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LSmeets-2653 asked DanielMierswa-2732 answered

Cant send signed e-mail after draft

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.

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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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Hi @LSmeets-2653,
Just checking in to see if above information was helpful. If you have any further updates on this issue, please feel free to post back.

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JeffYang-MSFT avatar image
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JeffYang-MSFT answered LSmeets-2653 commented

Hi @LSmeets-2653,

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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Hi @LSmeets-2653,
It has been a while, how is everything going?
If you have any update about this issue, please feel free to post back.

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"Concepts" are drafts. I'm experiencing same issue as well, so I can confirm product behavior. The only difference is that my certificate is stored on a smart card.

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@JeffYang-MSFT
Yes, an 'normal' e-mail is going fine. When I create a new e-mail and save this as draft (concept) and trying to re-send it the error appears. Translation from the error:

First screenshot: This message cannot be signed or encrypted in Microsoft Outlook because you do not have certificates to send messages from your email address

Second screenshot: When I press Beveiligingsinstelling wijzigen (Change security setting) screenshot 2 opens. Here can I select under Instelling wijzigen (Change settings) the certificate. When I select this one the error still appears.

@Crypt32 : Are you also working on an terminal?

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No, it happens to me locally. So I suspect it is related to Outlook itself rather than terminal. It could be terminal issue if you would use smart cards and smart card redirection may struggle sometimes. But if you do not use smart cards, then certificate is installed on a same machine where Outlook runs (on a terminal server), so it isn't related to terminal session. This means that I have same issue you do.

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Thanks for all your updates here.
Have you tried turning off e-mail matching for certificates in Outlook and see if the issue could have any difference there?
Please check the steps in this document: How to turn off e-mail matching for certificates in Outlook.
Any update, please feel free to post back.

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Thank you for the update @JeffYang-MSFT . I just tested it and it didn't help. Also the how to is for 2013 and below. I'm working with Office 2019. I followed the 2016 solution of this page but didnt work.


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JeffYang-MSFT avatar image
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JeffYang-MSFT answered JeffYang-MSFT edited

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:
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1. On two completely new devices, add my certificate into Outlook like below
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2. Then create new Outlook email messages, encrypted with signing
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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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LSmeets-2653 avatar image
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LSmeets-2653 answered Crypt32 commented

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.


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For me it's only a name and not an e-mailadres. Can that be a problem?

no, it is not.
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DanielMierswa-2732 avatar image
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DanielMierswa-2732 answered

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)

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