COUNTIF(SUM/SUMIF) from top to current row not adding automatically with new rows

This is something I have just learned to deal with for years of using Numbers as far back as I can remember (I used ClarisWorks spreadsheet back in the day, I don't know if it was an option then), but I thought I'd see if there's any alternative.

I am trying to COUNTIF a range from the top row to the row of the formula. Like After the header row, A2 counts A2:A2, A3 counts A2:A3, A4 counts A2:A4. So, I enter A$2:A2 in the top row.

A example version would look like this:

Name Times

John 1

Jill 1

Jack 1

Jane 1

Jane 2

Joe 1

Jeri 1

Judy 1

Joe 2

John 2

Jack 2

Jill 2

Jill 3

When I do

=COUNTIF(A$2:A2, [Name Column])

I get the correct numbers when copied and pasted down the entire column body (no cells inconsistent or blank). However, adding new rows does not automatically fill in the formula, but it does fill just about every other formula I throw at it.

I don't know if I am missing something or if there is a workaround. It's not the end of the world to just manually drag and fill the cells from the row above, but since everything else is automatic, I was wondering if there's another option. The related formulas like SUM, SUMIF, etc. have the same issue with not autofilling cells when new rows are added.

This is both in the desktop and iOS versions (both latest versions as of this point).

Thanks for any advice/responses