Publishing Nightmares: The Questions That'll Save Your Ass

Q

"Why does `twine upload` keep failing with 'HTTP 403: Invalid or non-existent authentication information'?"

A

Your API token is probably fucked. PyPI changed authentication in 2024 - legacy passwords are dead, and they didn't make it obvious in the UI. Fix it:

## Generate a new API token at https://pypi.org/manage/account/token/
pip install twine
twine upload dist/* --username __token__ --password pypi-your-actual-token-here

Pro tip: Store the token in ~/.pypirc so you don't have to type that shit every time:

[pypi]
username = __token__  
password = pypi-AgEIcHlwaS5vcmcyLongTokenStringHere
Q

"My package uploaded but when I install it, Python can't find my modules. What the fuck?"

A

Your pyproject.toml is lying about where your code actually is. Classic mistake when switching from setup.py.

This breaks:

[build-system]
requires = ["setuptools", "wheel"]
[project]
name = "mypackage"

This works:

[build-system]  
requires = ["setuptools>=61.0", "wheel"]
build-backend = "setuptools.build_meta"

[project]
name = "mypackage"
dynamic = ["version"]

[tool.setuptools.packages.find]  
where = ["src"]  # Tell setuptools your code is in src/
Q

"How do I avoid publishing packages that some asshole can hijack?"

A

Use Trusted Publishing - it's GitHub Actions that directly authenticates with PyPI without storing tokens anywhere.

Set it up:

  1. In PyPI: Account Settings → Publishing → Add a new pending publisher
  2. Fill out: your GitHub repo, workflow filename, environment name
  3. In GitHub: Create a "pypi" environment with required reviewers
  4. Use the official PyPA GitHub Action

No more token bullshit, no more credential leaks.

Q

"Someone created a typosquatting package that looks like mine. Now what?"

A

File a PyPI support request immediately with evidence. They take this shit seriously since the December 2024 Ultralytics attack.

Protect yourself:

  • Register common typos of your package name early
  • Monitor PyPI for similar names using PyPI-Scout
  • Set up Google Alerts for your package name
Q

"'error: Microsoft Visual C++ 14.0 is required' when building wheels. Help?"

A

Windows package building is fucked by design. Your package probably has C extensions that need compilation.

Quick fixes:

## Option 1: Let PyPI build the wheels for you
pip install build
python -m build --wheel  # Run this on multiple platforms

## Option 2: Use cibuildwheel for automated multi-platform builds  
pip install cibuildwheel
cibuildwheel --output-dir dist/

Or just tell Windows users to use conda and save everyone the pain.

Q

"I accidentally published my API keys in my package. How fucked am I?"

A

Pretty fucked, but recoverable if you move fast. Leaked credentials get scraped by bots within minutes - I've seen AWS keys get used before the commit notification email arrives.

Damage control:

  1. Immediately revoke the leaked credentials
  2. Delete the release from PyPI (you have 30 minutes before it's cached forever)
  3. Generate new credentials
  4. Add the leaked keys to your .gitignore and use environment variables
  5. Consider the compromised systems breached until proven otherwise
Q

"How do I know if my dependencies are secure and won't break user installs?"

A

Use pip-audit to scan for vulnerabilities and pipdeptree to visualize dependency hell:

pip install pip-audit pipdeptree safety
pip-audit  # Scans for known vulnerabilities
pipdeptree --warn conflict  # Shows dependency conflicts
safety check  # Alternative vulnerability scanner

Pin your dependencies with exact versions in production:

requests==2.31.0  # Not requests>=2.31.0
pandas==2.0.3     # Prevents surprise breakage

The Publishing Workflow That Won't Get You Hacked

Publishing Python packages in 2025 means dealing with an ecosystem under constant attack. PyPI faces a steady stream of malicious packages - thousands uploaded monthly - from typosquatting to supply chain attacks. The December 2024 Ultralytics breach where hackers injected Bitcoin mining malware into a popular computer vision package wasn't an anomaly - it's the new normal.

Modern Package Structure: src/ Layout Saves Lives

Forget everything you learned about Python package structure from tutorials written in 2019. The modern approach uses src layout - not because it's trendy, but because it prevents you from accidentally testing your local code instead of the installed package.

myproject/
├── src/
│   └── mypackage/
│       ├── __init__.py
│       └── core.py
├── tests/
├── pyproject.toml
└── README.md

Why this matters: When you run tests, Python can't import from your local working directory. It forces you to install and test the actual package, catching import errors before users do. I've seen packages with 50k+ downloads that don't work because the maintainer never tested the installed version.

pyproject.toml: The Only Config File You Need

setup.py is legacy garbage. Modern Python packaging uses pyproject.toml exclusively:

[build-system]
requires = ["setuptools>=61.0", "wheel"]
build-backend = "setuptools.build_meta"

[project]
name = "mypackage"  
version = "0.1.0"
description = "Does stuff without breaking"
authors = [{name = "Your Name", email = "you@domain.com"}]
license = {text = "MIT"}
dependencies = [
    "requests>=2.31.0,<3.0.0",  # Pin major versions
    "click>=8.0.0"
]
requires-python = ">=3.8"
classifiers = [
    "Development Status :: 4 - Beta",
    "License :: OSI Approved :: MIT License",
    "Programming Language :: Python :: 3.8",
    "Programming Language :: Python :: 3.9",
    "Programming Language :: Python :: 3.10",
    "Programming Language :: Python :: 3.11",
]

[project.urls]
Homepage = "https://github.com/yourusername/mypackage"
Repository = "https://github.com/yourusername/mypackage.git"
Issues = "https://github.com/yourusername/mypackage/issues"

[tool.setuptools.packages.find]
where = ["src"]

Trusted Publishing: No More Token Leakage

Traditional PyPI publishing requires storing API tokens as GitHub secrets. These get compromised regularly through various attack vectors. Trusted Publishing eliminates tokens entirely by letting PyPI authenticate GitHub Actions directly.

Setup takes 5 minutes:

  1. PyPI side: Account Settings → Publishing → Add a new pending publisher

    • Repository: yourusername/yourpackage
    • Workflow filename: publish.yml
    • Environment name: pypi (creates access control)
  2. GitHub side: Create a protected environment named pypi in your repo settings

    • Settings → Environments → New environment
    • Add "Required reviewers" - only these people can trigger releases
    • This prevents random contributors from publishing malicious updates
  3. Workflow: Use the official PyPA action:

name: Publish to PyPI
on:
  release:
    types: [published]  # Only on tagged releases

jobs:
  publish:
    runs-on: ubuntu-latest
    environment: pypi  # References the protected environment
    permissions:
      id-token: write  # Required for trusted publishing
    steps:
      - uses: actions/checkout@v4
      - uses: actions/setup-python@v4
        with:
          python-version: '3.11'
      - name: Build package
        run: |
          pip install build
          python -m build
      - uses: pypa/gh-action-pypi-publish@release/v1
        # No token needed - authenticates via OIDC

Security Scanning: Catch Problems Before Users Do

Dependency vulnerabilities are the most common attack vector. pip-audit scans your dependencies against the PyPA Advisory Database:

pip install pip-audit
pip-audit  # Scans current environment
pip-audit --desc  # Shows vulnerability descriptions
pip-audit --fix   # Attempts to upgrade to safe versions

Workflow vulnerabilities get scanned by zizmor, which catches template injection attacks like the one that compromised Ultralytics:

pip install zizmor
zizmor .github/workflows/  # Scans all workflows

Add both to your CI pipeline:

- name: Audit dependencies
  run: pip-audit --desc --format=json
- name: Audit workflows  
  run: zizmor --format=json .github/workflows/

Version Management: Semantic Versioning That Doesn't Suck

Your version numbers communicate compatibility to automated tools. Use Semantic Versioning:

  • 1.0.01.0.1: Bug fixes (safe to auto-update)
  • 1.0.01.1.0: New features (probably safe)
  • 1.0.02.0.0: Breaking changes (requires human review)

Automate versioning with bump2version:

pip install bump2version
bump2version patch  # 1.0.0 → 1.0.1
bump2version minor  # 1.0.1 → 1.1.0  
bump2version major  # 1.1.0 → 2.0.0

Testing Your Package: The Reality Check

Test the installed package, not your local code:

## Build and install in isolated environment
python -m build
pip install dist/*.whl --force-reinstall

## Test the installed version
python -c \"import mypackage; print(mypackage.__version__)\"
python -m pytest tests/  # Tests should still pass

Common gotchas that only show up in the installed version:

  • Missing __init__.py files
  • Incorrect package paths in pyproject.toml
  • Missing data files not included in MANIFEST.in
  • Import errors due to incorrect module structure

Release Process: The Human Firewall

Automated publishing is convenient but dangerous. Implement human oversight:

  1. Code review: All changes require PR approval
  2. Protected environments: Only trusted maintainers can publish
  3. Release checklist: Document the manual steps
  4. Staging repository: Test on TestPyPI first

TestPyPI workflow:

## Upload to TestPyPI first
twine upload --repository testpypi dist/*

## Test install from TestPyPI
pip install --index-url https://test.pypi.org/simple/ mypackage

## If it works, upload to real PyPI
twine upload dist/*

This caught a bug in my last release where the package imported fine locally but failed on fresh installs due to a missing dependency declaration.

Pro tip: Always test your wheel installation on a completely fresh Python environment. I've seen packages that work with pip install -e . but fail when installed normally because they're importing from the local development directory.

Advanced Publishing Hell: The Gotchas That'll Ruin Your Week

Q

"My package builds fine locally but fails on different Python versions. What now?"

A

Testing on one Python version is like testing your code on localhost and calling it production-ready.

Use tox to test multiple versions:bashpip install tox# tox.ini [tox]envlist = py38,py39,py310,py311[testenv]deps = pytestcommands = pytest tests/Or use GitHub Actions matrix builds:yamlstrategy: matrix: python-version: ["3.8", "3.9", "3.10", "3.11"]Common version-specific failures:

  • f-strings (Python 3.6+)
  • pathlib.Path.readtext() (Python 3.5+)
  • Type hints syntax changes
  • Deprecated standard library functions
Q

"How do I handle package dependencies that conflict with each other?"

A

Welcome to dependency hell

  • the reason Docker exists.

Check conflicts with pipdeptree:bashpip install pipdeptreepipdeptree --warn conflictSolutions that actually work:

  • Loose pinning: requests>=2.28.0,<3.0.0 (allows patch updates)
  • Dependency groups:

Use [project.optional-dependencies] for dev tools

  • Version constraints: Let pip's resolver figure it out, don't over-constrainAvoid exact pinning (==) unless you have a specific reason. It causes more problems than it solves.
Q

"My C extension package won't install on M1 Macs. Users are pissed."

A

Apple silicon broke half the Python ecosystem in 2021.

Use cibuildwheel to build universal wheels:```yaml# .github/workflows/wheels.yml

  • name:

Build wheels uses: pypa/cibuildwheel@v2.16.2 env:

CIBW_ARCHS_MACOS: x86_64 arm64  # Both Intel and M1    CIBW_ARCHS_LINUX: x86_64 aarch64  # Both x64 and ARM Linux```This builds wheels for every major platform/architecture combo and uploads them to PyPI. Users get pre-compiled binaries instead of compilation errors.
Q

"Someone forked my package, made minimal changes, and is republishing under a similar name. Legal?"

A

Probably legal if your license allows it, but shitty behavior. Document the original with clear attribution requirements:python# In your __init__.py__author__ = "Your Name"__original__ = "https://github.com/yourusername/original-package" __license__ = "MIT"MIT/BSD licenses require attribution. If they're not providing it, you have grounds for a DMCA takedown.

Q

"How do I deprecate old versions without breaking existing installations?"

A

Semantic versioning + deprecation warnings + clear communication:```pythonimport warningsdef old_function(): warnings.warn( "old_function() is deprecated, use new_function() instead. " "This will be removed in version 2.0.0", Deprecation

Warning, stacklevel=2 ) return new_function()```Timeline for breaking changes:

  1. Version 1.5.0:

Add deprecation warnings 2. Version 1.6.0: More warnings, update docs 3. Version 2.0.0: Remove deprecated featuresGive users at least 3 months and 2 minor versions to migrate.

Q

"My package got flagged by corporate security tools. How do I prove it's not malware?"

A

Corporate security tools flag anything that:

  • Makes network requests

  • Accesses file system

  • Has dependencies with CVEs

  • Comes from unknown publishersDocument your package's behavior clearly:```markdown## Security InformationThis package:

  • ✅ Makes HTTPS requests to api.example.com only

  • ✅ Reads/writes files only in user-specified directories

  • ✅ Dependencies scanned with pip-audit (see CI results)

  • ✅ Published via GitHub Actions with signed commits

  • ❌ Does NOT access sensitive system resources

  • ❌ Does NOT make unexpected network connections```

Q

"I want to transfer ownership of my package but keep some control. How?"

A

PyPI supports multiple maintainers with different permission levels: 1.

Add co-maintainers: Manage → Collaborators → Add collaborator2.

Set permissions: Owner (full access) vs Maintainer (can't delete project) 3. Document succession plan in README 4. Use GitHub's "transfer repository" feature for the source codeDon't just abandon packages

  • either transfer ownership or mark them as deprecated. Abandoned packages become attack targets.
Q

"How do I know if my package is being used in production somewhere important?"

A

Check reverse dependencies and download stats:

  • Libraries.io shows what packages depend on yours
  • PyPI download stats: pip install pypistats && pypistats overall mypackage
  • Git

Hub's "Used by" tab shows dependent repositories

  • Search for your package name in GitHub code searchIf major companies depend on your package, consider:

  • More rigorous testing procedures

  • Security-focused development practices

  • Communication channels for security issues

  • Succession planning (bus factor > 1)High-impact packages get more scrutiny but also more responsibility.

Publishing Methods Compared: Pick Your Poison

Method

Security

Ease of Use

Maintenance

Best For

Worst For

Manual twine

🟡 Token storage risk

🔴 Error-prone

🔴 Constant token rotation

Learning, one-offs

Team projects, automation

GitHub Actions (token)

🟡 Secret leakage risk

🟢 Set it and forget it

🟡 Token management

Legacy workflows

Security-focused teams

Trusted Publishing

🟢 No stored secrets

🟢 Zero token management

🟢 Automatic auth

Production packages

Complex multi-repo setups

GitLab CI

🟢 OIDC support

🟡 Requires setup

🟡 GitLab-specific

GitLab-centric teams

GitHub users

Local build + upload

🔴 Dev machine compromise

🔴 Forgot to test again?

🔴 Bus factor of 1

Emergency fixes

Any serious project

Essential Resources for Package Publishing

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