If I have roots on both ends of a cutting would it be wise to cut it in half and plant both halves in cups?

I think it would depend on the size of the cutting.  If it is small then no, if it is large - 10" or more then I just might!

I am with Chris, the more roots the best it is for new growth, and the cutting will find its way to send out the bud. You can burry all the roots, unless of course you have a 15" cutting, in that case, I would cut in half, with the cut just below the node.  so the upper portion will have a good chance to also grow.

A little clarification of this question is needed. You are saying you have roots on both ends of your cutting and your going to plant in cups. If you cut the cutting in half and stick both vertically in cups roots down. One will be upside down. A picture would help along with dimensions. 

I received 4 Black Madeira cuttings this year. All rooted great. One on both ends. I cut it in half and now have 5 plants. The ones that were halfs are slighty behind the others but doing great. I now wish the other three had also rooted on both ends. By the way from this experience I fail to see what some call a difficult variety to root. Cuttings came from longtime very knowledgeable member.

Jake

Plant it horizontal about 1 inch deep

This has happened to me many times, sometimes just under a shoot, roots will appear in the air in the humidity cup!  I just leave them alone.  Don't need more trees per variety.  One is enough for me, but if I had the space, I like the horizontal suggestion!  I've done it outside in spring, and they do well under those conditions!

Suzi

Mike, that's exactly what I was considering doing. Cutting an inch off the top and planting in horizontally. Should I leave a little sticking out or completely submerge it? The cuttings about ten inches long, I'd post pic but I don't have a camera.

I plant the whole thing horizontal and cover it with about 1 inch of perlite/promix and have as many roots facing downward
as possible