When you run the 'install python on Windows' task there is a difference in behavior if when you run on the Windows2016 OS compared with the Windows2019. This happens with python 3.8.0 and 3.8.1. Please note: while the warning mentions pip, this is not about pip!
[debug]System.Management.Automation.RemoteException: WARNING: You are using pip version 19.2.3, however version 20.0.2 is available.
[error]WARNING: You are using pip version 19.2.3, however version 20.0.2 is available._
Hosted agent pool: 'vs2017-win2016'
_WARNING: You are using pip version 19.2.3, however version 20.0.2 is available.
You should consider upgrading via the 'python -m pip install --upgrade pip' command.
It seems that on the Windows 2019 OS warnings are perceived as errors and the task is put in FAILED status. It even happens when you use dependencies that are not compatible and gives a warning put the task in failed mode. This is not only on the hosted agents but also on my own self-hosted agents.
When you run the 'install python on Windows' task there is a difference in behavior if when you run on the Windows2016 OS compared with the Windows2019. This happens with python 3.8.0 and 3.8.1. Please note: while the warning mentions pip, this is not about pip!
Hosted agent pool: 'windows-2019' _##[debug]Leaving Invoke-VstsTool.
[debug]Leaving D:\a_tasks\InstallPython_6095fbbe-853d-4f2e-bc15-a88c92a78b4d\1.0.13\InstallPython.ps1.
[debug]Caught exception from task script.
[debug]Error record:
[debug]WARNING: You are using pip version 19.2.3, however version 20.0.2 is available.
[debug] + CategoryInfo : NotSpecified: (:) [], RemoteException
[debug] + FullyQualifiedErrorId : RuntimeException
[debug]
[debug]Script stack trace:
[debug]
[debug]Exception:
[debug]System.Management.Automation.RemoteException: WARNING: You are using pip version 19.2.3, however version 20.0.2 is available.
[error]WARNING: You are using pip version 19.2.3, however version 20.0.2 is available._
Hosted agent pool: 'vs2017-win2016' _WARNING: You are using pip version 19.2.3, however version 20.0.2 is available. You should consider upgrading via the 'python -m pip install --upgrade pip' command.
[debug]Exit code: 0
[debug]Leaving Invoke-VstsTool.
[debug]Leaving D:\a_tasks\InstallPython6095fbbe-853d-4f2e-bc15-a88c92a78b4d\1.0.13\InstallPython.ps1.
It seems that on the Windows 2019 OS warnings are perceived as errors and the task is put in FAILED status. It even happens when you use dependencies that are not compatible and gives a warning put the task in failed mode. This is not only on the hosted agents but also on my own self-hosted agents.