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Are you updating the content within the same emails as were previously used in the Stream?
If so, the Engagement Program won't send those to the same individual, even if you remove and re-add them to the Stream.
If you're updating content, I suggest creating new emails, adding those to the stream, then deactivating and archiving the old versions. That way, for any lead within (or exhausted) in the Stream, the new emails won't have been sent, so will be available for sending in the next Cast.
Alex is right. Engagement programs "remember" which email assets have already been sent to which leads in a stream cast. So simply editing the email assets does not necessarily mean the email is a new asset.