Ultimate Ears UE-11 Pro Headphones Reviewed (Verdict: Painful!)
Being one of the first to try the Ultimate Ears UE-11 Pro, a $1150 pair of headphones with four drivers inside, might seem like a sweet score. (Especially when you're not paying for the unit and, since they're custom molded to fit in your ears, won't have to return them.)
Not so, says CrunchGear's Mike Kobrin:
A couple of weeks later, I got the UE-11's, pictured above, in a nice custom metal case, complete with my initials on the inside of one of the earphones. I spent the next 45 minutes or so trying to insert the earphones, which are made of hard plastic -- no doubt to protect the $1150 worth of miniaturized electronics inside. By the time I was able to get them in, I was sweating, and they were far from comfortable. Actually, they gave me a headache within a few minutes, despite the incredibly glorious sound.
The AudioFile: My Violated Ears [CrunchGear]

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Check out the ProPhonic 2X-S model from Sensaphonics. They are used as widely in the industry as the Ultimate Ears models, but are made from a soft gel silicone and are much more comfortable. The sound is on par with the UE stuff.
It also seems that the audiologist that did your impressions may have been part of the problem. I've never heard of anyone biting down continuously while the mold was cast. Usually you're encouraged to open and close your mouth during the process to ensure that the variations in your ear canal are accounted for. This may have lead to an improper fit in the end result.
One area where the UE IEMs shine are the detachable cable that makes replacement stupidly simple. Most other brands are permanently affixed and have to be sent back to the manufacturer for replacement.
I second the comment about the impressions. I make ear impressions as well as "instant" type silicon ear plugs (for shooting sports). Impressions should be made with the client flexing their jaw, swallowing, and otherwise moving their ear canals around. Krobin should have also made certain to point out his odd ear canals to the person making the impressions; he states in the article his ear canals are small and one has an "odd bend".
Before making the instant plugs, we always ask them if they had any issues with their ears, or fit of other ear plugs. If so, we talk to them about the trouble and try to figure out a way to make ours work for them. After the plugs are finished, we have the clients put them in (demonstrating the technique) to check the fit. If the plugs didn't feel comfortable, we wouldn't charge them. For something so sensitive to many people, these are important customer service points.
A couple of months ago I bought the HT820 wireless (bluetooth indeed) headset from Motorola, the specs were good and the sound was great but the design was somehow painful to wear, I could not wear them for more than 30 mins.
This reviewer has to be kidding me. I tried the UE 11 at NAMM 2007 before it was announced and honestly unless you go to the UE web site and watch the video on how to insert your monitors, you can't say they're hard to put in. I've been using UE for a long time and they are the best in ear monitors made, highest quality, custom fitted, and once they get broken in a bit, comfortable. Truly.
Not to mension the UE-11 actually has 3 tuned drivers. Two of them are dual driver (one inside another) making for an absolutely incredible sound.
You need to visit: http://www.ultimateears.com and check out the instructional video. It helps a lot. UE is uncompromised audio, the highest grade far superior to the competition (all of which I have used) and I stand by them 100%.
The thing to remember is to have the volume source off when plugging them in and then to listen at a lower volume than usual as they have a huge amount of power. The clarity and low end is unsurpassed as well.
One reason UE moved away from soft molds is they had a tendency to give out and eventually break down where as UE's molds can withstand the riggors of the road much better. A good mold is the key to a good fit. One of the best things about UE is their molds. Also one price for any color, cord length, or custom logo is nice as well. Their customer support and artist relations department has had nothing but respect and personal attention for me as well.