My hosting provider (DreamHost, which is generally great) has a webmail interface that can only graciously be called “classic”. They use SquirrelMail, whose user interface was pretty cool in the early 90s but hasn’t evolved since then.

One path to better webmail is Google Apps for Your Domain‘s Gmail, which is the very model of a modern major webmail app. Google Apps is a great service, mostly. Google Apps lets you use Gmail with your own domain, which is theoretically very sweet.

However, for a couple months I’ve been wrestling with a serious email delivery problem since I switched to Google Apps. After hour-upon-frustrating-hour of research and testing, here’s what I’ve learned:

Gmail (including Gmail for Google Apps) blocks your POP email client from receiving posts you make to mailing lists. It apparently blocks any email it thinks you’ve sent to yourself, even if it didn’t come directly from you.

I emailed the support address for Google Apps on January 8, but haven’t heard back. After two weeks, it’s unlikely that I ever will. I tried to ping Keith Coleman, Google’s Gmail product manager, but he’s done a great job of keeping his email address out of his employer’s index. (My hope is that everyone suffering from the same problem will at least find this post and take a little comfort that It’s Not Just Them.)

Let’s categorize this email block as a Google Is Smarter Than You problem, or GISTY. GISTY is the magical unicorn that lives in (feeds on?) the hearts and minds of all Google employees. The really annoying thing about magical unicorns like GISTY is that she knows — knows! — what you would want if you just knew better.

GISTY’s magical thinking is, Hey, since you’ve already seen this email, I’ll just block your email client from getting it. And I’m not going to file it in spam where you could whitelist it, or give you any other way to get it. That’s okay, right? But she doesn’t actually tell you this. And then she stabs you in the ass with her alicorn, making you wonder what the hell that was all about.

Stupid unicorns.

This GISTY problem makes it difficult to use mailing lists, since it means no local archiving, no local search, and no way to confirm whether and when your email was posted to a list, at least not without performing serious email acrobatics.

“Ahhh!”, you say. “Just create another nickname for the user in Google Apps, and then subscribe to the email list with both nicknames, and then post email with one nickname and receive it with the other!” Tried it, doesn’t work…again, GISTY knows better.

I’m afraid that we’ll see more and more of GISTY as Google calcifies, which it gradually seems to be doing.

It’d be nice if this post got the attention of someone at Google, because I know from trolling forums that lots of people are having problems, and that nobody from Google is even acknowledging the issue. In the meantime, I’ll keep trying to find a product manager that cares, and I’ll report back if anything changes.