On 26 Jun 2013 22:30, "Luke Taylor" <luke@returnvoid.info> wrote:
> Thanks to everyone for the fantastic advice, much appreciated.
> Nothing back from Microsoft yet, I won't be holding my breath.

Just to set your expectations, we had a recent case where order confirmation emails were being dropped silently by hotmail and their response was essentially: we can't tell you why it was dropped.

We sent the email with the same contents and it arrived.

The best advice I can offer is to repeat what Andy said about asking customers to put your sending email address in their hotmail address books.
> If the situation doesn't improve soon then I'll probably try Mandrill (thanks for the tip Richard), I don't see myself building up a decent rep with such a low mail volume any time soon.

Our emails are delivered from Sendgrid from an IP address we've used to deliver millions of solicited emails over the past few years. We still have problems delivering to hotmail.

I wouldn't bother moving email sending. AFAICT dealing with hotmail and their ilk is just a regrettable cost of doing business.