Dendrobium Spectabile when to repot?

[Syrinth]

Dear Heavens that was a pain.

I'm not used to Dendrobium roots, are they supposed to/can they be brown and flatish? They didn't feel squishy *most of them*

Good thing I did this too, I hadn't noticed that the canes that were facing the window had all turned purple. I guess they were getting a bit too much sun.

Lastly, I couldn't get them back into the pot they were in at first. Put them in a pot about two inches bigger than the previous one. I added some clay pellets to make it drain faster and provide more aeration but I'm seriously considering trying to cram it back into the last pot.

*When I took it out of the last pot it was essentially a big root ball surrounded by sphagnum