When this happens I get a message that the printer was expecting a different size paper and to load proper paper. Sometimes it will run the envelope through but nothing is printed on the envelope. (Even though the tray is loaded with several envelopes) Sometimes I will get a printer out of paper message.
Under Printing Options select printer auto select for the tray Under Options Tab, then Envelope Options, select Size 6 3/4 (3 5/8 x 6 1/2 in)
Trying unsuccessfully to print envelopes using Word.