So you're doing this manually for 300 - 600 images per file? For safety, you really should be saving these to disk, cropped so that each image represents one student, before adding them to Word. If you don't, you risk losing the lot if the document becomes corrupted - which it's already showing signs of.

FWIW, if you're using the docx format your existing images can easily be extracted by changing the file's extension to .zip, then opening the file as a zip archive from where you can readily copy the images to a folder.

As for the cropping concerns, perhaps you could explain the current process? In any half-decent graphics program (even Windows Paint) you should be able to select an area then save the selection as a new file (copying to a new file might be required first).

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Cheers,
Paul Edstein
[Fmr MS MVP - Word]