We just encountered an interesting problem with the edu 2.0 email system that I thought I'd share.
When we first launched the site, we decided to use the Gmail SMTP server for sending emails. Everything worked fine until we hit the 500 user mark, at which point we noticed that some emails were not being sent successfully. The reason: Gmail imposes a 500-emails per day limit to prevent spamming.
We decided that the best alternative strategy was to use the sendmail program which comes pre-installed on LINUX servers. We switched over to sendmail (a single line modification in Rails) and everything seemed to be fine. We tested the system by sending a few emails to our test accounts; no problems.
A day later, I noticed that the number of people joining our site seemed to decrease, but I attributed this to a natural fluctuation in early users. However, after a while I noticed that some people just weren't getting emails that the system sent to them. After some debugging, we finally got a big clue; all the people who had recently joined our site had a Gmail account!
It turns out that we didn't have the more modern "postfix" sendmail utility and the one that was installed didn't process DNS correctly. The result was that Gmail accepted our emails and other systems rejected them. Sure enough, I found that around 100 people who had recently tried to join had never received their activation codes. Oops!
The good news is that we found the bug and switched over to the new system. We'll do some more testing with accounts that aren't on Gmail (Yahoo, AOL, HotMail at the minimum) and send apology emails to the people who recently tried to join. The other bit of good news is that our user base has actually been expanding, although it wasn't showing up due to the email issue.
It's good to get these kinds of issues straighted out early. I wonder how many more of them are lurking?
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