Case Sensitive Stylistic Sets?

I’ve been trying to find the answer to this but haven’t so far. I apologize in advance for my ignorance.

I’m looking for a way to make contextually case sensitive characters within the same stylistic set? I’m including a titling cap (AKA drop cap) feature for my font and would like to have all of them be in the “.ss01” stylistic set. Instances like the “C”, however, present a problem because one version works well with lower case characters but not for upper case letters. This is because the original “C” works best overhanging the x-height of the lower case characters but needs to be taller to overhang the cap height of capital letters (and the lower case letters that extend to the cap height). So, I am hoping to create contextually case sensitive versions of these titling caps to solve most instances where this would be an issue (namely, the capital letters), so “C.ss01” would automatically switch to “C.ss01.case” if it precedes a capital letter.

Is this possible and/or is this the best way to approach this issue? Any guidance on this will be appreciated!

I’m not really sure what you mean. Can you post some screenshots?

The case feature is not for letters, but for punctuation, symbols, and figures:

You could add a contextual alternates (calt) feature that switches the letter:

sub C.ss01' @Uppercase by C.ss01.UC;

I think this is what I needed. Thanks, @mekkablue!