An error after an upload can describe a failed follow-up operation rather than a failed content transfer. Read the complete WinSCP message before sending the same file again, particularly when the destination automatically imports each arriving file.

Record the destination path, filename, attempt time and the full error details. Preserve the local source. The important question is which stage failed: transferring content, applying metadata, or processing the file in the receiving application.

Interpret the post-transfer failure narrowly

WinSCP documents a message stating that upload succeeded but setting permissions or a timestamp failed. Possible reasons include an account that can write content without owning the file, a server that does not support the requested metadata operation, or a receiving process that already moved or deleted the uploaded file.

The detail helps distinguish these cases. A permission denial, an unsupported-operation response and a missing-path response are different evidence. None should automatically be relabelled as a broken connection or proof that the remote content never arrived.

For an automated import folder, ask the responsible operator to check the receiving application's records for that exact attempt. A missing file in the incoming folder may mean it was consumed; uploading again before resolving that state can create another submission.

Decide whether the metadata requirement can change

If the workflow does not require the failing metadata operation, WinSCP documents disabling Set permissions or Preserve timestamp, or using Ignore permission errors as appropriate. Make that decision against the delivery requirements rather than merely hiding an inconvenient message.

Timestamp-based synchronization needs special care: disabling timestamp preservation also requires reconsidering the modification-time comparison criterion. Do not change that assumption in a working synchronization task without reviewing what it uses to decide which files differ.

Use a harmless sample for the revised settings, then check both the remote content and the metadata that still matters. Where a consumer is involved, confirm its recorded outcome separately. A quiet transfer dialog is not sufficient if a required permission or import result remains wrong.

Only retry the original delivery after establishing whether it is missing and whether a repeat is appropriate. Keep the accepted settings and the recipient's outcome with the attempt record. This turns an ambiguous red error into a specific, reviewable status without inventing a failure or duplicating work already received.

Sources: WinSCP documentation.