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Email not being received/possibly being perceived as spam?

Posted on 2014-10-28
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Last Modified: 2014-11-08
Hi,

Our situation is that a couple of managers sent out 30 or so emails in very quick succession, all with the same subject heading, to customers as a personalized after sales courtesy call. These emails had delivery receipts but none appear to have been delivered. Individual emails are coming through and being sent out without issue and our spam filter is working inbound only(just checked with our provider). Our email (Exchange 2003 /server 2003)is sent out via smart host smtp.btconnect.com.  Is it likely that BT think this is spam? We were able to send out Christmas opening times last year in a similar way without any problems....any thoughts? Thanks..
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Question by:Paul Welsh
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by:MadHatterAdmin
ID: 40408192
Is your mail being forwarded thru an external smarthost?

I would try http://mxtoolbox.com/ to see if you're being blacklisted by any providers as they might be blocking you as spam.
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by:Paul Welsh
ID: 40408223
HI - yes we are going through bt smart host - smtp.btconnect.com - like I mentioned -all other emails are working fine - we have no problems at all with standard email send /receive and do not appear to be blacklisted. Its only when our guys try to send out a group of 30 or so emails, that this happens. There is a 0.5 mb attachment on 30 emails  -so 15mb or thereabouts  - but I understand BT limit is 20 or 25mb...
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by:Paul Welsh
ID: 40408225
If I change from using a smart host to DNS - would this be worse, i.e. look even more spammy and invite blacklisting?
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MadHatterAdmin earned 500 total points
ID: 40408607
No, There's really no need to relay outbound mail thru an smtp smarthost. Using your DNS would be more beneficial because your email headers will contain your mail server info BUT if it's relayed externally it might be more recognizable as spam. General practice is using a smarthost for virus and spam filtering inbound, not usually outbound.  

Please follow best practices for exchange with dns and make sure you have a reverse look up and a couple other things in place or you WILL get flagged as spam.

Try this and test to see what happens.
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Expert Comment

by:hecgomrec
ID: 40411629
Can you take one of those email addresses and send it with the same attachment?  can you without it?

Sometimes, is the attachment that is consider the dangerous and the filter will not allow it; Also the amount of email that can be send simultaneously can be an issue, this one you will have to discuss with your ISP (smtp smart host) to know/increase your limits.
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