Have you tried a scarf (a la "I Love Lucy")?

My hair isn't as short as yours, but since my cut I've had to adjust my sleep method. I use mix of clips and short pineapples, all high enough on my head so that it doesn't hurt. I'm not sure your hair is long enough to do it though.
Originally Posted by curlyjenn10
My scalp is a deva. The reason I don't want to have to deal with clips and such is that I always wake up with a bad headache. Not a fun way to start the day. I haven't tried a scarf because I don't have a suitable one. I'm not a scarf girl haha. All of my scarves are the practical kind (big, thick, wool, and warm). I worry that I wouldn't be able to keep it on during the night too.

You should check out xcptnl thread about the night of many experiments. She said sleeping pre-scrunching was promising. She also has shorter hair.

The Night of many Experiments
Originally Posted by whatsercurl
Thanks for the link I haven't been on as much lately due to midterms and I'd missed that thread entirely. I'll have to take a detailed look
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Fine/thin 2c/3a, Low-Medium Porosity, Dry!