I'd check the nameservers for that domain are correctly setup for that domain and fully propagated, if US DNS checks fail, LE usually will fail. Propagation for NS records can take 24-48 hours.
LE Timeout will happen after X number of tries that fail, you'll also have to wait a little time for your server IP to release to perform updated checks again. (LE safely measure)
You'll probably find the logs under appcd on the server the website is on. I've had that error before and it was a misaligned domain NS records.