Sounds almost like you blocked the site at some point for some reason. I know the software "phones home" to check for updates, and many users don't like that behavior in their software and take steps to prevent it from occurring using a firewall or hosts file. Not saying that it was is going on with Outpost on your machine, but I haven't seen or heard of any reason that the site would be blocked.
I used to go crazy blocking "phoning home" on every single application that I used. Sometimes I went as far as adding an entry into the hosts file to prevent access. Months later I would become convinced that a major developer had gone under or been hacked when I couldn't get to their website. Or, I would try to manually update the program using a built in function and wonder why it couldn't connect. Since then, I have relaxed quite a bit.