OP, I am almost positive I have your problem pegged.
I was having the same exact problem with my 10/22. This is not a problem with the extractor/ bolt... This is an out of battery detonation caused by a tight chamber.
Turns out my barrel was a Target chamber, so a bit tighter then the standard chamber. When used with most brands of non-target/match ammo, the cartridge will not fully seat in the chamber. Due to the design of the 10/22, it will still fire when out of battery, causing the exact set of circumstances your photos show.
You will not be able to tell with a snap cap, as seen here...
However, if you drop a live round in the chamber, you will see that it is about 1/8" OOB.
Resulting in blowouts like the one on the left, and mangled and stretched cases like the two in the middle when it doesn't blow, if you looked through your fired brass they would look like these. A .22 fired from a properly functioning gun looks like the one on the right.
You will need to ream out the chamber with a standard .22lr reamer if you want to use bulk ammo, your only other option is to use the very high end match ammunition.
The final result will be that you can drop in the cartridge no problem.
Hope this helps you out OP.