How do I print addresses directly on envelopes with Penmark?

Step by step

1. Open the book and click Print, then the Envelopes pill.
2. Choose a size. The picker groups them: Popular (A7, US #10), US card and announcement sizes, US commercial sizes, International (DL, C6, C5, C4), and "Custom size…" for anything else between 3 and 15 inches a side.
3. Pick a style from the nine presets (Classic, Script, Elegant, Editorial, Gallery, Modern, Casual, Minimal, Holiday) and, if you like, a recipient size (small / medium / large), an accent color and an ornament.
4. Set the return address: Front, upper left (the default for a new envelope setup), Back flap (printed as a second pass), or No return address. Type the sender's name and address; an optional heading line can sit above the name.
5. Select the recipients in the list (filter, SELECT ALL, or ONLY beside one name to print just that envelope). The preview pages through them; PREVIEW LONGEST ADDRESS jumps to the one hardest to fit.
6. Click Download PDF. Before the download, a "Check your print settings" sheet repeats the paper size to choose and how to load the envelope if Penmark knows your printer.
7. Print the PDF. When printing, choose the envelope's paper size (the sheet names it, for example "Envelope A7" for A7). If your print settings do not list it, add a custom paper size of 7.25 × 5.25 in. Leave the scale setting at its default.

The first time: let Penmark learn your printer

Printers differ in how an envelope has to be loaded. The "Envelope printing setup" card walks through one test envelope in four steps (load one envelope, print the test page, say how it came out, save) and then remembers the loading direction and any alignment nudge for that printer and size. See How do I load envelopes into my printer?.

What a batch looks like

One PDF, one page per recipient, in the order you selected them. Print the whole stack, or a subset, or a single envelope again with ONLY. After a jam, "Start printing at №" continues from where the stack stopped. See reprint one envelope or resume.

Printing from a phone or tablet

The designer, the preview and the download work in a phone or tablet browser. In our testing, printing an envelope PDF from Safari on an iPad through AirPrint to an HP OfficeJet Pro 8030-series printer worked correctly once the printer itself was set to the envelope size: with the printer configured for a 6¾ envelope, AirPrint offered the paper size "Envelope - Personal" and the 6¾ PDF printed at full size with the addresses where the preview showed them.

The limitation: AirPrint offered only the paper sizes the printer advertised. With the printer set for Letter, AirPrint offered only Letter for a #10 envelope PDF, and the preview showed the envelope scaled onto a Letter page. If your print dialog offers only Letter, configure the envelope size on the printer itself first (its control panel or settings app), then reopen the print dialog. iPadOS offered no custom paper size in our testing, so a size your printer does not advertise (such as A7 on this HP) may not be printable from an iPad even though Penmark's A7 PDF is correct; print those from a computer. Other printers and print apps can behave differently.