I typically cup when roots are visible (1/4 inch) and the bottom end has started to callus. These cuttings are actually part of a test. They had been in an unheated room (45-65 deg F) for 2 months in Sphagnum Moss, I placed them in the 75-80 deg F. rooting cabinet 9 days ago, They had not grown mold in that entire time.
I usually cup the cuttings once I get callus formation and use "humidity domes" for only 2 additional weeks (at 75 deg F) then introduce the cutting to a south facing widow at room temperature. By that time there is visible root growth in the 16oz clear cups. That usually takes 4-5 weeks.