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+
+                        <h1 id="managing-dependencies-with-poetry"><a class="header" href="#managing-dependencies-with-poetry">Managing dependencies with Poetry</a></h1>
+<p>This is a quick cheat sheet for developers on how to use <a href="https://python-poetry.org/"><code>poetry</code></a>.</p>
+<h1 id="background"><a class="header" href="#background">Background</a></h1>
+<p>Synapse uses a variety of third-party Python packages to function as a homeserver.
+Some of these are direct dependencies, listed in <code>pyproject.toml</code> under the
+<code>[tool.poetry.dependencies]</code> section. The rest are transitive dependencies (the
+things that our direct dependencies themselves depend on, and so on recursively.)</p>
+<p>We maintain a locked list of all our dependencies (transitive included) so that
+we can track exactly which version of each dependency appears in a given release.
+See <a href="https://github.com/matrix-org/synapse/issues/11537#issue-1074469665">here</a>
+for discussion of why we wanted this for Synapse. We chose to use
+<a href="https://python-poetry.org/"><code>poetry</code></a> to manage this locked list; see
+<a href="https://github.com/matrix-org/synapse/issues/11537#issuecomment-1015975819">this comment</a>
+for the reasoning.</p>
+<p>The locked dependencies get included in our &quot;self-contained&quot; releases: namely,
+our docker images and our debian packages. We also use the locked dependencies
+in development and our continuous integration.</p>
+<p>Separately, our &quot;broad&quot; dependencies—the version ranges specified in
+<code>pyproject.toml</code>—are included as metadata in our &quot;sdists&quot; and &quot;wheels&quot; <a href="https://pypi.org/project/matrix-synapse">uploaded
+to PyPI</a>. Installing from PyPI or from
+the Synapse source tree directly will <em>not</em> use the locked dependencies; instead,
+they'll pull in the latest version of each package available at install time.</p>
+<h2 id="example-dependency"><a class="header" href="#example-dependency">Example dependency</a></h2>
+<p>An example may help. We have a broad dependency on
+<a href="https://pypi.org/project/phonenumbers/"><code>phonenumbers</code></a>, as declared in
+this snippet from pyproject.toml <a href="https://github.com/matrix-org/synapse/blob/release-v1.57/pyproject.toml#L133">as of Synapse 1.57</a>:</p>
+<pre><code class="language-toml">[tool.poetry.dependencies]
+# ...
+phonenumbers = &quot;&gt;=8.2.0&quot;
+</code></pre>
+<p>In our lockfile this is
+<a href="https://github.com/matrix-org/synapse/blob/dfc7646504cef3e4ff396c36089e1c6f1b1634de/poetry.lock#L679-L685">pinned</a>
+to version 8.12.44, even though
+<a href="https://pypi.org/project/phonenumbers/#history">newer versions are available</a>.</p>
+<pre><code class="language-toml">[[package]]
+name = &quot;phonenumbers&quot;
+version = &quot;8.12.44&quot;
+description = &quot;Python version of Google's common library for parsing, formatting, storing and validating international phone numbers.&quot;
+category = &quot;main&quot;
+optional = false
+python-versions = &quot;*&quot;
+</code></pre>
+<p>The lockfile also includes a
+<a href="https://github.com/matrix-org/synapse/blob/release-v1.57/poetry.lock#L2178-L2181">cryptographic checksum</a>
+of the sdists and wheels provided for this version of <code>phonenumbers</code>.</p>
+<pre><code class="language-toml">[metadata.files]
+# ...
+phonenumbers = [
+    {file = &quot;phonenumbers-8.12.44-py2.py3-none-any.whl&quot;, hash = &quot;sha256:cc1299cf37b309ecab6214297663ab86cb3d64ae37fd5b88e904fe7983a874a6&quot;},
+    {file = &quot;phonenumbers-8.12.44.tar.gz&quot;, hash = &quot;sha256:26cfd0257d1704fe2f88caff2caabb70d16a877b1e65b6aae51f9fbbe10aa8ce&quot;},
+]
+</code></pre>
+<p>We can see this pinned version inside the docker image for that release:</p>
+<pre><code>$ docker pull matrixdotorg/synapse:v1.57.0
+...
+$ docker run --entrypoint pip matrixdotorg/synapse:v1.57.0 show phonenumbers
+Name: phonenumbers
+Version: 8.12.44
+Summary: Python version of Google's common library for parsing, formatting, storing and validating international phone numbers.
+Home-page: https://github.com/daviddrysdale/python-phonenumbers
+Author: David Drysdale
+Author-email: dmd@lurklurk.org
+License: Apache License 2.0
+Location: /usr/local/lib/python3.9/site-packages
+Requires:
+Required-by: matrix-synapse
+</code></pre>
+<p>Whereas the wheel metadata just contains the broad dependencies:</p>
+<pre><code>$ cd /tmp
+$ wget https://files.pythonhosted.org/packages/ca/5e/d722d572cc5b3092402b783d6b7185901b444427633bd8a6b00ea0dd41b7/matrix_synapse-1.57.0rc1-py3-none-any.whl
+...
+$ unzip -c matrix_synapse-1.57.0rc1-py3-none-any.whl matrix_synapse-1.57.0rc1.dist-info/METADATA | grep phonenumbers
+Requires-Dist: phonenumbers (&gt;=8.2.0)
+</code></pre>
+<h1 id="tooling-recommendation-direnv"><a class="header" href="#tooling-recommendation-direnv">Tooling recommendation: direnv</a></h1>
+<p><a href="https://direnv.net/"><code>direnv</code></a> is a tool for activating environments in your
+shell inside a given directory. Its support for poetry is unofficial (a
+community wiki recipe only), but works solidly in our experience. We thoroughly
+recommend it for daily use. To use it:</p>
+<ol>
+<li><a href="https://direnv.net/docs/installation.html">Install <code>direnv</code></a> - it's likely
+packaged for your system already.</li>
+<li>Teach direnv about poetry. The <a href="https://github.com/direnv/direnv/wiki/Python#poetry">shell config here</a>
+needs to be added to <code>~/.config/direnv/direnvrc</code> (or more generally <code>$XDG_CONFIG_HOME/direnv/direnvrc</code>).</li>
+<li>Mark the synapse checkout as a poetry project: <code>echo layout poetry &gt; .envrc</code>.</li>
+<li>Convince yourself that you trust this <code>.envrc</code> configuration and project.
+Then formally confirm this to <code>direnv</code> by running <code>direnv allow</code>.</li>
+</ol>
+<p>Then whenever you navigate to the synapse checkout, you should be able to run
+e.g. <code>mypy</code> instead of <code>poetry run mypy</code>; <code>python</code> instead of
+<code>poetry run python</code>; and your shell commands will automatically run in the
+context of poetry's venv, without having to run <code>poetry shell</code> beforehand.</p>
+<h1 id="how-do-i"><a class="header" href="#how-do-i">How do I...</a></h1>
+<h2 id="reset-my-venv-to-the-locked-environment"><a class="header" href="#reset-my-venv-to-the-locked-environment">...reset my venv to the locked environment?</a></h2>
+<pre><code class="language-shell">poetry install --extras all --remove-untracked
+</code></pre>
+<h2 id="delete-everything-and-start-over-from-scratch"><a class="header" href="#delete-everything-and-start-over-from-scratch">...delete everything and start over from scratch?</a></h2>
+<pre><code class="language-shell"># Stop the current virtualenv if active
+$ deactivate
+
+# Remove all of the files from the current environment.
+# Don't worry, even though it says &quot;all&quot;, this will only
+# remove the Poetry virtualenvs for the current project.
+$ poetry env remove --all
+
+# Reactivate Poetry shell to create the virtualenv again
+$ poetry shell
+# Install everything again
+$ poetry install --extras all
+</code></pre>
+<h2 id="run-a-command-in-the-poetry-virtualenv"><a class="header" href="#run-a-command-in-the-poetry-virtualenv">...run a command in the <code>poetry</code> virtualenv?</a></h2>
+<p>Use <code>poetry run cmd args</code> when you need the python virtualenv context.
+To avoid typing <code>poetry run</code> all the time, you can run  <code>poetry shell</code>
+to start a new shell in the poetry virtualenv context. Within <code>poetry shell</code>,
+<code>python</code>, <code>pip</code>, <code>mypy</code>, <code>trial</code>, etc. are all run inside the project virtualenv
+and isolated from the rest o the system.</p>
+<p>Roughly speaking, the translation from a traditional virtualenv is:</p>
+<ul>
+<li><code>env/bin/activate</code> -&gt; <code>poetry shell</code>, and</li>
+<li><code>deactivate</code> -&gt; close the terminal (Ctrl-D, <code>exit</code>, etc.)</li>
+</ul>
+<p>See also the direnv recommendation above, which makes <code>poetry run</code> and
+<code>poetry shell</code> unnecessary.</p>
+<h2 id="inspect-the-poetry-virtualenv"><a class="header" href="#inspect-the-poetry-virtualenv">...inspect the <code>poetry</code> virtualenv?</a></h2>
+<p>Some suggestions:</p>
+<pre><code class="language-shell"># Current env only
+poetry env info
+# All envs: this allows you to have e.g. a poetry managed venv for Python 3.7,
+# and another for Python 3.10.
+poetry env list --full-path
+poetry run pip list
+</code></pre>
+<p>Note that <code>poetry show</code> describes the abstract <em>lock file</em> rather than your
+on-disk environment. With that said, <code>poetry show --tree</code> can sometimes be
+useful.</p>
+<h2 id="add-a-new-dependency"><a class="header" href="#add-a-new-dependency">...add a new dependency?</a></h2>
+<p>Either:</p>
+<ul>
+<li>manually update <code>pyproject.toml</code>; then <code>poetry lock --no-update</code>; or else</li>
+<li><code>poetry add packagename</code>. See <code>poetry add --help</code>; note the <code>--dev</code>,
+<code>--extras</code> and <code>--optional</code> flags in particular.
+<ul>
+<li><strong>NB</strong>: this specifies the new package with a version given by a &quot;caret bound&quot;. This won't get forced to its lowest version in the old deps CI job: see <a href="https://github.com/matrix-org/synapse/blob/4e1374373857f2f7a911a31c50476342d9070681/.ci/scripts/test_old_deps.sh#L35-L39">this TODO</a>.</li>
+</ul>
+</li>
+</ul>
+<p>Include the updated <code>pyproject.toml</code> and <code>poetry.lock</code> files in your commit.</p>
+<h2 id="remove-a-dependency"><a class="header" href="#remove-a-dependency">...remove a dependency?</a></h2>
+<p>This is not done often and is untested, but</p>
+<pre><code class="language-shell">poetry remove packagename
+</code></pre>
+<p>ought to do the trick. Alternatively, manually update <code>pyproject.toml</code> and
+<code>poetry lock --no-update</code>. Include the updated <code>pyproject.toml</code> and poetry.lock`
+files in your commit.</p>
+<h2 id="update-the-version-range-for-an-existing-dependency"><a class="header" href="#update-the-version-range-for-an-existing-dependency">...update the version range for an existing dependency?</a></h2>
+<p>Best done by manually editing <code>pyproject.toml</code>, then <code>poetry lock --no-update</code>.
+Include the updated <code>pyproject.toml</code> and <code>poetry.lock</code> in your commit.</p>
+<h2 id="update-a-dependency-in-the-locked-environment"><a class="header" href="#update-a-dependency-in-the-locked-environment">...update a dependency in the locked environment?</a></h2>
+<p>Use</p>
+<pre><code class="language-shell">poetry update packagename
+</code></pre>
+<p>to use the latest version of <code>packagename</code> in the locked environment, without
+affecting the broad dependencies listed in the wheel.</p>
+<p>There doesn't seem to be a way to do this whilst locking a <em>specific</em> version of
+<code>packagename</code>. We can workaround this (crudely) as follows:</p>
+<pre><code class="language-shell">poetry add packagename==1.2.3
+# This should update pyproject.lock.
+
+# Now undo the changes to pyproject.toml. For example
+# git restore pyproject.toml
+
+# Get poetry to recompute the content-hash of pyproject.toml without changing
+# the locked package versions.
+poetry lock --no-update
+</code></pre>
+<p>Either way, include the updated <code>poetry.lock</code> file in your commit.</p>
+<h2 id="export-a-requirementstxt-file"><a class="header" href="#export-a-requirementstxt-file">...export a <code>requirements.txt</code> file?</a></h2>
+<pre><code class="language-shell">poetry export --extras all
+</code></pre>
+<p>Be wary of bugs in <code>poetry export</code> and <code>pip install -r requirements.txt</code>.</p>
+<p>Note: <code>poetry export</code> will be made a plugin in Poetry 1.2. Additional config may
+be required.</p>
+<h2 id="build-a-test-wheel"><a class="header" href="#build-a-test-wheel">...build a test wheel?</a></h2>
+<p>I usually use</p>
+<pre><code class="language-shell">poetry run pip install build &amp;&amp; poetry run python -m build
+</code></pre>
+<p>because <a href="https://github.com/pypa/build"><code>build</code></a> is a standardish tool which
+doesn't require poetry. (It's what we use in CI too). However, you could try
+<code>poetry build</code> too.</p>
+<h1 id="troubleshooting"><a class="header" href="#troubleshooting">Troubleshooting</a></h1>
+<h2 id="check-the-version-of-poetry-with-poetry---version"><a class="header" href="#check-the-version-of-poetry-with-poetry---version">Check the version of poetry with <code>poetry --version</code>.</a></h2>
+<p>The minimum version of poetry supported by Synapse is 1.2.</p>
+<p>It can also be useful to check the version of <code>poetry-core</code> in use. If you've
+installed <code>poetry</code> with <code>pipx</code>, try <code>pipx runpip poetry list | grep poetry-core</code>.</p>
+<h2 id="clear-caches-poetry-cache-clear---all-pypi"><a class="header" href="#clear-caches-poetry-cache-clear---all-pypi">Clear caches: <code>poetry cache clear --all pypi</code>.</a></h2>
+<p>Poetry caches a bunch of information about packages that isn't readily available
+from PyPI. (This is what makes poetry seem slow when doing the first
+<code>poetry install</code>.) Try <code>poetry cache list</code> and <code>poetry cache clear --all &lt;name of cache&gt;</code> to see if that fixes things.</p>
+<h2 id="remove-outdated-egg-info"><a class="header" href="#remove-outdated-egg-info">Remove outdated egg-info</a></h2>
+<p>Delete the <code>matrix_synapse.egg-info/</code> directory from the root of your Synapse
+install.</p>
+<p>This stores some cached information about dependencies and often conflicts with
+letting Poetry do the right thing.</p>
+<h2 id="try---verbose-or---dry-run-arguments"><a class="header" href="#try---verbose-or---dry-run-arguments">Try <code>--verbose</code> or <code>--dry-run</code> arguments.</a></h2>
+<p>Sometimes useful to see what poetry's internal logic is.</p>
+
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