How to save an email as a PDF with the attachments still in it

Print to PDF, pick the PDF printer, save. That works in every mail client and takes about four seconds. It also hands back a document with the attachments missing and the routing headers stripped, which nobody notices until the file has a job to do.

What the print dialog actually hands you

Printing renders the reading pane onto paper-sized pages. That pane was assembled for your convenience, not for the record: the sender's display name instead of their address, the timestamp converted into your time zone, the thread folded down to what fits on screen.

Three things do not survive the trip, and only one of them is obvious.

Attachments are listed by filename in the header block and left where they were. A PDF that reads Invoice_4471.pdf (212 KB) across the top does not contain Invoice_4471.pdf.

The internet headers go with them. Every server that handled the message added a Received line on the way through, and the server that delivered it recorded whether the sending domain had authorised that route. The format is set out in RFC 5322, and none of it is rendered on screen, so none of it prints.

Anything collapsed stays collapsed. Older messages sit behind a control in long threads, and quoted replies hide behind a trimmed content button. Print what is showing and you print the summary.

The steps, client by client

All of these produce the same kind of file, so use whichever is in front of you. Microsoft's Outlook documentation lists the same paths for the classic desktop app, the new one and the web version.

That last row is worth knowing, because iOS offers no PDF printer to select. The print preview is already a PDF. Pinch outwards on the page thumbnail and it opens as a document you can save to Files or pass straight to another app, which beats hunting for a printer that was never there. Gmail's print help documents the gesture for its own iPhone app, and it works from anything that can print.

Which file you get when you save the original

Saving the message rather than printing it produces one of two things, and you do not get to pick. Where you are saving from decides it.

Outlook writes .msg, a compound container that keeps the body, the properties Exchange tracks and each attachment as separate streams inside a single file. Everything else writes .eml, which is the message as it actually travelled: headers at the top, body underneath, attachments encoded into text and appended.

Keeping the attachments

Classic Outlook has a checkbox for this that almost nobody finds. In the print dialog, open Print Options and tick Print attached files. Outlook then sends each attachment through the same print job, so they land in the PDF behind the message.

It only covers attachments Windows knows how to print. A Word file or another PDF goes through. A .zip, a nested .msg, a CAD drawing or anything else without a print handler is skipped, and skipped quietly, which is the failure mode you want least.

The dependable route is to keep the original and convert that. Save the message, then run the saved file through a converter that writes the attachments into the PDF instead of naming them.

The headers, and when they turn out to be the point

The From line on a printed email is display text. It says whatever the sending client put there.

What sits underneath is much harder to arrange. Each server that touched the message stamped a Received line with its own name and clock, in order, so the chain reads backwards from your inbox to the machine that sent it. The Message-ID belongs to that message alone. The delivering server recorded whether the sending domain publishes a record authorising that server, and whether the signature over the body verified.

None of that appears in the reading pane, so none of it prints. It lives in the .msg or the .eml.

A long thread, or a whole folder

Gmail prints a conversation as one document, oldest message first, as long as you expand anything collapsed before you hit print. Outlook prints the message you selected and nothing else, so a fifteen message thread is fifteen jobs unless you switch to the conversation view first.

For a batch, select the messages, save them in one go, convert them, then merge the results into a single file in whatever order you need. That is also the only sane way to produce one PDF from a thread that Outlook insists on treating as separate messages.

Expect the result to be large. A 4 MB scan attached to the message is still 4 MB once it is inside the PDF, and a thread with several of them adds up quickly. If the archive has to be emailed onwards, compress it once at the end rather than compressing each piece on the way in.