Sending an encrypted email from Outlook Desktop Client to gmail or yahoo.

Question

Have setup AIP and policies and labels and they do work when I send an encrypted email from OWA to gmail.

When I try and send an encrypted email from Outlook Desktop Client (version Microsoft 365 Apps for enterprise, [I have an A5 license]}, to my gmail account, I am unable to read message. I am not sending an encrypted email but rather an encrypted email.

This is what I get....

---

This message is protected with Microsoft Information Protection. You can open it using Microsoft Outlook, which is available for iOS, Android, Windows, and Mac OS. Get Outlook for your device here: https://aka.ms/protectedmessage.

Microsoft Information Protection allows you to ensure your emails can't be copied or forwarded without your permission. Learn more at https://microsoft.com/rms.
Attachments area

I get the message.rpmsg attachement which tells me it is an encrypted email.

---

How do I open this file in my gmail account? Is the only way to send an encrypted email to gmail is via OWA? Why is this not working with the Outlook Desktop Client?

Answer 1

Hi @Zambrano Jr, Ismael C ,

Are you testing with the same two email accounts? If not, to avoid possible issues from different email accounts, please try using the same two email accounts to test and see if the issue has any difference.

I did some research about sending encrypted messages with AIP and your error prompts. First of all, it is suggested for you to check the steps of encrypting Outlook messages in this article and see if you have operated properly. (Note: Since the web site is not hosted by Microsoft, the link may change without notice. Microsoft does not guarantee the accuracy of this information.)

Besides, are there multiple email accounts in your Outlook client? In order to avoid confusion between multiple accounts, it is suggested for you to add your email account to a new single Outlook profile via Control Panel > Mail > Show profile and see if your issue has any difference.

By the way, can this message be opened normally if you configure your Gmail account to your Outlook client? If so, I found this similar thread External users cannot open encrypted email, the discussion of the third party solution might could be helpful to you, please check it.

Any updates, please feel free to let me know.

---

If an Answer is helpful, please click "Accept Answer" and upvote it.
Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.