When I started in engineering 30 years ago, an older engineer told me then "nothing will ring your phone in your career more than hardware and springs". He was right!
In a properly designed joint, the energy spent tightening a bolt is stored by stretching it. So, the joint must be ridged and the bolt stretches like rubber. The joint is held from slipping by the clamp of the bolt. When clamp alone won't hold, you add bolts (more clamp) or a mechanical means such as a pin. Your joint appears to be doing this. I wouldn't drill it out.
Know that most lock washers, lock nuts, etc are bandaids that actually soften the joint and make it harder to put energy into the bolt where you want it. Avoid them! Instead, use high grade hardware and torque the joint to proof. Remember: torque is what we do. Tension is what we want.