Text Ends Compressing on Cylinder. How Would You?

You can also add a curve, shrinkwrap that to the surface and use a curve modifier on the text to get it following the curve. Remember to have plenty of subdivisions in the curve.
This allows you to bend the text the other way - like a rainbow. You may want to add some curve that way to make the text align better with the surface below it.
And a curve allows you to tilt the text…

Curve Tilt

Select one point or many to tilt.

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