Licensed version has an incorrect dependency on PowerShell assemblies and will only load v3 and above

[ferventcoder]

tl;dr, if you have a licensed version, you should upgrade to at least 1.4.1.

choco upgrade chocolatey.extension - this package is only available for licensed versions of choco

After further review, we determined it is actually an issue with how the licensed version was taking a dependency on System.Management.Automation that was incorrect, causing it to attempt to load only v3 and above. This means that if you were running PowerShell v2, the licensed assembly would not load correctly, causing other issues when trying to install packages.

This is easily seen if you run into it attempting to load the same version of System.Management.Automation several times.

Could not load file or assembly 'System.Management.Automation, Version=3.0.0.0, 
Culture=neutral, PublicKeyToken=31bf3856ad364e35' or one of its dependencies. The system cannot find the file specified.' 
Could not load file or assembly 'System.Management.Automation, Version=3.0.0.0, 
Culture=neutral, PublicKeyToken=31bf3856ad364e35' or one of its dependencies. The system cannot find the file specified.' 
Could not load file or assembly 'System.Management.Automation, Version=3.0.0.0, 
Culture=neutral, PublicKeyToken=31bf3856ad364e35' or one of its dependencies. The system cannot find the file specified.' 

Original

An issue was uncovered that attempting to upgrade PowerShell with Chocolatey creates a lock on the binaries that PowerShell is attempting to upgrade.

When attempting to install/upgrade PowerShell, there could be an issue that occurs that sets the system into a state where Chocolatey is not able to be used:

Could not load file or assembly 'System.Management.Automation, Version=3.0.0.0, 
Culture=neutral, PublicKeyToken=31bf3856ad364e35' or one of its dependencies. The system cannot find the file specified.' 

It cycles through all of the possibilities and can not find a suitable PowerShell to install.

We can attempt to do one of the following:

• create a copy of those binaries and use those for the dependencies and then delete them after the run.
• automatically fall back to system PowerShell when we see a particular update that is for PowerShell libraries.
• something else

Of course my vote is for option 1.

[laurinkeithdavis]

So, I'm not sure what you mean by "attempting to upgrade PowerShell with Chocolatey". I'm not attempting to upgrade anything when this issue occurs. At most, I'm attempting to install a package, but not PowerShell. Do you mean a package that I am attempting to install is doing this (though, I'm pretty sure this last time, I was not actually installing anything)?

[ferventcoder]

It's based on best guess of what could be going on. Does an upgraded WMF get pushed out as part of Windows Update/System Policy?

Looking at what we know so far:

• Choco loads the PowerShell assemblies (which may lock the files) while choco.exe is running.
• These are assemblies in the GAC.
• Later when choco.exe runs, the assemblies are missing and it gives the errors above.

[ferventcoder]

Looks like I got a little ahead of myself. After further review, we determined it is actually an issue with how the licensed version was taking a dependency on System.Management.Automation that was incorrect, causing it to attempt to load only v3 and above. This means that if you were running PowerShell v2, the licensed assembly would not load correctly, causing other issues when trying to install packages.