diff --git a/db/models.py b/db/models.py
index 8adbda0..091bca6 100644
--- a/db/models.py
+++ b/db/models.py
@@ -40,6 +40,14 @@ class OrdersPool(BaseModel):
     time = TextField(null=True)
     confirm_delay = IntegerField(null=True)
 
+    punishment_pool = ForeignKeyField(
+        'self',
+        column_name='punishment_pool_id',
+        field='id',
+        backref='punishments_for',
+        null=True
+    )
+
     def to_dict(self):
         return {
             'id': self.id,
@@ -50,6 +58,7 @@ class OrdersPool(BaseModel):
             'weekends': self.weekends,
             'time': self.time,
             'confirm_delay': self.confirm_delay,
+            'punishment_pool_id': self.punishment_pool_id,
             'orders': [{
                 'id': order.id,
                 'name': order.name,
@@ -90,19 +99,10 @@ class OrderAddOn(BaseModel):
 #
 # Order State
 #
-class PunishmentStatus(BaseModel):
-    confirmed_at = DateTimeField(null=True)  # TIMESTAMP
-    created_at = DateTimeField()  # TIMESTAMP
-    mastodon_id = TextField()
-    text = TextField()
-
-    class Meta:
-        table_name = 'punishment_status'
-
 class OrderStatus(BaseModel):
     confirmed_at = DateTimeField(null=True)  # TIMESTAMP
     created_at = DateTimeField()  # TIMESTAMP
-    due_at = DateTimeField()  # TIMESTAMP
+    due_at = DateTimeField(null=True)  # TIMESTAMP
     mastodon_id = TextField()
     text = TextField()
 
@@ -121,6 +121,14 @@ class OrderStatus(BaseModel):
         backref='statuses',
         null=False
         )
+    
+    punishment_for = ForeignKeyField(
+        'self',
+        column_name='punishment_for_id',
+        field='id',
+        backref='punishment',
+        null=True
+    )
 
     class Meta:
         table_name = 'order_status'
diff --git a/db/queries.py b/db/queries.py
index 952a6e5..ee7d607 100644
--- a/db/queries.py
+++ b/db/queries.py
@@ -1,14 +1,13 @@
 import datetime
 
-from .models import database, User, OrdersPool, DomSubUsers, Repeat, SkipDay, OrderStatus, PunishmentStatus
+from .models import database, User, OrdersPool, DomSubUsers, Repeat, SkipDay, OrderStatus
 
 def initdb():
   database.connect()
   database.create_tables([
     Repeat,
     SkipDay,
-    OrderStatus,
-    PunishmentStatus
+    OrderStatus
   ])
 
 def user_add(username, chat_id):
@@ -90,24 +89,20 @@ def skip_day_contains(date):
   q = SkipDay.select().where(SkipDay.date == date)
   return len(q) > 0
 
-def order_status_put(orders_pool, user, mastodon_id, created_at, due_at, text):
+def order_status_put(orders_pool, user, mastodon_id, created_at, due_at, text, punishment_for=None):
   return OrderStatus.create(
     orders_pool_id=orders_pool.id,
     user_id=user.id,
     mastodon_id=mastodon_id,
     created_at=created_at,
     due_at=due_at,
-    text=text
+    text=text,
+    punishment_for=punishment_for
   )
 
 def order_status_by_id(order_status_id):
   return OrderStatus.get(id=order_status_id)
 
-def order_status_outstanding():
-  return OrderStatus.select().where(
-    (OrderStatus.confirmed_at.is_null()) & (OrderStatus.punishment_id.is_null())
-  )
-
 def order_status_confirm(id, confirmed_at):
   q = OrderStatus.update(
     confirmed_at=confirmed_at
@@ -115,17 +110,3 @@ def order_status_confirm(id, confirmed_at):
     OrderStatus.id == id
   )
   return q.execute()
-
-def punishment_status_put(order_status_id, mastodon_id, created_at, text):
-  punishment_status = PunishmentStatus.create(
-    mastodon_id=mastodon_id,
-    created_at=created_at,
-    text=text
-  )
-
-  q = OrderStatus.update(
-    punishment_id=punishment_status.id
-  ).where(
-    OrderStatus.id == order_status_id
-  )
-  q.execute()
diff --git a/flask/api.py b/flask/api.py
index d6cd334..8d074b3 100644
--- a/flask/api.py
+++ b/flask/api.py
@@ -152,6 +152,14 @@ def sub_order_set(username, set_id, sub):
       try:
         op.name = request.json['name']
 
+        if ('punishment_pool_id' in request.json and
+            request.json['punishment_pool_id'] in [
+              op.id for op in orders_pool_list(sub.id)
+            ]):
+          op.punishment_pool_id = request.json['punishment_pool_id']
+        else:
+          op.punishment_pool_id = None
+
         op.scheduled = request.json['scheduled']
         if op.scheduled:
           op.probability = request.json['probability']
@@ -198,4 +206,14 @@ def sub_order_set(username, set_id, sub):
     op.delete_instance(recursive=True)
     return ('', 204)
 
-  return jsonify(op.to_dict())
+  return jsonify({
+    "orderSets": [
+      {
+        'id': op.id,
+        'name': op.name,
+      }
+      for op
+      in orders_pool_list(sub.id)
+    ],
+    "orderSet": op.to_dict()
+    })
diff --git a/flask/vite/src/OrderSet.tsx b/flask/vite/src/OrderSet.tsx
index bd4d3e6..39be9d5 100644
--- a/flask/vite/src/OrderSet.tsx
+++ b/flask/vite/src/OrderSet.tsx
@@ -15,6 +15,7 @@ import {
   Collapse,
   NumberInput,
   Text,
+  Select,
 } from "@mantine/core";
 import { notifications } from "@mantine/notifications";
 import { TimeInput } from "@mantine/dates";
@@ -68,24 +69,41 @@ type FormOrderSetOrder = Omit<OrderSetOrder, "id" | "add_ons"> & {
   add_ons: FormOrderSetOrderAddOn[];
 };
 
-type FormOrderSet = Omit<OrderSet, "orders"> & {
+type FormOrderSet = Omit<OrderSet, "orders" | "punishment_pool_id"> & {
   orders: FormOrderSetOrder[];
+  punishment_pool_id?: string | number;
 };
 
 export const OrderSet: React.FC = () => {
   const navigate = useNavigate();
   const { username, set_id } = useParams();
-  const orderSet = useLoaderData<OrderSet>();
+  const { orderSets, orderSet } = useLoaderData<{
+    orderSets: Pick<OrderSet, "id" | "name">[];
+    orderSet: OrderSet;
+  }>();
   const [showScheduling, setShowScheduling] = React.useState(
     orderSet?.scheduled,
   );
 
+  const punishmentOptions = React.useMemo(
+    () =>
+      orderSets.map(({ id, name }) => ({ id, value: `${id}`, label: name })),
+    [orderSets],
+  );
+
   const form = useForm<Partial<FormOrderSet>>({
     mode: "uncontrolled",
-    initialValues: orderSet ?? {
-      scheduled: false,
-      orders: [],
-    },
+    initialValues: orderSet
+      ? {
+          ...orderSet,
+          punishment_pool_id: orderSet.punishment_pool_id
+            ? `${orderSet.punishment_pool_id}`
+            : undefined,
+        }
+      : {
+          scheduled: false,
+          orders: [],
+        },
     validate: {
       name: (value: string) =>
         value.length < 1 ? "Please enter a name" : null,
@@ -105,12 +123,22 @@ export const OrderSet: React.FC = () => {
             value.length < 1 ? "Please enter a name" : null,
         },
       },
+      punishment_pool_id: (value: string) =>
+        !value || orderSets.some(({ id }) => id === Number(value))
+          ? null
+          : "Please select a valid pool",
     },
     onValuesChange: (values) => {
       if (values.scheduled !== showScheduling) {
         setShowScheduling(values.scheduled);
       }
     },
+    transformValues: (values) => ({
+      ...values,
+      punishment_pool_id: values.punishment_pool_id
+        ? Number(values.punishment_pool_id)
+        : undefined,
+    }),
   });
 
   const handleSubmit = React.useCallback(
@@ -235,6 +263,13 @@ export const OrderSet: React.FC = () => {
             />
           </Paper>
         </Collapse>
+        <Select
+          clearable
+          label="Punishment Pool"
+          description="Orders Pool to issue punishments from"
+          data={punishmentOptions}
+          {...form.getInputProps("punishment_pool_id")}
+        />
 
         <Title order={2} mt="lg" mb="sm">
           Orders
diff --git a/flask/vite/src/index.d.ts b/flask/vite/src/index.d.ts
index 2faef75..b7d0ea8 100644
--- a/flask/vite/src/index.d.ts
+++ b/flask/vite/src/index.d.ts
@@ -22,4 +22,5 @@ type OrderSet = {
     weekends: boolean;
     time: string;
     confirm_delay: string;
+    punishment_pool_id?: number;
 }
diff --git a/generate.py b/generate.py
index b4bfd1c..f2ee9f9 100644
--- a/generate.py
+++ b/generate.py
@@ -59,9 +59,10 @@ def generate_order(orders_pool):
         "orders": result
     }
 
-def generate_punishment():
-    orders_config = read_config()
+def generate_punishment(orders_pool):
+    # Pick new orders
+    (result, repeat_p) = pick_order(orders_pool.orders)
 
-    (result, repeat_p) = pick_order(orders_config['punishments'])
-
-    return result
+    return {
+        "orders": result
+    }
diff --git a/migrations/009_delete_punishment_status.py b/migrations/009_delete_punishment_status.py
new file mode 100644
index 0000000..b3d4b64
--- /dev/null
+++ b/migrations/009_delete_punishment_status.py
@@ -0,0 +1,55 @@
+"""Peewee migrations -- 009_delete_punishment_status.py.
+
+Some examples (model - class or model name)::
+
+    > Model = migrator.orm['table_name']            # Return model in current state by name
+    > Model = migrator.ModelClass                   # Return model in current state by name
+
+    > migrator.sql(sql)                             # Run custom SQL
+    > migrator.run(func, *args, **kwargs)           # Run python function with the given args
+    > migrator.create_model(Model)                  # Create a model (could be used as decorator)
+    > migrator.remove_model(model, cascade=True)    # Remove a model
+    > migrator.add_fields(model, **fields)          # Add fields to a model
+    > migrator.change_fields(model, **fields)       # Change fields
+    > migrator.remove_fields(model, *field_names, cascade=True)
+    > migrator.rename_field(model, old_field_name, new_field_name)
+    > migrator.rename_table(model, new_table_name)
+    > migrator.add_index(model, *col_names, unique=False)
+    > migrator.add_not_null(model, *field_names)
+    > migrator.add_default(model, field_name, default)
+    > migrator.add_constraint(model, name, sql)
+    > migrator.drop_index(model, *col_names)
+    > migrator.drop_not_null(model, *field_names)
+    > migrator.drop_constraints(model, *constraints)
+
+"""
+
+from contextlib import suppress
+
+import peewee as pw
+from peewee_migrate import Migrator
+
+
+with suppress(ImportError):
+    import playhouse.postgres_ext as pw_pext
+
+
+def migrate(migrator: Migrator, database: pw.Database, *, fake=False):
+    """Write your migrations here."""
+    
+    migrator.remove_model('punishment_status')
+
+
+def rollback(migrator: Migrator, database: pw.Database, *, fake=False):
+    """Write your rollback migrations here."""
+    
+    @migrator.create_model
+    class PunishmentStatus(pw.Model):
+        id = pw.AutoField()
+        confirmed_at = pw.DateTimeField(null=True)
+        created_at = pw.DateTimeField()
+        mastodon_id = pw.TextField()
+        text = pw.TextField()
+
+        class Meta:
+            table_name = "punishment_status"
diff --git a/migrations/010_add_order_status_punishment_for.py b/migrations/010_add_order_status_punishment_for.py
new file mode 100644
index 0000000..4d818a5
--- /dev/null
+++ b/migrations/010_add_order_status_punishment_for.py
@@ -0,0 +1,51 @@
+"""Peewee migrations -- 010_add_order_status_punishment_for.py.
+
+Some examples (model - class or model name)::
+
+    > Model = migrator.orm['table_name']            # Return model in current state by name
+    > Model = migrator.ModelClass                   # Return model in current state by name
+
+    > migrator.sql(sql)                             # Run custom SQL
+    > migrator.run(func, *args, **kwargs)           # Run python function with the given args
+    > migrator.create_model(Model)                  # Create a model (could be used as decorator)
+    > migrator.remove_model(model, cascade=True)    # Remove a model
+    > migrator.add_fields(model, **fields)          # Add fields to a model
+    > migrator.change_fields(model, **fields)       # Change fields
+    > migrator.remove_fields(model, *field_names, cascade=True)
+    > migrator.rename_field(model, old_field_name, new_field_name)
+    > migrator.rename_table(model, new_table_name)
+    > migrator.add_index(model, *col_names, unique=False)
+    > migrator.add_not_null(model, *field_names)
+    > migrator.add_default(model, field_name, default)
+    > migrator.add_constraint(model, name, sql)
+    > migrator.drop_index(model, *col_names)
+    > migrator.drop_not_null(model, *field_names)
+    > migrator.drop_constraints(model, *constraints)
+
+"""
+
+from contextlib import suppress
+
+import peewee as pw
+from peewee_migrate import Migrator
+
+
+with suppress(ImportError):
+    import playhouse.postgres_ext as pw_pext
+
+
+def migrate(migrator: Migrator, database: pw.Database, *, fake=False):
+    """Write your migrations here."""
+    
+    migrator.add_fields(
+        'order_status',
+
+        punishment_for=pw.ForeignKeyField(column_name='punishment_for_id', field='id', model='self', null=True))
+
+
+def rollback(migrator: Migrator, database: pw.Database, *, fake=False):
+    """Write your rollback migrations here."""
+    
+    migrator.remove_fields('order_status', 'punishment_for')
+
+    migrator.drop_index('order_status', 'punishment_for')
diff --git a/migrations/011_add_orders_pool_punishment_pool.py b/migrations/011_add_orders_pool_punishment_pool.py
new file mode 100644
index 0000000..46ffde0
--- /dev/null
+++ b/migrations/011_add_orders_pool_punishment_pool.py
@@ -0,0 +1,51 @@
+"""Peewee migrations -- 011_add_orders_pool_punishment_pool.py.
+
+Some examples (model - class or model name)::
+
+    > Model = migrator.orm['table_name']            # Return model in current state by name
+    > Model = migrator.ModelClass                   # Return model in current state by name
+
+    > migrator.sql(sql)                             # Run custom SQL
+    > migrator.run(func, *args, **kwargs)           # Run python function with the given args
+    > migrator.create_model(Model)                  # Create a model (could be used as decorator)
+    > migrator.remove_model(model, cascade=True)    # Remove a model
+    > migrator.add_fields(model, **fields)          # Add fields to a model
+    > migrator.change_fields(model, **fields)       # Change fields
+    > migrator.remove_fields(model, *field_names, cascade=True)
+    > migrator.rename_field(model, old_field_name, new_field_name)
+    > migrator.rename_table(model, new_table_name)
+    > migrator.add_index(model, *col_names, unique=False)
+    > migrator.add_not_null(model, *field_names)
+    > migrator.add_default(model, field_name, default)
+    > migrator.add_constraint(model, name, sql)
+    > migrator.drop_index(model, *col_names)
+    > migrator.drop_not_null(model, *field_names)
+    > migrator.drop_constraints(model, *constraints)
+
+"""
+
+from contextlib import suppress
+
+import peewee as pw
+from peewee_migrate import Migrator
+
+
+with suppress(ImportError):
+    import playhouse.postgres_ext as pw_pext
+
+
+def migrate(migrator: Migrator, database: pw.Database, *, fake=False):
+    """Write your migrations here."""
+    
+    migrator.add_fields(
+        'orders_pool',
+
+        punishment_pool=pw.ForeignKeyField(column_name='punishment_pool_id', field='id', model='self', null=True))
+
+
+def rollback(migrator: Migrator, database: pw.Database, *, fake=False):
+    """Write your rollback migrations here."""
+    
+    migrator.remove_fields('orders_pool', 'punishment_pool')
+
+    migrator.drop_index('orders_pool', 'punishment_pool')
diff --git a/migrations/012_add_order_status_null_due_at.py b/migrations/012_add_order_status_null_due_at.py
new file mode 100644
index 0000000..7d2a55a
--- /dev/null
+++ b/migrations/012_add_order_status_null_due_at.py
@@ -0,0 +1,50 @@
+"""Peewee migrations -- 012_add_order_status_null_due_at.py.
+
+Some examples (model - class or model name)::
+
+    > Model = migrator.orm['table_name']            # Return model in current state by name
+    > Model = migrator.ModelClass                   # Return model in current state by name
+
+    > migrator.sql(sql)                             # Run custom SQL
+    > migrator.run(func, *args, **kwargs)           # Run python function with the given args
+    > migrator.create_model(Model)                  # Create a model (could be used as decorator)
+    > migrator.remove_model(model, cascade=True)    # Remove a model
+    > migrator.add_fields(model, **fields)          # Add fields to a model
+    > migrator.change_fields(model, **fields)       # Change fields
+    > migrator.remove_fields(model, *field_names, cascade=True)
+    > migrator.rename_field(model, old_field_name, new_field_name)
+    > migrator.rename_table(model, new_table_name)
+    > migrator.add_index(model, *col_names, unique=False)
+    > migrator.add_not_null(model, *field_names)
+    > migrator.add_default(model, field_name, default)
+    > migrator.add_constraint(model, name, sql)
+    > migrator.drop_index(model, *col_names)
+    > migrator.drop_not_null(model, *field_names)
+    > migrator.drop_constraints(model, *constraints)
+
+"""
+
+from contextlib import suppress
+
+import peewee as pw
+from peewee_migrate import Migrator
+
+
+with suppress(ImportError):
+    import playhouse.postgres_ext as pw_pext
+
+
+def migrate(migrator: Migrator, database: pw.Database, *, fake=False):
+    """Write your migrations here."""
+    
+    migrator.change_fields('order_status', due_at=pw.DateTimeField(null=True))
+
+    migrator.drop_not_null('order_status', 'due_at')
+
+
+def rollback(migrator: Migrator, database: pw.Database, *, fake=False):
+    """Write your rollback migrations here."""
+    
+    migrator.change_fields('order_status', due_at=pw.DateTimeField())
+
+    migrator.add_not_null('order_status', 'due_at')
diff --git a/orders.py b/orders.py
index f1ab3f7..fbcc3f9 100644
--- a/orders.py
+++ b/orders.py
@@ -4,7 +4,7 @@ import asyncio
 
 from util import make_session
 from generate import generate_order, generate_punishment
-from db.queries import order_status_by_id, order_status_put, punishment_status_put, order_status_outstanding, order_status_confirm
+from db.queries import order_status_by_id, order_status_put, order_status_confirm
 from mastodon import Mastodon
 from telegram.telegram import Telegram
 from settings import MASTODON_USERNAME, ORDER_TIMEOUT, ENV
@@ -91,6 +91,7 @@ async def order_issue(orders_pool):
           )
 
 async def punishment_mastodon_post(session, punishment_str, reply_id=None):
+    # TODO: Get user's mastodon username
     post = "@%s has failed to post proof of compliance. Here is the punishment -\n\n" % MASTODON_USERNAME
     post += punishment_str + "\n\n"
     if ENV == 'dev':
@@ -104,7 +105,7 @@ async def punishment_mastodon_post(session, punishment_str, reply_id=None):
         in_reply_to_id=reply_id
     )
 
-async def punishment_telegram_post(session, punishment_str, m_url):
+async def punishment_telegram_post(session, orders_pool, punishment_str, m_url):
     post = "You failed to show proof of compliance. Here is your punishment -\n\n"
     post += punishment_str + "\n\n"
     post += m_url
@@ -112,34 +113,40 @@ async def punishment_telegram_post(session, punishment_str, m_url):
         post += "\n\n⚠️ DEV"
 
     t = Telegram(session)
-    await t.message_send(post)
+    await t.message_send(orders_pool.user.telegram_chat_id, post)
 
-async def punishment_issue(session, outstanding_order):
-    # TODO: Generate a punishment
+async def punishment_issue(session, order_status):
+    if order_status.pool is None or order_status.pool.punishment_pool is None:
+        logger.info(f'Unable to issue a punishment for {order_status.id}, no punishment pool for order pool {order_status.pool.name}')
+        # TODO: No punishment mastodon/telegram posts
+        return
 
-    logger.info('TODO: Generate a punishment')
-    return
+    punishment_pool = order_status.pool.punishment_pool
 
-    punishment = generate_punishment()
-    punishment_str = "\n".join(punishment)
+    punishment = generate_punishment(punishment_pool)
+    punishment_str = "\n".join(punishment['orders'])
 
     punishment_status = await punishment_mastodon_post(
         session,
         punishment_str,
-        outstanding_order.mastodon_id,
+        order_status.mastodon_id,
     )
 
     await punishment_telegram_post(
         session,
+        punishment_pool,
         punishment_str,
         punishment_status['url']
     )
 
-    punishment_status_put(
-        outstanding_order.id,
+    order_status_put(
+        punishment_pool,
+        order_status.user,
         punishment_status['id'],
         punishment_status['created_at'],
-        punishment_str
+        None,
+        punishment_str,
+        punishment_for=order_status
     )
 
 order_check_lock = asyncio.Lock()
@@ -148,6 +155,10 @@ async def order_check(order_status_id):
         async with make_session() as session:
             order_status = order_status_by_id(order_status_id)
 
+            if order_status.punishment.count() > 0:
+                logger.info(f'Punishment already issued for {order_status.id}')
+                return
+
             m = Mastodon(session)
             context = await m.statusContext(order_status.mastodon_id)
 
diff --git a/scheduling.py b/scheduling.py
index c26d51d..e3f4a99 100644
--- a/scheduling.py
+++ b/scheduling.py
@@ -6,7 +6,7 @@ from scheduler.asyncio import Scheduler
 
 from settings import TIMEZONE
 from orders import order_issue, order_check
-from db.queries import order_status_outstanding, orders_pool_by_id, orders_pool_scheduled, skip_day_contains
+from db.queries import orders_pool_by_id, orders_pool_scheduled, skip_day_contains
 from util import order_time
 
 logger = logging.getLogger(__name__)