tt position in the aerobars?
or road bike on the hoods?

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Kat Hunter reports on the San Dimas Stage Race from inside the GC winning team
Aeroweenie.com -Compendium of Aero Data and Knowledge
Freelance sports & outdoors writer Kathryn Hunter

road bike on the hoods

Same problem. I switched to wider bars and it got a little better. I just deal with it. Left side is worse for whatever reason. FWIW, I've also been diagnosed with very mild carpal tunnel syndrome. Not sure if they are related. And only on the road bike. TT is fine.

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I wanna go fast!

nevermind.

Lots of potential causes, could include but not limited to the following:

• Bars too low/need adjusting
  
• Lack of flexibility
• Poor or improper bike fit
• Loading too much weight in the shoulders
• Not engaging your core to support body weight
• Switch bar tape to something more comfortable

I occasionally have this problem, for me it is loading too much in the shoulders and not engaging my core.

my experience in the FWIW department is that it's the pressure on a nerve in the hand that's causing the sleep sensation. I switched to gloves with the thickest pads I could find and the problem was greatly reduced.

Or just ride your tt bike all the time. ;)

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The difference between stupidity and genius is that genius has its limits. -- A fake Albert Einstein "quote"

Classic symptom of too much weight on the hands while ridding.

Under a moderate pedaling effort you should be able to take your hands off the handle bars and your body remain in the same position with very little core strength effort. Falling forward (down) is usually an indication that the saddle is in the wrong position relative to the BB, usually to compensate for the wrong size bike or stem. Your hands coming back towards your body is an indication the bike is too big (or the stem is too long)

If you have trainer check what happens when you lift your hands, then adjust the saddle forward slightly and check again. If it is better, move a little more, if it is worse go back (unlikely). You can also do it on the road.

Once you have the saddle in the correct position you may need to change stem length (or maybe not). If you get your body balanced and your stem shortened but your hands still come back naturally you have bike size problem

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"...the street finds its own uses for things"

Do you wear gloves when you ride your road bike? If so, what kind? Is your bar tape padded? What's the quality of the roads you typically ride on?

Road vibrations can lead to numbness/tingling/hands falling asleep. What material is your fork, stem and handlebars? Not suggesting that you upgrade everything to carbon fiber, but carbon fiber forks cut out a lot of road vibration.