Some accounts cannot send to some Hotmail recipients
Question asked by Martin Eising - 5/27/2015 at 8:34 AM
Answered
We just switched our VPS plan to HostMySite.com, and I'm having a terrible problem with Hotmail emails!
 
Some of our "healthquotes.ca" email users can send an email to some Hotmail people but not other Hotmail accounts.
 
Background info:
 
- we have SPF and PTR records created
- some of our email users can send to Hotmail accounts, while other people in our office cannot send to Hotmail
- when the email fails there is no bounce message
- when the email fails to get to the Hotmail user, the SmarterMail log file indicates the email was successfully delivered
- the PTR/SPF records use our primary IP
- the "sender IP" address in the email headers (of email sent to Hotmail account) is NOT using the primary IP, for some strange reason. (I've contacted HostMySite.com to see if this can be fixed).
 
What is baffling is that some of the people in the office can send reliably to some Hotmail accounts but not other Hotmail accounts.
 
Has anyone seen a similar problem? Any help is greatly appreciated, I'm stuck!
 
Thanks in advance for any help.
 
Martin
 

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0
Bruce Barnes Replied
Are any of the non-delivered accounts originating on accounts hosted on SmarterMail and sending to accounts hosted on the same server which are forwarding to the Hotmail accounts?
 
Do you have SRS enabled?
Bruce Barnes
ChicagoNetTech Inc
brucecnt@comcast.net

Phonr: (773) 491-9019
Phone: (224) 444-0169

E-Mail and DNS Security Specialist
Network Security Specialist

Customer Service Portal: https://portal.chicagonettech.com
Website: https://www.ChicagoNetTech.com
Security Blog: http://networkbastion.blogspot.com/

Web and E-Mail Hosting, E-Mail Security and Consulting
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Martin Eising Replied
Thanks very much for the reply Bruce :)

SRS was not enabled, I've done so and re-started the SmarterMail service, but I'm still having the same problem.

I'm not sure I understand the first question you asked. We send email from our office using PostMail (PHP), which is then relayed to the destination email address using our SmarterMail server, hosted on our VPS.

We started having problems right after we migrated to a new VPS.

It is so strange that only some users in the office have problems, and out of those users they only have problems with some hotmail accounts, not all hotmail accounts.

Martin

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Martin Eising Replied
P.s. problem is fixed!! I changed the outgoing IP address for SmarterMail to match the IP used with the PTR/SPF records and now everyone can send to Hotmail addresses!!
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Matt Petty Replied
Employee Post
Might want to move this to a reply that way I can be better tracked and marked as the answer.
Matt Petty
Software Developer
SmarterTools Inc.
(877) 357-6278
www.smartertools.com
1
Martin Eising Replied
Marked As Answer
P.s. problem is fixed!! I changed the outgoing IP address for SmarterMail to match the IP used with the PTR/SPF records and now everyone can send to Hotmail addresses!!
0
Martin Eising Replied
Done :)

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