First look straight down on the edge with magnification, if you see reflection while tilting the blade back and forth, the edge is damaged. Looking from the side will tell you the extent of the damage. If deep, it will need to be refreshed on a hone.

Typically new stroppers damage the edge while stropping, buy stropping with too much pressure, lifting the spine or flipping while the blade is moving forward. Doing any of the above with a pasted strop will increase any damage.

When you have an issue, looking at the edge will always tell you what is going on and what will be needed to repair it.

If the damage to the edge is lite, a pasted strop may revive it, but pressure will only cause more damage. A refresh is probably you best bet. As your stropping skill improves, so too will your edges and the length of time between a visits to the hones.