Glad you found this thread for your question. I got rabbitholed in the process

The main point is the cutting needs areoles (where the spines are) to generate pups. If you position your cactus with one side persistently shade, it may develop aerial roots like my TBM(short) has. I'm yet to take a cutting, but it seems highly likely that some pre-existing roots would help hasten the establishment of your cuttings once they meet the soil. Either way, it may involve a year's wait, but at least aerial roots would provide an easy visual clue - better than persistently digging up an already-planted specimen.

I also wonder if potato juice or similar may help to encourage root formation - some of the more competent gardeners out there must have a few tips in that direction.