More Email Redirection

I've written before about some of my email behaviors. I thought I would share some more with how I manage personal email and how I got bitten by it this month.

I have used a personal domain name for quite a few years now. These are sometimes called "private label" or "vanity" domains. There are a number of reasons why I do this. It used to be because I ran my own mail server, but any more it's probably just a matter of branding and the ability to choose any email address I want.

When Gmail became available (my oldest message is dated October 2004), I signed up for an account to see what it was all about. I liked it so much that I wanted it to become my primary email application. I quickly moved my personal email over to my new Gmail account and configured my personal address to forward to my Gmail address. This allowed me to respond to mail regardless of which address it was delivered to. The ability to set a custom From: address meant that I could still have messages that I sent from my Gmail account be marked with my personal domain address which provided some consistency for those who pay attention to where messages come from.

I operated in this fashion for a few years. I ultimately got bored with configuring my own SMTP server and started using a webhost to do this for me. I went through a couple of services before I found one that I liked for the amount I was willing to pay. Recently, Google started up another service called Google Apps. This is a free service that will host your personal mail and web space among a few other things. They don't have as many features as some other places, but the price is right.

I switched my personal domain over to be hosted by Google Apps about a year ago now. The experience has been pretty good, although not perfect. Now that my personal domain email actually lived on Google's servers, the dilemma that I faced was whether or not to maintain my @gmail.com address and continue to use the Gmail application.

As for my main inbox, I prefer the Gmail application over the Google Apps mail application for my personal domain. The main reason is that the public Gmail application seems to get new features long before they release them to Google Apps. A secondary reason is because many of my friends already have my Google Talk login (@gmail.com) and I don't want to go through the hassle of getting them all to change. :)

Once that decision was made, I configured my personal address, once again, to simply forward all mail to my @gmail.com address. This works well except for the way that Google has chosen to implement a forwarding mail alias. I say alias, because on other webhosts (and, indeed, in Sendmail itself) it is quite easy to create an alias that merely forwards everything to a real mailbox. Google's Apps offering does not offer that functionality. You have to create a real mailbox for every address that you want. Then, if you want it to forward mail, you must login to the mailbox and configure it to forward mail to another address. This means maintaining another username/password as well. I don't really like this approach, but, let's face it, it isn't painful enough to make me switch to another webhost.

Now that you have a background (hopefully, you aren't just plain confused) of how my personal email ultimately flows to my inbox, I will share with you how this approach has let me down over the past few weeks. It all comes down to spam; where should it be filtered?

Google does a wonderful job fighting spam. I rarely see spam in my inbox anymore. It is just something that hasn't been an issue for quite a long time. One of the very common methods that mail providers use to ensure that they don't incorrectly mark a message as spam is to check to see if it is from a person in your address book or contacts list. They assume (correctly) that if a person you know is sending you a message, it probably isn't spam. Well, for me, that breaks down.

Recall a couple paragraphs ago, that I have an actual mailbox for my personal domain address. All this mailbox does is forward to my @gmail.com address. However, since it is a mailbox and not just a forwarding alias, Gmail checks all messages coming to that address for spam. This approach is fine, I suppose. Although, it would be perfectly acceptable if they just forwarded the spam messages and let my @gmail.com address handle it. Since I never login directly to that address, I obviously don't manage my contacts there. Therein lies the problem. I realized yesterday that a few of my messages from dear friends of mine have been getting flagged as spam because I don't have any contacts listed in that mailbox. These messages hit the spam folder and never get forwarded to the @gmail.com address that I monitor.

This has been happening only for the last few weeks, which leads me to believe they have done something to get more aggressive lately, or (sinking feeling) I just don't have anything in the spam folder older then the last few weeks and this problem has been happening all along.

My short term fix for this is to export my contacts from my @gmail.com account and import them into my personal domain account. I don't like this approach because it is a high maintenance solution, but it will have to do until I get some time to research this further.


Feel free to comment if you are using an interesting approach to email and let me know what you do and don't like about it.