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Note #4: Gmail update (2007.10.19)

Three days ago, I posted a letter to Gmail that expressed my frustration with our relationship. It was painful to write, and I’d rather not relive the experience, so go read it if you want the background.

When I wrote the letter, I wasn’t really expecting to hear from Gmail. I wasn’t expecting anyone from their team to email me and tell me that they were working on the problem. I didn’t expect a random stranger to email me with a silver bullet that would allow me to vanquish my Gmail demons. I will admit that it would have been cool had either of these things happened, but I wasn’t holding my breath.

Instead, I expected to get mail from regular readers sympathizing with my plight and/or trying to help out in any way they could. I expected this because my regular readers are all awesome people. This is indeed what happened, and this was more than enough for me. I just needed to make myself heard, and it was nice to know that there were people out there who did in fact hear me, even if they didn’t work for Gmail.

But things didn’t go exactly as I had expected—if they had, I wouldn’t need to post an update. Gord emailed me with a possible solution and a generous offer to help implement it. As I was writing up my reply to him, I decided to go to my contact form and send an email to myself so I could look at the headers and maybe narrow down what was happening. I used a dummy name and a dummy email address to make sure it went into my spam folder. Except it didn’t—it went into my inbox. I was perplexed, and then figured I had maybe used that dummy address in a previous test and somehow Gmail recognized it. So I went back and tried again, twice, with completely random email addresses that I was sure I hadn’t used before, but I got the same result.

I mentioned this to Gord and asked if he would try sending me a comment using an email address that he hadn’t used to email me before. I realize that it doesn’t really matter who sends the message, since everything originates from the same server, but I just couldn’t believe my eyes. Gord sent me four messages using four different addresses, and they all got through to my inbox.

The chances of someone at Gmail reading my letter and then immediately fixing the problem without any specific input from me are slim to none, but the timing is uncanny. Right before I posted the letter I checked the form one last time to make sure I wouldn’t have egg on my face, and sure enough the message ended up on the spam pile. So the problem still existed when the entry was posted. Now, though, the problem is solved (update, 2007.10.23 - I just got my first “new contact” email since posting the original letter, and it went straight into my inbox, so the problem is definitely solved).

Although I didn’t mention it in my letter, I have a fairly good idea as to the cause of the problem. It was never about the email addresses, because messages were being tossed out indiscriminately. What did these messages all have in common? They came from my server. So that must have been it. I could never figure out why this mattered, but my best guess is that the server had somehow gotten on a Gmail blacklist. I have no idea if this is really the case, or if Gmail even has blacklists, but it’s the most reasonable explanation I can think of.

Of course, knowing (or at least having a good idea) what the problem is doesn’t help when you can’t communicate with the people you need to talk to. As I mentioned in the letter, I tried to contact Gmail a number of times but never got a reply, not even an automated response. Don’t get me wrong—I’m psyched that the problem is fixed, but an underlying problem still exists: the difficulty in getting in touch with Gmail to report problems. If your problem doesn’t fit into their predetermined hierarchy of problems, you’re pretty much out of luck.

So I still love Gmail, and I’m very happy that things seem to be working properly now, but that nagging doubt is still eating away at the corner of my mind. What if the server goes back on a blacklist? Do I have any recourse but to sit around and wait for the problem to be fixed? Whatever the case, as I told Gord, I’m not going to be looking this gift horse in the mouth. The best I can do now is hope that I don’t have to go through this again.

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