pages not rotating in preview

I'm having the same problem but it only happens with pdf's from one person. All the others work like they should. I figured out a work-around. Open your file, Go File>Export As PDF Then when the Export/Save window pops up, select "Show Details" and select Landscape orientation. Then the new exported pdf will be the way you want it.

Preview will rotate the entire PDF page by 90 ° increments to its original orientation. The image does not rotate independent of the effected PDF page.

Uncertain why this is not working for you. Might have to do with PDF properties (document restrictions), or the internal structure of the PDF itself. Even if you were viewing this PDF at 200% or 50%, it should rotate with the document.

Does this lack of drawing rotation exist when using the current version of Adobe Acrobat Reader DC? When opened in Acrobat Reader, press ⌘+d to open the document properties panel, and then select the Security tab to look at the current document restrictions.

See Image and note the Tool Bar at Top. Icon second to Last ( Box with Arrow ) will Rotate the entire thing

OP issue was PDF, not an image. Preview will rotate an entire image, in 90° increments, that is opened separately from a PDF document.