If I don't restart my laptop after changing my password, I'm saving up for a whole load of shit. The proxy logins may, or may not, continue to work, but it's highly likely that at some point in the next few hours, Outlook is going to trigger 3 failed password checks and lock me out of my mailbox.

And that's assuming it expires when I'm in the office, whereas what seems to happen roughly half the time is it expires when I'm connected via the VPN.