How do I load envelopes into my printer so Penmark prints the right way up?

The four steps

1. Load one envelope. Follow your printer's own guidance (look for an envelope icon by the tray or a prompt on its screen), then use the three controls and the tray diagram to tell Penmark how you loaded it: printing side faces up or down, top edge points left or right, and the envelope sits left, center or right in the tray. No spare envelope? Cut plain paper to the envelope's size.
2. Print the test page. Download the test PDF and print it with the paper size shown. The page is covered in landmarks: edge labels, a crosshair, and a box where the return address prints.
3. How did it come out? Choose one: Perfect, Upside down, Printed on the wrong side, Shifted or clipped, or Wrong size. Upside down means turn the envelope around in the tray and print the same PDF again; wrong side means flip it; shifted leads to the alignment nudges; wrong size leads to the paper-size check. The PDF itself never changes orientation.
4. Save this setup. Give the printer a name ("HP OfficeJet Pro 8035e", or just "Office printer"). Penmark saves the loading instruction and any nudge for that printer and that envelope size.

What Penmark remembers, and where it shows up

The saved setup is per printer and per size. The Print tab's printer card reads "Ready to print A7 envelopes" with the loading sentence, and the sheet before each download repeats it. A second size on the same printer starts from the first size's loading settings and only needs its own quick test print. Printer setups follow you, not the book.

Why Penmark asks you instead of guessing

Two printers of the same model can feed envelopes differently depending on the tray, the feed path and the driver. One test envelope verified by you is more reliable than a database of models, so Penmark keeps no such database and never rotates or flips the PDF to compensate.

Printing from a phone or tablet

The setup and its test page can be run from a phone or tablet browser. In our testing on an iPad (Safari, AirPrint, an HP OfficeJet Pro 8030-series), the envelope-sized PDF printed correctly once the printer itself was set to the envelope size, which made AirPrint offer that paper size ("Envelope - Personal" for 6¾). AirPrint offered only the sizes the printer advertised: with the printer set for Letter, only Letter was offered and the page was scaled. So on a tablet, set the envelope size on the printer first, then reopen the print dialog; for a size your printer does not advertise, run the setup from a computer. Other printers and print apps can behave differently.