Hi Jamie,
That sounds to me like your job has hung for some reason. It should say that it is running simulated annealing, and should have lines in the log such as "...trying gamma 0.500000, weight 30.000000" to indicate that gamma/weight pair has been started. The coordinate minimization step is usually quite fast, even for large structures.
What version of Phenix are you using? It would be worth trying to run:
libtbx.python /path_to_phenix/phenix_regression/den_restraints/tst.py to see if DEN works correctly on your system. That should complete in under a minute.
Jeff