Emails from one user to another show up as Untitled Attachment
Question asked by Eric Tykwinski - 10/6/2021 at 12:50 PM
SmarterMail Enterprise Build 7914 (Sep 1, 2021)

Never seen this before, we have two users, Alex and Aaron on the same domain.  It looks like Alex is sending contacts and it's breaking both MAPI and Webmail, but not when using Outlook with IMAP.
Alex is sending with Outlook on normal SMTP with attachments in Outlook to Aaron who is using Outlook with MAPI.  When Aaron opens the emails it show blank with 2 attachments both titled Untitled Attachment.

1st just a text file with "This attachment is a MAPI 1.0 embedded message and is not supported by this mail system."
2nd seems to be the contact possibly in RTF.

I tested with my webmail and Outlook 2019 on MAPI with the same results, but a seperate account with just checking with IMAP works fine.

It only happens when you click Outlook Item as attachment, using a Business Card (vcf) seems to work fine.

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Zach Sylvester Replied
Employee Post Marked As Answer

Thanks for reaching out. I just tested this and it appears to be working on the latest build. Please upgrade and let me know if you have anymore issues with this. 

Best Regards, 

Zach Sylvester

System/Network Administrator
SmarterTools Inc.
(877) 357-6278
Eric Tykwinski Replied
Alright, I'm getting sort of pissed on this now.
So I updated to the latest build, and tested the issue. As of this morning it was 7950.
Here's the response, I received:
> Thanks for the fast response. Do you think you could upgrade to the latest build? There were some fixes done
> recently with attachments. 

Here's the release notes: 

Build 7957 (Oct 14, 2021)

  • Fixed: Extra space on DKIM-signature line can cause DKIM issues.
Obviously nothing about re-encoding attachments.  I really think now this is related:

Considering that CI/CD is good for developers, but ITIL is required to announce downtime for end users of enterprise systems, this is basically incompatible with legal requirements.  Why do you think Microsoft uses update Tuesdays to deliver updates?  It's also why everyone is pissed about update 7944, https://portal.smartertools.com/community/a94421/build-7944-do-not-install-serious-issue.aspx

If you are really patching this issue, it should be in the notes.  If you are stalling, just say you are working on it...  I can't risk loosing clients because of you are lax on testing releases, and I'm sure many others here will agree.

Sébastien Riccio Replied
We agree
Sébastien Riccio
System & Network Admin

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