Preview Rotating and Cropping Upon Export or Print
There are multiple questions about a bug in Preview rotating some images when we try to export or print it. Since they're all outdated like this one (Disabling EXIF rotation in finder & previ… - Apple Community) and none of the ideas worked for me I thought I should submit a workaround that does.
Right before printing rotate the image yourself (25 degrees either direction). You'll immediately see it switch in the Print dialogue back to landscape orientation.