Hi rcportz,
Welcome to the HP Forums.
I see that you are having some issues printing the envelopes.
I will be happy to help you.
Then envelope is put in the priority tray printed side up. Adjust the side media guides against the envelope to prevent paper jams. There are 3 little pictures stamped on the priority tray but very hard to make out.
In Word, Click on Tools, select Letters and Mailing/Envelopes and labels, the envelope box will open, in the envelope tab enter your address, click on Options, click the Printing Options tab, you will need to change the Feed to Auto, it is likely set to Manual. Check the feed method to make sure it is set correctly.
Try printing from the main tray to see if you have the same results. Remove all the paper first to prevent skewed printing or a paper jam.
You might already have this document, but I wanted to include it just in case.
Please let me know if you need further assistance.
Thank you for posting on the HP Forums.
Have a great day.