A remote recycle bin configured in WinSCP is useful only when you understand which operations use it. It is a client setting that changes how WinSCP performs certain remote actions, not evidence that every program or server job now has a recovery policy.

First inspect the relevant site's Advanced settings and its Recycle Bin page. Record the remote bin directory and who can access it. Do not confuse this location with the Windows desktop Recycle Bin or a separate retention feature provided by the server.

Separate deletion from overwrite protection

Preserve deleted remote files to recycle bin moves deleted files into the specified remote directory. Preserve overwritten remote files to recycle bin is a separate option, documented for SFTP only; it relocates the existing remote file before an uploaded replacement overwrites it.

WinSCP adds a deletion timestamp to the relocated filename. The bin also applies to modifications during synchronization. Deleting or overwriting an item already inside that remote bin is permanent under this mechanism, so do not use the bin itself as the destination for another test overwrite.

Because this behaviour belongs to the configured client operation, do not infer protection for a deletion issued by another client or by a server process. Establish those systems' actual retention arrangements separately.

Rehearse recovery with disposable versions

In a test folder under your control, create a text file containing a clear version marker. With the intended deletion option enabled, delete only that disposable sample through WinSCP. Inspect the configured remote bin and identify its timestamped entry by content as well as name.

Copy the recovered sample to a new recovery folder and open it. Keep the original test location separate so the rehearsal does not overwrite newer work. This verifies the usable recovery path and your account's access to it.

If overwrite protection is also required, conduct a separate SFTP rehearsal using two recognisable versions. Confirm the current destination contains the replacement and the bin contains the earlier version. A successful deletion rehearsal does not establish overwrite protection.

Document the tested site, options and recovery directory with the workflow. Plan server backups and retention independently: moving a file elsewhere on the same server does not demonstrate that it survives a server failure or a later cleanup of that directory.

Sources: WinSCP documentation.