So, let’s cut to the chase: The answer to this question is, “possibly...eventually...but probably not before you have a chance to eat them.” In other words, pickles stay safe to eat for a very long time, regardless of what the ‘best by’ date says. (While we’re on the subject, it’s worth noting that ‘best by’ and ‘sell by’ dates actually have no bearing on the safety of a food product—they are actually labels slapped on by manufacturers to indicate best quality.)
Pickles are especially hardy, though, and are likely to stay fresh in both the pantry and the fridge for one to two years past that (misleading) expiration date, provided they’re properly sealed, the experts at Healthy Canning tell us. In fact, staying power is kind of the point of the pickling process. The highly acidic and uber salty brine that makes pickles possible was once the go-to method for preserving all types of food, and for good reason: The pickled environment is particularly inhospitable to bad bacteria. So, yeah, once a boring cuke undergoes that transformation, there’s really no turning back...or, erm, bad.
But wait, is it possible for a pickle to go bad? Yes, but it’s highly unlikely. First of all, there’s no reason it should take you two years to make your way through a jar of dill pickles—unless, say, you never liked them to begin with and bought them by accident. Even after two years, the odds that a pickle will make you sick are pretty slim. However, it is still a possibility—especially if you didn’t properly reseal the jar after opening it. When it comes to pickles that have been hanging around a little too long, the far more likely outcome is simply that they will lose their satisfying crunch.