Why "Encrypt" button in Outlook is not showing or enabled as it was enabled using below PowerShell cmdlets?

Hello, @Mytoast Admin,

Welcome to the Microsoft Q&A platform!

Based on your description, the "Encrypt" button in your Outlook account is not showing or enabled as it was enabled using below PowerShell cmdlets.

According to the Microsoft official document, the SimplifiedClientAccessEncryptOnlyDisabled parameter specifies whether to disable Encrypt only in Outlook on the web. If you want to enable Encrypt only in Outlook on the web, you need to set the value to $False.

To verify that this parameter is valid, I performed the following test.

1.Use Get-IRMConfiguration cmdlet to get the current value.

2.Use the following cmdlet to disable Encrypt only in Outlook on the web and wait for a while to make it effective.

 Set-IRMConfiguration -SimplifiedClientAccessEncryptOnlyDisabled $True

3.Change the value from $True to $False in order to enable Encrypt only again.

The result shows that the commands I used above do disable or enable the “Encrypt” feature in OWA. One difference between us is that your “Encrypt” button is grayed out but it just disappeared in my test, so your problem should not be related to powershell commands, but to other settings.

So I ran a new test and successfully reproduced your question. If you check the “Encrypt this message (S/MIME)” box in the “More Options” section of OWA, then you get the ” Encrypt” button will be grayed out as shown below.

To solve this issue, you just need to uncheck “Encrypt this message (S/MIME)”.

If you do not choose the option after check, I suggest you log in to another account using your device and browser or log in to your account using another device and browser to see if the same problem occurs.

Should you need more help on this, you can feel free to post back. 

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Thank you for your support and understanding.

Best Wishes,

Alex Zhang