We can't really tell what is going on without logs. More information on that below.
The remote version of Astrometry.NET was down for a day or so a few days ago... not sure if this intersected with your problems... I highly recommend a local install (ANSVR). @Andy has made it easier than it has any right to be...
Anyhow, your description, while real, only leads me to ask 20 more questions... the answers to which are all in your log files (you will need to reproduce the issue or dig out the log file that shows the issues).