If it loses all its leaves in winter then it’s done from my experience.

Late to the party... I'm in Texas, I clipped mine down to the base during the winter and it has grown back.

I’m in central NC. Today I saw a red petal on my pineapple sage and assumed that it had been blown onto it from a nearby flowering plant.

But it’s the pineapple sage! It has one loom and some bright crimson buds ready to pop. I’m flabbergasted since it’s not supposed to flower until (in my experience here) early October.

Just sharing because this is so unusual. I bought it in April in a 1qt container and put it in a large container immediately. It will be interesting to see if to fully blooms early and then continues, or not.

Update and opinions wanted. I’m the OP. I had several small blooms in May, then just foliage growth (as normal). It’s large and healthy, but no flowers or buds that I can see yet. It’s September 23rd and I expected it to pop by now.

I’m in Raleigh NC. Do Y’all think it may still bloom? I can’t recall when they’ve bloomed in past years, but this seems late. It’s in the same spot. TIA.

Cut pineapple sage down to a few inches above the ground after the blooming period ends in late fall or early winter. This pruning helps the shrub grow back thicker and lusher each year.

Pineapple Sage typically is a Fall bloomer, which is why it's usually only grown where there is long, warm Fall weather. I've never had it winter-over in my zone 9B gardens.