Room drop timing?

I was trying to book a second preferred room for my parents at Caribbean Beach for our trip in Mid Dec. with the free dining plan, but sadly it appeared to be sold out for the last two weeks. When I logged on this evening, it looked like it was available but when I went to enter my credit card info it crashed and when my browser reloaded the rooms were gone. Does WDW release additional rooms at regular intervals or do I just need to keep checking? Any tips on what times might be good to check for newly released rooms? Is this a lost cause and should I just book something else?