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LaserJet Pro M102w

I used to be able to print on envelopes just fine. Then one day, I printed one envelope fine and then the next didn't work right. I put the envelope in the same way as always, go through the envelope printing menu in Word, but then I get the flashing exclamation point on the printer. If I click the button, it will print the envelope, but it prints the address up at the top of the envelope. I've tried unplugging the printer and plugging it back in and fiddling with all the settings in Word and no matter what I change, it still prints the address in wrong place. 

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It sounds like the printer thinks it may be using plain paper instead of a #10 envelope. It's important to make sure the driver settings are correct coming from the software program, but also make sure the priority tray slot is set to #10 envelope. A windows 10 update can change your print driver settings.

 

1. From the software program, select the Print option.
2. Select the printer from the list of printers, and then click or tap the Properties or Preferences button to
open the print driver.
NOTE: The name of the button varies for different software programs.

3. Click or tap the Paper/Quality tab.
4. In the Paper source drop-down list, select the tray to be used.
5. In the Media drop-down list, select Envelope.
6. Click the OK button to close the Document Properties dialog box.
7. In the Print dialog box, click the OK button to print the job

I am not a HP employee. I am a service tech on these forums researching topics and offering my best guess to aide in your troubleshooting.
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