Yes, it would be nice to have WinSCP automatically ignore timestamp errors.
I'm having issues uploading files with WinSCP script method.
If the timestamp is invalid (just a time for example, no date) WinSCP just dies and quits when attempting to modify the timestamp.
There should be an option (scriptable too!) that tells WinSCP to ignore any errors while attempting to modify the timestamp.
I think the solution is here: https://winscp.net/eng/docs/library_from_script_transfer_settings
$transferOptions = New-Object WinSCP.TransferOptions
$transferOptions.FilePermissions = $Null # This is default
$transferOptions.PreserveTimestamp = $False
Unfortunately, I do not know how to implement it in a script.