Why won't IIS send my email?
February 5, 2008 6:50 AM   Subscribe

Seemingly random undeliverable email using IIS's built in SMTP server. Please hope me!

Hello everyone
I have a windows server 2003 dedicated machine, which randomly fails to send email. I've been using CDO for years now, and have never come across such an annoying problem, i've literally spent days trying to fix this problem!!

Basically i have a website hosted there, with a really simple CDO send script. It look like this:

for x = 1 to Request.Form.count()
  themessage=themessage & Request.Form.key(x) & vbcrlf
  themessage=themessage & Request.Form.item(x) & vbcrlf & vbcrlf

Set MailMessage = server.createobject("CDO.message")
MailMessage.to = "info@flexytron.com"
MailMessage.from = "info@flexytron.com"
MailMessage.subject = "RFQ from website"
MailMessage.textbody = themessage

Now about 50% of these emails come through.

The rest give me a 5.3.5 "Delivery to the following recipients failed (info@flexytron.com)

The from address in the bounce email is given as postmaster@DSVR003430.livemail.co.uk

Reporting-MTA: dns;flexyweb.co.uk
Received-From-MTA: dns;DSVR003430
Arrival-Date: Tue, 5 Feb 2008 14:29:42 +0000
Final-Recipient: rfc822;info@flexytron.com
Action: failed
Status: 5.3.5

I can't understand why this is happening. Can anyone work out why my email won't send? It's driving me completely spare, especially as one minute it works, and the next it doesn't!
Thanks a lot
posted by derbs to Computers & Internet (4 answers total) 1 user marked this as a favorite
The most likely explanation is that one of the inbound mail servers is down. From a dig on this domain, this looks like smtpin.livemail.co.uk. - you may wish to contact them and see if they are having issues.
posted by jenkinsEar at 7:05 AM on February 5, 2008

Turn on the logging for the SMTP server. You can get to it through the IIS control panel.

If this is a production box don't forget to turn it off afterwards.
posted by XMLicious at 9:30 AM on February 5, 2008

Try another mail-sending component besides CDO. I know there are plenty of commercial IIS hosting services that don't allow CDO. There are plenty of alternatives out there. The one I use on my site is Persits' ASPEmail. It's free, but there's a premium version that actually does queueing (the free version expects you to point it to an SMTP server that does the final delivery). For a mail server, I run CommuniGate Pro, which is also free for five accounts or fewer.
posted by kindall at 5:03 PM on February 5, 2008

Oh, and the reason it's bouncing is probably anti-spam at the receiving server. I would not be surprised to hear that CDO is used to send a lot of spam from various VB apps and scripts.
posted by kindall at 5:05 PM on February 5, 2008

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