Envelopes are being printed upside down.

[RMittelman1]

I've always been able to print envelopes from Word by loading them upside-down in the paper tray with the flaps on the left. Now they have started to be printed upside-down, meaning the flap is on the bottom after printing rather than on the top.

[Hawks_Eye]

Hi @RMittelman1 

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

Thanks for explaining that so clearly—it’s definitely frustrating when something that used to work suddenly flips the script (literally!). Let’s get your envelopes printing right-side-up again. 💌

🛠️ Why This Is Happening

This issue is often caused by:

• A Word or printer driver update that changed the default feed orientation
• A mismatch between paper type settings and how the printer expects envelopes to be loaded
• The printer interpreting the envelope as photo paper or another media type

✅ Steps to Fix Envelope Orientation

1. Set the Correct Feed Method in Word

• In Word, go to Mailings → Envelopes → Options
• Click the Printing Options tab
• Choose the correct Feed Method (usually face down, flap left for HP inkjets)
• Make sure Clockwise rotation is unchecked

2. Confirm Envelope Size and Type

• In the same dialog, go to the Envelope Options tab
• Select the correct envelope size (e.g., #10 Envelope)
• Click OK and try printing again

3. Load Envelopes in the Main Tray

• Load envelopes face down, flap to the left
• Avoid using the photo tray—it doesn’t support envelopes

4. Update or Reinstall Printer Driver

• Go to HP’s support page for the 7955e
• Download and install the latest full feature software and driver
• Restart your computer and printer

5. Check Printer Settings

• On the printer’s touchscreen, go to Settings → Paper Setup
• Confirm the tray is set to Envelope and not Photo or Plain Paper

If the issue persists, you can also try printing from WordPad or another app to see if the behavior is consistent. Let’s get those envelopes looking sharp again! 💪📬

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

[RMittelman1]

Not sure how pertinent this is, but I'm running Windows on my MacBook using Parallels. In the Windows version of Word, the paper always comes out upside down, which means I need to always rotate the envelope 180 degrees so the address is oriented properly on the envelope. This happens regardless of whether I check the "rotate" checkbox.

On Word for Mac, everything works properly, with the envelope oriented the right way. Strangely, in Word for Mac, checking the "rotate" checkbox also does not change how the envelope is printed.

So I will now re-install the printer driver in Windows. BTW, I have 2 different printer drivers defined in Windows for my printer. I  should probably uninstall both before installing new Windows driver, right?

[RMittelman1]

Removed and re-installed printer driver for my printer. Same problem occurs. default in word seems to be feeding envelope face-up. switched to face-down. tried printing without rotating envelope. rotate box unchecked. printed upside down. clicked on to rotate, and nothing changed except the graphic showing what the envelope looks like in paper tray. but still prints upside down.

[Hawks_Eye]

@RMittelman1 

Thanks for laying out all the details—it really helps paint a clear picture. I can imagine how annoying it must be to wrestle with envelope orientation every time you print, especially when things work fine on the Mac side but go haywire in Windows via Parallels.

Let’s try a few targeted steps to get those envelopes printing right-side up:

🛠️ Fixing Upside-Down Envelope Printing in Word (Windows via Parallels)

Remove Duplicate Printer Drivers

• Yes, it’s a good idea to uninstall both printer entries in Windows to avoid conflicts.
• Go to Control Panel > Devices and Printers, right-click each printer, and choose Remove device.
• Then reinstall the correct driver from the HP support site.

Adjust Word Envelope Settings

• In Word, go to Mailings > Envelopes > Options > Printing Options.
• Try toggling the “Clockwise rotation” checkbox—some users report this flips the output correctly.
• Also, confirm the feed method matches how you’re loading the envelope (face-up vs. face-down, flap orientation).

Set Correct Paper Size and Orientation

• In File > Print > Printer Properties, manually set the paper size to Envelope #10 and orientation to Landscape.
• Avoid relying on Word’s auto-detection—explicit settings tend to work better in virtual environments.

Check Parallels Printer Mapping

• Parallels may be passing the printer through as a generic device.
• Open Parallels > Devices > USB & Bluetooth, and ensure the printer is connected directly to Windows, not shared from macOS.
• If possible, install the printer as a network printer in Windows rather than USB passthrough.

Test with a Custom Envelope Template

• Create a blank Word document, set custom page size to match your envelope, and manually position the address blocks.
• This bypasses Word’s envelope wizard and gives you full control over layout.

Let me know how it goes or if you'd like help walking through any of these steps. We’ll get those envelopes behaving properly—no more upside-down surprises! ✉️😄

Regards,

Hawks_Eye

[RMittelman1]

Thanks for the reply. First 3 things I had already tried. No change.

I can't figure out how to check Parallels printer mapping. I found Parallels Desktop settings, but there is nothing under

Devices > USB and Bluetooth about printers. How do I go to Parallels > Devices?

I found something somewhere about sharing with the Mac printer settings and turned it off. Now the printer disappeared from Windows entirely. It can't find the printer when I click Add Printer. The HP Smart app knows about the printer, but Windows does not. There is no way to install the printer.

I found a setting on the Mac to share network devices and turned it on. Once rebooting Windows, I could then add the printer back in Windows. But its description includes the fact that it's a Mac printer being shared. This is the only way Windows can recognize the printer at all.

Now I can print in Windows, but the envelope still prints upside down from Word regardless of whether I check the box to rotate the envelope, and regardless of the setting for envelope being upside down or not.

This is frustrating, because it used to work just fine. Also, I print envelopes from Access using Word automation, so I don't have the luxury of changing the settings the way I can do in Word > Mailings > Envelopes.

[Max3Aj]

@RMittelman1, Thank you for your response. 
@Hawks_Eye is away for now. 

This needs one-on-one interaction hence I'm sending a private message to assist you with the next action. 

  

Please check your Private message icon on the upper right corner of your HP Community profile Next, to your profile Name, you should see a little blue envelope, please click on it or simply click on this link. 

  

I hope this helps! Keep me posted. 

  

Max3Aj

HP Support