I can't reply to digitally signed emails in OWA. I don't have a digital signature and don't need one. The message is not encrypted. I only need to reply back. I get this message when sending: An error occurred while sending this S/MIME message. The certificate used to sign this message isn't valid. Is there a way to ignore this?

@Jackie Butler What's the detailed version of your Exchange servers? You can check with the following command: Get-ExchangeServer | Format-List Name,Edition,AdminDisplayVersion Do you get the same error alert when send a new message or reply to other messages without digitally signed? Is there a ribbon icon when you reply the message? Like this: Please check the S/MIME settings in your OWA. Options > Mail > S/MIME, make sure "Add a digital signature to all messages I send" is not selected: If the response is helpful, please click " Accept Answer " and upvote it. Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.

Can't reply to digitally signed emails in OWA

Accepted answer

Lydia Zhou - MSFT 2,376 Reputation points Microsoft Employee

2020-09-24T02:23:10.01+00:00
@Jackie Butler

What's the detailed version of your Exchange servers? You can check with the following command:

Get-ExchangeServer | Format-List Name,Edition,AdminDisplayVersion

Do you get the same error alert when send a new message or reply to other messages without digitally signed?
Is there a ribbon icon when you reply the message? Like this:

Please check the S/MIME settings in your OWA. Options > Mail > S/MIME, make sure "Add a digital signature to all messages I send" is not selected:

If the response is helpful, please click "Accept Answer" and upvote it.
Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.
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Jackie Butler 236 Reputation points

2020-09-24T12:33:39.66+00:00

No problems sending a new email.
The selections for S/MIME are not selected.
No ribbon icon

Edition : Standard
AdminDisplayVersion : Version 15.0 (Build 1497.2)

Lydia Zhou - MSFT 2,376 Reputation points Microsoft Employee

2020-09-25T09:31:24.3+00:00

@Jackie Butler

When you reply the message, click More actions > Show message options, make sure "Digitally sign this message (S/MIME)" is not selected:

You have mentioned that "I don't have a digital signature and don't need one", does your organization configure S/MIME recently? If so, we have to check and make sure the certificate is valid.

What browser do you use? You can try with different browsers to see if the issue persists.

If the response is helpful, please click "Accept Answer" and upvote it.
Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.

Lydia Zhou - MSFT 2,376 Reputation points Microsoft Employee

2020-09-28T09:40:05.7+00:00

@Jackie Butler

Just checking in to see if above information was helpful. If you have any questions or need further help on this issue, please feel free to post back.

If the response is helpful, please click "Accept Answer" and upvote it.
Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.
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Can't reply to digitally signed emails in OWA

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