Under Settings go to Reconnect.
Select all three available options:
- Auto Reconnect Enabled
- Do not start downloads if others wait for a Reconnect
- Reconnects can interrupt resumable downloads
Under Reconnect Method select: External Batch Reconnect
Under Interpreter type: /bin/bash -c
Under Batch Script type:
./expressvpn background enable
./expressvpn disconnect
./expressvpn connect
Finally under Start in (application folder) type: /usr/local/bin
Took me a while to figure this out. Sharing here for posterity.