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Yes, Silverfin supports syncing documents from Octopus. Once a document is linked to a transaction in Octopus, it also appears in Silverfin. Depending on the number of documents, it may take some time for all of them to become visible in Silverfin after the sync is complete.
If the DMS (Documents) module in Octopus is disabled, Silverfin cannot retrieve document references. In that case, documents are skipped during synchronisation and no error is shown.