Set-AuthenticodeSignature UnknownError (Windows 2019 Server)

Trying the simplest of commands while trying to sign a file.

$Cert = Get-PfxCertificate -FilePath "myCert.pfx"
Set-AuthenticodeSignature "MyApp.app" -Certificate $Cert

To put some background around my issues, I am trying to run this on a newly created Azure Windows 2019 server. (The same certificate and file types work as expected on the “old” Azure Windows 2016 server.)

To make it more frustrating, I can sign a “.ps1” file on the new 2019 server. I can either create the “.ps1” file as new or even renaming the “.app” file to “.ps1” allows signing correctly.

Any help with this would be appreciated. I can’t seem to find any logs for the UnknownError so it’s very difficult know what the issue is.

SignerCertificate                         Status                                                         Path                                                         
-----------------                         ------                                                         ----                                                         
                                          UnknownError                                                   MyApp.app 

[iSazonov]

@TimothyWatkins Thanks for sharing more info. The issue is not PowerShell related. I believe you should use Windows Server feedback (open a support case, use Feedback tool, use a forum).

You could enable CAPI logs on your system and look events there.

[msftbot[bot]]

This issue has been marked as external and has not had any activity for 1 day. It has been be closed for housekeeping purposes.