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PekkaPekkonen-2967 asked PekkaPekkonen-2967 commented

Cannot encrypt email on Mac Outlook

Hello

One of our customer is unable to encrypt email in Mac Outlook.
She gets the following error after pressing encrypt button.

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I think she has a mail account from two different tenant added to Outlook. The other should have working settings, but the other we do not manage.

In web version encryption works.

Any ideas, what could be the issue?

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Hi @PekkaPekkonen-2967 ,

Welcome to our forum!

In order to further research this case, please take time to provide relevant information about the following questions:
· Are there any differences between the customer with those customers who can encrypt emails normally? Such as the version of outlook client and account, please check your outlook version(Outlook>About Outlook) and make sure you have upgraded your Outlook to the latest version.
· About "a mail account from two different tenant" you mentioned, do you mean the two accounts in a profile or any else?
· What is your encryption button like? And which encryption method is used(S/MIME encryption or Microsoft 365 Message Encryption)?
· Does this issue happen only when encrypting a particular email or every email?

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Thank you @ChristyZhang-MSFT

Right now I don't have access to this computer but I will try to provide the information.

I checked that there is no updates for Outlook so I assume it is the latest version.

I think there is two accounts in a single profile.
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The customer used Encrypt button in Options tab.
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I think the encryption method is Office 365 Message Encryption (OME).

Due to limited time I didn't do extensive testing on the customer computer. But this was the first time she tried it.

There is only one other user/computer in the tenant. The other is a Windows computer, and with that encryption has been successful before.

I hope these would help us further.

Regards,
PekkaPek

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I ran into character limit, but I add here:
the other user/computer in the tenant also had problems with encryption at the same time.
A draft could not be encrypted, nothing happened when pressing the button.
Instead, a new message got encrypted successfully with the other user account and computer.

Regards,
PekkaPek

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Hi @PekkaPekkonen-2967 ,

Thanks for your reply!

But I'm sorry that it seems to I haven’t fully understood your question, according to my understanding: two accounts are configured in one profile, emails can be encrypted successfully when using an account, but the error prompts after pressing encrypt button when using another account, right?

For further research, It's recommended to configure the account that couldn't work normally in other clients to check if it has any differences there.

In addition, as I know, the error usually prompts when messages are opened, so does this issue happens when you click the encrypt button in a new message only ,or it also prompts when opening an encrypted message?

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