An inserting system is provided for securing an envelope having a window. The system includes a deck slidably supporting the envelope, where the deck defines an insertion area, and a securing mechanism in the insertion area securing the envelope in an insertion location during insertion of a collation. The securing mechanism includes a first securing element selectively securing a first portion of the envelope between the window and an open edge of the envelope and a second securing element selectively securing a second portion of the envelope between the window and a closed edge of the envelope. The inserting system may also include a deflection element disposed on the deck between the first securing element and the second securing element, wherein the deflection element guides the collation away from an edge of the window.