Hi Matt,
By default transfer tasks will continue to attempt to retry most errors for up to three days before expiring. If your task still shows up in the Activity page when you search for active tasks then it is still periodically attempting to make progress and should pickup where it left off if the underlying issue can be resolved.
The error you're getting seems to be coming from your file system. I would recommend investigating the path in the error message locally to see if you can determine the cause of the issue. If you need assistance we might be able to help more in a support ticket, although issues with the filesystem itself are out of our control.
If you do need to resubmit the task or submit a new task with potential for overlap you can enable the sync option to only transfer files that are not found at the destination and avoid re-transferring the files that have already been transferred.