Forwarding encrypted e-mails with images render the e-mail unreadable

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Forwarding encrypted e-mails with images render the e-mail unreadable

Łukasz Szczygielski 1

Hello, Our company footer contains an image and when forwarding it the amount of the images stack. We noticed that when the amount of images is >=2 the next recipient is not able to open the encrypted message. We are running a Exchange 2016 Standard server.

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Answer 1

Lucas Liu-MSFT 6,196

Hi @Łukasz Szczygielski ,
In order to better solve the issue, I would like to confirm the following information with you:

How do you encrypt emails?
Have all users encountered this issue?
I noticed that you mentioned the forwarded email. If you send an encrypted email with more than two pictures, can it be opened normally?
Please try to following the steps:
Please try to send an encrypted email that does not contain pictures to a user who has encountered the issue, and see if the user open it normally after forwarding.
Please try to open the encrypted email on OWA.
Are there any prompts or errors when the encrypted mail cannot be opened? If so, please share with us, but please pay attention to covering your personal privacy.

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Lucas Liu-MSFT 6,196 Reputation points

2021-01-14T10:02:05.71+00:00

Hi @Łukasz Szczygielski ,
I am writing here to confirm with you how thing going now? If the above suggestion helps, please click “Accept as answer” to mark helpful reply as an answer.Your action would be helpful to other users who encounter the same issue and read this thread.
Thanks for your understanding.

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Lucas Liu-MSFT 6,196 Reputation points

2021-01-19T06:34:35.9+00:00

Hi @Łukasz Szczygielski ,
I am writing here to confirm with you how thing going now? If the above suggestion helps, please click “Accept as answer” to mark helpful reply as an answer.Your action would be helpful to other users who encounter the same issue and read this thread.
Thanks for your understanding.

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Łukasz Szczygielski 1 Reputation point

2021-01-19T10:19:33.61+00:00
Hello @Lucas Liu-MSFT
Thanks for the reply!

we use S/MIME

Yes

That will need more testing from out site

We already tried most of these scenarios:

In this case it works

We do not have the option to read encrypted e-mails at all using OW
Lucas Liu-MSFT 6,196 Reputation points

2021-01-21T06:43:16.97+00:00
Hi @Łukasz Szczygielski ,

According to the research on information you prevoided, Sending and viewing encrypted email messages requires both sender and recipient to share their digital ID certificate. This means that you and the recipient each must send the other a digitally signed message, which enables you to add the other person’s certificate to your Contacts. So please make sure the recipient has the corresponding digital ID certificates.
You could check the settings of certificate following: File-> Options -> Trust Center -> Trust Center Settings -> Email Security.
For more information: Get a digital ID

Did this issued happen suddenly? Have any changes been made before this issue? If all users have this issue, you also could check whether the certificate installed successfully.
Lucas Liu-MSFT 6,196 Reputation points

2021-01-21T06:43:53.817+00:00

In addition, please make sure that sender and recipient must have a mail application that supports the S/MIME standard. If you using the outlook client, please upgrade outlook to last version.

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Lucas Liu-MSFT 6,196 Reputation points

2021-01-26T09:46:58.607+00:00

Hi @Łukasz Szczygielski ,
It long time no receive your feedback, is there any update?

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Łukasz Szczygielski 1 Reputation point

2021-01-26T10:01:38.55+00:00
Hello,

Yes, both the sender and recipient have the correct certificates installed.

It was probably always, we discovered it as we enabled auto encryption across the organization.
Lucas Liu-MSFT 6,196 Reputation points

2021-01-29T09:43:32.57+00:00

Hi @Łukasz Szczygielski ,
Please try to re-install the sender’s key on recipient computer and try to open the encrypted e-mail again.
What the result if you send an encrypted email containing two pictures directly to the recipient?

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Forwarding encrypted e-mails with images render the e-mail unreadable

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