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Recently (6/17) I began having issues with uploaded JPG images being pulled/seen on an object report. Could it have been me? I've only been doing this for 12 years. Well - I'm not sure if it was me, Safari on a Mac, the image except the PowerSchool Community (Roger, Matt, Adam, John, Mark, and Brian) helped me figure it out that some images have EXIF data attached to them and PS doesn't like that anymore. Engineers at PS knew about this and Brian has making some changes for the mid summer (2017) update. There is a KB Article 7054 - Photos Missing from Object Report which states

Issue: Photo files containing EXIF or other (sometimes hidden) information may not display properly in object reports. EXIF information captures meta-information from digital cameras, such as camera makes and models, shutter speed, focal length, and so on, and stores that information in the JPEG image file. If photos appear properly in PowerSchool's web interface, but not on object reports, the report engine may be having problems with the attached EXIF data. Not all JPEG EXIF data causes this problem.

JPEG images without attached EXIF or other data may still not display properly on object reports.  In this case it may be that the photo is not in a standard JPEG/JFIF format.  Please see Knowledgebase Article 9830 for more information about JPEG/JFIF.

Workaround: Removing EXIF information from image files will solve this problem. Using a third-party graphics application that allows you to strip EXIF or other data from files, or that does not support EXIF data (and thus discards the EXIF information), open the affected image file(s) and save them without the EXIF or other data, making sure that the format is JPEG/JFIF.  Some applications allow "batch" photo editing, so that you can access all photos at once.

I attempted to strip off the EXIF data with Photoshop with little success. I'm sure it can be done but Mark Messias from ParkBench Software suggested using the Preview app on the Mac. Open the file, select all, copy it, then create a new file... a new image will appear - Save AS and change PNG format back to jpg. Title it and increase the quality to BEST - store in your images location. This creates a CLEAN EXIF free images and will need to be uploaded again to your server. Good Luck!