7451 S/MIME Broken
Problem reported by Robert Simpson - 5/28/2020 at 9:10 AM
Testing out MAPI with a digital signature today ... sent an e-mail via MAPI to my work account, and it appears botched on my work account (Office 365)

I digitally signed the e-mail and sent via SM Beta over MAPI.  The received e-mail I got had a blank body, and a message that "Outlook blocked an unsafe atttachment file.tmp"

It looks OK in my Sent Items folder inside Outlook, but it's definitely NOT OK on the SM Web Interface Sent Items folder.

6 Replies

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Robert Simpson Replied
This is what it looks like in Outlook's Sent Items folder:

The above e-mail was sent with "Add a digital signature to this message" checked, but not the "Send this message as clear text signed" checked.

And this is what it looks like in the SM web interface Sent Items folder (raw data)

From: "Robert Simpson" <robert@domain.com>
To: <robert.simpson@workdomain.com>
Subject: Test
Date: Thu, 28 May 2020 09:06:50 -0700
Reply-To: robert@domain.com
Message-ID: <03dcdc0e83a840579eb7c7cc04010ac8@>
MIME-Version: 1.0
Content-Type: multipart/mixed; boundary=fcc03c411c224a95a85703af64480075

This is a multipart message in MIME format.

Content-Type: text/plain;
Content-Transfer-Encoding: quoted-printable

Content-Type: application/pkcs7-mime
Content-Transfer-Encoding: base64
Content-Disposition: attachment;


There's quite a lot wrong with this.  If I check the "Send this message as clear text signed" as well, I get a different output, but it's still wrong, and Exchange still can't understand it.

Robert Simpson Replied
Sending via EAS works fine.  Raw data in SM Sent Items looks like this:
To: "Robert Simpson" <robert.simpson@workdomain.com>
Subject: Activesync signed test
Date: Thu, 28 May 2020 09:40:57 -0700
Message-ID: <01ef01d6350e$c36133f0$4a239bd0$@domain.com>
MIME-Version: 1.0
Content-Type: application/pkcs7-mime;
Content-Transfer-Encoding: base64
Content-Disposition: attachment;
X-Mailer: Microsoft Outlook 16.0
Thread-Index: AdY1DnWKzI5aeUdPSNSvJQ4r3eR3uw==
Content-Language: en-us
From: "Robert Simpson" <robert@domain.com>

Larry Duran Replied
Employee Post
Hey Robert, thanks for reporting this.  We'll be taking a look at it and we'll let you know what we find.
Larry Duran Software Developer SmarterTools Inc. (877) 357-6278 www.smartertools.com
Benjamin Breedlove Replied
It is May 30, 2023, what is the updated status on this problem?
Zach Sylvester Replied
Employee Post
Hey Benjamin, 

Thanks for the question. This issue was resolved a long time ago. 

Zach Sylvester System/Network Administrator SmarterTools Inc. (877) 357-6278 www.smartertools.com
Oliver Replied
I'm a bit confused.
I have reported problems with S/MIME signed mails in Outlook connected via MAPI to the support. They told me that SM does not support S/MIME.

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