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Step-by-step build — 5 steps. Also available as a print sheet.
Lay the four fence picket boards side by side so the overall width is about 23". Place the two 20" backer strips on top with roughly 1-1/2" of clearance on each end (the picket's stem shape is 1-1/2" wide, so it makes a handy spacing guide). Glue and staple the backers to the face boards — two staples per overlap.
Flip the assembly and add two more staples per overlap from the front side into the backers, staying at least 1" from the outer edges where there's no backer support underneath.
Starting about 3" up from the bottom edge, draw a pumpkin outline across the joined boards, keeping the shape clear of the backer strips underneath so the jigsaw has clean material to cut through. Keep it organic — a smaller curve up top and a bigger, rounder bulge at the bottom reads more like a real pumpkin than a symmetrical circle.
Clamp the panel securely with the area to be cut overhanging the bench edge, and confirm it's solid before cutting. Cut the outline with the jigsaw, unclamping and repositioning as needed to keep the cut area clear of the bench.
Cut and attach a stem shape to the back of the pumpkin cutout with glue and staples.
Glue and staple the front of the box to the sides. Apply glue along three edges of the bottom panel and set it inside the front/side assembly, then staple along the side and front edges to lock it in.
Set the box open-side up. Run glue along the top edges, then set the pumpkin cutout on top, aligning its bottom edge and the start of the pumpkin curve with the box's outside corners. Staple the pumpkin to the bottom of the box, then use a straight edge as a guide while stapling it to the sides.