Encountered challanges during Ansible upgrade.

Ansible-core 2.17.7 and Python 3.8 on Ubuntu18.04

Issue:

By default ubuntu18.04 has preinstalled python3.6. However Ansible 2.17.7 requires Python 3.7 or above on target host.

(Link to Ansible Matrix)[https://docs.ansible.com/ansible/latest/reference_appendices/release_and_maintenance.html#ansible-core-support-matrix]

However, ansible 2.17.7 still uses /usr/bin/python3 instead takes the defined ansible_python_interpreter variable.

Error in due execution:

Traceback (most recent call last):
  File "<stdin>", line 107, in <module>
  File "<stdin>", line 99, in _ansiballz_main
  File "<stdin>", line 44, in invoke_module
  File "<frozen importlib._bootstrap>", line 971, in _find_and_load
  File "<frozen importlib._bootstrap>", line 951, in _find_and_load_unlocked
  File "<frozen importlib._bootstrap>", line 894, in _find_spec
  File "<frozen importlib._bootstrap_external>", line 1157, in find_spec
  File "<frozen importlib._bootstrap_external>", line 1131, in _get_spec
  File "<frozen importlib._bootstrap_external>", line 1112, in _legacy_get_spec
  File "<frozen importlib._bootstrap>", line 441, in spec_from_loader
  File "<frozen importlib._bootstrap_external>", line 544, in spec_from_file_location
  File "/tmp/ansible_setup_payload_gkarwtna/ansible_setup_payload.zip/ansible/module_utils/basic.py", line 5
SyntaxError: future feature annotations is not defined

Solution #1:

To install python3.8 via apt and OS has two python versions python3.6 and python3.8.

apt install python3.8

Install python3-apt

apt install python3-apt

Update symlinks for packages

cd /usr/lib/python3/dist-packages
ln -s apt_pkg.cpython-36m-x86_64-linux-gnu.so apt_pkg.so
ln -s apt_inst.cpython-36m-x86_64-linux-gnu.so apt_inst.so

Solution #2:

Update symlink for python3

ln -s /usr/bin/python3.8 /usr/bin/python3

Ansible-core 2.17.7 and Ubuntu24.04

Issue:

***********************************************************************************************
fatal: [HOSTNAME]: FAILED! => changed=false 
  cmd:
  - /usr/bin/python3
  - -m
  - pip.__main__
  - install
  - stormssh
  - pyopenssl
  msg: |-
    stdout: Collecting stormssh
      Using cached stormssh-0.7.0-py3-none-any.whl
    Requirement already satisfied: pyopenssl in /usr/local/lib/python3.12/dist-packages (25.0.0)
    Collecting flask (from stormssh)
      Using cached flask-3.1.0-py3-none-any.whl.metadata (2.7 kB)
    Collecting paramiko (from stormssh)
      Using cached paramiko-3.5.0-py3-none-any.whl.metadata (4.4 kB)
    Requirement already satisfied: six in /usr/lib/python3/dist-packages (from stormssh) (1.16.0)
    Requirement already satisfied: termcolor in /usr/local/lib/python3.12/dist-packages (from stormssh) (2.5.0)
    Requirement already satisfied: cryptography<45,>=41.0.5 in /usr/lib/python3/dist-packages (from pyopenssl) (41.0.7)
    Requirement already satisfied: typing-extensions>=4.9 in /usr/local/lib/python3.12/dist-packages (from pyopenssl) (4.12.2)
    Requirement already satisfied: Werkzeug>=3.1 in /usr/local/lib/python3.12/dist-packages (from flask->stormssh) (3.1.3)
    Requirement already satisfied: Jinja2>=3.1.2 in /usr/local/lib/python3.12/dist-packages (from flask->stormssh) (3.1.5)
    Requirement already satisfied: itsdangerous>=2.2 in /usr/local/lib/python3.12/dist-packages (from flask->stormssh) (2.2.0)
    Requirement already satisfied: click>=8.1.3 in /usr/lib/python3/dist-packages (from flask->stormssh) (8.1.6)
    Collecting blinker>=1.9 (from flask->stormssh)
      Using cached blinker-1.9.0-py3-none-any.whl.metadata (1.6 kB)
    Requirement already satisfied: bcrypt>=3.2 in /usr/lib/python3/dist-packages (from paramiko->stormssh) (3.2.2)
    Requirement already satisfied: pynacl>=1.5 in /usr/lib/python3/dist-packages (from paramiko->stormssh) (1.5.0)
    Requirement already satisfied: MarkupSafe>=2.0 in /usr/local/lib/python3.12/dist-packages (from Jinja2>=3.1.2->flask->stormssh) (3.0.2)
    Requirement already satisfied: cffi>=1.4.1 in /usr/local/lib/python3.12/dist-packages (from pynacl>=1.5->paramiko->stormssh) (1.17.1)
    Requirement already satisfied: pycparser in /usr/local/lib/python3.12/dist-packages (from cffi>=1.4.1->pynacl>=1.5->paramiko->stormssh) (2.22)
    Using cached flask-3.1.0-py3-none-any.whl (102 kB)
    Using cached paramiko-3.5.0-py3-none-any.whl (227 kB)
    Using cached blinker-1.9.0-py3-none-any.whl (8.5 kB)
    Installing collected packages: blinker, flask, paramiko, stormssh
      Attempting uninstall: blinker
        Found existing installation: blinker 1.7.0

    :stderr: ERROR: Cannot uninstall blinker 1.7.0, RECORD file not found. Hint: The package was installed by debian.

Cause:

The blinker package was installed via apt repository instead pip.

Solution #1: More safety way.

Determinate the package that is used as a dependency and try to install via apt. In our case, the Flask version 3.1.0 requires blinker version 1.9.0. However blinker package was installed via apt and python cannon overwrite it. If install Flask package via apt repository it will install Flask version 3.0.2 version which works with blinker version 1.7.0.

Solution #2: Less safety way.

Lets using directly execution pip with param as --break-system-packages

pip install --force-reinstall blinker==1.9.0 --break-system-packages