Hey Darthclide,
I signed my bot(KubosKubot) up for 2-Factor Auth, and some folks say that
whispers can't be sent from a bot unless the bot is whispered first. Maybe that's our issue? Next time you're online, I'll whisper your bot and we'll see if that works. I only mention this because perhaps in our efforts to ensure our bots work(like a responsible coder should), perhaps we opened the figurative window on accident for our bots to send us whispers, and since we only need open the window once, we haven't noticed the "pattern".
I know this is a janky workaround, but any workaround is better than no workaround.
