From 664cd32f81cd2d9c3a27a45a611d4f52cd07d517 Mon Sep 17 00:00:00 2001
From: MrMeeb <mrmeeb@noreply.git.mrmeeb.stream>
Date: Mon, 20 Jan 2025 12:00:06 +0000
Subject: [PATCH] 4.63.0

---
 app/.github/workflows/main.yml  |  57 ++--
 app/.python-version             |   1 +
 app/CONTRIBUTING.md             |  27 +-
 app/Dockerfile                  |  48 ++--
 app/app/admin_model.py          |  10 +-
 app/app/models.py               |   8 +-
 app/email_handler.py            |  11 +
 app/pyproject.toml              | 213 ++++++++-------
 app/requirements-dev.lock       | 469 ++++++++++++++++++++++++++++++++
 app/requirements.lock           | 392 ++++++++++++++++++++++++++
 app/scripts/new-migration.sh    |   4 +-
 app/scripts/reset_local_db.sh   |   4 +-
 app/scripts/reset_test_db.sh    |   2 +-
 app/scripts/run-test.sh         |   4 +-
 app/tests/api/test_alias.py     |   2 +-
 app/tests/test_contact_utils.py |   2 +-
 app/tests/test_email_handler.py |  13 +
 17 files changed, 1083 insertions(+), 184 deletions(-)
 create mode 100644 app/.python-version
 create mode 100644 app/requirements-dev.lock
 create mode 100644 app/requirements.lock

diff --git a/app/.github/workflows/main.yml b/app/.github/workflows/main.yml
index b14160a..48211ba 100644
--- a/app/.github/workflows/main.yml
+++ b/app/.github/workflows/main.yml
@@ -1,6 +1,12 @@
-name: Test and lint
+name: SimpleLogin actions
 
-on: [push, pull_request]
+on:
+  push:
+    branches:
+      - master
+    tags:
+      - v*
+  pull_request:
 
 jobs:
   lint:
@@ -9,35 +15,30 @@ jobs:
       - name: Check out repo
         uses: actions/checkout@v3
 
-      - name: Install poetry
-        run: pipx install poetry
-
-      - uses: actions/setup-python@v4
+      - name: "Install rye"
+        id: setup-rye
+        uses: eifinger/setup-rye@v4
         with:
-          python-version: '3.10'
-          cache: 'poetry'
+          version: '0.43.0'
+          checksum: 'ca702c3d93fd6ec76a1a0efaaa605e10736ee79a0674d241aad1bc0fe26f7d80'
+          enable-cache: true
 
       - name: Install OS dependencies
-        if: ${{ matrix.python-version }} == '3.10'
         run: |
           sudo apt update
           sudo apt install -y libre2-dev libpq-dev
 
       - name: Install dependencies
-        if: steps.cached-poetry-dependencies.outputs.cache-hit != 'true'
-        run: poetry install --no-interaction
+        if: steps.setup-rye.outputs.cache-hit != 'true'
+        run: rye sync --no-lock
 
       - name: Check formatting & linting
         run: |
-          poetry run pre-commit run --all-files
+          rye run pre-commit run --all-files
 
 
   test:
     runs-on: ubuntu-latest
-    strategy:
-      max-parallel: 4
-      matrix:
-        python-version: ["3.10"]
 
     # service containers to run with `postgres-job`
     services:
@@ -69,24 +70,23 @@ jobs:
       - name: Check out repo
         uses: actions/checkout@v3
 
-      - name: Install poetry
-        run: pipx install poetry
-
-      - uses: actions/setup-python@v4
+      - name: Install rye
+        id: setup-rye
+        uses: eifinger/setup-rye@v4
         with:
-          python-version: ${{ matrix.python-version }}
-          cache: 'poetry'
+          version: '0.43.0'
+          checksum: 'ca702c3d93fd6ec76a1a0efaaa605e10736ee79a0674d241aad1bc0fe26f7d80'
+          enable-cache: true
+          cache-prefix: 'rye-cache'
 
       - name: Install OS dependencies
-        if: ${{ matrix.python-version }} == '3.10'
         run: |
           sudo apt update
           sudo apt install -y libre2-dev libpq-dev
 
       - name: Install dependencies
-        if: steps.cached-poetry-dependencies.outputs.cache-hit != 'true'
-        run: poetry install --no-interaction
-
+        if: steps.setup-rye.outputs.cache-hit != 'true'
+        run: rye sync --no-lock
 
       - name: Start Redis v6
         uses: superchargejs/redis-github-action@1.1.0
@@ -95,7 +95,8 @@ jobs:
 
       - name: Run db migration
         run: |
-          CONFIG=tests/test.env poetry run alembic upgrade head
+          rye install alembic
+          CONFIG=tests/test.env rye run alembic upgrade head
 
       - name: Prepare version file
         run: |
@@ -104,7 +105,7 @@ jobs:
 
       - name: Test with pytest
         run: |
-          poetry run pytest
+          rye run pytest
         env:
           GITHUB_ACTIONS_TEST: true
 
diff --git a/app/.python-version b/app/.python-version
new file mode 100644
index 0000000..251b350
--- /dev/null
+++ b/app/.python-version
@@ -0,0 +1 @@
+3.10.16
diff --git a/app/CONTRIBUTING.md b/app/CONTRIBUTING.md
index 008ea11..819822d 100644
--- a/app/CONTRIBUTING.md
+++ b/app/CONTRIBUTING.md
@@ -20,7 +20,7 @@ SimpleLogin backend consists of 2 main components:
 ## Install dependencies
 
 The project requires:
-- Python 3.10 and poetry to manage dependencies
+- Python 3.10 and rye to manage dependencies
 - Node v10 for front-end.
 - Postgres 13+
 
@@ -28,7 +28,7 @@ First, install all dependencies by running the following command.
 Feel free to use `virtualenv` or similar tools to isolate development environment.
 
 ```bash
-poetry sync
+rye sync
 ```
 
 On Mac, sometimes you might need to install some other packages via `brew`:
@@ -55,7 +55,7 @@ brew install -s re2 pybind11
 We use pre-commit to run all our linting and static analysis checks. Please run
 
 ```bash
-poetry run pre-commit install
+rye run pre-commit install
 ```
 
 To install it in your development environment.
@@ -160,25 +160,25 @@ Here are the small sum-ups of the directory structures and their roles:
 The code is formatted using [ruff](https://github.com/astral-sh/ruff), to format the code, simply run
 
 ```
-poetry run ruff format .
+rye run ruff format .
 ```
 
 The code is also checked with `flake8`, make sure to run `flake8` before creating the pull request by
 
 ```bash
-poetry run flake8
+rye run flake8
 ```
 
 For HTML templates, we use `djlint`. Before creating a pull request, please run
 
 ```bash
-poetry run djlint --check templates
+rye run djlint --check templates
 ```
 
 If some files aren't properly formatted, you can format all files with
 
 ```bash
-poetry run djlint --reformat .
+rye run djlint --reformat .
 ```
 
 ## Test sending email
@@ -236,18 +236,11 @@ There are several ways to setup Python and manage the project dependencies on Ma
 # we haven't managed to make python 3.12 work
 brew install python3.10
 
-# make sure to update the PATH so python, pip point to Python3
-# for us it can be done by adding "export PATH=/opt/homebrew/opt/python@3.10/libexec/bin:$PATH" to .zprofile
+# Install rye using the official installation script, found on https://rye.astral.sh/guide/installation/
 
-# Although pipx is the recommended way to install poetry,
-# install pipx via brew will automatically install python 3.12
-# and poetry will then use python 3.12
-# so we recommend using poetry this way instead
-curl -sSL https://install.python-poetry.org | python3 -
-
-poetry install
+# Install the dependencies
+rye sync
 
 # activate the virtualenv and you should be good to go!
 source .venv/bin/activate
-
 ```
\ No newline at end of file
diff --git a/app/Dockerfile b/app/Dockerfile
index 851b7d2..21822ae 100644
--- a/app/Dockerfile
+++ b/app/Dockerfile
@@ -4,43 +4,45 @@ WORKDIR /code
 COPY ./static/package*.json /code/static/
 RUN cd /code/static && npm ci
 
-# Main image
-FROM python:3.10
+FROM --platform=linux/amd64 ubuntu:22.04
+
+ARG RYE_VERSION="0.43.0"
+ARG RYE_HASH="ca702c3d93fd6ec76a1a0efaaa605e10736ee79a0674d241aad1bc0fe26f7d80"
 
 # Keeps Python from generating .pyc files in the container
-ENV PYTHONDONTWRITEBYTECODE 1
+ENV PYTHONDONTWRITEBYTECODE=1
 # Turns off buffering for easier container logging
-ENV PYTHONUNBUFFERED 1
+ENV PYTHONUNBUFFERED=1
 
-# Add poetry to PATH
-ENV PATH="${PATH}:/root/.local/bin"
 
 WORKDIR /code
 
-# Copy poetry files
-COPY poetry.lock pyproject.toml ./
+# Copy dependency files
+COPY pyproject.toml requirements.lock requirements-dev.lock .python-version ./
 
-# Install and setup poetry
-RUN pip install -U pip \
-    && apt-get update \
-    && apt install -y curl netcat-traditional gcc python3-dev gnupg git libre2-dev cmake ninja-build\
-    && curl -sSL https://install.python-poetry.org | python3 - \
-    # Remove curl and netcat from the image
-    && apt-get purge -y curl netcat-traditional \
-    # Run poetry
-    && poetry config virtualenvs.create false \
-    && poetry install  --no-interaction --no-ansi --no-root \
-    # Clear apt cache \
-    && apt-get purge -y libre2-dev cmake ninja-build\
+# Install deps
+RUN apt-get update \
+    && apt-get install -y curl netcat-traditional gcc python3-dev gnupg git libre2-dev build-essential pkg-config cmake ninja-build bash clang \
+    && curl -sSL "https://github.com/astral-sh/rye/releases/download/${RYE_VERSION}/rye-x86_64-linux.gz" > rye.gz \
+    && echo "${RYE_HASH}  rye.gz" | sha256sum -c - \
+    && gunzip rye.gz \
+    && chmod +x rye \
+    && mv rye /usr/bin/rye \
+    && rye toolchain fetch `cat .python-version` \
+    && rye sync --no-lock --no-dev \
+    && apt-get autoremove -y \
+    && apt-get purge -y curl netcat-traditional build-essential pkg-config cmake ninja-build python3-dev clang\
+    && apt-get autoremove -y \
     && apt-get clean \
     && rm -rf /var/lib/apt/lists/*
 
+# Copy code
+COPY . .
+
 # copy npm packages
 COPY --from=npm /code /code
 
-# copy everything else into /code
-COPY . .
-
+ENV PATH="/code/.venv/bin:$PATH"
 EXPOSE 7777
 
 #gunicorn wsgi:app -b 0.0.0.0:7777 -w 2 --timeout 15 --log-level DEBUG
diff --git a/app/app/admin_model.py b/app/app/admin_model.py
index 2123e36..f49654b 100644
--- a/app/app/admin_model.py
+++ b/app/app/admin_model.py
@@ -791,7 +791,7 @@ class EmailSearchResult:
         self.query: str
 
     @staticmethod
-    def from_email(email: str) -> EmailSearchResult:
+    def from_request_email(email: str) -> EmailSearchResult:
         output = EmailSearchResult()
         output.query = email
         alias = Alias.get_by(email=email)
@@ -803,7 +803,11 @@ class EmailSearchResult:
                 .all()
             )
             output.no_match = False
-        user = User.get_by(email=email)
+        try:
+            user_id = int(email)
+            user = User.get(user_id)
+        except ValueError:
+            user = User.get_by(email=email)
         if user:
             output.user = user
             output.user_audit_log = (
@@ -912,7 +916,7 @@ class EmailSearchAdmin(BaseView):
         email = request.args.get("email")
         if email is not None and len(email) > 0:
             email = email.strip()
-            search = EmailSearchResult.from_email(email)
+            search = EmailSearchResult.from_request_email(email)
 
         return self.render(
             "admin/email_search.html",
diff --git a/app/app/models.py b/app/app/models.py
index e5f6453..32d017e 100644
--- a/app/app/models.py
+++ b/app/app/models.py
@@ -343,7 +343,7 @@ class Fido(Base, ModelMixin):
 class User(Base, ModelMixin, UserMixin, PasswordOracle):
     __tablename__ = "users"
 
-    FLAG_DISABLE_CREATE_CONTACTS = 1 << 0
+    FLAG_FREE_DISABLE_CREATE_CONTACTS = 1 << 0
     FLAG_CREATED_FROM_PARTNER = 1 << 1
     FLAG_FREE_OLD_ALIAS_LIMIT = 1 << 2
     FLAG_CREATED_ALIAS_FROM_PARTNER = 1 << 3
@@ -550,7 +550,7 @@ class User(Base, ModelMixin, UserMixin, PasswordOracle):
     # bitwise flags. Allow for future expansion
     flags = sa.Column(
         sa.BigInteger,
-        default=FLAG_DISABLE_CREATE_CONTACTS,
+        default=FLAG_FREE_DISABLE_CREATE_CONTACTS,
         server_default="0",
         nullable=False,
     )
@@ -640,7 +640,7 @@ class User(Base, ModelMixin, UserMixin, PasswordOracle):
         # If the user is created from partner, do not notify
         # nor give a trial
         if from_partner:
-            user.flags = User.FLAG_CREATED_FROM_PARTNER
+            user.flags = user.flags | User.FLAG_CREATED_FROM_PARTNER
             user.notification = False
             user.trial_end = None
             Job.create(
@@ -1189,7 +1189,7 @@ class User(Base, ModelMixin, UserMixin, PasswordOracle):
     def can_create_contacts(self) -> bool:
         if self.is_premium():
             return True
-        if self.flags & User.FLAG_DISABLE_CREATE_CONTACTS == 0:
+        if self.flags & User.FLAG_FREE_DISABLE_CREATE_CONTACTS == 0:
             return True
         return not config.DISABLE_CREATE_CONTACTS_FOR_FREE_USERS
 
diff --git a/app/email_handler.py b/app/email_handler.py
index 9eb88ba..da273f9 100644
--- a/app/email_handler.py
+++ b/app/email_handler.py
@@ -600,6 +600,17 @@ def handle_forward(envelope, msg: Message, rcpt_to: str) -> List[Tuple[bool, str
         else:
             reply_to_contact = get_or_create_reply_to_contact(reply_to, alias, msg)
 
+    if alias.user.delete_on is not None:
+        LOG.d(f"user {user} is pending to be deleted. Do not forward")
+        EmailLog.create(
+            contact_id=contact.id,
+            user_id=contact.user_id,
+            blocked=True,
+            alias_id=contact.alias_id,
+            commit=True,
+        )
+        return [(True, status.E502)]
+
     if not alias.enabled or contact.block_forward:
         LOG.d("%s is disabled, do not forward", alias)
         EmailLog.create(
diff --git a/app/pyproject.toml b/app/pyproject.toml
index a09e019..3e9409b 100644
--- a/app/pyproject.toml
+++ b/app/pyproject.toml
@@ -1,20 +1,100 @@
+[project]
+name = "SimpleLogin"
+version = "0.1.0"
+description = "SimpleLogin partner API"
+authors = [ {name="SimpleLogin", email="dev@simplelogin.io"}]
+license = "MIT"
+repository = "https://github.com/simple-login/app"
+keywords = ["email", "alias", "privacy", "oauth2", "openid"]
+packages = [
+    { include = "app/" },
+    { include = "migrations/" },
+]
+include = ["templates/*", "templates/**/*", "local_data/*.txt"]
+
+requires-python = "~=3.10"
+
+dependencies = [
+    "flask ~= 1.1.2",
+    "flask_login ~= 0.5.0",
+    "wtforms ~= 2.3.3",
+    "unidecode ~= 1.1.1",
+    "gunicorn ~= 20.0.4",
+    "bcrypt ~= 3.2.0",
+    "python-dotenv ~= 0.14.0",
+    "ipython ~= 7.31.1",
+    "sqlalchemy_utils ~= 0.36.8",
+    "psycopg2-binary ~= 2.9.3",
+    "sentry_sdk ~= 2.20.0",
+    "blinker ~= 1.4",
+    "arrow ~= 0.16.0",
+    "Flask-WTF ~= 0.14.3",
+    "boto3 ~= 1.35.37",
+    "Flask-Migrate ~= 2.5.3",
+    "flask_admin ~= 1.5.6",
+    "flask-cors ~= 3.0.9",
+    "watchtower ~= 0.8.0",
+    "sqlalchemy-utils == 0.36.8",
+    "jwcrypto ~= 0.8",
+    "yacron>=0.19.0",
+    "flask-debugtoolbar ~= 0.11.0",
+    "requests_oauthlib ~= 1.3.0",
+    "pyopenssl ~= 19.1.0",
+    "aiosmtpd ~= 1.2",
+    "dnspython == 2.6.1",
+    "coloredlogs ~= 14.0",
+    "pycryptodome ~= 3.9.8",
+    "phpserialize ~= 1.3",
+    "dkimpy ~= 1.0.5",
+    "pyotp ~= 2.4.0",
+    "flask_profiler ~= 1.8.1",
+    "facebook-sdk ~= 3.1.0",
+    "google-api-python-client ~= 1.12.3",
+    "google-auth-httplib2 ~= 0.0.4",
+    "python-gnupg ~= 0.4.6",
+    "webauthn ~= 0.4.7",
+    "pyspf ~= 2.0.14",
+    "Flask-Limiter == 1.4",
+    "memory_profiler ~= 0.57.0",
+    "gevent ~= 24.11.1",
+    "email-validator ~= 1.1.3",
+    "PGPy == 0.5.4",
+    "coinbase-commerce ~= 1.0.1",
+    "requests ~= 2.25.1",
+    "newrelic ~= 8.8.0",
+    "flanker ~= 0.9.11",
+    "pyre2 ~= 0.3.6",
+    "tldextract ~= 3.1.2",
+    "flask-debugtoolbar-sqlalchemy ~= 0.2.0",
+    "twilio ~= 7.3.2",
+    "Deprecated ~= 1.2.13",
+    "MarkupSafe~=1.1.1",
+    "cryptography ~= 37.0.1",
+    "SQLAlchemy ~= 1.3.24",
+    "redis ~= 4.5.3",
+    "newrelic-telemetry-sdk ~= 0.5.0",
+    "aiospamc == 0.10",
+    "itsdangerous ~= 1.1.0",
+    "werkzeug ~= 1.0.1",
+]
+
 [tool.black]
 target-version = ['py310']
 exclude = '''
 (
-  /(
-      \.eggs         # exclude a few common directories in the
-    | \.git          # root of the project
-    | \.hg
-    | \.mypy_cache
-    | \.tox
-    | \.venv
-    | _build
-    | buck-out
-    | build
-    | dist
-    | migrations    # migrations/ is generated by alembic
-    | app/events/generated
+ /(
+   \.eggs         # exclude a few common directories in the
+   | \.git          # root of the project
+   | \.hg
+   | \.mypy_cache
+   | \.tox
+   | \.venv
+   | _build
+   | buck-out
+   | build
+   | dist
+   | migrations    # migrations/ is generated by alembic
+   | app/events/generated
   )/
 )
 '''
@@ -27,7 +107,6 @@ exclude = [".venv", "migrations", "app/events/generated"]
 indent = 2
 profile = "jinja"
 blank_line_after_tag = "if,for,include,load,extends,block,endcall"
-
 # H006: Images should have a height attribute
 # H013: Images should have an alt attribute
 # H016: Missing title tag in html. | False positive on template
@@ -43,92 +122,26 @@ blank_line_after_tag = "if,for,include,load,extends,block,endcall"
 # T001: Variables should be wrapped in a single whitespace. | Messes up with comments
 ignore = "H006,H013,H016,H017,H019,H021,H025,H030,H031,T003,J004,J018,T001"
 
-[tool.poetry]
-name = "SimpleLogin"
-version = "0.1.0"
-description = "open-source email alias solution"
-authors = ["SimpleLogin <dev@simplelogin.io>"]
-license = "MIT"
-repository = "https://github.com/simple-login/app"
-keywords = ["email", "alias", "privacy", "oauth2", "openid"]
-packages = [
-  { include = "app/" },
-  { include = "migrations/" },
+[tool.uv]
+dev-dependencies = [
+    "pytest ~= 7.0.0",
+    "pytest-cov ~= 3.0.0",
+    "pre-commit ~= 2.17.0",
+    "black ~= 22.1.0",
+    "djlint ~= 1.3.0",
+    "pylint ~= 2.14.4",
+    "ruff ~= 0.1.5",
 ]
-include = ["templates/*", "templates/**/*", "local_data/*.txt"]
-
-[tool.poetry.dependencies]
-python = "^3.10"
-flask = "^1.1.2"
-flask_login = "^0.5.0"
-wtforms = "^2.3.3"
-unidecode = "^1.1.1"
-gunicorn = "^20.0.4"
-bcrypt = "^3.2.0"
-python-dotenv = "^0.14.0"
-ipython = "^7.31.1"
-sqlalchemy_utils = "^0.36.8"
-psycopg2-binary = "^2.9.3"
-sentry_sdk = "^2.16.0"
-blinker = "^1.4"
-arrow = "^0.16.0"
-Flask-WTF = "^0.14.3"
-boto3 = "^1.15.9"
-Flask-Migrate = "^2.5.3"
-flask_admin = "^1.5.6"
-flask-cors = "^3.0.9"
-watchtower = "^0.8.0"
-sqlalchemy-utils = "^0.36.8"
-jwcrypto = "^0.8"
-yacron = "^0.11.1"
-flask-debugtoolbar = "^0.11.0"
-requests_oauthlib = "^1.3.0"
-pyopenssl = "^19.1.0"
-aiosmtpd = "^1.2"
-dnspython = "^2.0.0"
-coloredlogs = "^14.0"
-pycryptodome = "^3.9.8"
-phpserialize = "^1.3"
-dkimpy = "^1.0.5"
-pyotp = "^2.4.0"
-flask_profiler = "^1.8.1"
-facebook-sdk = "^3.1.0"
-google-api-python-client = "^1.12.3"
-google-auth-httplib2 = "^0.0.4"
-python-gnupg = "^0.4.6"
-webauthn = "^0.4.7"
-pyspf = "^2.0.14"
-Flask-Limiter = "^1.4"
-memory_profiler = "^0.57.0"
-gevent = "22.10.2"
-email_validator = "^1.1.1"
-PGPy = "0.5.4"
-coinbase-commerce = "^1.0.1"
-requests = "^2.25.1"
-newrelic = "8.8.0"
-flanker = "^0.9.11"
-pyre2 = "^0.3.6"
-tldextract = "^3.1.2"
-flask-debugtoolbar-sqlalchemy = "^0.2.0"
-twilio = "^7.3.2"
-Deprecated = "^1.2.13"
-cryptography = "37.0.1"
-SQLAlchemy = "1.3.24"
-redis = "^4.5.3"
-newrelic-telemetry-sdk = "^0.5.0"
-aiospamc = "0.10"
-
-[tool.poetry.dev-dependencies]
-pytest = "^7.0.0"
-pytest-cov = "^3.0.0"
-black = "^22.1.0"
-djlint = "^1.3.0"
-pylint = "^2.14.4"
-
-[tool.poetry.group.dev.dependencies]
-ruff = "^0.1.5"
-pre-commit = "^3.8.0"
 
 [build-system]
-requires = ["poetry>=0.12"]
-build-backend = "poetry.masonry.api"
+requires = ["hatchling"]
+build-backend = "hatchling.build"
+
+[tool.hatch.metadata]
+allow-direct-references = true
+
+[tool.hatch.build.targets.sdist]
+include = ["app", "local_data", "migrations", "templates"]
+
+[tool.hatch.build.targets.wheel]
+packages = ["app", "local_data", "migrations", "templates"]
diff --git a/app/requirements-dev.lock b/app/requirements-dev.lock
new file mode 100644
index 0000000..1e5c91f
--- /dev/null
+++ b/app/requirements-dev.lock
@@ -0,0 +1,469 @@
+# generated by rye
+# use `rye lock` or `rye sync` to update this lockfile
+#
+# last locked with the following flags:
+#   pre: false
+#   features: []
+#   all-features: false
+#   with-sources: false
+#   generate-hashes: false
+#   universal: false
+
+-e file:.
+aiohappyeyeballs==2.4.4
+    # via aiohttp
+aiohttp==3.11.11
+    # via yacron
+aiosignal==1.3.2
+    # via aiohttp
+aiosmtpd==1.4.6
+    # via simplelogin
+aiosmtplib==3.0.2
+    # via yacron
+aiospamc==0.10.0
+    # via simplelogin
+alembic==1.14.0
+    # via flask-migrate
+appnope==0.1.4
+    # via ipython
+arrow==0.16.0
+    # via simplelogin
+astroid==2.11.7
+    # via pylint
+async-timeout==5.0.1
+    # via aiohttp
+    # via redis
+atpublic==5.0
+    # via aiosmtpd
+attrs==24.3.0
+    # via aiohttp
+    # via aiosmtpd
+    # via flanker
+    # via pytest
+backcall==0.2.0
+    # via ipython
+bcrypt==3.2.2
+    # via simplelogin
+black==22.1.0
+blinker==1.9.0
+    # via flask-debugtoolbar
+    # via simplelogin
+boto3==1.35.99
+    # via simplelogin
+    # via watchtower
+botocore==1.35.99
+    # via boto3
+    # via s3transfer
+cachetools==5.5.0
+    # via google-auth
+cbor2==5.6.5
+    # via webauthn
+certifi==2024.12.14
+    # via aiospamc
+    # via requests
+    # via sentry-sdk
+cffi==1.17.1
+    # via bcrypt
+    # via cryptography
+cfgv==3.4.0
+    # via pre-commit
+chardet==4.0.0
+    # via flanker
+    # via requests
+click==8.1.8
+    # via black
+    # via djlint
+    # via flask
+    # via typer
+coinbase-commerce==1.0.1
+    # via simplelogin
+colorama==0.4.6
+    # via djlint
+coloredlogs==14.3
+    # via simplelogin
+coverage==7.6.10
+    # via pytest-cov
+crontab==0.22.8
+    # via yacron
+cryptography==37.0.4
+    # via flanker
+    # via jwcrypto
+    # via pgpy
+    # via pyopenssl
+    # via simplelogin
+    # via webauthn
+decorator==5.1.1
+    # via ipython
+deprecated==1.2.15
+    # via jwcrypto
+    # via limits
+    # via simplelogin
+dill==0.3.9
+    # via pylint
+distlib==0.3.9
+    # via virtualenv
+djlint==1.3.0
+dkimpy==1.0.6
+    # via simplelogin
+dnspython==2.6.1
+    # via dkimpy
+    # via email-validator
+    # via simplelogin
+email-validator==1.1.3
+    # via simplelogin
+facebook-sdk==3.1.0
+    # via simplelogin
+filelock==3.16.1
+    # via tldextract
+    # via virtualenv
+flanker==0.9.11
+    # via simplelogin
+flask==1.1.2
+    # via flask-admin
+    # via flask-cors
+    # via flask-debugtoolbar
+    # via flask-httpauth
+    # via flask-limiter
+    # via flask-login
+    # via flask-migrate
+    # via flask-profiler
+    # via flask-sqlalchemy
+    # via flask-wtf
+    # via simplelogin
+flask-admin==1.5.8
+    # via simplelogin
+flask-cors==3.0.10
+    # via simplelogin
+flask-debugtoolbar==0.11.0
+    # via flask-debugtoolbar-sqlalchemy
+    # via simplelogin
+flask-debugtoolbar-sqlalchemy==0.2.0
+    # via simplelogin
+flask-httpauth==4.8.0
+    # via flask-profiler
+flask-limiter==1.4
+    # via simplelogin
+flask-login==0.5.0
+    # via simplelogin
+flask-migrate==2.5.3
+    # via simplelogin
+flask-profiler==1.8.1
+    # via simplelogin
+flask-sqlalchemy==2.5.1
+    # via flask-migrate
+flask-wtf==0.14.3
+    # via simplelogin
+frozenlist==1.5.0
+    # via aiohttp
+    # via aiosignal
+future==1.0.0
+    # via webauthn
+gevent==24.11.1
+    # via simplelogin
+google-api-core==2.24.0
+    # via google-api-python-client
+google-api-python-client==1.12.11
+    # via simplelogin
+google-auth==2.37.0
+    # via google-api-core
+    # via google-api-python-client
+    # via google-auth-httplib2
+google-auth-httplib2==0.0.4
+    # via google-api-python-client
+    # via simplelogin
+googleapis-common-protos==1.66.0
+    # via google-api-core
+greenlet==3.1.1
+    # via gevent
+gunicorn==20.0.4
+    # via simplelogin
+html-tag-names==0.1.2
+    # via djlint
+html-void-elements==0.1.0
+    # via djlint
+httplib2==0.22.0
+    # via google-api-python-client
+    # via google-auth-httplib2
+humanfriendly==10.0
+    # via coloredlogs
+identify==2.6.5
+    # via pre-commit
+idna==2.10
+    # via email-validator
+    # via flanker
+    # via requests
+    # via tldextract
+    # via yarl
+importlib-metadata==4.13.0
+    # via djlint
+iniconfig==2.0.0
+    # via pytest
+ipython==7.31.1
+    # via simplelogin
+isort==5.13.2
+    # via pylint
+itsdangerous==1.1.0
+    # via flask
+    # via flask-debugtoolbar
+    # via flask-wtf
+    # via simplelogin
+jedi==0.19.2
+    # via ipython
+jinja2==2.11.3
+    # via flask
+    # via yacron
+jmespath==1.0.1
+    # via boto3
+    # via botocore
+jwcrypto==0.9.1
+    # via simplelogin
+lazy-object-proxy==1.10.0
+    # via astroid
+limits==4.0.0
+    # via flask-limiter
+loguru==0.7.3
+    # via aiospamc
+mako==1.3.8
+    # via alembic
+markupsafe==1.1.1
+    # via jinja2
+    # via mako
+    # via simplelogin
+    # via wtforms
+matplotlib-inline==0.1.7
+    # via ipython
+mccabe==0.7.0
+    # via pylint
+memory-profiler==0.57.0
+    # via simplelogin
+multidict==6.1.0
+    # via aiohttp
+    # via yarl
+mypy-extensions==1.0.0
+    # via black
+newrelic==8.8.1
+    # via simplelogin
+newrelic-telemetry-sdk==0.5.1
+    # via simplelogin
+nodeenv==1.9.1
+    # via pre-commit
+oauthlib==3.2.2
+    # via requests-oauthlib
+packaging==24.2
+    # via limits
+    # via pytest
+parso==0.8.4
+    # via jedi
+pathspec==0.9.0
+    # via black
+    # via djlint
+pexpect==4.9.0
+    # via ipython
+pgpy==0.5.4
+    # via simplelogin
+phpserialize==1.3
+    # via simplelogin
+pickleshare==0.7.5
+    # via ipython
+platformdirs==4.3.6
+    # via black
+    # via pylint
+    # via virtualenv
+pluggy==1.5.0
+    # via pytest
+ply==3.11
+    # via flanker
+pre-commit==2.17.0
+prompt-toolkit==3.0.48
+    # via ipython
+propcache==0.2.1
+    # via aiohttp
+    # via yarl
+proto-plus==1.25.0
+    # via google-api-core
+protobuf==5.29.3
+    # via google-api-core
+    # via googleapis-common-protos
+    # via proto-plus
+psutil==6.1.1
+    # via memory-profiler
+psycopg2-binary==2.9.10
+    # via simplelogin
+ptyprocess==0.7.0
+    # via pexpect
+py==1.11.0
+    # via pytest
+pyasn1==0.6.1
+    # via pgpy
+    # via pyasn1-modules
+    # via rsa
+pyasn1-modules==0.4.1
+    # via google-auth
+pycparser==2.22
+    # via cffi
+pycryptodome==3.9.9
+    # via simplelogin
+pygments==2.19.1
+    # via flask-debugtoolbar-sqlalchemy
+    # via ipython
+pyjwt==2.10.1
+    # via twilio
+pylint==2.14.5
+pyopenssl==19.1.0
+    # via simplelogin
+    # via webauthn
+pyotp==2.4.1
+    # via simplelogin
+pyparsing==3.2.1
+    # via httplib2
+pyre2==0.3.6
+    # via simplelogin
+pyspf==2.0.14
+    # via simplelogin
+pytest==7.0.1
+    # via pytest-cov
+pytest-cov==3.0.0
+python-dateutil==2.9.0.post0
+    # via arrow
+    # via botocore
+    # via strictyaml
+python-dotenv==0.14.0
+    # via simplelogin
+python-gnupg==0.4.9
+    # via simplelogin
+pytz==2024.2
+    # via twilio
+    # via yacron
+pyyaml==6.0.2
+    # via djlint
+    # via pre-commit
+redis==4.5.5
+    # via simplelogin
+regex==2022.10.31
+    # via djlint
+    # via flanker
+requests==2.25.1
+    # via coinbase-commerce
+    # via facebook-sdk
+    # via google-api-core
+    # via requests-file
+    # via requests-oauthlib
+    # via simplelogin
+    # via tldextract
+    # via twilio
+requests-file==2.1.0
+    # via tldextract
+requests-oauthlib==1.3.1
+    # via simplelogin
+rsa==4.9
+    # via google-auth
+ruamel-yaml==0.17.4
+    # via yacron
+ruff==0.1.15
+s3transfer==0.10.4
+    # via boto3
+sentry-sdk==2.20.0
+    # via simplelogin
+    # via yacron
+setuptools==75.8.0
+    # via astroid
+    # via gunicorn
+    # via ipython
+    # via zope-event
+    # via zope-interface
+simplejson==3.19.3
+    # via flask-profiler
+six==1.17.0
+    # via coinbase-commerce
+    # via flanker
+    # via flask-cors
+    # via flask-limiter
+    # via google-api-python-client
+    # via google-auth-httplib2
+    # via jwcrypto
+    # via pgpy
+    # via pyopenssl
+    # via python-dateutil
+    # via sqlalchemy-utils
+    # via webauthn
+sqlalchemy==1.3.24
+    # via alembic
+    # via flask-debugtoolbar-sqlalchemy
+    # via flask-sqlalchemy
+    # via simplelogin
+    # via sqlalchemy-utils
+sqlalchemy-utils==0.36.8
+    # via simplelogin
+sqlparse==0.5.3
+    # via flask-debugtoolbar-sqlalchemy
+strictyaml==1.7.3
+    # via yacron
+tld==0.13
+    # via flanker
+tldextract==3.1.2
+    # via simplelogin
+toml==0.10.2
+    # via pre-commit
+tomli==2.2.1
+    # via black
+    # via coverage
+    # via djlint
+    # via pylint
+    # via pytest
+tomlkit==0.13.2
+    # via pylint
+tqdm==4.67.1
+    # via djlint
+traitlets==5.14.3
+    # via ipython
+    # via matplotlib-inline
+twilio==7.3.2
+    # via simplelogin
+typer==0.9.4
+    # via aiospamc
+typing-extensions==4.12.2
+    # via aiospamc
+    # via alembic
+    # via limits
+    # via multidict
+    # via typer
+unidecode==1.1.2
+    # via simplelogin
+uritemplate==3.0.1
+    # via google-api-python-client
+urllib3==1.26.20
+    # via botocore
+    # via newrelic-telemetry-sdk
+    # via requests
+    # via sentry-sdk
+virtualenv==20.29.0
+    # via pre-commit
+watchtower==0.8.0
+    # via simplelogin
+wcwidth==0.2.13
+    # via prompt-toolkit
+webauthn==0.4.7
+    # via simplelogin
+webob==1.8.9
+    # via flanker
+werkzeug==1.0.1
+    # via flask
+    # via flask-debugtoolbar
+    # via simplelogin
+wrapt==1.17.2
+    # via astroid
+    # via deprecated
+wtforms==2.3.3
+    # via flask-admin
+    # via flask-wtf
+    # via simplelogin
+yacron==0.19.0
+    # via simplelogin
+yarl==1.18.3
+    # via aiohttp
+zipp==3.21.0
+    # via importlib-metadata
+zope-event==5.0
+    # via gevent
+zope-interface==7.2
+    # via gevent
diff --git a/app/requirements.lock b/app/requirements.lock
new file mode 100644
index 0000000..449c9be
--- /dev/null
+++ b/app/requirements.lock
@@ -0,0 +1,392 @@
+# generated by rye
+# use `rye lock` or `rye sync` to update this lockfile
+#
+# last locked with the following flags:
+#   pre: false
+#   features: []
+#   all-features: false
+#   with-sources: false
+#   generate-hashes: false
+#   universal: false
+
+-e file:.
+aiohttp==3.8.4
+    # via google-auth
+    # via yacron
+aiosignal==1.2.0
+    # via aiohttp
+aiosmtpd==1.4.2
+    # via simplelogin
+aiosmtplib==1.1.4
+    # via yacron
+aiospamc==0.10.0
+    # via simplelogin
+alembic==1.4.3
+    # via flask-migrate
+appnope==0.1.0
+    # via ipython
+arrow==0.16.0
+    # via simplelogin
+async-timeout==4.0.2
+    # via aiohttp
+    # via redis
+atpublic==2.0
+    # via aiosmtpd
+attrs==20.2.0
+    # via aiohttp
+    # via aiosmtpd
+    # via flanker
+backcall==0.2.0
+    # via ipython
+bcrypt==3.2.0
+    # via simplelogin
+blinker==1.4
+    # via flask-debugtoolbar
+    # via simplelogin
+boto3==1.35.99
+    # via simplelogin
+    # via watchtower
+botocore==1.35.99
+    # via boto3
+    # via s3transfer
+cachetools==4.1.1
+    # via google-auth
+cbor2==5.2.0
+    # via webauthn
+certifi==2019.11.28
+    # via aiospamc
+    # via requests
+    # via sentry-sdk
+cffi==1.14.4
+    # via bcrypt
+    # via cryptography
+chardet==3.0.4
+    # via flanker
+    # via requests
+charset-normalizer==3.4.1
+    # via aiohttp
+click==8.0.3
+    # via flask
+    # via typer
+coinbase-commerce==1.0.1
+    # via simplelogin
+coloredlogs==14.0
+    # via simplelogin
+crontab==0.22.8
+    # via yacron
+cryptography==37.0.1
+    # via flanker
+    # via jwcrypto
+    # via pgpy
+    # via pyopenssl
+    # via simplelogin
+    # via webauthn
+decorator==4.4.2
+    # via ipython
+deprecated==1.2.13
+    # via simplelogin
+dkimpy==1.0.5
+    # via simplelogin
+dnspython==2.6.1
+    # via dkimpy
+    # via email-validator
+    # via simplelogin
+email-validator==1.1.3
+    # via simplelogin
+facebook-sdk==3.1.0
+    # via simplelogin
+filelock==3.15.4
+    # via tldextract
+flanker==0.9.11
+    # via simplelogin
+flask==1.1.2
+    # via flask-admin
+    # via flask-cors
+    # via flask-debugtoolbar
+    # via flask-httpauth
+    # via flask-limiter
+    # via flask-login
+    # via flask-migrate
+    # via flask-profiler
+    # via flask-sqlalchemy
+    # via flask-wtf
+    # via simplelogin
+flask-admin==1.5.7
+    # via simplelogin
+flask-cors==3.0.9
+    # via simplelogin
+flask-debugtoolbar==0.11.0
+    # via flask-debugtoolbar-sqlalchemy
+    # via simplelogin
+flask-debugtoolbar-sqlalchemy==0.2.0
+    # via simplelogin
+flask-httpauth==4.1.0
+    # via flask-profiler
+flask-limiter==1.4
+    # via simplelogin
+flask-login==0.5.0
+    # via simplelogin
+flask-migrate==2.5.3
+    # via simplelogin
+flask-profiler==1.8.1
+    # via simplelogin
+flask-sqlalchemy==2.5.1
+    # via flask-migrate
+flask-wtf==0.14.3
+    # via simplelogin
+frozenlist==1.3.3
+    # via aiohttp
+    # via aiosignal
+future==0.18.3
+    # via webauthn
+gevent==24.11.1
+    # via simplelogin
+google-api-core==1.22.2
+    # via google-api-python-client
+google-api-python-client==1.12.3
+    # via simplelogin
+google-auth==1.22.0
+    # via google-api-core
+    # via google-api-python-client
+    # via google-auth-httplib2
+google-auth-httplib2==0.0.4
+    # via google-api-python-client
+    # via simplelogin
+googleapis-common-protos==1.52.0
+    # via google-api-core
+greenlet==3.1.1
+    # via gevent
+gunicorn==20.0.4
+    # via simplelogin
+httplib2==0.22.0
+    # via google-api-python-client
+    # via google-auth-httplib2
+humanfriendly==8.2
+    # via coloredlogs
+idna==2.10
+    # via email-validator
+    # via flanker
+    # via requests
+    # via tldextract
+    # via yarl
+ipython==7.31.1
+    # via simplelogin
+ipython-genutils==0.2.0
+    # via traitlets
+itsdangerous==1.1.0
+    # via flask
+    # via flask-debugtoolbar
+    # via flask-wtf
+    # via simplelogin
+jedi==0.17.2
+    # via ipython
+jinja2==2.11.3
+    # via flask
+    # via yacron
+jmespath==0.10.0
+    # via boto3
+    # via botocore
+jwcrypto==0.8
+    # via simplelogin
+limits==1.5.1
+    # via flask-limiter
+loguru==0.7.2
+    # via aiospamc
+mako==1.2.4
+    # via alembic
+markupsafe==1.1.1
+    # via jinja2
+    # via mako
+    # via simplelogin
+    # via wtforms
+matplotlib-inline==0.1.3
+    # via ipython
+memory-profiler==0.57.0
+    # via simplelogin
+multidict==4.7.6
+    # via aiohttp
+    # via yarl
+newrelic==8.8.0
+    # via simplelogin
+newrelic-telemetry-sdk==0.5.0
+    # via simplelogin
+oauthlib==3.1.0
+    # via requests-oauthlib
+parso==0.7.1
+    # via jedi
+pexpect==4.8.0
+    # via ipython
+pgpy==0.5.4
+    # via simplelogin
+phpserialize==1.3
+    # via simplelogin
+pickleshare==0.7.5
+    # via ipython
+ply==3.11
+    # via flanker
+prompt-toolkit==3.0.7
+    # via ipython
+protobuf==5.27.1
+    # via google-api-core
+    # via googleapis-common-protos
+psutil==5.7.2
+    # via memory-profiler
+psycopg2-binary==2.9.3
+    # via simplelogin
+ptyprocess==0.6.0
+    # via pexpect
+pyasn1==0.4.8
+    # via pgpy
+    # via pyasn1-modules
+    # via rsa
+pyasn1-modules==0.2.8
+    # via google-auth
+pycparser==2.20
+    # via cffi
+pycryptodome==3.9.8
+    # via simplelogin
+pygments==2.7.4
+    # via flask-debugtoolbar-sqlalchemy
+    # via ipython
+pyjwt==2.4.0
+    # via twilio
+pyopenssl==19.1.0
+    # via simplelogin
+    # via webauthn
+pyotp==2.4.0
+    # via simplelogin
+pyparsing==2.4.7
+    # via httplib2
+pyre2==0.3.6
+    # via simplelogin
+pyspf==2.0.14
+    # via simplelogin
+python-dateutil==2.8.1
+    # via alembic
+    # via arrow
+    # via botocore
+    # via strictyaml
+python-dotenv==0.14.0
+    # via simplelogin
+python-editor==1.0.4
+    # via alembic
+python-gnupg==0.4.6
+    # via simplelogin
+pytz==2020.1
+    # via google-api-core
+    # via twilio
+    # via yacron
+redis==4.5.5
+    # via simplelogin
+regex==2023.12.25
+    # via flanker
+requests==2.25.1
+    # via coinbase-commerce
+    # via facebook-sdk
+    # via google-api-core
+    # via requests-file
+    # via requests-oauthlib
+    # via simplelogin
+    # via tldextract
+    # via twilio
+requests-file==1.5.1
+    # via tldextract
+requests-oauthlib==1.3.0
+    # via simplelogin
+rsa==4.6
+    # via google-auth
+ruamel-yaml==0.17.4
+    # via strictyaml
+    # via yacron
+s3transfer==0.10.4
+    # via boto3
+sentry-sdk==2.20.0
+    # via simplelogin
+    # via yacron
+setuptools==67.6.0
+    # via google-api-core
+    # via google-auth
+    # via gunicorn
+    # via ipython
+    # via zope-event
+    # via zope-interface
+simplejson==3.17.2
+    # via flask-profiler
+six==1.15.0
+    # via bcrypt
+    # via coinbase-commerce
+    # via flanker
+    # via flask-cors
+    # via flask-limiter
+    # via google-api-core
+    # via google-api-python-client
+    # via google-auth
+    # via google-auth-httplib2
+    # via limits
+    # via pgpy
+    # via pyopenssl
+    # via python-dateutil
+    # via requests-file
+    # via sqlalchemy-utils
+    # via webauthn
+sqlalchemy==1.3.24
+    # via alembic
+    # via flask-debugtoolbar-sqlalchemy
+    # via flask-sqlalchemy
+    # via simplelogin
+    # via sqlalchemy-utils
+sqlalchemy-utils==0.36.8
+    # via simplelogin
+sqlparse==0.4.4
+    # via flask-debugtoolbar-sqlalchemy
+strictyaml==1.1.0
+    # via yacron
+tld==0.12.6
+    # via flanker
+tldextract==3.1.2
+    # via simplelogin
+traitlets==5.0.4
+    # via ipython
+    # via matplotlib-inline
+twilio==7.3.2
+    # via simplelogin
+typer==0.9.0
+    # via aiospamc
+typing-extensions==4.8.0
+    # via aiospamc
+    # via typer
+unidecode==1.1.1
+    # via simplelogin
+uritemplate==3.0.1
+    # via google-api-python-client
+urllib3==1.26.20
+    # via botocore
+    # via newrelic-telemetry-sdk
+    # via requests
+    # via sentry-sdk
+watchtower==0.8.0
+    # via simplelogin
+wcwidth==0.2.5
+    # via prompt-toolkit
+webauthn==0.4.7
+    # via simplelogin
+webob==1.8.7
+    # via flanker
+werkzeug==1.0.1
+    # via flask
+    # via flask-debugtoolbar
+    # via simplelogin
+wrapt==1.15.0
+    # via deprecated
+wtforms==2.3.3
+    # via flask-admin
+    # via flask-wtf
+    # via simplelogin
+yacron==0.19.0
+    # via simplelogin
+yarl==1.9.2
+    # via aiohttp
+zope-event==5.0
+    # via gevent
+zope-interface==7.2
+    # via gevent
diff --git a/app/scripts/new-migration.sh b/app/scripts/new-migration.sh
index da11a75..5456857 100755
--- a/app/scripts/new-migration.sh
+++ b/app/scripts/new-migration.sh
@@ -12,10 +12,10 @@ docker run -p 25432:5432 --name ${container_name} -e POSTGRES_PASSWORD=postgres
 sleep 3
 
 # upgrade the DB to the latest stage and
-env DB_URI=postgresql://postgres:postgres@127.0.0.1:25432/sl poetry run alembic upgrade head
+env DB_URI=postgresql://postgres:postgres@127.0.0.1:25432/sl rye run alembic upgrade head
 
 # generate the migration script.
-env DB_URI=postgresql://postgres:postgres@127.0.0.1:25432/sl poetry run alembic revision --autogenerate $@
+env DB_URI=postgresql://postgres:postgres@127.0.0.1:25432/sl rye run alembic revision --autogenerate $@
 
 # remove the db
 docker rm -f ${container_name}
diff --git a/app/scripts/reset_local_db.sh b/app/scripts/reset_local_db.sh
index 422c2a8..42dae95 100755
--- a/app/scripts/reset_local_db.sh
+++ b/app/scripts/reset_local_db.sh
@@ -3,5 +3,5 @@
 export DB_URI=postgresql://myuser:mypassword@localhost:15432/simplelogin
 echo 'drop schema public cascade; create schema public;' | psql  $DB_URI
 
-poetry run alembic upgrade head
-poetry run flask dummy-data
+rye run alembic upgrade head
+rye run flask dummy-data
diff --git a/app/scripts/reset_test_db.sh b/app/scripts/reset_test_db.sh
index 2546601..234cef3 100755
--- a/app/scripts/reset_test_db.sh
+++ b/app/scripts/reset_test_db.sh
@@ -3,4 +3,4 @@
 export DB_URI=postgresql://myuser:mypassword@localhost:15432/test
 echo 'drop schema public cascade; create schema public;' | psql  $DB_URI
 
-poetry run alembic upgrade head
+rye run alembic upgrade head
diff --git a/app/scripts/run-test.sh b/app/scripts/run-test.sh
index b403b76..531a9aa 100755
--- a/app/scripts/run-test.sh
+++ b/app/scripts/run-test.sh
@@ -10,10 +10,10 @@ docker run -d --name sl-test-db -e POSTGRES_PASSWORD=test -e POSTGRES_USER=test
 sleep 3
 
 # migrate the DB to the latest version
-CONFIG=tests/test.env poetry run alembic upgrade head
+CONFIG=tests/test.env rye run alembic upgrade head
 
 # run test
-poetry run pytest -c pytest.ci.ini
+rye run pytest -c pytest.ci.ini
 
 # Delete the test DB
 docker rm -f sl-test-db
diff --git a/app/tests/api/test_alias.py b/app/tests/api/test_alias.py
index dd39e13..010b396 100644
--- a/app/tests/api/test_alias.py
+++ b/app/tests/api/test_alias.py
@@ -549,7 +549,7 @@ def test_create_contact_route_free_users(flask_client):
     assert r.status_code == 201
 
     # End trial and disallow for new free users. Config should allow it
-    user.flags = User.FLAG_DISABLE_CREATE_CONTACTS
+    user.flags = User.FLAG_FREE_DISABLE_CREATE_CONTACTS
     Session.commit()
     r = flask_client.post(
         url_for("api.create_contact_route", alias_id=alias.id),
diff --git a/app/tests/test_contact_utils.py b/app/tests/test_contact_utils.py
index 0b4b985..d0fa574 100644
--- a/app/tests/test_contact_utils.py
+++ b/app/tests/test_contact_utils.py
@@ -135,7 +135,7 @@ def test_create_contact_free_user():
     assert result.contact is not None
     assert not result.contact.automatic_created
     # Free users with the flag should be able to still create automatic emails
-    user.flags = User.FLAG_DISABLE_CREATE_CONTACTS
+    user.flags = User.FLAG_FREE_DISABLE_CREATE_CONTACTS
     Session.flush()
     result = create_contact(random_email(), alias, automatic_created=True)
     assert result.error is None
diff --git a/app/tests/test_email_handler.py b/app/tests/test_email_handler.py
index 1c9c650..e77a971 100644
--- a/app/tests/test_email_handler.py
+++ b/app/tests/test_email_handler.py
@@ -2,6 +2,7 @@ import random
 from email.message import EmailMessage
 from typing import List
 
+import arrow
 import pytest
 from aiosmtpd.smtp import Envelope
 
@@ -387,3 +388,15 @@ def test_preserve_headers(flask_client):
     msg = sent_mails[0].msg
     for header in headers_to_keep:
         assert msg[header] == header + "keep"
+
+
+def test_not_send_to_pending_to_delete_users(flask_client):
+    user = create_new_user()
+    alias = Alias.create_new_random(user)
+    user.delete_on = arrow.utcnow()
+    envelope = Envelope()
+    envelope.mail_from = "somewhere@lo.cal"
+    envelope.rcpt_tos = [alias.email]
+    msg = EmailMessage()
+    result = email_handler.handle(envelope, msg)
+    assert result == status.E504