Re: Timeout when calculating the remote checksum
You can instead disable (or prolong) the reconnect on stall:
https://winscp.net/eng/docs/ui_pref_resume
https://winscp.net/eng/docs/ui_pref_resume
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sha256sum
process on the remote server continues to run).
sha256sum
does not seem to provide any "--progress" or something, thus I'm not sure if there's an easy way to monitor the real progress. Maybe, as a better workaround, it is possible to add something like "expected minimum sha256sum speed (MB/s)" setting in WinSCP and calculate the actual timeout based on the file size.