Prep and cook the potatoes: Rinse baby potatoes and place them in a pot. Cover with cold water by 1 inch, add a big pinch of salt, and bring to a boil. Simmer 12–15 minutes, until just tender when pierced with a fork.
Do not overcook.
Cool and halve: Drain and let the potatoes cool until comfortable to handle. Halve them lengthwise so they look like little “boats.” If any halves wobble, slice a thin piece off the bottom to help them sit flat.
Scoop the centers: Using a small spoon or melon baller, gently scoop a small cavity from each half. Set the potato “shells” aside on a tray.
Place the scooped potato centers in a mixing bowl.
Roast (optional for flavor): For sturdier shells and extra flavor, toss the hollowed halves with olive oil, salt, and pepper, then roast at 400°F (200°C) for 10–12 minutes until lightly golden. Let cool.
Make the filling: To the bowl with the scooped potato, add vegan mayo, Dijon, lemon juice, chopped pickles, pickle brine (if using), garlic powder, onion powder, smoked paprika, hot sauce (if using), salt, and pepper. Mash until smooth and creamy.
Stir in chopped chives or dill.
Adjust seasoning: Taste the filling and adjust the tang and salt. For more zing, add a splash of lemon or pickle brine. For smokiness, add a pinch more paprika.
Pipe or spoon the filling: Transfer filling to a piping bag with a star tip (or a zip-top bag with the corner snipped) and pipe generous swirls into each potato shell.
You can spoon it in if you prefer a rustic look.
Decorate “spooky” toppings: Make little spiders by halving olives for bodies and slicing thin legs from additional olive pieces. Arrange on top of the filling. Dust with smoked paprika for color.
Add capers or pepper strips for extra flair.
Chill and serve: Chill for at least 20–30 minutes to set the filling. Serve on a platter lined with greens or parchment for easy lifting.