Problems sending specific attachments

57010 pts.
Tags:
Development
E-business
Microsoft Exchange
Microsoft Office
Software
I am the exchange administrator for my organization. We have 3 exchange clusters (exchange 2000 SP4), a front end server, and use an SMTP connector to send outbound mail. We use a third-party vendor as a smart host for all our outbound email. My problem is this: I am getting complaints that specific emails are routinely not getting sent, and users are getting delay notifications, and then NDR's. It appears to be limited to emails with .tif attachments. The complaint is coming from my finance department, so this is high profile and very urgent. We are in communication with the third party vendor, but so far they are telling us the issue is on our end. Now they have told us that before about issues with inbound email that they also handle for us, and we have proven them wrong at least three different times now, so I am not ruling out that the issue could still be with them. Has anyone had an issue like this and found a solution? I would greatly appreciate some suggestions, thanks!

Answer Wiki

Thanks. We'll let you know when a new response is added.

.tif files are generally quite large and may be to large for your server. To remedy this have your IT increase the size of out-going files or change the the extention to .doc.

This should be the answer. I have had this problem with large photo and vidio files. It is best to increase the file allouance in the server as changing the extention is a pain in the butt.

Discuss This Question: 6  Replies

 
There was an error processing your information. Please try again later.
Thanks. We'll let you know when a new response is added.
Send me notifications when members answer or reply to this question.

REGISTER or login:

Forgot Password?
By submitting you agree to receive email from TechTarget and its partners. If you reside outside of the United States, you consent to having your personal data transferred to and processed in the United States. Privacy
  • Technochic
    I have no size limit set on my outgoing mail and the size of the files we have had issues with has been 1MB or less, so that is not the issue. In fact, I sent 8 emails to an external address today with 8 different types of attachments, some of which were greater than 2MB, and they all went through successfully. I tried resending one that I got an NDR on last week directly after this test, and again it was not sent. I will get an NDR on it tomorrow I am sure. Thanks for the suggestion though. Any other ideas? I'm really stumped here!
    57,010 pointsBadges:
    report
  • Petroleumman
    Hello, Can you disable email routing through this third-party host? If so, do that and test your outbound messages containing .tif images directly from your server. If the problem goes away then you can saftley say the source is with the third party mail vendor. It is highly possible that the vendor is performing some type of virus or spam screening of your outbound messages which is finding fault with *.tif files. Since you have a history of vendor related problems I would push them hard to assist in the trouble-shooting process since their service does create an additional point of failure. Good luck!
    0 pointsBadges:
    report
  • Technochic
    We do have the third party vendor involved and have an open work order with them asking for assistance. I have not gone so far as to disable the smart host forwarding yet, but will do try that as well. Thanks.
    57,010 pointsBadges:
    report
  • Ursulus
    Hi, I would try routing the mail yourself as a test.. depending on how you want to handle it, you could schedule an outage one evening, change the email routing to use DNS and try sending a .tif.. My hunch is that the problem lay with the email forwarding crowd as there is nothing in Exchange that will prevent .tif that I'm aware of. Ursulus
    0 pointsBadges:
    report
  • Technochic
    Thanks ursulus, That's my hunch too, and we are going to remove the third party tomorrow for exactly the test you suggested. Here's the really odd part, every single time we have gotten the third party on the phone about this (three times now), those attachments fly through like greased lightning! Happened again today. My supervisor called them, and I was just hearing the conversation when I saw my email that I had already gotten a delay notification on arrive in my external email account. While on the phone with them we both successfully sent 7 more. All the while they are telling us the issue is on our end. As soon as we got off the phone with them, the next tests we sent were again hung up in the SMTP queue and still have not been delivered. I'm flummoxed! Something is just not right there! We're trying sending directly tomorrow and will know for sure where the issues lies thereafter. Thanks for your input, I am of the same mind as you are on this.
    57,010 pointsBadges:
    report
  • Technochic
    Found it!!!!! I was talking to a team mate about this issue, and my Network Security Admin asked me for more details. Then he told me that HE was filtering out .tiff files at the external firewall and had been for months! He said he didn't think it was going to affect anyone!!!! As far as I know he never asked our team if this would cause a problem, nor let us know that he was going to do it. He said it was a "knee-jerk" reaction to the wmf security issue we had at the beginning of the year. *sigh* so much for change control, and not doing anything until it is discussed and agreed on first huh? My supervisor, who has been working with me on this for the last two months, was LIVID! Oh well, at least it is finally resolved and my finance department is happy now!
    57,010 pointsBadges:
    report

Forgot Password

No problem! Submit your e-mail address below. We'll send you an e-mail containing your password.

Your password has been sent to:

To follow this tag...

There was an error processing your information. Please try again later.

REGISTER or login:

Forgot Password?
By submitting you agree to receive email from TechTarget and its partners. If you reside outside of the United States, you consent to having your personal data transferred to and processed in the United States. Privacy

Thanks! We'll email you when relevant content is added and updated.

Following