Comments on: Email encryption in Outlook: how to encrypt messages with digital ID

Learn how to use Outlook email encryption to protect your email messages against unauthorized reading in Outlook 2016 and 2013. What Exchange hosted encryption is and how send secure encrypted emails between Outlook and other emails clients. Continue reading →

Comments page 2. Total comments: 54

  1. Hi Svetlana, your posting has been extremely helpful. I have another question: S/MIME is not working on my corporate environment. they send me the certificates for encryption but after importing then to the local system, and to email user in the same group, encryption failed. But some for some user when I sent an email to itself, it works. I use Outlook 2013 on a Win 7 environment.

  2. Last year (2014) i also had my emails hacked and i have been looking into and i have been looking into email encryption softwares. I found some good information from this website http://www.hackedemails.com/email-encryption/ and hope that it might be useful for you also.

  3. Hi,
    I have added certificates to a couple users on my network. (Outlook 2010)
    We want to send encrypted mails between those users. The only problem is that I need to configure that all the outgoing mail will be encrypted.

    Can I configure that a mail will be encrypted if I send it to specific contacts. So not to all outgoing mail.
    Thanks

  4. Thanks for this great article!

    Is there a way to automatically sign emails from only one of multiple accounts?
    I have one personal account which I now have a Digital ID for, and one company Exchange account which don't have EHE enabled. I would like for all emails sent from my personal account to be automatically sigend, and the ones sent from my company account not to be signed. is this possible in Outlook 2013?

    Thanks

  5. I have an employee with the following encryption problem. He can receive my encrypted emails, can open and read them, he can also send me encrypted emails which I have no problem opening or reading, However, if he replies to my encrypted emails they fail to send/encrypt even though he can me "new" encrypted email with no problems.

    What are we doing wrong?

    1. I'm sorry, we haven't encountered this problem before and that is why I am unable to help. You can probably contact Microsoft support service (support.microsoft.com) for assistance.

  6. Why is it that to be able to send encrypted emails via outlook, you have to go through the trouble of adding the public cert of that person to his address book contact

    In Apple Mail, this is ALL AUTOMATIC ( and invisible to our most simplistic user ! )

    I sync my contacts with google, I cant attach the cert to the contact as when the contacts are synced, the cert is then lost again

    this is a major problem for me and my company and has caused us to start transferring our users to Apple platforms.

    The odd thing is that, the only thing that the departments miss is Publisher, which has to be run in Parallels

    annoying we have to go to these lengths for something which most definitely doesn't work as it should

    thanks

    1. Hello Adrian,

      Unfortunately, I cannot address any of your questions because I do not work for Microsoft : )

  7. Hey Sveti,

    Is it possible in some way to make sure IT administrator can't read my mails?
    Is there any way to do it? (I was thinking about them logging in to my profile with administrator rights and launch Outlook.) Any ideas? Thank you.

  8. Hi Svetlana,

    I received my COMODO certificate and I can see it in my certificate store but I am not able to select it in Outlook 2013, it just says that I have "no certificates meet the application criteria".

    I also am not able to export the private key of the certificate because it's greyed out.

    Any ideas?

  9. I too have a lot problems which I would like to discuss with you.Great information about email encryption outlook...Thanks for sharing! A great help to the public.

  10. Hi Svetlana,
    I have an strange issue,I'm sending mails with signed messages (using comodo email certificate) (without any attachments) to one of the organisation , but the recipients are receiving my mail as an attachment which can not be opened. The recipients have saved my email address in their address book, still they are unable to view my email contents on the body of a email. Could you please help me here?

  11. I can find the way to encript everything that you send out but is there a way to have outlook automatically encript all attachments but not every single email?
    thanks!

  12. Okay, I have another question for you, Svetlana. Above in your article you have described how to exchange the digital ID's with each other by right-clicking on the person's name in Contacts and clicking Add to Contacts. This also adds the digital public key of the recipient with whom we want to send messages to. And if that contact already exists in Outlook contacts, then select "Update information in the Duplicate Contact Detected dialog". I'm using Outlook 2013 and I do not find the Duplicate Contact Detected dialog box anywhere. Where should I look to Update information for the contact that already exists ??
    Thanks.

  13. Hi Svetlana Cheusheva,
    Okay. You have showed how to install the digital ID into Outlook. But you have not shown how to share the digital ID with another person through Outlook. How do we share our digital ID within Outlook with another person ?

      1. Thanks Svetlana for walking me through how to configure and setting this up. It's working wonderfully now !

  14. Hi,

    Please correct me if I'm wrong. In order to communicate between Outlook 2013 and Gmail, I thought I needed to exchange digital ID's. Hence, I went to the COMODO site and filled in the details for my Gmail account and got a success message for the certificate to have been installed. I then opened IE, tools -> options -> Content tab -> certificates. I could see the my Gmail email address listed there. Then I exported the certificate to the desktop and wrote myself an email from Gmail and attached this certificate along with my mail to my Outlook account. After that I right-clicked on my account name in contacts and added the Gmail account into Outlook. I looked in the People group and clicked on Certificates, then imported the Gmail certificate into Outlook and saved the closed the window. Then I wrote myself another email from Outlook to my Gmail account. I clicked on the Encrypt button to encrypt the message and clicked the sent button. But when I do that, I always get a message "Microsoft Outlook had problems encrypting the message ....... because recipients had missing or invalid certificates ... "

    What did I do wrong here ? I tried to follow your instructions exactly, but why does it give me this error ??

    ~Thanks

    1. Hi Maneesh,

      We have done some research and found out that to be able to send / receive encrypted messages via Gmail, a special plugin is required to be installed in your web-browser.

      For example, you can check out Penango (https://www.penango.com/download). It works with Firefox and IE.

  15. Hi Svetlana,

    I'm using Outlook 2013. I would like to know how to work with Outlook 2013 mail client and Gmail. I've set up the Outlook part by installing the Digital certificate from COMODO and then wrote myself an email on my gmail account. The first thing I did was to send an plain text mail attaching my public ID to my gmail account. Then I installed another digital certificate from COMODO for my gmail account and did the same to send my public key to my Outlook account. After this I sent an encrypted email from Outlook 2013 to my Gmail account. The email sure did come, but I cannot see anything written in the mail, except a small attachment called "smime.p7m" of 11 kb size. How do I decrypt the mail sent from my Outlook 2013 and read it in my Gmail account ??

    Thanks for helping.

    1. Hi Maneesh,

      Could you please provide more details on how exactly you installed another digital certificate from COMODO for your gmail account?

  16. I'd say it's a bug... Simply can't make it work. Will try on 2013 just to verify...

    Thanks,

    Per

    1. Per,

      I am very interested to know the result and will really appreciate if you take a minute to post it here. Thank you!

  17. Hi all!

    I have two Exchange accounts aimed at two different servers in my profile. In Outlook 2011 for Mac this works as advertised, but in Outlook 2010 for Windows Outlook is never able to distinguish between the two certificates and e-mail addresses. It will always use the last added certificate, regardless of auto select, default select or manual select.

    I have two different named security settings in trust center, each with the correct certificate for the e-mail address. I have seen people do this with Outlook 2013 but I have failed with 2010.

    Any ideas?

    All the best,

    Per

    1. Hi Per!
      I am sorry, we have never encountered this problem before. You can probably contact Microsoft support service for assistance or search for a solution on stackoverflow.com or answers.microsoft.com. Really sorry for not being able to help you better.

  18. FYI, message encryption is broken in Windows 8, you can send but you can't read received encrypted messages. Message signing works though.

  19. These instructions seem backwards. I thought my public key makes it possible for others to send me encrypted messages. Not to open messages from me. It makes no sense for a public key to be able to open an encrypted file. Conversely, I should need to have the public key of each correspondent to whom I want to send encrypted email.

    Do I have it backwards, or is the Outlook system vulnerable to interception by anyone with my public key?

    1. Hello Robert,

      You are absolutely right. You share your public key with others so that they can send you encrypted messages (your private key enables you to read them).

      > Conversely, I should need to have the public key of each correspondent to whom I want to send encrypted email.
      Absolutely so. I couldn't have put it better.

      I've revised the article and made a few corrections to convey exactly this meaning. Thank you very much for your feedback!

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