Heat a large frying pan over medium heat, cook the bacon with the oil until its fat is rendered but the bacon is still juicy, about 10 minutes.

Transfer cooked bacon to a paper towel-lined plate, then increase the heat to medium-high/high. (If you have a lot of fat in the pan, drain some, but you'll want to keep most of it as the sprouts are going to soak it up).

Add the Brussels sprouts to the pan, using tongs to ensure cut side is facing down. Sear without disturbing them for 5-7 minutes, until sprouts are charred and beginning to blacken. (I had to do this step in two batches, as my pan isn't large enough to hold a full pound of halved sprouts.) Flip the sprouts, then season with salt and pepper.

Add the dried cherries and cooked bacon to the pan, toss, then continue cooking until the sprouts begin to color - another 2-3 minutes.

Add the stock, a little bit at a time, to the pan. Using a wooden spoon, smash the cherries into the sauce, thereby breaking them into smaller pieces as the sauce reduces. Once the cherries are almost fully incorporated (several minutes), add the vinegar.

Continuing cooking another 2-3 minutes, or until the sauce is thick enough it is coating the Brussels sprouts. Do NOT reduce too much, otherwise the sauce will become overly sweet.

The sprouts should be well-charred on the outside, but still bright green on the inside and bite-tender.

Serve warm.