diff --git a/docker/Dockerfile b/docker/Dockerfile
index 24b5515eb9..6009da7db7 100644
--- a/docker/Dockerfile
+++ b/docker/Dockerfile
@@ -14,20 +14,61 @@
# DOCKER_BUILDKIT=1 docker build -f docker/Dockerfile --build-arg PYTHON_VERSION=3.10 .
#
+# Irritatingly, there is no blessed guide on how to distribute an application with its
+# poetry-managed environment in a docker image. We have opted for
+# `poetry export | pip install -r /dev/stdin`, but there are known bugs in
+# in `poetry export` whose fixes (scheduled for poetry 1.2) have yet to be released.
+# In case we get bitten by those bugs in the future, the recommendations here might
+# be useful:
+# https://github.com/python-poetry/poetry/discussions/1879#discussioncomment-216865
+# https://stackoverflow.com/questions/53835198/integrating-python-poetry-with-docker?answertab=scoredesc
+
+
+
ARG PYTHON_VERSION=3.9
###
-### Stage 0: builder
+### Stage 0: generate requirements.txt
###
-FROM docker.io/python:${PYTHON_VERSION}-slim as builder
+FROM docker.io/python:${PYTHON_VERSION}-slim as requirements
-# install the OS build deps
-#
# RUN --mount is specific to buildkit and is documented at
# https://github.com/moby/buildkit/blob/master/frontend/dockerfile/docs/syntax.md#build-mounts-run---mount.
-# Here we use it to set up a cache for apt, to improve rebuild speeds on
-# slow connections.
+# Here we use it to set up a cache for apt (and below for pip), to improve
+# rebuild speeds on slow connections.
+RUN \
+ --mount=type=cache,target=/var/cache/apt,sharing=locked \
+ --mount=type=cache,target=/var/lib/apt,sharing=locked \
+ apt-get update && apt-get install -y git \
+ && rm -rf /var/lib/apt/lists/*
+
+# We install poetry in its own build stage to avoid its dependencies conflicting with
+# synapse's dependencies.
+# We use a specific commit from poetry's master branch instead of our usual 1.1.12,
+# to incorporate fixes to some bugs in `poetry export`. This commit corresponds to
+# https://github.com/python-poetry/poetry/pull/5156 and
+# https://github.com/python-poetry/poetry/issues/5141 ;
+# without it, we generate a requirements.txt with incorrect environment markers,
+# which causes necessary packages to be omitted when we `pip install`.
#
+# NB: In poetry 1.2 `poetry export` will be moved into a plugin; we'll need to also
+# pip install poetry-plugin-export (https://github.com/python-poetry/poetry-plugin-export).
+RUN --mount=type=cache,target=/root/.cache/pip \
+ pip install --user git+https://github.com/python-poetry/poetry.git@fb13b3a676f476177f7937ffa480ee5cff9a90a5
+
+WORKDIR /synapse
+
+# Copy just what we need to run `poetry export`...
+COPY pyproject.toml poetry.lock README.rst /synapse/
+
+RUN /root/.local/bin/poetry export --extras all -o /synapse/requirements.txt
+
+###
+### Stage 1: builder
+###
+FROM docker.io/python:${PYTHON_VERSION}-slim as builder
+
+# install the OS build deps
RUN \
--mount=type=cache,target=/var/cache/apt,sharing=locked \
--mount=type=cache,target=/var/lib/apt,sharing=locked \
@@ -45,30 +86,27 @@ RUN \
zlib1g-dev \
&& rm -rf /var/lib/apt/lists/*
-# Copy just what we need to pip install
-COPY MANIFEST.in README.rst setup.py /synapse/
-COPY synapse/__init__.py /synapse/synapse/__init__.py
-COPY synapse/python_dependencies.py /synapse/synapse/python_dependencies.py
-
# To speed up rebuilds, install all of the dependencies before we copy over
-# the whole synapse project so that we this layer in the Docker cache can be
+# the whole synapse project, so that this layer in the Docker cache can be
# used while you develop on the source
#
-# This is aiming at installing the `install_requires` and `extras_require` from `setup.py`
+# This is aiming at installing the `[tool.poetry.depdendencies]` from pyproject.toml.
+COPY --from=requirements /synapse/requirements.txt /synapse/
RUN --mount=type=cache,target=/root/.cache/pip \
- pip install --prefix="/install" --no-warn-script-location \
- /synapse[all]
+ pip install --prefix="/install" --no-warn-script-location -r /synapse/requirements.txt
-# Copy over the rest of the project
+# Copy over the rest of the synapse source code.
COPY synapse /synapse/synapse/
+# ... and what we need to `pip install`.
+# TODO: once pyproject.toml declares poetry-core as its build system, we'll need to copy
+# pyproject.toml here, ditching setup.py and MANIFEST.in.
+COPY setup.py MANIFEST.in README.rst /synapse/
-# Install the synapse package itself and all of its children packages.
-#
-# This is aiming at installing only the `packages=find_packages(...)` from `setup.py
+# Install the synapse package itself.
RUN pip install --prefix="/install" --no-deps --no-warn-script-location /synapse
###
-### Stage 1: runtime
+### Stage 2: runtime
###
FROM docker.io/python:${PYTHON_VERSION}-slim
|