Few things to note:

• Coder Connect stops itself on device sleep, and starts on device wake to workaround the issue described in Improve Coder Connect tunnel reconnect handling internal#563
• macOS calls wake on system VPNs even whilst the lid is closed.
• A new .dylib is downloaded on Coder Connect start whenever the hash of the one on the Coder deployment changes.
  • For https://dev.coder.com, this is whenever there's a push to coder/coder main (exacerbating this issue).
• When a new .dylib is downloaded, the user must approve it's execution by entering their password (see fix: unquarantine dylib after download #38 for why).
  • If that dialog times out, this is the error message returned.

Once coder/internal#563 (in review) is resolved, Coder Connect won't turn itself off on sleep, which will mean it won't restart on wake and attempt to download the latest .dylib, which will mean you won't see this anymore. but you'll still need to enter your password whenever you start Coder Connect against a fresh build of dev.coder.com.

Once #135 is complete, the user won't be prompted to enter their password when a new .dylib is downloaded, the privileged helper will take care of it.