I have tried printing envelopes on several digital (toner based) digital print engines and in my experience there is no way to get away from wrinkling the envelope. The only thing I have found that seems to work to some extent is to run the envelopes with the flap open and the longest edge (after opening the flap) as the leading edge (on #10's the flap is open and is the trailing edge). For #10 envelopes this means opening the flaps (not as bad as it sounds for small quantities) and using a custom page size. There is a fair amount of jamming (approx 3-4 jams per 100) but for short runs of 100 envelopes it's the only game in town unless you get a small inkjet printer to print them on.
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