S/MIME Decryption Issue OWA

Question

S/MIME Decryption Issue OWA

Dan R4 6

I have the most up to date version of Windows 11, Microsoft Edge and the S/MIME extension installed on my home computer. I have added the domain for my work website but when I try to open an encrypted e-mail in Edge on the OWA site, I get this response: "The S/MIME message wasn't decrypted successfully. An unexpected S/MIME error occurred." I have tried reinstalling the S/MIME and restarting Edge and my computer after doing so but I continue to have the same issue. I have ensured I have the appropriate certificates installed as well.

Anonymous

2022-06-13T08:59:27.673+00:00

Hi @Dan R4 ,

Since this question is related to Office Exchange, I've added corresponding tag so that relevant community experts can help you.
Ahmed Abdalla Bazazo 6 Reputation points

2022-06-20T08:57:31.767+00:00

v.good
J H 0 Reputation points

2024-01-30T12:13:53.53+00:00

I tried Private Mode and unable to open encrypted emails yet i can send digitally signed and encrypted emails via OWA just fine.

2 answers

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Anonymous

2022-06-13T08:59:27.673+00:00

Hi @Dan R4 ,

Since this question is related to Office Exchange, I've added corresponding tag so that relevant community experts can help you.
Ahmed Abdalla Bazazo 6 Reputation points

2022-06-20T08:57:31.767+00:00

v.good
J H 0 Reputation points

2024-01-30T12:13:53.53+00:00

I tried Private Mode and unable to open encrypted emails yet i can send digitally signed and encrypted emails via OWA just fine.

Answer 1

Aaron Xue-MSFT 2,596 Microsoft External Staff

Hi @Dan R4

Based on your description, I’d like to confirm few questions for identifying the issue.

1.Could you open the encrypted email from Outlook client?
2.Please try to open OWA in Edge with in Private mode and check if the encrypted message can be opened.
3.Try to use other browser like Chrome to open the encrypted email.

Please kindly provide us your updated after you performing above mentioned information. Thanks!

If the response is helpful, please click "Accept Answer" and upvote it.

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Aaron Xue-MSFT 2,596 Reputation points Microsoft External Staff

2022-06-17T09:47:32.867+00:00

Hi @Dan R4 ,
It's been a while, is there any update?
Ahmed Abdalla Bazazo 6 Reputation points

2022-06-20T08:58:18.49+00:00

v.good
Tom Jackson 56 Reputation points

2022-07-20T13:34:19.763+00:00

I have the same issue and I can attest that the emails can be decrypted fine from Outlook while on-site, logged onto my work computer that resides on my work domain, but when accessing OWA on a home computer that is not part of that domain, this is the point when it fails - and that's whether on Edge (regular or InPrivate), or Chrome (regular or incognito).

It doesn't matter if you go into the Control Panel - Network and Internet - Internet Options - Security tab - Trusted sites - Sites button - add the site and 'OK' your way back out and refresh the page, nor does it work after that to go into the same area and hit Custom level on the Trusted sites icon area - Allow ActiveX Filtering and set this to Disable and refresh the page, again. I've seen both of these suggested in Microsoft forums. It also doesn't matter if it's after a reboot following doing this and logging back into OWA and retrying the email.

When you're in the OWA page and you go to the gear icon, then 'View all Outlook settings' - Mail tab on sidebar - S/MIME, it says I have the latest control installed (4.0800.20.21.804.1). But if I try to decrypt something it will say 'Your message couldn't be retrieved. Please try again later.' or the decryption failed.

I saw text on the same S/MIME settings screen when I pulled up Edge's InPrivate mode saying it wasn't installed, though in regular mode it is. Clicked the link to install it - takes me to the Microsoft App Store S/MIME page, says it's already installed, shows a 'Remove' button.

Answer 2

شرين قاسم محمد سليمان 1

Good Cores

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S/MIME Decryption Issue OWA

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