I have also done rosemary this way.
When I plant cuttings with new roots, there is a diference with transplanting something that was in soil:
the roots stick to each other instead of spreading (as they did in water).
So I thought about a trick, maybe useless, may be it helps....
I prepare some thin DRY soil that I reserve.
I make a hole that I fill with water, and quickly put the rooted cutting in, so that the roots spread as they did in the bottle.
I add the thin dry soil so that it sticks well among the roots.
More soil around...
It does not matter if it is very wet for a start, the cutting was in water at first.
My soil has drenage, but here I really have to care about watering
enough my rosemary.
And I noticed that transplanting old ones is very delicate.
I tried some basilicum cuttings in water, a woody type, and the result was much better with direct planting.