Wash jars, lids, and bands in hot, soapy water and rinse well. Place jars upright in a large canning pot or deep stockpot, cover with water, and bring to a gentle simmer to keep them hot and clean. Keep lids in a small pan of very hot (not boiling) water off to the side.

Rinse pickling cucumbers under cool water and scrub gently to remove any dirt or prickles. Slice off 1/16–1/8 inch from the blossom end of each cucumber (the end opposite the stem) to remove softening enzymes. Trim stem ends if desired.

Decide on spears or chips. For spears: cut each cucumber lengthwise into 4–6 wedges. For chips: slice crosswise into 1/4-inch rounds. You can mix and match in different jars.

In a medium pot, combine water, distilled white vinegar, pickling salt, and granulated sugar (if using). Bring to a gentle boil over medium-high heat, stirring until the salt dissolves completely. Once it reaches a boil and the salt is dissolved, reduce heat to low and keep the brine hot but not at a hard boil.

Using a jar lifter, remove one hot jar from the canning pot, pouring the water back into the pot. Place the jar on a folded kitchen towel. Add to the bottom of each pint jar: 1 head fresh dill (or about 1/2 teaspoon dill seeds), 1 lightly smashed garlic clove (or 2 for extra garlicky pickles), and a pinch of black peppercorns, mustard seeds, and red pepper flakes if using. Pack the jar firmly with cucumber spears standing upright or chips stacked tightly, leaving about 1/2 inch headspace at the top.

Using a ladle and canning funnel, pour the hot brine over the cucumbers, maintaining 1/2 inch headspace at the top. Pour slowly so the brine can flow around the cucumbers and tap the jar gently on the towel to help it settle.

Slide a bubble remover or thin plastic spatula down the inside of the jar to release any trapped air bubbles. Add more brine if needed to restore 1/2 inch headspace.

Wipe the jar rim with a clean, damp cloth to remove any brine or salt. Place a warm lid on the jar and screw on the band until fingertip-tight (snug but not overly tight).

Place the filled jar back into the canning pot. Repeat packing and filling with remaining jars, cucumbers, and brine. Ensure jars are covered by 1–2 inches of water. Bring to a full rolling boil, then process pint jars for 10 minutes (quart jars for 15 minutes), starting timing once the water returns to a full boil. Adjust processing time for altitude according to trusted guidelines if above 1,000 feet.

Turn off heat and let jars rest in the hot water for 5 minutes. Using a jar lifter, carefully lift jars straight up and set them on a towel-lined counter without tilting. Let cool undisturbed for 12–24 hours. Once cool, check seals: the center of each lid should be concave and not flex up and down when pressed.

Remove bands, wipe jars if needed, and label with the date. Store sealed jars in a cool, dark place. For best flavor, let pickles sit for at least 1–2 weeks before opening so the dill and garlic can fully infuse the cucumbers.