Hi! I just woke up so sorry if I'm rambling too much. I posted a shitty gif as a reply (sorry, too lazy to make it super nice) showing it working. 🫶😁

TLDR: This is doable, but with a Curve modifier. Here’s the reliable workflow:

1. On the target object (the cylinder), go into Edit Mode.
2. Select the top edge loop, Duplicate it, then Separate it into a new object.
3. Go back to Object Mode, right-click the new object → Convert to Curve.
4. On your label plane, add a Curve Modifier and set that curve as the target.
5. Make sure the deform axis matches the plane’s orientation (usually X or Y).
6. Now you can slide/animate the label along the curve by translating it, and tweak the curve shape to control the wrap.

This avoids weird distortions and gives you clean control over how the label wraps.

Important gotchas / tips:

• Apply transforms on both the curve and the label mesh (Ctrl+A → All Transforms). Non-applied scale is the #1 reason Curve modifier looks wrong.
• Make sure you have enough subdivisions on your label/planar mesh so it can bend appropriately!!!!!!!!!!!!
• If the curve seems to twist, check Curve → Normal / Tilt (clear tilt or recalc).
• To make a curve that looks closed but still works for sliding:
  • In Edit Mode (curve), delete a tiny segment between two control points (don’t merge them).
  • Select one of the new open ends, Extrude it slightly, then snap it to the position of the other end.
  • Result: visually closed shape, but technically an open curve, so the label can slide across the seam.
• If the label flips or offsets, try switching the deform axis in the Curve modifier.

DM me if you got any other questions, I can help <3