Welcome to the Orchid Board!
Yes, photos will help.
Your plant is probably not getting enough water. That may be from you not watering enough, or it may be because the root system is poor. Orchid roots need lots of air around them. Suffocation is the commonest cause of root loss.
Catts. in sphagnum moss need to be watered so the moss doesn't stay soggy wet. That will suffocate roots.
The time to repot is when new roots are just forming. Repotting in between can damage old roots and the plant may not be able to take up enough water until the next period of root growth, which might be months. I never cut off old roots when repotting. It's usually not possible to tell what is alive or dead.
If you plant is in a bark mixture, watering every 2 weeks is probably not often enough.
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