If there's already a 5th in the chord/scale. C major 7th has a G, so it would be an F# which is a #11.
Same reason why a #9 chord isn't just called a minor 3rd. You already have a major third in a C#9 chord, so the added note is a D# on top, not an Eb (which would be b10).
Although there are some chord/scales or melody lines where you have no choice but to have duplicate letter names, e.g. a chromatic run, or the 8 note diminished scale, or the altered scale (which has both b9 and #9).
Another guideline, for more chromatic type of lines, is # ascending and b descending.
This is related to why you'll occasionally see Cb or Fb instead of B or E, or E# and B# instead of F and C.
e.g if you wanted a G# Major or Dominant chord (leading to C# minor, for example), It would be spelled G# B# D#. It wouldn't be G# C D#, because C is four letters from G.... it would be a diminished 4th! Of course, you could call the chord Ab, but that wouldn't be a 5th above C#...
It might seem complicated but it actually simplifies things. For example it's easier to memorize chords if you know that some kind of F is always the 3rd of some kind of D, etc.
#4I know the two tones are enharmonic, but I'm just trying to better understand extended harmony.
Is it a major/minor thing? Like if I'm playing over Cmaj7 and hit an F#/Gb is that a #11 or a b5?
Is there a rule for this?
Thanks in advance.
Here's something that I wrote a while back that explains that and more: https://www.thegearpage.net/board/i...how-chord-naming-works.1122189/#post-13635907