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In Outlook 2016, I can't send encrypted email to "some" people but I can to others. RRS feed

  • Question

  • I work in an environment that requires that when I send PII or personally identifiable information like SS#'s and such in an email, I have to encrypt the email. I used to send such email to three people that I now get "The following recipient is NOT in an approved domain to receive PII..." I can send encrypted email to the majority of those I need to except for the three.

    I have gone to the PKI site and downloaded their certificates and installed them, I have also checked that I did get the certificate and they are in my contacts. I've also deleted the old certificate I had for them which made the new certificate the new default. I also published my own certificate to the Gallery. But still I cannot send them email. Outlook still say's the error message above and then it say's it can't find their certificate after I click out of the error box. 

    Any help will be greatly appreciated,  

    Thank you.

    Thursday, June 25, 2020 8:28 PM

Answers

  • Hi ,

    Can other users in your working environment send encrypted emails successfully to this specific three users?

    If other users in your working environment have the same issue as you, I'm afraid that the key of this issue might be related to this specific three users. Please try to troubleshot from the perspective of this specific three accounts themselves and see if there is any difference.

    If other users in your working environment can send encrypted emails successfully to this specific three users. As I know, to completely eliminate the influence from the old certificate, it is suggested to remove this specific three 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.

    Regards,

    Jeff Yang


    Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact tnsf@microsoft.com.

    Friday, June 26, 2020 6:18 AM

All replies

  • Hi ,

    Can other users in your working environment send encrypted emails successfully to this specific three users?

    If other users in your working environment have the same issue as you, I'm afraid that the key of this issue might be related to this specific three users. Please try to troubleshot from the perspective of this specific three accounts themselves and see if there is any difference.

    If other users in your working environment can send encrypted emails successfully to this specific three users. As I know, to completely eliminate the influence from the old certificate, it is suggested to remove this specific three 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.

    Regards,

    Jeff Yang


    Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact tnsf@microsoft.com.

    Friday, June 26, 2020 6:18 AM
  • Thank you Jeff!!! It worked!

    I just deleted the users from my contacts and auto-complete and voila! I sent them encrypted emails just fine.

    Thanks a million sir!

    Monday, June 29, 2020 8:12 PM