An outsert application system is disclosed that includes a vacuum assembly and a pivot arm. The vacuum assembly is for accommodating passage of a vacuum to an engagement surface at a first end thereof for engaging an outsert. The pivot arm is rotatably coupled at a first end thereof to a second end of the vacuum assembly, and the vacuum assembly is adapted to rotate with respect to the pivot arm about a first axis. A second end of the pivot arm is adapted for rotation about a second axis that is substantially parallel with the first axis. The system further includes a translation device that causes the first axis to move with respect to the second axis as the vacuum assembly rotates about the first axis.