Cyndi..tell your guy it needs to be hand cancelled and see what he says. That's where the extra 20 cents comes in. Our soft squishies get caught in their cancelling machines and stops the whole process, tears up our envelopes and sometimes the fabric in them. better to be safe and pay the extra! I don't even take my envelopes to the window, I buy forty 65cent stamps, put them on the envelopes and drop them in the slot. I've never had a postage due issue or a torn up one. Maybe this helps clear things up a little!