Hi, we use outlook 2013 in our company. we use certificate\private-key (S/MIME) to encrypt and decrypt some of our e-mails.

sometime outlook mis-encrypts the e-mails and it makes them un-decryptable by the recipient and by the sender.

also - sometimes while sending normal unencrypted mail, outlook sends blank e-mails instead.

both cases makes original e-mail content lost forever and causes us data loss and great frustration.

Is this a known bug?

Is there an algorithm \ key length unsupported by outlook?

thanks!

Nadav.

Hi,

Does this issue happen to all users?

Did you have any antivirus software installed in your environment? If so, please temporarily turn off them to check if the problem persists.

In addition, if the issue only happen to several users, we can try to create a new mail profile in Control Panel to check the result. See:

http://support.microsoft.com/kb/829918/en-us

Please let me know the result.

Best Regards,

Steve Fan
TechNet Community Support

• Marked as answer by Steve FanMicrosoft contingent staff, Moderator Sunday, March 02, 2014 4:56 PM

Hi Steve, thanks for your answer,

Sadly, this already happend to more than 50% of the users (although, in a very low rate)

regarding the Anvi-Virus programs - currently each user uses a different anti-virus software and the problem seems to occur even to users using MS's windows-defender.

Can you think of any other reason to this?

Many Thanks!

Nadav

We also have this problem with Outlook 2013, in that a mail is encrypted after we have pressed the 'Send Unencrypted' button on the pop-up window that appears when a recipient has no certificate installed in their Outlook contact record.  When this occurs, the sent email cannot be opened and so all contents are effectively lost.  Of course, the recipient also receives an email that they cannot read.

The problem apparently only occurs if the email is set to Encrypt under the Options tab for the mail being sent.  (If email is configured to be encrypted under the Trust Center Settings, then this Options selection to Encrypt is automatically set for each email.)