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Payloads are not generating

I have repeated the same steps well enough that they haunt my sleep. At this point I am almost quite literally repeating the instructional material in my sleep. I've revisited the payload generation step where all stageless payloads are generated, yet REGARDLESS OF WHAT DIRECTORY I select ... nothing seems to work. The Cobalt Strike application is perfectly happy LYING TO ME about it's successful action. I've repeated these steps, rebooted the VMs, reverted back to snapshot and yet it still haunts like a RAVEN....EVERMORE.
Please help, my poor lab hours have suffered enough.