Cant send signed e-mail after draft

L. Smeets 76 Reputation points
2021-03-10T20:45:43.33+00:00

Hi,

A couple of years I'm using a email Signing Certificates from Sectigo for signing my e-mails. I just renewed my certificate and reinstalled it in Outlook. When I'm sending an new 'normal' e-mail it's signed and working properly.

When I create an email and save it to my concepts and send it after 1 minute I got an error;

76328-1.png
This message cannot be signed or encrypted in Microsoft Outlook because you do not have certificates to send messages from your email address

When I press on change security settings I can select my certificate (where now Automatisch / Automatically stands) but the error still occurs.

76427-2.png

Outlook version: Outlook 2019 16.0.10371.20060 - 64 bits but also occurs on Outlook 2016. I'm working on an terminal server.

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Outlook: A family of Microsoft email and calendar products.Management: The act or process of organizing, handling, directing or controlling something.
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4 answers

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  1. JeffYang-MSFT 6,241 Reputation points Microsoft Vendor
    2021-03-11T06:06:12.533+00:00

    Hi @L. Smeets ,

    Welcome!

    When I'm sending an new 'normal' e-mail it's signed and working properly.
    So, here, may I understand that you could successfully create a new email message, encrypt it and send it out but will get troubles when using "concepts"?
    If yes, what does the "concepts" you mentioned here mean?

    By the way, currently in Microsoft Q&A we only support English, so could you please provide us with English error screenshot so that we can conduct more researches about your issue?

    Any update, please feel free to post back.

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  2. JeffYang-MSFT 6,241 Reputation points Microsoft Vendor
    2021-04-05T08:56:35.28+00:00

    Hi all,

    Thanks for you update.

    Sorry for my delay here. I'm here to share some of my updates about your issue. I tried to reproduce your issue in my Outlook 2016 and Outlook 2019 versions, with the steps below to test:
    84471-10.jpg 84395-2.jpg

    1. On two completely new devices, add my certificate into Outlook like below
      84404-3.jpg
    2. Then create new Outlook email messages, encrypted with signing
      84377-4.jpg
    3. Save to Draft folder
    4. Wait for a while and restart my Outlook, check the Draft folder and send those encrypted emails out
    5. Emails can be successfully send out without any issues and the recipients can receive them normally.

    Tests result just work fine and could not reproduce your issue.

    I noticed that you selected automatic security settings in your Security Properties, what if your tried manually choose your certificates and restart your Outlook to see if the issue could be resolved then?
    84451-5.jpg

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  3. L. Smeets 76 Reputation points
    2021-05-06T14:16:18.837+00:00

    Hi @JeffYang-MSFT

    Sorry for my delay. Below are the screenshots:
    94436-cert10.png94406-cert11.png

    94437-cert12.png

    When I try to switch the Security Settings I can select the certificate. When I press OK the same error appears: This message cannot be signed or encrypted in Microsoft Outlook because you do not have certificates to send messages from your email address.

    I also added a screenshot from the certificate. What I saw on your first screenshot that your signing certificate contains probaly the e-mailadres ******.com. For me it's only a name and not an e-mailadres. Can that be a problem? If it would, it would be strange that I can send an 'normal' (not an draft) e-mail signed.

    Apologies for the late reply.

  4. Daniel Mierswa 1 Reputation point
    2022-04-07T13:51:26.577+00:00

    Had the same problem on one of our laptops.

    Got it resolved by fixing a seemingly unrelated credentials problem that user had with an unrelated mail-account.

    One of their other accounts, had that problem, where outlook doesn't properly save your credentials and asks for the same credentials everytime you start outlook and never properly saves them.

    So I fixed that problem by removing the credentials for that other account from the credentialmanager and reentering them. And for some reason after that everything worked again even the saving and sending of signed emails.
    Not sure if that was actually the reason it started working again, but it sure look that way.
    (before that I readded the the certificate and restarted outlook a couple of times. But that didn't really help)