I'm having an issue where portals placed on my rotating panels will only be oriented one specific way relative to the prop_dynamic (panel) inside of them. Here is a big, simple version of the problem I'm facing.

File Name: TestBox-panelsize.zip
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Click here to download Portals on Panels, Issue Clarification

rotate the panels until the portal are at the desired rotation, the only way to know if thi is right is to keep trying and dont befooled by an upside down portal. I have never had this problem so all I know is to keep trying till you get it right.

Try placing an info_placement_helper or a func_portal_orientation (if your using the first portal engine) You can specify the direction you want the 'lower part' of the portal to be aimed at.