The upgrade to macOS Catalina deleted my WireGuard VPN client configuration, includes my private key 
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Seems stable now for me (after I re-configured the tunnel).
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Just happened again. After restart the tunnel configuration disappeared. Fortunately I’ve saved a backup of the config... Using the latest version of the client (macOS) and server (Ubuntu).
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I can only offer that the 3 times I've experienced it so far, each time it's been after waking my MacBook Pro. The WireGuard tunnel dialog box is front and center showing that my tunnels are gone.
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Will follow up via DM for additional debugging you can help with.
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