I've been using my @portal42.net address as my mail e-mail address for a couple of years now, but have always been too lazy to set up Gmail to use One.com's SMTP server for sending the e-mail. (One.com was my webhost since 2006 until I transferred the domain into private administration at Godaddy.com.) Gmail can insert any e-mail addres you want into the From: header of e-mails, as long as you can verify you indeed have access to that address. However, to prevent itself from getting blacklisted by spamfilters, it still inserts a Sender: header with the actual Gmail address to tell the receiving mail server that the e-mail wasn't actually sent by an official mail server for the address in the From: header. Generally this is fine but Microsoft's Outlook and derivatives portray this in a horrible manner in their layout. Instead of simply crediting the address in the From: header as the sender (like any other sane mail application ever created) it credits the address in the Sender: header and only names the other address as having ordered the mail to be sent. It looks like this:

From: address@gmail.com On Behalf Of Your Name

Yes, it doesn't even cite the e-mail address, just the name that is sent along with it. Now generally this wouldn't be such a huge problem if not for the fact that I wanted to send mail with my portal42.net address to mask my gmail address. My Google username is an old nickname which I've mostly abandoned by now, but I can't create a replacement account with my new nickname because "jelco" is 5 characters and Google enforces a 6-characters-minimum policy on usernames. Hence my desire to mask the address.

For a long time I didn't set this up properly because I didn't care enough - few people I mail still use any Outlook-ish application anyway. However, with setting up a new mail server I decided I'd give it a go and configure Gmail to send e-mail through the portal42.net server so that it can finally abandon the stupid Sender: header practice.

I've been tinkering with this for a long while and in the end it was set up properly, but Gmail simply refused to work. For those who want to get technical, I'm using exim4 on debian lenny and set up SMTP AUTH with TLS with the minimal required configuration tweaks. My test with the locally installed copy of Outlook 2007 worked fine, but Gmail didn't budge and kept saying my server was being stupid.

After about two hours of experimenting, the solution turned out to be as simple as turning off secure authentication. Not on my server's end, but on Gmail's end. Keeping in mind that Outlook authenticates perfectly fine over TLS and the exim logs didn't even say anything about Gmail trying to initiate a connection (and failing), this seems like a very strange outcome. In the end I've come to the conclusion that Gmail probably doesn't understand TLS and tries SSL instead. I'm not sure why Google did this. It seems like one of the most unprofessional shortcomings I've seen in one of Google's products in a long time (except Google Wave probably, in which the biggest unprofessional shortcoming is the reason someone ever made such a useless and overhyped nonsense product). Setting up exim to use SSL next to TLS seems like it shouldn't be necessary (most tutorials claim you inadvertedly set up SSL when you set up TLS) but I've tested it with Outlook and that confirms that currently my server doesn't answer to SSL. It's probably doable and I'll definitely look into it, but that doesn't disguise the fact that on this end, Google fails miserably with authentication support. There's a good reason everything has TLS support these days, and not only is it best practice to prefer the newer technology over the old one, many services have even abandoned SSL in favour of TLS because of its flaws. I'm not saying that my e-mail password needs as much protection as, say, the credentials to my bank account, but it's just stupid to deny one the choice.

In other news, I'm currently home alone here on the University of Twente campus. I'm going back to my parents' for Christmas and will stay until December 30th, but I'm pretty sure if I stay too long my parents and I will just get on each other's nerves again (like it was when I still lived there - moving out of the house is one of the main reasons I wanted to go to Uni so bad). Hence I'm staying here until December 25th, and in that time I've seen the entire campus turn quiet. Currently the only two left in this house of 9 are me and the house cat. What I've found interesting about these days alone is that occasionally it does feel somewhat lonely. This is interesting because until a couple of years ago I was a loner who wouldn't mind being alone up in his room for days. I knew high school changed a lot about me but it hadn't really dawned on me that it'd be this big a difference that I actually miss the company of some housemates after just a few days. I guess that while these are not the most interesting days I've ever spent here, I'm thankful for the experience.

And just to break away from the melancholical spirit: after some stress testing yesterday done by my friends from the Introversion community, we found out my Team Fortress 2 server suffered from the occasional lag. It seems to be solved just about entirely, so if you have some time to spare you're welcome to try out the server! You can connect to tf2.portal42.net:27015 in Steam and it'll do the rest for you.

Jelco