Printing envelopes in Microsoft 365/Word

[E9Luke]

I use Microsoft 365/Word in Windows 11 in a Parallels VM on a MacBook Pro (14-in, 2023). In Word, I start a new document, then click the Mailings tab and choose Envelopes. I fill in the To: information; my return address is already filled in. Then I Add to Document and save the envelope setup.

Next I try to print, and here's where the trouble begins. (I use an HP Envy Inspire 7955e printer.) The Print Preview looks just fine--it looks just like the envelope should in landscape orientation. When it prints, however, the envelope emerges from the printer with only the return address showing, and it's printed as if it were set to print in portrait orientation. That is, the return address prints across the short dimension of the envelope! I try again after changing the orientation to portrait, but I get the same result.

I started my search for help in the Microsoft 365 support community. There I read a post that loosely resembled my problem. The "best" response recommended that I update the printer drivers and then uninstall and reinstall the printer from scratch. 

This printer is installed and working well otherwise on both the Mac and Windows sides. I don't recall how I installed the printer on the Windows side—it's been a while. Perhaps I'm using the printer in Windows just as it came when I installed it on the Mac side. Anyway, how do I proceed? Do I first uninstall the printer in Windows 11 >> Printers & Scanners? Then  what?

Will uninstalling the printer in Windows in any way affect the printer installation on the Mac side?

[Hawks_Eye · Accepted solution]

Hi @E9Luke 

Welcome to the HP Support Community! We're here to help you get back up and running.

Here’s how you can address the envelope printing issue step by step:

Step 1: Verify Envelope Settings in Word

• Open your saved envelope document in Word.
• Go to Mailings > Envelopes > Options.
• Under Envelope Options, confirm the correct envelope size is selected.
• Under Printing Options, check the feed method and orientation. Make sure it matches how your printer expects envelopes to be loaded.

 

Step 2: Check Printer Properties Before Printing

• When you go to File > Print, select your HP Envy Inspire 7955e.
• Click Printer Properties or Preferences.
• Ensure the Paper Size matches the envelope size chosen in Word.
• Set the Paper Type to “Envelope” if available.
• Confirm the orientation matches the way the envelope is loaded (usually landscape for most HP printers).

 

Step 3: Load the Envelope Correctly

• Place the envelope in the input tray according to the printer’s envelope guide.
• Typically, envelopes are loaded with the print side facing down and the flap on the left or top, depending on tray design.
• Double-check the printer’s control panel or tray markings for the correct orientation.

 

Step 4: Reinstall the Printer in Windows

If the issue persists, reinstalling the printer on the Windows side can help:

1. Go to Settings > Bluetooth & devices > Printers & scanners.
2. Select your HP printer and choose Remove device.
3. Restart Windows.
4. Reinstall the printer:
   • Go back to Printers & scanners.
   • Click Add device and let Windows detect your HP printer.
   • If prompted, install the full driver/software package using the HP App.

 

Step 5: Clarification on Mac vs. Windows

• Removing the printer in Windows will not affect the installation on the macOS side. Each operating system manages its own printer drivers and settings independently.

If after reinstalling the printer and adjusting the envelope feed/orientation settings the issue continues, the most common cause is a mismatch between Word’s envelope orientation and the printer’s feed orientation. Carefully aligning those two usually resolves the problem.

If my response helped, please mark it as an Accepted Solution! ✅ It helps others and spreads support. 💙 Also, tapping "Yes" on "Was this reply helpful?" makes a big difference! Thanks! 😊

Take care, and have an amazing day!

Regards, 

Hawks_Eye

[E9Luke]

Thank you, Hawks_Eye! The one thing I had failed to do was to adjust the Printer Properties >> Paper size from Letter to Envelope #10.  I did change that setting on the printer's control panel, but not in Word >> File >> Print >> Printer Properties.  That's where I went wrong. My printer was trying to print an envelope on letter size paper!

I did find one little oddity as I stepped through your instructions. Envelope Options defaults to laying the blank envelopes in the tray with face up. My printer's instructions (as they appear in the main feed tray) tell me to place the envelope face down, so I ticked the Face down button. Then Word showed the envelope lying with the flap on the right. The printer wants the flap on the left, so I ticked the box for "Clockwise rotation." When I changed the setting in Envelope Options to comply with the printer's instructions, I got the message, "You have changed Word's default envelope handling method for this printer. These changes could be incorrect." Well, as it  turns out,  placing the envelope face down is correct, but clockwise rotation got me an envelope with the address printed upside down. Which is no big deal, of course. I got my envelope printing problem fixed.