The serial/wifi debugger has to inject code into the temp build copy of the code. It injects onto the end of the code line which means inside an IF statement if the breakpoint is placed on an IF. 

In this case I suspect the IF statement the breakpoint is on resolved to false and therefore the breakpoint is not hit.

Because it is an injected code debugger you can move the breapoint up one line to an empty line if you need it to execute the breakpoint outside of the line you have selected.