I donīt know. Winternight in general was very much anti-Matrix and Fry in particular had a pathological fear of the matrix.
I think I remember that there was a rather big controversy in the group whether to ally with ExPacis or not, to destroy the matrix (Pax didnīt tell them, that she really wanted to change it, but not destroy it, IIRC) - though I donīt recall, who was on which side of the discussion.
They had this Berserker & God BTLs going on, but otherwise they didnīt do anything matrix related, to the point that they wouldnīt even use it for communication of any kind. Winternights other technical fields of interest where Drones (their primary means of communication, by remote delivery of datachips) and WMDs (nukes, Surtr nanites & Ymir chemical agents).