I just did a quick test, and I can also confirm this. Since obviously nothing has changed on the Oak end, Particle must have changed something on their end - perhaps disabling the fastupdate routine or changing something in the protocol, hence the Oak has had to revert to the slower programming mode. The Arduino IDE is only saying that it has timed out as it expects the Oak to be programmed within 90-120 seconds (can't remember which), so bugs out once that time has elapsed. Someone can probably enable to debug mode on the Oak to see if the handshake indicates what is going on, it won't be me as I dont have time for that atm.
However, yes, it is taking almost exactly five minutes for me to do uploads too :-/