Failing Forward

In a previous post, I talked about how some email clients will mangle the display of your name (“on behalf of” yourself) when you use Gmail as a client for other addresses.  This is because, when using Gmail as a hub for other email accounts, when you send email via SMTP, it’s Gmail sending the mail, not your mailserver du jour.  And so, to avoid the message looking like spam, Gmail tacks on some extra headers.  In certain clients (such as Microsoft Outlook), these headers would get displayed in awkward ways.

A post to the Gmail Blog yesterday, however, informs us that this no longer need be the case.  Gmail now features an option to send mail properly via your email hosts SMTP server.

Wonderful – now my personal address won’t be revealed in emails I send for work or school.  To configure the new feature is a breeze, and there are already tons of material on it, so I’m not going to duplicate that content.  However, it’s not so easy if you want to use Gmail as a funnel for a Live/Outlook account.

Back in May, my school migrated from in-house email hosting, to using the Microsoft Live platform.  That’s fine – less strain on the campus network sounds good to me.  Setting up POP access to an Outlook account was easy when the change happened.  The server is just outlook.com, running on port 995 for SSL.  Great.  So shouldn’t the SMTP setup be as simple?

Hah.  “Should.”  My favorite word.

If you’re thinking “set the SMTP host to smtp.outlook.com, and use SSL port 465,” as per the standard practice – you’d be wrong.  No, in fact they do not expose their SMTP hosts directly.  You actually have to log into your Outlook Web Access account using the ugly address https://pod51000.outlook.com/owa, and then once OWA loads, it will redirect you to a new ugly host (for example, pod51015.outlook.com, or something like that).  That host is your SMTP server.  Once you jump through the flaming hoop… no SSL.  Only TLS, which Gmail doesn’t support.  So port 25 is all you get.

Oh well, at least it works.  Hopefully Microsoft will start using a more friendly SMTP system, and roll SSL into the package (or Google will add TLS to the secure connection options).

Update: It seems that, while this solution does work, it’s not a permanent miracle.  Evidently the exact address can change from time to time, necessitating that you repeat this process in the future.