Sending, receiving, and organizing email in Outlook.com
Hi Zoe,
The two page PDF happens because the web and new Outlook print views often collapse parts of a conversation at print time. The way to capture everything is to print the whole thread as individual messages from Outlook for Windows classic using Memo Style.
Open Outlook classic, go to the folder that contains the thread, expand the conversation so you can see each message, click the oldest message, then hold Shift and click the newest so all messages in the thread are selected in order. Press Ctrl+P, choose Microsoft Print to PDF as the printer, select Print Options if you see it, make sure Memo Style is selected and not Table Style, confirm the list is sorted oldest to newest so the PDF reads top to bottom, then click Print and save the file.
If anything in those steps does not match what you see, tell me exactly where it differs and I will adjust the path.