[R_burke]

Looking for some kind of IEM canal headphones that are small/comfortable enough to fall asleep while wearing them

Prefer not to spend more than $200 for a pair

[TheChairGuy]

I think you'd have to get custom fitted ones to even approach falling gently asleep with them (I'm a side sleeper...if you can sleep face up, than a bunch of models might suffice)

Westone does custom fitted units - I find the standard UM2 to be comfortable enough.  I think they are closer to $300 tho, now.

The UM1's is their single driver model that is comfortable below $200

John

[funkmonkey]

Check out JAYS qJAYS.  last I checked they had a MSRP around $170.  They sound fantastic, and are extremely small, sitting almost entirely inside your ear canal.  With the cords wrapped around my ears and cinched up tight behind my neck I can fall asleep very easy with them.  Though I prefer to use my Yuin PK2 ear buds, simply because they will pop out of my ears sometime after I have fallen asleep and have rolled over once or twice.  The qJAYS tend to stay put, especially when using foam tips (like Comply) rather than the silicone ones.

[Tyson]

Sensaphonics makes the most comfortable IEM because it's a soft, silicon like material.  I have a pair and the sound is perfect for portable devices - warm and musical.