I tried soooo many TWS for sleeping and while the 1more Comfobuds Z were ok for side sleeping, the battery lasted only 2.5h in the beginning and became less and less rather quickly
Then I realized that for sleeping, I am not too fuzzy about sound quality, since I listen mainly to binaural / meditation / sleep music ... and for that check amazon.fr for musicozy sleep headbands ... I got my first for as low as 10€ ... and I wear it every night now! Battery lasts over 12h, I don't feel anything when laying on the side ... just a thought, I wish I had tried those earlier, would have saved me some TWS money
Till now I didn't want to use a hot headband for sleeping.. and I was afraid that the drivers would be still thick and uncomfortable to sleep on the side on them...
As they are really cheap, I think I will probably give a try..
Actually, I use some IEM for many years now for sleeping and some are really comfortable enough for sleeping with a convincing sound quality ( which I would like to keep for the first hour when I usually read some books in my bed) ...
Based on my experience, I would classify my sleeping IEMs like this as my preferred order as sleeping IEM :
1) Soundmagic E11C (40€) + iFi Go blu, this amazing IEM are so cheap, with the proper tips SQ is very very good and they disappears almost completely in the ears .. We don't feel them at all when sleeping on the side.. they provide more than 11 hours playing time on one charge in LDAC mode (I could never drain completely the battery till now)..
2) Beyerdynamic Xelento (1000€) + FIIO BTR7, only max 7 hours playing time, they are very comfortable for sleeping on the side, they are much more expansive, but with a very nice sound quality. Unfortunately the Xelento is incompatible at low level volume with the iFi Go Blu in "balanced mode" with a permanent little background hiss (no issue in unbalanced mode).
3) Sennheiser IE600/IE900 (600/1600€) + iFi Go blu more than 12 hours playing time, perfect sound quality, very comfortable too for sleeping on the side.. but the MMCX connector is definitely a real bull/garbage connector and I broke almost all my IEMs with MMCX (even IER 1ZR, Vision Ears EXT)=> I will never buy again IEM a mmcx connectors, though only the Xelento could survive till now)...
4) Jabra Elite 7 Pro (130€) rather comfortable to sleep on the side though it depends on the position in the ears which can hurt a bit sometimes in the middle of the night and need to reposition the driver in the ear, a very good/impressive sound quality with more than 10 hours playing time (I would say 11h or more available, as I never drained fully the battery till now, I always had at least 30% left).
5) nearly on par with Elite 7 ..... the Samsung Galaxy Buds2 pro & Galaxy Buds pro (a little bit bigger) ... 150/200€ they are rather comfortable to sleep though it depends on the position in the ears which can hurt a bit sometimes in the middle of the night and need to reposition a driver in the ear, of course a very good sound quality for Samsung smartphone users.. less than 8 hours playing time AAC codec + without ANC (which can be too short for the end of the evening plus a full night)