Post by RachHow do I stop OneNote from inserting PDFs sideways?
--I just had the same question (now it is 2016)
For those interested, here is the answer from a developer who worked on it:
Hi ejlev, I am the developer of Onetastic addin and also a developer in the Microsoft OneNote team.
To explain the situation a bit, when you insert a PDF file into OneNote, you are actually printing it, that is why it is called "File Printout". OneNote does not know anything about the PDF file format (or other files that you are inserting through File Printout command). The way it ends up in OneNote is that OneNote invokes a "print" command on the file which launches the application that is registered for the file format (in this case Adobe Reader) which then prints it to OneNote. The registered application decides which orientation the page should be printed. The result of the printing is a bunch of images in OneNote which we call "printouts".
OneNote has a rotate feature for images, but not for printouts. Printouts work differently then images so the image rotate feature doesn't work on printouts. OneNote has to do something different to handle the case of printouts, which it isn't doing. Why is this feature missing? Well, it was missing in 2010, and I don't know why because I wasn't part of the OneNote team back then. We tried to bring this to 2013 but the issue was a bit complicated and we didn't have enough time to solve it completely and properly. Therefore it was left out. You see when you spend time on one feature, you can't spend that time on another. So you have to prioritize your work and spend your time on the most important things. You may call this as "the MS engineers just get too tired to include this very basic, totally necessary feature", but engineering is a trade off. I wish we had all the necessary features for our customers, but at the same time we have to stop somewhere to be able to ship the software.
After we ended up not doing this for 2013, I decided to write an add-in for this and give it away freely. This was actually how I started working on Onetastic.
One suggestion I can give is, instead of using Insert > File Printout, open the file first and then use Print command in the application (e.g. Adobe) and choose your orientation there. This will do the same insertion, but with the correct orientation.
Let me know if you have further questions. I know that what I tried to explain won't help with your frustration of not having this built-in. Hopefully you like Onetastic.
Omer Atay
OneNote developer
Onetastic - A cool free OneNote add-in: http://omeratay.com/onetastic