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Show preview of MBOX files content of any platform in a safe mode. Convert MBOX files or emails to Adobe PDF selectively. Option to Save or Export the MBOX file search results to PDF format. Preview emails of MBOX file as well as associated attachments. Switch Screen View: Horizontal and Vertical Screen mode. Supports MBOX files created by 15+ Email Clients.
A agree with Bruce and Leland's advice, but it's not clear to me if it fully addresses your question. To create PDFs, you need some sort of PDF Creator, such as Nitro PDF, PDFill PDF Tools (Free) or PDF Creator. These allow you to 'print' to PDF.
Outlook allows you to print multiple messages in one go, though I'm less certain about the attachments (what's the right place to print an attachment anyway? Where it was embedded in the message, after the message, completely separately?). Finally, you mention 'headers' but do you need the bear minimum (From: To: Subject: Date) full (a page or two per message) or something in between? If you want to have full control over printing, your best bets are a VBA script to print each message, enclosed in a loop to deal with each message selected. Alternatively, import the messages into a different mail client (e.g. Thunderbird) and process them there. By default, Outlook prints (basic) headers with the email.
If you go to File - Print - Print Options, there is a checkbox to print the attachments as well. The only drawback to this (the last time I tried using it) is that it will print out all of the emails first, then all of the attachments. My preferred order would be each email immediately followed by its attachments, but apparently Microsoft doesn't see the logic in that one.
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You may be able to achieve this effect by writing your own VBA script to handle the printing for you although I haven't tried anything remotely like it since Outlook 2000. To dump it to a PDF, you just need to have Adobe Acrobat (not just the Reader), or something like novaPDF, or Nitro PDF Reader (comes with a PDF print driver as well).
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You just need to select the appropriate 'printer' to create your PDF file.