It turned out that I was missing "askpass" in my VPN config. This was
not required before but now is.

With this new option in place, things work well and the password prompt
is broadcast to all the consoles thanks to systemd-ask-password-wall.

Since I don't wanted the "wall" like behaviour, I changed it to only the
invoking console using those commands:

  systemctl disable systemd-ask-password-wall.service
  systemctl disable systemd-ask-password-wall.path
  systemctl stop systemd-ask-password-wall.service
  systemctl stop systemd-ask-password-wall.path
  systemctl enable systemd-ask-password-console.service
  systemctl start systemd-ask-password-console.service

** Changed in: openvpn (Ubuntu)
       Status: New => Invalid

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https://bugs.launchpad.net/bugs/1530674

Title:
  Trouble unlocking a password-locked private key

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