I upvoted this post over on the Super User site that tells a remote machine to use a command line PIN entry program rather than the default GUI Passphrase dialog (screenshot). This helped me when SSHing from a Pixelbook to an Intel NUC Skull Canyon running Ubuntu 18.04. I am using pass (Unix Password Manager) to grab a password. The GUI prompt was appearing on the remote machine blocking the Pixelbook.

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