Updating Database from Windows

Tried every solution that’s already been offered around here but I simply cannot update an SQLite database. Tried this and got permission denied (yes I have proxy running in another window)
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I’m not able to use sftp because it refuses to overwrite files that already exist on the VM. (I’m only limited to cd, ls, get, put, and chmod commands.)
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Attempting to register an SSH key to my local agent results in this error:
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What should I do now?