cannot read attachment of encrypted mails

Question

Ralf_F Author

Level 1

21 points

cannot read attachment of encrypted mails

I updated to Sierra last week.

I cannot store/read attachments of encrypted mails anymore.

Body of mails can be read any time.

It does not depend on account type, imap, MSExchange, iCloud.

I can read and store same attachment and mail under IOS 10.0.2., i.e.

iPad/Iphone can handle it.

any solution ? or do I have to wait for an APPLE Update.

Thanks for help

Ralf

MacBook Pro (Retina, 15-inch, Mid 2014), macOS Sierra (10.12)

Posted on Sep 28, 2016 4:54 AM

Reply

Answer 1

chuck_3rd

Community Specialist

Sep 28, 2016 6:41 PM in response to Ralf_F

Hello Ralf_F,
Thank you for using Apple Support Communities.

I understand from your post that after updating to macOS Sierra you are no longer able to store or read attachments from encrypted emails. I know how important it is for you to be able to read all your emails on your Mac. I recommend using the information from the following article to help resolve this type of issue:

Mail for Mac: If Mail can’t decrypt messages

If you receive an email that Mail can’t decrypt, it’s possible your digital certificate or its private key is missing from a keychain. Try these suggestions.

If you have a backup of your keychain (created when you export your digital certificate and private key), import the Personal Information Exchange (.p12) file. For more information, see Import and export keychain items.

If your digital certificate and private key are stored on a Common Access Card (“smart card”), insert the card in your Mac, then try again.

If you no longer have your digital certificate or its private key, obtain a new certificate. For more information, see Use personal certificates in Mail.

Best Regards.

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Answer 2

Ralf_F Author

Level 1

21 points

Sep 28, 2016 11:34 PM in response to chuck_3rd

Dear alex_h1

I thank you for your kind reply.

No keys are missing and as stated I can read the also encrypted body of emails wirth or without attachemnts enclosed, though.

It's the attachment on my Macbook und apple mail, which cannot be read or stored. Although encryption of the attachment seems to be o.k., as the same mail and atachement can both be read on my IOS device using the same certificate.

It looks like that the attachment does not run through decryption mode after downloading the mail or isn't downloaded at all.

Anyway, thanks again.

best regards

Ralf

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Answer 3

8hur

Level 1

13 points

Oct 3, 2016 8:33 AM in response to Ralf_F

Hi Ralph, same here, I found no answer yet. Mails sent with a certificate (and or not encrypted) and received by Mail on macOS Sierra show 0 bytes for the attachments.

When sending with Mail on macOS Sierra if you turn off the use of a certificate, the attachments arrive properly in Mail macOS Sierra.

Not receiving 'certified, and/or not encrypted' attachments is true for all attachments, even a tiny logo png shows up as a question mark in a square.

I also notice the order of the headers in a received Mail message is different in Mail macOS Sierra: From - Subject - To. In Yosemite it is: From - To: - Subject - (and with a certificate:) Security: 'V' Signed (by: sender email). "V' is in the seal icon. So in macOS Sierra Mail you don't see the message sender has used a certificate.

The same mails received by my non-upgraded Mac with Yosemite show up fine, signed and encrypted and including all attachments. The Mac I'm testing macOS Sierra on is a fresh clone (CCC) of this Mac with Yosemite.

Arthur

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