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I have a collection of mailing list messages in an Outlook 2007 folder that I need to save as a single, chronologically ordered PDF.

When exporting to PDF, Outlook generates a PDF Portfolio in which each message is a separate document. The messages are indexed by a header that mimics the appearance of an email client. From Acrobat Pro, the contents of this portfolio can be saved as individual files (Select All, then Extract From Portfolio), creating a collection of individual files with filenames based on the subject of each message. In theory, these could be combined back into a single PDF.

The problem with this solution is that extracting the individual messages from the portfolio strips them of their original time and date stamp, which is stored in the portfolio index. Instead, the messages become organized alphabetically by subject, and each individual file has a time/date based not on the original message but on the time/date it was extracted from the portfolio. So I can create an alphabetically ordered PDF, but not a chronological one.

Is there a solution to this problem that doesn't involve buying a third-party add-on?

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Turns out you can do this from within Outlook. The Adobe PDF plugin includes the option to disable the creation of PDF portfolios (Adobe PDF -> Change Conversion Settings.) Not sure how I missed this...

When portfolio creation is disabled, Outlook will export the contents of a folder as a single PDF in reverse chronological order. AFAICT there's no way to change this arrangement (it'll do this regardless of how the folder is displayed in Outlook), but it's a good enough solution for my needs.

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