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Homebrew, OpenSSL and PowerShell

On Mac, PowerShell really, really wants to specifically use OpenSSL version 1.0.

Unfortunately, homebrew switched to OpenSSL version 1.1 in v2.2, because OpenSSL 1.0 is end-of-life.

This fixes it (for now at least):

brew uninstall openssl --ignore-dependencies
brew uninstall openssl --ignore-dependencies
brew install https://github.com/tebelorg/Tump/releases/download/v1.0.0/openssl.rb

References:

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Powershell, O365 & Teams PSTN calling

Unfortunately you need a Windows system to administer Office 365 with PowerShell. It’s only API calls, but it’s not (yet, hopefully) migrated to .NET Core. So Mac & Linux users are out of luck, although .NET Core should be more than capable to do this.

Anyhow.

If you want to administer Teams with PowerShell, you … are in trouble. It’s barely documented, and it sucks. Those are the steps to be done:

> $sess = New-CsOnlineSession ... 
> Import-Module SkypeOnlineConnector ... 
> Import-PSSession $sess

… and this should be it. Now all the PowerShell commands for Teams (in my case: Grant-CsTeamsUpgradePolicy) should be available.