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Maybe the flap is getting caught on something. Try rotating the envelope 180 degrees so the flap is on the other side, and use your ptinter's "rotated print" function to print the addresses in the correct orientation?
I had this problem too! My solution was to slide a regular piece of 8 1/2 x 11 paper in between the flap and the envelope. Then I sent them through on that. Not a single one jammed or went in crooked. You have to feed them through individually though so it's time-consuming.
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So, FI has a very nice photo printer, and we used it to address a few of our invitation envelopes (most were done by the invitation printer, but a couple had to be redone, as a couple of people moved or got divorced). The invitation envelopes were 7-inches square.
Now I'm doing rehearsal dinner invitations, and tried to run the envelopes through the printer last night. They are 5.25 x 7.25 inches, rectangular. And they won't pull through straight. No matter how carefully I line them up, the address is a little crooked. The envelopes are the same weight as the wedding invitation envelopes. Any advice?