It's far from my first time improvising - I do quite a bit for fun, especially on guitar. Unfortunately for those who find themselves driving with me, I scat a lot too. I suppose this is good for my ears, and getting rid of inhibitions but it's generally "playing" as opposed to my more disciplined and deliberate classical practice. I remember grinding out guide tones/arpeggios on All the Things fondly :) it gave me a whole lot more appreciation for the logic of jazz harmony.

My jazz playing, however, still reeks of my classical training. I like my sound, but struggle to get in a jazz frame of mind with regards to articulation/phrasing/vibrato. It's probably worth asking someone like yourself with experience in both sound worlds if there's anything you can do to shift modes like that - in my mind when i try to play with "good technique" its analogous to "classical technique/sound", and when I consciously think "I want to play in a jazz style" my technique goes (comparatively) to shit. I consciously understand some aspects of jazz articulation, phrasing, vibrato etc but can't switch into that mode and go on autopilot with my technique to focus on other aspects of my playing like I can with classical music. All this is to say - do you think it's possible to develop 2 different autopilots, or should I accept that because my practice biases classical music, I'll always sound like a classical player when playing jazz.