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We were looking to migrate to Files as a first step to prep for a Lightning migration and noticed a potential useful setting:

"Files uploaded to the Attachments related list on records are uploaded as Salesforce Files, not as attachments"

(Customize > Salesforce Files > Settings > General Settings)

I noticed that when when this setting is enabled it does not behave as expected. In fact it performs the opposite as it describes. It creates an Attachment when uploading a File as opposed to creating a File when uploading a legacy Attachment.

Is this the expected behavior... it seems backwards to me? Why would I enable this setting in my org, is there a valid use case? Does anyone have a link I can read more about this?

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I just had to use this functionality today itself. And it works absolutely fine when enabled in my Org.

Initially all files uploaded when getting dumped in 'Attachments' & then when i enabled it, started to get dumped in 'Files' object.

You have to do some additional steps for legacy files.

Refer below link - https://blogs.perficient.com/2018/11/02/transitioning-from-notes-and-attachments-to-files-in-salesforce/

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