I believe you must use the 'Save as Adobe PDF' item off the main File menu rather than doing a Save As. What version of Word are you using? I work with Word 2010, and I have no problem having my table of contents and Level 1 and 2 headings translating into Adobe Acrobat. Is there a way to change the format so that when I print to PDF, a user can just click on the text in the table of contents and it takes them to that page or do you have to manually enter a table of contents to do this? The headings are correct and the table of contents table works well in Word (CTRL + left click) taking to you the appropriate page. I have a word document with a table of contents that I inserted using Word's built-in option.