Customer has constant email issues

S

sonata

Perch
I have a client who constantly has email issues. What is currently happening is that they get a message saying it "doesn't go through", at which point they keep on sending the email. Then they get a message from the recipient saying that they got the message several times.

This customer typically sends emails with large attachments (usually documents in graphics format), which I believe to be the problem. However, the error messages are confusing because they indicate the email didn't go through when, in fact, it did.

I am at my wit's end on this. I do not know what to tell them at this point because I see no errors or traffic problems on his mail server (which is also the one I use). I have had him change his timeout, look at his antivirus settings, etc. None of it is working.

If ANYONE has anything to suggest for this, please let me know. The customer is using Outlook 2003 as their email client. I'm not certain of the current antivirus software.
 
What AV is being used? I have seen this with Symantec and also with Avast that have a email "proxy" server for incoming/outgoing mail, it makes it think some error happened becuase the end of transmission command doesn't come, yet in reality the proxy has it and is sending after scanning, properly.
 
Stephen,

They are using PCCillin. I don't know if everyone is using it and whether they are all on the same version. I've asked the question and will post the response when I get it.

I suspect the AV is the problem because I use AVG, just sent out 6 emails, each one with a 10MB attachment, and had no problems; they all went through. I'm going to see what I can find out about the AV.
 
Client is using TrendMicro PC-Cillin Internet Security 2006 (Version 14.1). I'm trying to track down whether this version uses a proxy or could be causing these SMTP problems.
 
Also, check what they have for how often Outlook is performing a send/receive. The email send may not be completing before the next timed "send/receive" interval. Therefore it executes the send on the Outbox again. Likely their interval is some low setting like 2 minutes or something. I think the suggested standard interval is around 10 minutes.
 
cmjacobsen said:
Also, check what they have for how often Outlook is performing a send/receive. The email send may not be completing before the next timed "send/receive" interval. Therefore it executes the send on the Outbox again. Likely their interval is some low setting like 2 minutes or something. I think the suggested standard interval is around 10 minutes.
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I've forwarded this to the customer, but haven't gotten any response. Thanks for the input.
 
sonata said:
Client is using TrendMicro PC-Cillin Internet Security 2006 (Version 14.1). I'm trying to track down whether this version uses a proxy or could be causing these SMTP problems.
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I always recommend disabling virus checking on outgoing email. Not only does it cause a lot of unnecessary hassle, I can't see the sense of using it. If your computer sends infected email, it is because it is already infected, which means the AV software wasn't able to detect the infection. So it's highly unlikely that it will detect the infection in an outgoing message.
 
nzkiwi said:
I always recommend disabling virus checking on outgoing email. Not only does it cause a lot of unnecessary hassle, I can't see the sense of using it. If your computer sends infected email, it is because it is already infected, which means the AV software wasn't able to detect the infection. So it's highly unlikely that it will detect the infection in an outgoing message.
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i'll second this. outgoing email virus scanning is "feel-good" stuff. definitely causes more pain than it's worth.
 
Thanks, everyone, for your input. I've passed the suggestions on and will keep them in mind for the future.

As usual, this customer got incredibly upset, until I started suggesting things for him to check (because there is nothing wrong on my end). At that point, he drops it and life goes on...:rolleyes:
 
I have a customer who has been complaining about the same thing. He has McAfee AV and disabling email scan has not solved the problem. He uses Outlook express and automatically sends and receives every 10 min.

Is there anything else that could be causing this problem?
 
The "10 minutes" is relative really. For troubleshooting purposes, to somewhat eliminate the circular sending issue, disable the auto send & receive while sending a large attachment. It depends on the connectivity from the client to the mail server and how quickly the mail server receives the message/attachment.
 
The problem with some of these AV suites is that you can never be sure what they are really doing under the hood. For example when you turn off scanning of out-going mail, is the proxy disabled, or does the mail still go through the proxy, but without being scanned? If the latter, there couold still be timing issues with very large emails.

Try extending the timeout limits. I think they are 30 secs in OE. It may be necessary to set the limit to slightly longer than the time it takes to send a long message.

The other thing you can do is to enable SMTP logging. If you are not sure how to do this, there is some help on About.com
 
The other thing you can do is to enable SMTP logging. If you are not sure how to do this, there is some help on About.com
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Thanks for that tidbit - I'll suggest that next time my customer complains.
 
Thanks for the advice. It turned out though, that the problem was caused by a corrupt "Sent Items" folder. So the mail in the outbox was sent, but couldn't be moved to the "sent items" folder so it stayed in the outbox and was constantly re-sent.

I had to create a new identity in Outlook Express and import all the mails and mail accounts from the old one. That solved the problem.
 
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