> That's ridiculous that Dropbox has never thought that someone might need an upgrade to their account before their next "open-enrollment" style system. Just of

> That's ridiculous that Dropbox has never thought that someone might need an upgrade to their account before their next "open-enrollment" style system. Just off the cuff thinking would suggest applying whatever money has already been paid for the existing account, prorating it for what has been already used, and then subtract that from the fee to be collected for the upgrade. Then flip the switch in the database. Sure, it might be out-of-bounds for normal workflow. Seriously, I implemented this in a few minutes on my crappy little side project. If you want to downgrade, it's "contact support" so we discuss any issues and sort out a refund or credit as appropriate - but if you want to upgrade and pay more, that should be the fattest, shiniest, most automatic button available and give a fair, prorated deal with no hassle, those are customers who have experience with your service, like it and want more of it. The kind you want to keep the most. It seems like the most basic business sense.