Jason,
I appreciate you jumping in with an answer, however that is not true (at least not with the experience I have).
I travel all the time, and often cannot get a connection to the internet. I have learned to log in and make sure I am validated before a trip, because I have been stung in the past.
It appears that a "phone home" MUST BE DONE within a 30 day window. Anthing beyond that length of time will results in an error that tells me I need to connect to the internet in order to validate! That is why I am so concerned. If Web Assist went out of business tomorrow none of us will have extensions that load within a month!
If I am mistaken, or if this is simply a setting, please let me know. I am only going from my own experience!