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I believe it will only do this if all the duplicates were at the same Cast and Content stage. If they entered the Engagement at different points, then each record may receive a different piece of content at the next Cast.
Let's have Cheryl confirm this, or check on the original docs.
The engagement program de-dupes at both the program level and stream level. So you should never have a duplicate lead receive content, or even enter into the same engagement program.