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If you look in the "number of measures" field, you can see it's just the number 1...so when it is SUMed (as its aggregate) it is the number of records...
You're current test is a row level one (in that there is no aggregate)...so Tableau is doing is 1>=5000 on every row, and returning that they are not!
if you wrap it in a SUM it will do what you want, so...
IF SUM([Number of Records]) >= 5000
Although if each bar (in your example) is >5000 will depend on the VizLoD. You might find this useful, on the different types of calculation in Tableau (and how to think of them)
Hope that helps, but let me know if that doesn't make sense.
Thank You Simon!!