Web admin not working after reboot

Expected Behaviour:

Web interface should be accessible after a reboot following initial install or pihole -r.

Actual Behaviour:

Web admin does not resolve at static IP address after reboot following either initial install or pihole -r. Web admin is available following install or a pihole -r reconfiguration, but fails to resolve once OS is rebooted. Another symptom: http://pi.hole/admin is also inaccessible.

Status check indicates DNS is running and blocking is enabled following reboot.

Debug Token:

1optk28s5c

What is the output of sudo service lighttpd status after a reboot?

Posted below, and I have also generated a new debug token (1optk28s5c) because the other expired.

● lighttpd.service - Lighttpd Daemon
   Loaded: loaded (/lib/systemd/system/lighttpd.service; enabled; vendor preset: enabled)
   Active: active (running) since Sun 2018-10-21 16:21:42 EDT; 21s ago
  Process: 651 ExecStartPre=/usr/sbin/lighttpd -tt -f /etc/lighttpd/lighttpd.conf (code=exited, status=0/SUCCESS)
 Main PID: 674 (lighttpd)
   CGroup: /system.slice/lighttpd.service
           ├─674 /usr/sbin/lighttpd -D -f /etc/lighttpd/lighttpd.conf
           ├─683 /usr/bin/php-cgi
           ├─684 /usr/bin/php-cgi
           ├─685 /usr/bin/php-cgi
           ├─686 /usr/bin/php-cgi
           └─687 /usr/bin/php-cgi

Oct 21 16:21:42 haus systemd[1]: Starting Lighttpd Daemon...
Oct 21 16:21:42 haus systemd[1]: Started Lighttpd Daemon.

I don't see any issues in your log. What is the output of curl http://pi.hole/admin/api.php?summary

{"domains_being_blocked":"129,536","dns_queries_today":"52","ads_blocked_today":"4","ads_percentage_today":"7.7","unique_domains":"11","queries_forwarded":"22","queries_cached":"26","clients_ever_seen":"4","unique_clients":"4","dns_queries_all_types":"55","reply_NODATA":"12","reply_NXDOMAIN":"0","reply_CNAME":"0","reply_IP":"28","status":"enabled","gravity_last_updated":{"file_exists":true,"absolute":1540106105,"relative":{"days":"0","hours":"13","minutes":"12"}}}

Are you unable to access the web interface still? I don't see any issues so far.

Correct, Pi-hole static ip is timing out: ERR_CONNECTION_TIMED_OUT

I'm going to check my Ubiquiti USG and switch to see if there is something I am missing. It's odd that it happens after reboot from fresh Pi-hole installs

Do you only get that error when trying to access the web page from another device? Are you able to load the web interface on the Pi-hole device (at least via curl)?

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