Seems since 4.0.7 (and maybe 4.0.6) after suspend WireGuard doesn't always seem to connect.
It might be related to "Block all incoming connections" is enabled in macOS firewall, but the VPN (/Applications/eduVPN.app/Contents/PlugIns/TunnelExtension-macOS.appex) is explicit allowed, so in the past there was no issue.
In Connection log:
2026年06月04日 09:04:15.094 Network change detected with satisfied route and interface order [en9, en9, utun8, en0]
2026年06月04日 09:04:15.094 Routine: receive incoming v6 - stopped
2026年06月04日 09:04:15.094 Routine: receive incoming v4 - stopped
2026年06月04日 09:04:15.095 UDP bind has been updated
2026年06月04日 09:04:15.095 Routine: receive incoming v4 - started
2026年06月04日 09:04:15.095 peer(NKrI...arBc) - Sending keepalive packet
2026年06月04日 09:04:15.095 Routine: receive incoming v6 - started
2026年06月04日 09:04:26.663 peer(NKrI...arBc) - Retrying handshake because we stopped hearing back after 15 seconds
2026年06月04日 09:04:26.664 peer(NKrI...arBc) - Sending handshake initiation
2026年06月04日 09:04:31.772 peer(NKrI...arBc) - Handshake did not complete after 5 seconds, retrying (try 2)
2026年06月04日 09:04:31.773 peer(NKrI...arBc) - Sending handshake initiation
2026年06月04日 09:04:36.996 peer(NKrI...arBc) - Handshake did not complete after 5 seconds, retrying (try 3)
2026年06月04日 09:04:36.997 peer(NKrI...arBc) - Sending handshake initiation
2026年06月04日 09:04:41.928 peer(NKrI...arBc) - Retrying handshake because we stopped hearing back after 15 seconds
2026年06月04日 09:04:42.253 peer(NKrI...arBc) - Handshake did not complete after 5 seconds, retrying (try 2)
2026年06月04日 09:04:42.253 peer(NKrI...arBc) - Sending handshake initiation
2026年06月04日 09:04:47.488 peer(NKrI...arBc) - Handshake did not complete after 5 seconds, retrying (try 3)
2026年06月04日 09:04:47.488 peer(NKrI...arBc) - Sending handshake initiation
2026年06月04日 09:04:52.802 peer(NKrI...arBc) - Handshake did not complete after 5 seconds, retrying (try 4)
2026年06月04日 09:04:52.802 peer(NKrI...arBc) - Sending handshake initiation
2026年06月04日 09:04:56.978 peer(NKrI...arBc) - Retrying handshake because we stopped hearing back after 15 seconds
2026年06月04日 09:04:57.924 peer(NKrI...arBc) - Handshake did not complete after 5 seconds, retrying (try 2)
The double "en9" interface is weird and am seeing this on other devices too.
Have disabled "Block all incoming connections" in firewall to experience if this "solves" the issue.