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Here's a vote against the Shure Olives. I haven't developed a taste for their effect on sound sig on my Image S4s, and as noted above they can actually stick on the phone and become VERY difficult to remove (almost to the point of breaking the stalk).

As far as the Klipsch Gels, I too have had fit issues with my ears and the S4s (apparently I lost the originals shipped in the box). I had been using the Shure large grey silicon tips which fit great, but the boomy S4 bass is made super-bloated by those. Just ordered/received the 'Medium/Large' biflanges (that was listed on the packaging, when I ordered them I THOUGHT they actually called them 'Large' on the website). I have notoriously large ear canals and knew there'd be a problem the minute I looked at their size. I have found that one way to get a decent seal without that 'brainScratch' to which you refer is NOT lift my ear during insertion (which has become base habit since using IEMs), and sort of push back of the phones 'headward'. Seems to wedge them at a slightly different angle that creates seal and fulls back the bass. Otherwise the insertion has that 'empty' feeling and bass (while still there) is wierdly hollow. I'm just straight-up more used to a 'full' feeling of inserted IEMs given by Shure large greys, Ety yellow foamies, etc.

I'll be receiving Image X10s first of next week, and will be careful to not lose tip fit kit. It'll be my first stab at using Klipsch large single flange gels, which I'll install on both the X10s and S4s and see what happens. Can report back if you'd like.

 

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Got the X10s today!! Initial impression with the large single-flange gel tips...Beautiful. A little persnickity in achieving a working seal because the little beasties are so dang small. You NEED to get a perfect seal to get these to fly -- you can unfortunately arrive at a pseudo-seal with them and start to think,"huh, these sound funny, what's the big deal??"

I ended up wetting (very slightly) the tips with a dab of tap water, or my ear canals themselves. Careful, very little is best, I avoided getting any on the copper phones. Same deal as the S4s though.. you have to push in at the optimal angle -- in my case, shoving cable-ends inward toward the lobes while inserting. I'm experienced enough to know when seal-nirvana has been obtained, and was rewarded with a truly sublime experience. These aren't as middled up as my SE530s, and initially that leaves you feeling oddly about the tonal character of the sound. Just need a minute or two for psych-burn-in though and the X10s prove they can play all day while they provide rich enjoyment and never get tiring. I experienced a similar, "what gives", reaction upon re-inserting the SE530s after listening to the X10s - with MP3Gained/Bass Boost iPod nano 3G files for the Shures sounding smooshy/middly in contrast to the easier-listening Klipsch IEMs. Put my S4s up for sale almost immediately - nothing wrong with them, just not needed any more.