I can make a 2nd MIDI track in ableton and play the notes from the first MIDI track that I recorded while recording me twiddling the filter Frequency knob on the OB-6 and even though i don't see anything change on that 2nd MIDI track (the line stays dotted and doesn't change or move) it does appear to record the MIDI data back when i hit play on it and both MIDI tracks play to the OB-6, the notes i played, and the filter knob twiddling i played.
However if i use a softsynth, and hit A" even on the original one MIDI track (which is how i always did it before) it DOES show whichever parameter i last clicked on as what is live for MIDI automation and allows me to draw in MIDI automation for that parameter like I wanted it to (however after programming this automation if i click a different parameter, but then go back to the original parameter i automated, it no longer shows the automation i programmed but just a straight doted line like before programming, but it DOES play back the automation?)
I do not get it for the life of me. Inserting all the screenshots I figured would be pertinent:
First 2 are the Ableton MIDI preferences settings:


Then the Ableton arrangement view with the notes recorded from the OB-6 and the 2nd MIDI track not letting me automate any knob/CC data, yet recording it and playing it back while not showing any automation data that's being played back:

The Session view/mixer view of those tracks and their I/O:

Using a softsynth where the automation IS working mostly correctly and if i click on a parameter that parameter shows up as what is automatable in ableton and lets me draw in automation:

Any idea how I can do this? As I recall this never used to be an issue, automation used to just work nice and easy and simply (and without having to his the "A" key)?
Thanks!