Yes, I would. Without space to the sides, pups have a harder time finding/pushing up to the surface.

It looks a little scorched there On the tips. Is it getting too much sun or not enough water?

Repotting would definitely make the plant happier Just don't go more than the next size up. A 4 inch terra cotta pot would be perfect.

How is your plant doing, Nana?

Hi Tiffany, thanks for asking. I will post a couple of pictures . I know she looks rather crowded in that pot. I'm afraid to separate them. Any ideas ?

Just let it dry out, take as much dirt off the roots as you can and then repot it in a 4 inch clay or plastic pot using fresh potting soil mixed half with perlite (unless you have a gritty mix to use already).

Looking good! I agree about letting the old soil fall away, and you'll
be able to tell then what kind of separation is possible (but not
necessary unless you just want to separate.) But would use a MUCH
bigger pot than 4". W/o the confines of a pot, the pups come up several
inches away from the mama. Needs room to grow.