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At what point do you close your old questions?
Total Questions: 4 (4 unresolved)
DataGuard cannot, but you can do this with ACFS (Oracle Cloud Filesystem) Replication in addition to DataGuard, to keep file (BFiles) and the database in Sync.
Alternatively you could put the pdf into DBFS (Database Filesystem), so that the file would be saved inside the DB, hence replication via. the normal DG mechanism.