When it comes to email, Google apps has been a Godsend. It enables small companies to run efficient cloud based email systems that are protected and secure. This service is provided by Google for free for up to 10 users, allowing small companies to avoid the high cost of an exchange server entirely. Unfortunately, free is not always free, since a service like this does not come with any technical support. That is where we come in. We recently had a client with an issue with their Google apps account. The account worked fine, but when someone with an MSN, Live, or Hotmail email address would try to contact them, they would get an undeliverable error, its available after the break.

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From: postmaster@mail.hotmail.com [mailto:postmaster@mail.hotmail.com]
Sent: Tuesday, November 29, 2011 9:51 AM
To: xxxxxxxxx@msn.com
Subject: Delivery Status Notification (Failure)

This is an automatically generated Delivery Status Notification.

Delivery to the following recipients failed.

xxxxxxxx@xxxxxxxx.org 

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Obviously, this was not acceptable. It had been working fine, until we moved to a dedicated host, at which point it began to give us this issue with the MSN-Hotmail-Live emails. In the end the fix was actually very simple. We ended up doing 2 things. First, we removed all the existing MX records from the host, which left us with a clean start. Then we put in new MX records. I think part of the key lies in the fact that originally I had capitalized the MX records, and Linux based servers are case sensitive, whereas Windows servers are not. I believe this could be part of the reason. Secondly, we had a lot more MX records in the system than on our other Google apps accounts so we streamlined to what you see below:

MX (0)             aspmx.l.google.com.
MX (5)              alt1.aspmx.l.google.com.
MX (5)              alt2.aspmx.l.google.com.
MX (10)            aspmx2.googlemail.com.
MX (10)            aspmx3.googlemail.com.
TXT                    v=spf1 include:_spf.google.com ~all

The combination of lowercase MX records and the streamlined records (we had 7 plus the SPF record) fixed the issue for us, and we can now send and receive emails from all the providers.