column(default=0)
+	rehab: Mapped[Optional[int]] = mapped_column(default=0)
+	longpost: Mapped[Optional[int]] = mapped_column(default=0)
+	bird: Mapped[Optional[int]] = mapped_column(default=0)
+	email: Mapped[Optional[str]] = mapped_column(deferred=True)
+	css: Mapped[Optional[str]]
+	profilecss: Mapped[Optional[str]] = mapped_column(deferred=True)
+	passhash: Mapped[str] = mapped_column(deferred=True)
+	post_count: Mapped[int] = mapped_column(default=0)
+	comment_count: Mapped[int] = mapped_column(default=0)
+	received_award_count: Mapped[int] = mapped_column(default=0)
+	created_utc: Mapped[int]
+	admin_level: Mapped[int] = mapped_column(default=DEFAULT_ADMIN_LEVEL)
+	last_active: Mapped[int]
+	coins_spent: Mapped[int] = mapped_column(default=0)
+	coins_spent_on_hats: Mapped[int] = mapped_column(default=0)
+	lootboxes_bought: Mapped[int] = mapped_column(default=0)
+	chud: Mapped[int] = mapped_column(default=0)
+	queen: Mapped[Optional[int]] = mapped_column(default=0)
+	chud_phrase: Mapped[Optional[str]]
+	email_verified: Mapped[bool] = mapped_column(default=False)
+	shadowbanned: Mapped[Optional[user_id_fk]]
+	chudded_by: Mapped[Optional[user_id_fk]]
+	slurreplacer: Mapped[int] = mapped_column(default=1)
+	profanityreplacer: Mapped[int] = mapped_column(default=1)
+	flairchanged: Mapped[Optional[int]] = mapped_column(default=0)
+	namechanged: Mapped[Optional[int]] = mapped_column(default=0)
+	newtab: Mapped[bool] = mapped_column(default=False)
+	newtabexternal: Mapped[bool] = mapped_column(default=True)
+	frontsize: Mapped[int] = mapped_column(default=25)
+	bio: Mapped[Optional[str]] = mapped_column(deferred=True)
+	bio_html: Mapped[Optional[str]]
+	sig: Mapped[Optional[str]] = mapped_column(deferred=True)
+	sig_html: Mapped[Optional[str]]
+	show_sigs: Mapped[bool] = mapped_column(default=True)
+	progressivestack: Mapped[Optional[int]] = mapped_column(default=0)
+	deflector: Mapped[Optional[int]] = mapped_column(default=0)
+	friends: Mapped[Optional[str]] = mapped_column(deferred=True)
+	friends_html: Mapped[Optional[str]] = mapped_column(deferred=True)
+	enemies: Mapped[Optional[str]] = mapped_column(deferred=True)
+	enemies_html: Mapped[Optional[str]] = mapped_column(deferred=True)
+	is_banned: Mapped[Optional[user_id_fk]]
+	unban_utc: Mapped[Optional[int]]
+	ban_reason: Mapped[Optional[str]] = mapped_column(deferred=True)
+	shadowban_reason: Mapped[Optional[str]] = mapped_column(deferred=True)
+	is_muted: Mapped[bool] = mapped_column(default=False)
+	login_nonce: Mapped[int] = mapped_column(default=0)
+	coins: Mapped[int] = mapped_column(default=DEFAULT_COINS)
+	truescore: Mapped[int] = mapped_column(default=0)
+	marseybux: Mapped[int] = mapped_column(default=DEFAULT_MARSEYBUX)
+	mfa_secret: Mapped[Optional[str]] = mapped_column(deferred=True)
+	is_private: Mapped[bool] = mapped_column(default=False)
+	stored_subscriber_count: Mapped[int] = mapped_column(default=0)
+	defaultsortingcomments: Mapped[str] = mapped_column(default="hot")
+	defaultsorting: Mapped[str] = mapped_column(default="hot")
+	defaulttime: Mapped[str] = mapped_column(default=DEFAULT_TIME_FILTER)
+	custom_filter_list: Mapped[Optional[str]]
+	original_username: Mapped[Optional[str]]
+	extra_username: Mapped[Optional[str]]
+	prelock_username: Mapped[Optional[str]]
+	referred_by: Mapped[Optional[user_id_fk]]
+	currently_held_lottery_tickets: Mapped[int] = mapped_column(default=0)
+	total_held_lottery_tickets: Mapped[int] = mapped_column(default=0)
+	total_lottery_winnings: Mapped[int] = mapped_column(default=0)
+	last_viewed_modmail_notifs: Mapped[int] = mapped_column(default=0)
+	last_viewed_post_notifs: Mapped[int] = mapped_column(default=0)
+	last_viewed_log_notifs: Mapped[int] = mapped_column(default=0)
+	last_viewed_offsite_notifs: Mapped[int] = mapped_column(default=0)
+	bite: Mapped[Optional[int]] = mapped_column(default=0)
+	owoify: Mapped[Optional[int]] = mapped_column(default=0)
+	sharpen: Mapped[Optional[int]] = mapped_column(default=0)
+	marsify: Mapped[Optional[int]] = mapped_column(default=0)
+	rainbow: Mapped[Optional[int]] = mapped_column(default=0)
+	spider: Mapped[Optional[int]] = mapped_column(default=0)
+	lifetimedonated: Mapped[int] = mapped_column(default=0)
+	lifetimedonated_visible: Mapped[bool] = mapped_column(default=False)
+	blacklisted_by: Mapped[Optional[user_id_fk]]
+	grinch: Mapped[bool] = mapped_column(default=SITE_NAME != 'rDrama') #don't put in an if condition, it will cause an error bc it has a not-null constraint
+	group_creation_notifs: Mapped[bool] = mapped_column(default=False)
+	effortpost_notifs: Mapped[bool] = mapped_column(default=False)
 
 	if SITE_NAME == 'WPD':
 		nitter = False
@@ -158,37 +159,37 @@ class User(Base):
 		pronouns = 'they/them'
 		earlylife = 0
 		hole_creation_notifs = False
-		hidevotedon = Column(Boolean, default=False)
-		hide_cw = Column(Boolean, default=False)
+		hidevotedon: Mapped[bool] = mapped_column(default=False)
+		hide_cw: Mapped[bool] = mapped_column(default=False)
 	else:
-		nitter = Column(Boolean, default=False)
-		imgsed = Column(Boolean, default=False)
-		controversial = Column(Boolean, default=False)
-		reddit = Column(String, default='old.reddit.com')
-		pronouns = Column(String, default='they/them')
-		earlylife = Column(Integer, default=0)
-		hole_creation_notifs = Column(Boolean, default=True)
+		nitter: Mapped[bool] = mapped_column(default=False)
+		imgsed: Mapped[bool] = mapped_column(default=False)
+		controversial: Mapped[bool] = mapped_column(default=False)
+		reddit: Mapped[str] = mapped_column(default='old.reddit.com')
+		pronouns: Mapped[str] = mapped_column(default='they/them')
+		earlylife: Mapped[Optional[int]] = mapped_column(default=0)
+		hole_creation_notifs: Mapped[bool] = mapped_column(default=True)
 		hidevotedon = False
 		hide_cw = False
 
 	if IS_HOMOWEEN():
-		zombie = Column(Integer, default=0) # > 0 vaxxed; < 0 zombie
-		jumpscare = Column(Integer, default=0)
+		zombie: Mapped[int] = mapped_column(default=0) # > 0 vaxxed; < 0 zombie
+		jumpscare: Mapped[int] = mapped_column(default=0)
 
-	badges = relationship("Badge", order_by="Badge.created_utc", back_populates="user")
-	subscriptions = relationship("Subscription", back_populates="user")
-	following = relationship("Follow", primaryjoin="Follow.user_id==User.id", back_populates="user")
-	followers = relationship("Follow", primaryjoin="Follow.target_id==User.id", back_populates="target")
-	blocking = relationship("UserBlock", lazy="dynamic", primaryjoin="User.id==UserBlock.user_id", back_populates="user")
-	blocked = relationship("UserBlock", lazy="dynamic", primaryjoin="User.id==UserBlock.target_id", back_populates="target")
-	authorizations = relationship("ClientAuth", back_populates="user")
-	apps = relationship("OauthApp", back_populates="author")
-	awards = relationship("AwardRelationship", primaryjoin="User.id==AwardRelationship.user_id", back_populates="user")
-	referrals = relationship("User", primaryjoin="User.id==User.referred_by", order_by="User.created_utc")
-	designed_hats = relationship("HatDef", primaryjoin="User.id==HatDef.author_id", back_populates="author")
-	owned_hats = relationship("Hat", back_populates="owners")
-	hats_equipped = relationship("Hat", lazy="raise", viewonly=True)
-	hole_mods = relationship("Mod", primaryjoin="User.id == Mod.user_id", lazy="raise")
+	badges: Mapped[list["Badge"]] = relationship(order_by="Badge.created_utc", back_populates="user")
+	subscriptions: Mapped[list["Subscription"]] = relationship(back_populates="user")
+	following: Mapped[list["Follow"]] = relationship(primaryjoin="Follow.user_id==User.id", back_populates="user")
+	followers: Mapped[list["Follow"]] = relationship(primaryjoin="Follow.target_id==User.id", back_populates="target")
+	blocking: DynamicMapped["UserBlock"] = relationship(primaryjoin="User.id==UserBlock.user_id", back_populates="user")
+	blocked: DynamicMapped["UserBlock"] = relationship(primaryjoin="User.id==UserBlock.target_id", back_populates="target")
+	authorizations: Mapped[list["ClientAuth"]] = relationship(back_populates="user")
+	apps: Mapped[list["OauthApp"]] = relationship(back_populates="author")
+	awards: Mapped[list["AwardRelationship"]] = relationship(primaryjoin="User.id==AwardRelationship.user_id", back_populates="user")
+	referrals: Mapped[list["User"]] = relationship(primaryjoin="User.id==User.referred_by", order_by="User.created_utc")
+	designed_hats: Mapped[list["HatDef"]] = relationship(primaryjoin="User.id==HatDef.author_id", back_populates="author")
+	owned_hats: Mapped[list["Hat"]] = relationship(back_populates="owners")
+	hats_equipped: Mapped[list["Hat"]] = relationship(lazy="raise", viewonly=True)
+	hole_mods: Mapped[list["Mod"]] = relationship(primaryjoin="User.id == Mod.user_id", lazy="raise")
 
 	def __init__(self, **kwargs):
 
diff --git a/files/classes/userblock.py b/files/classes/userblock.py
index 7e17ebf4b..e25694259 100644
--- a/files/classes/userblock.py
+++ b/files/classes/userblock.py
@@ -1,19 +1,24 @@
 import time
+from typing import Optional, TYPE_CHECKING
 
-from sqlalchemy import Column, ForeignKey
-from sqlalchemy.orm import relationship
+from sqlalchemy.orm import Mapped, relationship
 from sqlalchemy.sql.sqltypes import *
 
 from files.classes import Base
+from files.helpers.types import user_id_fk_pk
+
+if TYPE_CHECKING:
+	from files.classes import User
+
 
 class UserBlock(Base):
 	__tablename__ = "userblocks"
-	user_id = Column(Integer, ForeignKey("users.id"), primary_key=True)
-	target_id = Column(Integer, ForeignKey("users.id"), primary_key=True)
-	created_utc = Column(Integer)
+	user_id: Mapped[user_id_fk_pk]
+	target_id: Mapped[user_id_fk_pk]
+	created_utc: Mapped[Optional[int]]
 
-	user = relationship("User", primaryjoin="User.id==UserBlock.user_id", back_populates="blocking")
-	target = relationship("User", primaryjoin="User.id==UserBlock.target_id", back_populates="blocked")
+	user: Mapped["User"] = relationship(primaryjoin="User.id==UserBlock.user_id", back_populates="blocking")
+	target: Mapped["User"] = relationship(primaryjoin="User.id==UserBlock.target_id", back_populates="blocked")
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
diff --git a/files/classes/usermute.py b/files/classes/usermute.py
index 10db9750d..af5ad1741 100644
--- a/files/classes/usermute.py
+++ b/files/classes/usermute.py
@@ -1,19 +1,24 @@
 import time
+from typing import Optional, TYPE_CHECKING
 
-from sqlalchemy import Column, ForeignKey
-from sqlalchemy.orm import relationship
+from sqlalchemy.orm import Mapped, relationship
 from sqlalchemy.sql.sqltypes import *
 
 from files.classes import Base
+from files.helpers.types import user_id_fk_pk
+
+if TYPE_CHECKING:
+	from files.classes import User
+
 
 class UserMute(Base):
 	__tablename__ = "usermutes"
-	user_id = Column(Integer, ForeignKey("users.id"), primary_key=True)
-	target_id = Column(Integer, ForeignKey("users.id"), primary_key=True)
-	created_utc = Column(Integer)
+	user_id: Mapped[user_id_fk_pk]
+	target_id: Mapped[user_id_fk_pk]
+	created_utc: Mapped[Optional[int]]
 
-	user = relationship("User", primaryjoin="User.id==UserMute.user_id")
-	target = relationship("User", primaryjoin="User.id==UserMute.target_id")
+	user: Mapped["User"] = relationship(primaryjoin="User.id==UserMute.user_id")
+	target: Mapped["User"] = relationship(primaryjoin="User.id==UserMute.target_id")
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
diff --git a/files/classes/views.py b/files/classes/views.py
index b8984db8f..725d64313 100644
--- a/files/classes/views.py
+++ b/files/classes/views.py
@@ -1,22 +1,27 @@
 import time
+from typing import Optional, TYPE_CHECKING
 
-from sqlalchemy import Column, ForeignKey
-from sqlalchemy.orm import relationship
+from sqlalchemy.orm import Mapped, relationship
 from sqlalchemy.sql.sqltypes import *
 
 from files.classes import Base
 from files.helpers.lazy import *
 from files.helpers.sorting_and_time import make_age_string
+from files.helpers.types import user_id_fk_pk
+
+if TYPE_CHECKING:
+	from files.classes import User
+
 
 class ViewerRelationship(Base):
 	__tablename__ = "viewers"
 
-	user_id = Column(Integer, ForeignKey('users.id'), primary_key=True)
-	viewer_id = Column(Integer, ForeignKey('users.id'), primary_key=True)
-	last_view_utc = Column(Integer)
-	created_utc = Column(Integer)
+	user_id: Mapped[user_id_fk_pk]
+	viewer_id: Mapped[user_id_fk_pk]
+	last_view_utc: Mapped[int]
+	created_utc: Mapped[Optional[int]]
 
-	viewer = relationship("User", primaryjoin="ViewerRelationship.viewer_id == User.id")
+	viewer: Mapped["User"] = relationship(primaryjoin="ViewerRelationship.viewer_id == User.id")
 
 	def __init__(self, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
diff --git a/files/classes/votes.py b/files/classes/votes.py
index a2d96e112..6f987afdc 100644
--- a/files/classes/votes.py
+++ b/files/classes/votes.py
@@ -1,23 +1,28 @@
 import time
+from typing import TYPE_CHECKING
 
-from sqlalchemy import Column, ForeignKey
-from sqlalchemy.orm import relationship
+from sqlalchemy.orm import Mapped, mapped_column, relationship
 from sqlalchemy.sql.sqltypes import *
 
 from files.classes import Base
 from files.helpers.lazy import lazy
+from files.helpers.types import comment_id_fk_pk, post_id_fk_pk, user_id_fk_pk
+
+if TYPE_CHECKING:
+	from files.classes import User
+
 
 class Vote(Base):
 	__tablename__ = "votes"
 
-	post_id = Column(Integer, ForeignKey("posts.id"), primary_key=True)
-	user_id = Column(Integer, ForeignKey("users.id"), primary_key=True)
-	vote_type = Column(Integer)
-	real = Column(Boolean, default=True)
-	coins = Column(Integer, default=1)
-	created_utc = Column(Integer)
+	post_id: Mapped[post_id_fk_pk]
+	user_id: Mapped[user_id_fk_pk]
+	vote_type: Mapped[int]
+	real: Mapped[bool] = mapped_column(default=True)
+	coins: Mapped[int] = mapped_column(default=1)
+	created_utc: Mapped[int]
 
-	user = relationship("User")
+	user: Mapped["User"] = relationship()
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
@@ -40,14 +45,14 @@ class CommentVote(Base):
 
 	__tablename__ = "commentvotes"
 
-	comment_id = Column(Integer, ForeignKey("comments.id"), primary_key=True)
-	user_id = Column(Integer, ForeignKey("users.id"), primary_key=True)
-	vote_type = Column(Integer)
-	real = Column(Boolean, default=True)
-	coins = Column(Integer, default=1)
-	created_utc = Column(Integer)
+	comment_id: Mapped[comment_id_fk_pk]
+	user_id: Mapped[user_id_fk_pk]
+	vote_type: Mapped[int]
+	real: Mapped[bool] = mapped_column(default=True)
+	coins: Mapped[int] = mapped_column(default=1)
+	created_utc: Mapped[int]
 
-	user = relationship("User")
+	user: Mapped["User"] = relationship()
 
 	def __init__(self, *args, **kwargs):
 		if "created_utc" not in kwargs: kwargs["created_utc"] = int(time.time())
diff --git a/files/helpers/types.py b/files/helpers/types.py
new file mode 100644
index 000000000..085070483
--- /dev/null
+++ b/files/helpers/types.py
@@ -0,0 +1,14 @@
+from typing import Annotated
+
+from sqlalchemy.sql.schema import ForeignKey
+from sqlalchemy.orm import mapped_column
+
+int_pk = Annotated[int, mapped_column(primary_key=True)]
+str_pk = Annotated[str, mapped_column(primary_key=True)]
+
+user_id_fk = Annotated[int, mapped_column(ForeignKey("users.id"))]
+user_id_fk_pk = Annotated[int, mapped_column(ForeignKey("users.id"), primary_key=True)]
+post_id_fk = Annotated[int, mapped_column(ForeignKey("posts.id"))]
+post_id_fk_pk = Annotated[int, mapped_column(ForeignKey("posts.id"), primary_key=True)]
+comment_id_fk = Annotated[int, mapped_column(ForeignKey("comments.id"))]
+comment_id_fk_pk = Annotated[int, mapped_column(ForeignKey("comments.id"), primary_key=True)]
\ No newline at end of file
diff --git a/typings/flask/__init__.pyi b/typings/flask/__init__.pyi
new file mode 100644
index 000000000..7f142f821
--- /dev/null
+++ b/typings/flask/__init__.pyi
@@ -0,0 +1,65 @@
+from files.classes.user import User
+from flask.ctx import _AppCtxGlobals
+from sqlalchemy.orm import Session
+from sqlalchemy.schema import Column
+import typing as t
+
+# According to PEP 484, "all objects imported into a stub using `from ... import *` are considered
+# exported", but this didn't work with Pyright for some reason, so everything has to be exported
+# manually. The alternative is to put `def __getattr__(name: str) -> t.Any: ...` here instead, but
+# then any symbol not in this file will be treated as Any, which prevents it from being checked.
+from flask import json as json
+from flask.app import Flask as Flask
+from flask.blueprints import Blueprint as Blueprint
+from flask.config import Config as Config
+from flask.ctx import after_this_request as after_this_request
+from flask.ctx import copy_current_request_context as copy_current_request_context
+from flask.ctx import has_app_context as has_app_context
+from flask.ctx import has_request_context as has_request_context
+from flask.globals import current_app as current_app
+from flask.globals import request as request
+from flask.globals import session as session
+from flask.helpers import abort as abort
+from flask.helpers import flash as flash
+from flask.helpers import get_flashed_messages as get_flashed_messages
+from flask.helpers import get_template_attribute as get_template_attribute
+from flask.helpers import make_response as make_response
+from flask.helpers import redirect as redirect
+from flask.helpers import send_file as send_file
+from flask.helpers import send_from_directory as send_from_directory
+from flask.helpers import stream_with_context as stream_with_context
+from flask.helpers import url_for as url_for
+from flask.json import jsonify as jsonify
+from flask.signals import appcontext_popped as appcontext_popped
+from flask.signals import appcontext_pushed as appcontext_pushed
+from flask.signals import appcontext_tearing_down as appcontext_tearing_down
+from flask.signals import before_render_template as before_render_template
+from flask.signals import got_request_exception as got_request_exception
+from flask.signals import message_flashed as message_flashed
+from flask.signals import request_finished as request_finished
+from flask.signals import request_started as request_started
+from flask.signals import request_tearing_down as request_tearing_down
+from flask.signals import template_rendered as template_rendered
+from flask.templating import render_template as render_template
+from flask.templating import render_template_string as render_template_string
+from flask.templating import stream_template as stream_template
+from flask.templating import stream_template_string as stream_template_string
+from flask.wrappers import Request as Request
+from flask.wrappers import Response as Response
+
+class Globals(_AppCtxGlobals):
+	agent: str
+	browser: t.Literal["webview", "firefox", "iphone", "mac", "chromium"]
+	db: Session
+	desires_auth: bool
+	is_api_or_xhr: bool
+	is_tor: bool
+	loggedin_chat: int
+	loggedin_counter: int
+	loggedout_counter: int
+	nonce: str
+	show_nsfw: bool
+	username: Column[str]
+	v: User | None
+
+g: Globals