Think I want to trade them for a new PortaPro if I don't find a solution soon. Does it just take more getting used to? Maybe an aftermarket tip? Something I'm missing?
Thanks in advance.
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The UE500s are pretty small and comfy IME. Have you tried the Comply Foam tips they come with? Foam tips are generally considered more comfortable than silicone tips. I also wouldn't recommend jamming them too far into your ears, just until you feel comfortable. In ears do take time to get used to if you're coming from ear buds, but they shouldn't be causing pain.
Hm... Try the foam tips, that should fix things up. To get rid of the vacuum seal, you can life the pinna (upper flap) of the ear that is causing you problems and push down on the IEM to break the seal... Then release the IEM, then the pinna. It'll recreate the seal, without a vacuum.
Sounds like the silicon tips are too small for your ears. Try using the larger tips that came with it, or see if you can use aftermarket tips (e.g. by Comply) instead.