Abstract: There is an envelope deskewing device provided with a mailing machine having a horizontal feed deck, with an elongate registration guide which extends along one side edge. Mail is fed along a feed path determined by the registration guide and a postage meter located downstream from the deskewing device. A support is mounted over the upper surface of the feed deck with a first rotary frictional drive mounted on the support for feeding the envelopes parallel to the registration guide along the feed path. A second rotary frictional drive is mounted upstream from the first rotary drive for receiving the envelopes in a random orientation ranging from parallel to the registration guide to a predetermined angle with respect to the registration guide. An abutment device mounted on the support adjacent to the second rotary drive prevents an envelope from being fed by the second rotary drive if the envelope is placed on the feed deck at an angle greater than the predetermined angle.