The answer is "It Depends".. Depending on: the envelope you are printing on. the number of sides you want to bleed off of (ie: 1, 2, 3, etc.). what the actual sides are (ie: top and bottom, top and left, etc). It may or may not be possible. Place your envelope order and enter a note that you want certain sides to bleed in the "Got Comments" comments section (found on file upload screen - see visual below), and one of our 4OVER4.COM reps will advise if doable and if any additional cost. Note: If your envelope is a full bleed envelope (bleeds on all 4 sides), please read this useful article.