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I’ve been through all of the tips over the past three weeks and, surprisingly, have now settled on the large tips even though they don’t go into my ear canal. Turns out, these AirPods work best sitting just against the opening of my ear. No more working themselves out when I chew, talk, or run. Completely different fit than any prior in-ear buds I’ve used.
 
I've had mine since launch day. On several occasions I've forgotten that they're still in (with Audio Transparency active) so yeah - I'd say they're definitely comfortable.
 
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