Not able to send encrypted email to a contact unless replying to signed message from the contect

Question

I can reply to signed emails (or encrypted) with an encrypted response however any emails I originate can only be sent in the clear. I have repeatedly imported the contracts certificate into their outlook contact certificates. I also had to remove the contact and create a new account as the !#$^ thing would not update. Is there a cache that needs to be flushed?
Outlook 2021, Microsoft providing company exchange services etc.

Answer 1

Hello @coinoperated

Thank you for sharing this on this community space.

I wonder if you have reviewed the next document down below and this might fit into your case scenario stated previously.

https://support.microsoft.com/en-us/office/encrypt-email-messages-373339cb-bf1a-4509-b296-802a39d801dc

Let me know if that was useful but if not, I can keep assisting you further.

Looking forward to your feedback,

Cheers,

Please "Accept the answer" if the information helped you. This will help us and others in the community as well.

Answer 2

Hi @coinoperated ,

As I know, to completely eliminate the influence from the old certificate, it is suggested to remove the users from your contact list and empty Auto-Complete List, then re-add them from GAL to see if the issue has any difference.

Besides, I found some similar threads about your issue, you may also check the other workarounds in these threads:
Unable to send encrypted email
Cannot send encrypted message to others
(Please 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.)

Hope this can be helpful.