What kind of printer are you using. Make model? Are you using the manual bypass tray?
I noticed that depending on the selections I made on the printer paper size setting itself and on the print driver, I got different results. i had to change the bypass paper tray setting to print labels and then when I changed it back, I selected “custom-r” instead of “custom” and it changed the print orientation.
What I did to get it to work:
1. Create new document in InDesign and changed document size to the envelope size (I think it was 7.25×5.25). I only used InDesign because I needed the ability to change/select glyphs for the font I was using and it gave me the flexibility to change spacing, kerning, and other fun things.
2. Once everything was done, I couldn’t print directly from InDesign or even Illustrator because the selections on the driver out of InDesign were too complicated and I couldn’t get it right. I saved it as a high quality PDF for print. I was familiar with this process because this was how I did all my invites and inserts and it was pretty much the same whether I created it in Illustrator or InDesign.
3. After I created the PDF, I found it easier for me to work out of Preview (but this is only for Macs) than in Adobe Viewer. (I don’t have Acrobat on my Mac but I do at work. The steps and selection are slighlty different depending on what software you are using and what print driver you are working with. At work we have PCL, Post Script, and Fiery drivers and the selections are a little different with each driver.)
4. When I select print, I have to change the paper size (I created a custom paper size because I couldn’t find it in the list of preset sizes on the driver.) I also de-selected scale to fit and auto-rotate. My print driver shows how it will look on the envelope.
5. So depending the paper size setting I have set on the menu on the actual printer, determines which direction I put my envelopes in to feed. I did test prints using same size paper as the envelopes, marking which way was face up and which way it fed so that when it prints, I know how to properly place the envelope. (This all worked until I had to change it to print some labels for another project so that’s why I have the oops envelope that printed sideways.)
This is what I did. I hope it helps. I remember trying to print envelopes on my work printer without a manual feed tray. I could never get it to work so I either handwrote addresses or printed them on my dymo thermal address printer.