Systems and methods which are adapted to generate multiple indicia in a single secure environment session are described. Embodiments provide for generation of a plurality of postage indicia in a single postage security device (PSD) transaction, whereby the PSD loads and unloads corresponding virtual PSD information a single time for generating the plurality of postage indicia (i.e., in a single secure environment session). The indicia generated in a same secure environment session according to embodiments of the invention may comprise a plurality of indicia requested by a same, single user. Additionally or alternatively, the indicia generated in the same secure environment session may comprise a plurality of indicia requested by multiple different users.