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I am on an iMac using OSX 10.5.8 and printing on an Epson R1800. With iWork, word processing module I set up the envelope to print and under the File menu, select page setup and choose #10 Envelope with Portrait orientation. I feed the envelope into the printer in the normal horizontal, top first, print surface up. In the File menu I select Print and hit Return. Most of the time this works. Sometimes the envelope feeds through without printing, and occasionally the envelope won't feed but the printer goes through the printing cycle. The R1800 is not the ideal envelope printer. It is made to print photos on photographic paper. I use an old fashioned typewriter to address envelopes.
Have you found a solution for this problem?? I have the same problem; happens sporadically but once it happens there's no fix. With the particular page I am printing I can't get it to correct itself.
I thought at first it was associated with Classic apps but that wasn't consistent. I just printed from Safari on a wireless iBook and this page is also reversed. Extremely frustrating!!!!!