Legacy PDFs searchable via Google ?

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Any ideas how I can remove legacy PDFs from the Hubspot environment so that they're no longer searchable via Google?

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Everything you upload to Hubspot with regards to files are indexed.  There's no way I'm aware of to not index these files short of just deleting them.  If you are archiving them, then I would remove them from Hubspot and move them to a backup server where you store other legacy documents.