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My recommenders have all allowed my recommendations to upload automatically to new applications on OSCAR. I sat down and did about fifteen applications two nights ago, and I noticed this morning that one of my recommendation letters did not attach to any of the new applications. This has not been an issue before, does anyone know how to sort this out?

Not a problem at all.

Just tell the professor to upload the letter again or to specifically apply it to the application.

Judges are used to electronic applications sometimes being incomplete. Two days is no time.