Date Comparison Incorrect Sometimes

I have three tables which contain dates, I have combined all of the unique dates into one date table. I am interested in creating a True/False condition where I can filter by the maximum date of one of our three tables. I calculate this max date as a measure where I just:

Measure = CALCULATE(MAX('Table 1'[Date]),'Table 1'[Fiscal Year] <= 2022)

So, now I create a column which checks if each row of our dates is less than our maximum date.

Check FY22 = if([Date] <= [Measure], True(), False())

This seems to create a bug where only those which dates are originally found only in Table 1 are filtered as expected. All other dates come in as False.

The measure used for filtering is returning this:

I've tried adding .Date to our date column and I'm getting the same results.

If I change our measure to just some defined static date, it works as expected which makes me think this is a bug of some sort?:

Measure = Date(2021, 9, 30)