The magically blocked PDF

This just started about six weeks ago.

Incomming mail arrives fine.
Outgoing mail is delivered fine, unless it contains a PDF attachment, and only if that PDF attachment is 2MB+ in size.  Should this 2MB attachment be split into two 1MB attachments, and sent one at a time, both arrive fine.

There are no send or receive limits set for Exchange.

These 2MB+ PDF messages just sit in the queue.  We first noticed this after 5 days had passed.

After a reboot, they are sent out and delivered as intended.  For a period everything works fine, then some random time later (few days to a week, no definate trigger,) process starts over again.  2MB+ of other files can get sent fine, PDFs 2MB+ sit in queue.  Reboot, delivered, rinse and repeat.  No significant errors being reported with OS, Exchange, DNS, AV.

Any ideas?
olivejarAsked:
Who is Participating?
I wear a lot of hats...

"The solutions and answers provided on Experts Exchange have been extremely helpful to me over the last few years. I wear a lot of hats - Developer, Database Administrator, Help Desk, etc., so I know a lot of things but not a lot about one thing. Experts Exchange gives me answers from people who do know a lot about one thing, in a easy to use platform." -Todd S.

ksharma4Commented:
Check the size of the mail being sent from ur exchange server.
0
kupzpennyCommented:
What kind of Firewall do you have?
Check this link. It looks like you firewall is interfering with the delivery.
http://www.experts-exchange.com/Networking/Email_Groupware/Exchange_Server/Q_21529275.html?query=PDF+stuck+on+exchange+queue&clearTAFilter=true

0
ksharma4Commented:
it should not be the firewall because user is saying that it is stuck in the smtp queue (Please tell me if i understand it incorrectly). It is not even going from exchange to firewall

Thanks
0
Has Powershell sent you back into the Stone Age?

If managing Active Directory using Windows Powershell® is making you feel like you stepped back in time, you are not alone.  For nearly 20 years, AD admins around the world have used one tool for day-to-day AD management: Hyena. Discover why.

olivejarAuthor Commented:
kupzpenny:

that is close, and gives me something to go on.  It's a watchguard firewall (x15 to be exact.)

That persons are being sent and resent.  In my case, some with PDFs are not being sent at all.  On the firewall, it's a lower model, so there are no proxys... it's simple port forwarding, so I am thinking that SMTP commands are not being filtered out.  In any case, I am also going to bother Watchguard with this now too.

ksharma4:  I do not think it is the firewall either, as there is no proxy/filter, and only port forwarding.  But, this would not be the first time I've encountered a Watchguard product fighting with another product/application.  If the firewall is playing with the SMTP commands, i can imagine Exchange thinking "ok, that didn't go so well. I will try to redeliver again later."

But I am not so sure it is the firewall anyway.  At one of their machines, I send three email to one of my accounts.  1) "Hello" 2) "hello" with 1MB PDF, and 3) "hello" with 2MB PDF.  #1 and #2 are delivered to me fine.  #3 sits in the Exchange queue until a reboot occurs.  Even "force connection" does nothing until rebooted.
0
olivejarAuthor Commented:
Made some headway, but not much.

took the firewall out of the loop.
attempted to send the PDF in question again.
Hits and sits in exchange queue.
1 hour passes and nothing.
"Force connection" and delivers as intended.

took the firewall out, so it's not the firewall.
AV? sure maybe, but 1) pdf is not a blocked extension, 2) sends fine when "force connection"
0
olivejarAuthor Commented:
Mcafee has a --feature-- for real-time scanning. Something about blocking large traffic over port 25, as it could be a worm.

disabled that and all is well.
0
CetusMODCommented:
PAQed with points refunded (500)

CetusMOD
Community Support Moderator
0

Experts Exchange Solution brought to you by

Your issues matter to us.

Facing a tech roadblock? Get the help and guidance you need from experienced professionals who care. Ask your question anytime, anywhere, with no hassle.

Start your 7-day free trial
It's more than this solution.Get answers and train to solve all your tech problems - anytime, anywhere.Try it for free Edge Out The Competitionfor your dream job with proven skills and certifications.Get started today Stand Outas the employee with proven skills.Start learning today for free Move Your Career Forwardwith certification training in the latest technologies.Start your trial today
Exchange

From novice to tech pro — start learning today.

Question has a verified solution.

Are you are experiencing a similar issue? Get a personalized answer when you ask a related question.

Have a better answer? Share it in a comment.