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We have an situation. Our customer can get sMIME encrypted mails and reply to that email. But when he wants to send it with new email he is getting an error message as if the recipient email does not have an public key.

So we have checked the certificate and it is valid (timewise). Also we tried to import that certificate to microsoft certificate. Nothing helped us to solve the problem. Customer has both terminal server and seperate laptop result is the same...

So microsoft website says : (https://support.office.com/en-us/article/encrypt-messages-by-using-s-mime-in-outlook-web-app-2e57e4bd-4cc2-4531-9a39-426e7c873e26)

S/MIME message encryption is supported only on messages sent to and from recipients in your organization’s address list. If you send an encrypted message to someone outside your organization, they will not be able to decrypt and read the message.

I have seen in stackexchange this question (Outlook 2010 cannot reply to encrypted email) but customer uses outlook2016 and that question was also not answered?

so here are the questions : 1- Where does outlook keep the (public) certificates of the received emails. 2- What is said in microsoft link above can that be correct? (i feel it is not correct) 3- To send an encrypted email should outlook first get the certificate of the recipient? if so how does this process work? which ports, protocols and what if there are spamgateways in the address shown by mx record?

Thank you.

CanBuyukburc
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1 Answers1

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1.You can view your own certificates or those that you receive in email messages in Certificates and Algorithms or by clicking icons on the Signed By line, detailed steps are listed here.

2.The statement is published by official so it must be correct.

3.To be able to exchange encrypted messages with certain contacts, you need to share your public keys first. And about Email encryption between Outlook and other email clients, you can have a read at this article to get a systematic knowledge, Email encryption in Outlook

Beverly Gao
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  • Any updates with your problem? – Beverly Gao Sep 03 '19 at 09:55
  • these have all been done already but we will connect to customers system today once more and recheck it. The systematic knowledge is there but to solve this problem in this case we need much more in depth details. – CanBuyukburc Sep 23 '19 at 06:32