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Update Privoxy base image to v4.0.0 #6

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🚀 Feature: Upgrade Privoxy to 4.0.0

📝 Motivation

Privoxy 4.0.0 includes important security fixes, performance improvements, and updated dependencies compared to the 3.x series. This PR updates the Dockerfile and test suite to build, run, and verify Privoxy 4.0.0.

📋 Key Changes

Dockerfile

  • Bumped ARG PRIVOXY_VERSION from 3.0.34 to 4.0.0.

  • Switched from pcre-dev to pcre2-dev, as required by Privoxy 4.x.

  • Added net-tools (e.g. netstat) for easier debugging.

  • Strip out any stray \r (“CRLF”) from shipped scripts and configs via sed -i 's/\r$//' so they work properly on Alpine/Linux.

  • Preserve original Privoxy defaults under /opt/privoxy-default for volume-based overrides.

Tests (pytest)

  • Updated default --privoxy-version to 4.0.0.

  • Update pytest matrix and fixtures to target 4.0.0.

  • Enhanced tests/conftest.py to detect Windows/macOS hosts and use 127.0.0.1 for proxy binding on those platforms.

  • Verified that all HTTP/HTTPS connectivity, blocking, and adblock filter tests pass locally.

⚠️ Note on Python support

We’re keeping the project and the CI on Python 3.12 for now because Poetry (and some dependencies, such as pydantic-core) fail to build on 3.13. Once those issues are resolved upstream, we can bump to 3.13+.

dosAnjosGustavo and others added 10 commits June 22, 2025 19:30
…lity

- Apply necessary changes to support Privoxy 4.0.0.
- Adjust settings as required by the new version.
- Add -addext options to openssl command for CA and key usage extensions.
- Ensure compatibility with new Privoxy 4.x requirements.
…ility

- Update entrypoint to repopulate /usr/local/etc/privoxy from /opt/privoxy-default if empty.
- Ensure all scripts use LF line endings and are executable.
- Add step to copy default config to /opt/privoxy-default during build.
- Bump python version to 3.13.5, python-on-whales to ^0.77.0, and pytest to ^8.4.1.
- Update poetry.lock accordingly.
- Add /.pytest_cache and /.venv to .gitignore for better local environment isolation.
- Update Dockerfile to build Privoxy 4.0.0 and switch to pcre2.
- Update GitHub Actions workflows to use PRIVOXY_VERSION 4.0.0.
- Update test matrix and pytest default version to 4.0.0.
- Improve Dockerfile build steps for better compatibility with Privoxy 4.x.
- Update .github/workflows/ci.yml matrix to
- Now matches the pyproject.toml ^3.13.5 constraint
- Add requests ^2.32.4 to [tool.poetry.dependencies] in pyproject.toml
- Regenerate poetry.lock via poetry lock so pytest’s conftest can import requests
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@Tardo Tardo left a comment

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Thanks for this update! needed and addressing some of the issues :)

Comment on lines +40 to +45
f'openssl req -new -x509 '
f'-key {ca_key_file} -sha384 -days 3650 '
f'-out {ca_bundle_file} '
f'-subj "{subj}" '
f'-addext "basicConstraints=critical,CA:TRUE" '
f'-addext "keyUsage=critical,keyCertSign,cRLSign"'
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ensure good interoperability

Suggested change
f'openssl req -new -x509 '
f'-key {ca_key_file} -sha384 -days 3650 '
f'-out {ca_bundle_file} '
f'-subj "{subj}" '
f'-addext "basicConstraints=critical,CA:TRUE" '
f'-addext "keyUsage=critical,keyCertSign,cRLSign"'
'openssl req -new -x509 '
f'-key {ca_key_file} -sha384 -days 3650 '
f'-out {ca_bundle_file} '
f'-subj "{subj}" '
'-addext "basicConstraints=critical,CA:TRUE" '
'-addext "keyUsage=critical,keyCertSign,cRLSign" '
'-addext "subjectKeyIdentifier=hash"'

Comment on lines +6 to +9
if [ ! -e /usr/local/etc/privoxy/config ] || [ -z "$(ls -A /usr/local/etc/privoxy)" ]; then
echo "[entrypoint] void config, populating defaults..."
cp -a /opt/privoxy-default/* /usr/local/etc/privoxy/
fi
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I think this should be documented in the README and warn that changing the configuration may break compatibility with the “privman” script (if not preserving the filterfile and actionsfile options).

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2 participants