This set of upgrades includes two major version jumps, both introducing significant breaking changes. The highest risk comes from the urllib3 and werkzeug upgrades, which require environment and code-level changes.

• urllib3: 1.23 → 2.6.3 (High Risk)

  • Python Support: Support for Python versions older than 3.9 has been dropped. [1]
  • Security Defaults: The minimum TLS version is now 1.2, and certificate hostname verification is stricter, no longer using the commonName field. [1, 2]

• werkzeug: 2.2.3 → 3.1.5 (High Risk)

  • Python Support: Support for Python 3.7 was dropped in v2.3. [13]
  • API Removals: Previously deprecated code has been removed. For example, the test client now returns a TestResponse object instead of a tuple, and generate_password_hash defaults to a different algorithm (scrypt). [13]

Recommendation: These upgrades require significant validation. Ensure your environment uses Python 3.9+ and that all external service connections are compatible with TLS 1.2. Review your code for usage of deprecated werkzeug APIs and test thoroughly, as behavior and return types have changed.

Notice 🤖: This content was augmented using artificial intelligence. AI-generated content may contain errors and should be reviewed for accuracy before use.