Unable to send email with TIF/TIFF attachments

Posted on 2008-10-28
Last Modified: 2013-11-30
I am unable to send emails with TIF/TIFF files attached outside our organisation.  Emailing them internally works fine, so my suspicions are with the ClearSwift MailSweeper for SMTP.  The following is logged in the event log

EventID 792
Network I/O error 10054 (0x00002746) encountered when sending message data to <mailserver>

I also receive regular emails stating that the email is delayed (see below);

Your message has been delayed and is still awaiting delivery to the following recipient(s):
Message delayed

I/O error encountered
during command: (message data)

Any help greatly appreciated.
Question by:JonathanCoupland
  • 3
  • 2
LVL 31

Expert Comment

ID: 22823589
TIF extensions should pass through without problem.  Try renaming the file without an extension to test whether that works.

What I would look at though is the size of these attachments.  TIF files can be pretty enormous in size.

Author Comment

ID: 22823623
The TIF file(s) are only around 120k.  I have tried renaming them, but the problem still persists.
LVL 31

Accepted Solution

moorhouselondon earned 500 total points
ID: 22823624
The wikipedia entry for TIFF does have this to say, which might be the cause of blocking:-

The TIFF file format is unusual in comparison to other image formats, in that it is composed of small descriptor blocks containing offsets into the file which point to the actual pixel image data (composed of bands of pixel rows). This means that incorrect offset values can cause programs to attempt to read erroneous portions of the file or attempt to read past the physical end of file. Like most other image file formats, improperly encoded packet or line lengths within the file can cause poorly written rendering programs to overflow their internal buffers. Properly-written image rendering programs generally avoid such pitfalls.
Multiple buffer overflows have been found in Libtiff.[1][2][3] Some of these have also been used to execute unsigned code on the PlayStation Portable,[4] as well as run third party applications on the iPhone and iPod Touch[citation needed].
LVL 31

Assisted Solution

moorhouselondon earned 500 total points
ID: 22823675
These mailsweeper "appliances" do seem to cause a lot of problems.  From the fact that you renamed the file and problem persists, it sounds like the mailsweeper thing is not parsing the outgoing mail stream correctly.  Have you tried zipping it?  

Author Closing Comment

ID: 31510651
The issue is now resolved.  I was able to zip the file and it would then get delivered to the recipient.  It turns out that it was getting blocked by one of our 'Intrusion Dectection' systems!  Many thanks for the advice

Featured Post

Is Your Active Directory as Secure as You Think?

More than 75% of all records are compromised because of the loss or theft of a privileged credential. Experts have been exploring Active Directory infrastructure to identify key threats and establish best practices for keeping data safe. Attend this month’s webinar to learn more.

Question has a verified solution.

If you are experiencing a similar issue, please ask a related question

Suggested Solutions

Title # Comments Views Activity
exchange, scripts 30 77
Exchange Passive Recynchronization 2 27
Log event for Exchange Active sync mailbox removal on mobile device 1 14
exchange, outlook 2 26
We are happy to announce a brand new addition to our line of acclaimed email signature management products – CodeTwo Email Signatures for Office 365.
Disabling the Directory Sync Service Account in Office 365 will stop directory synchronization from working.
In this video we show how to create a Distribution Group in Exchange 2013. We show this process by using the Exchange Admin Center. Log into Exchange Admin Center.: First we need to log into the Exchange Admin Center. Navigate to the Recipients >>…
The basic steps you have just learned will be implemented in this video. The basic steps are shown to configure an Exchange DAG in a live working Exchange Server Environment and manage the same (Exchange Server 2010 Software is used in a Windows Ser…

911 members asked questions and received personalized solutions in the past 7 days.

Join the community of 500,000 technology professionals and ask your questions.

Join & Ask a Question

Need Help in Real-Time?

Connect with top rated Experts

18 Experts available now in Live!

Get 1:1 Help Now