Setting up plus alias addressing with Exchange 365, easily

For those of us out there who use Exchange 365 for our email services, and have lamented the lack of plus-style alias addressing, this feature finally arrived in Septemeber 2020.

However, those of us without too much experience in Powershell, or use Mac desktops as our primary platforms, may need a little extra help on getting this activated.

Why do it?

In simple terms – it makes it easier to track if/when data leaks, or when your email address has been sold or shared without your consent or intent.

By using a unique alias for each site you interact with, it makes tracking down the source of the leak pretty easy, and also to cut the address off when someone sends you a lot of junk and it’s obvious they’re not the type of entity that follows the law or respects unsubscribe links.

How to do it

Here’s a quick guide on how to set this up simply.

1. Using a Mac? Don’t mess around with Powershell solutions on your Mac, just download VirtualBox and the free Windows 10 Developer Environment for VirtualBox. Once installed and download, run it.
   
2. Open Powershell as Administrator.
   
3. Install PowerShellGet

Install-PackageProvider -Name NuGet -Force
Install-Module -Name PowerShellGet -Force

4. Allow PowerShell to run scripts:

Set-ExecutionPolicy RemoteSigned

5. Install ExchangeOnlinePowershell:

Install-Module -Name ExchangeOnlineManagement

6. Connect to ExchangeOnlinePowershell:

Import-Module ExchangeOnlineManagement
Connect-ExchangeOnline -UserPrincipalName navin@contoso.com -ShowProgress $true

Remember: Replace navin@contoso.com with your administrator email address, so you can actually connect successfully to your Exchange instance and make these changes.

7. Enable plus addressing:

Set-OrganizationConfig -AllowPlusAddressInRecipients $true

7. Bonus: Enable sending mail with your alias address:

If you’re a smart cookie, and you’ve created a totally seperate email address to use with aliasing (i.e. alias@yourdomain.com, as an alias for youraccount@yourdomain.com) so you can really stick it to those internet marketers who suck at their data analysis, here’s how you enable the ability to send emails on behalf of your alias address:

Set-OrganizationConfig -SendFromAliasEnabled $true

And that’s it. Go ahead, send something to username+alias@yourdomain.com. And once you’ve confirmed it’s working, go and update your usernames and personal information en masse (which sadly is going to take a little while to do).