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Installing PowerShell on macOS for remote administration of Microsoft 365

There are a couple of catches to install PowerShell on macOS and have it work for remote sessions to Microsoft 365 / Azure AD / Exchange Online.

First, install the latest release version of PowerShell from GitHub:

https://github.com/PowerShell/PowerShell/releases

Then, install MacPorts

https://github.com/macports/macports-base/releases

After you have installed MacPorts, install the older version of OpenSSL that PowerShell requires. In Terminal, type:

sudo port install openssl10

After installing OpenSSL 1.0, make a symlink so that PowerShell can find it where it is looking for it

sudo mkdir -p /usr/local/opt/openssl
sudo ln -s /opt/local/lib/openssl-1.0 /usr/local/opt/openssl/lib

Once this has been done, you can connect to MS365:

pwsh
$UserCredential = Get-Credential
$Session = New-PSSession -ConfigurationName Microsoft.Exchange -ConnectionUri https://outlook.office365.com/powershell-liveid/ -Credential $UserCredential -Authentication Basic -AllowRedirection
Import-PSSession $Session

5 thoughts on “Installing PowerShell on macOS for remote administration of Microsoft 365

    1. Yes, good point – if this is not a clean install of macOS and Mac Ports, then there may be cruft remaining from previous installations that needs to be removed.

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