Debugging with breakpoint - Evaluate and log - Not writing to debug output

This should be reproducible in any solution.

In a simple console application I have 5 breakpoints enabled in my solution with "Evaluate and log" option checked for each. These breakpoints are on 5 unique methods on their only return statements. Although the breakpoints are being hit, only 2 out of 5 are logging their outputs to the "Debug Output" window.

To troubleshoot, I changed the expression to an integer for consistent testing. Still nothing.