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.

You're assuming it works. Where I work we have an intranet-based web app that pushes the new password to all the various corporate systems. We're forced to choose a new password every 90 days. I'd say 1 time out of 3 something doesn't work, and I have to open a support ticket. While I'm waiting for support, I'm not getting emails, or can't log in to some systems, etc. Multiply that by hundreds of users at my company.

Twice, support resolved the issue by resetting my password and telling me the new one... which is my last name plus 4 digits. Then I can live with a very insecure password for 90 days, or try the reset app roulette again.