Press fresh pineapple through a juicer and measure exactly 2 cups juice. Measure the sour cream, raw honey, and homemade vanilla.
Put all four ingredients in a 4-cup glass measure or bowl with a pour spout. Whisk until completely smooth with no white sour-cream streaks or sticky honey ribbons.
Divide evenly among 6 to 8 stainless popsicle molds, leaving a little headroom. Center the sticks.
Freeze for at least 6 hours or overnight, until rigid through the center.
Run the outside of the mold briefly under hot water, then pull gently on the stick to release.