There’s Sadly Not Many Instances Throughout The Canons Of Tails Wagging His Tails, However, Most Of

There’s sadly not many instances throughout the canons of Tails wagging his tails, however, most of the time we see it, he wags them in a circle, accidentally causing him to fly.

In the Sonic Boom canon, this seems to be a behavior that Sonic is used to.

In Sonic Origins, the cutscene implies this behavior (wagging his tails so fast he accidentally flies) is the very reason Tails first learned he could fly.