DNS server stops responding constantly

Expected Behaviour:

-operating system Linux Ubuntu 16.04.6
-hardware VM on a QNAP TS-451a

Expecting pi-hole to run like it did previously on 4.4.4.

Actual Behaviour:

As soon as I updated to 5.0, the issues began with the DNS resolution after the reboot of the VM or the server. Attempted fresh install of the OS as well as several different configurations, problems do not stop. If left for a couple of days, the server stops responding to any DNS requests. Please can you help me fix this once and for all?

Debug Token:

(Moderator edit: removed explicit debug log from public view)

[✗] There was an error uploading your debug log.

  • Please try again or contact the Pi-hole team for assistance.
  • A local copy of the debug log can be found at: /var/log/pihole_debug.log

Your debug log shows some problems in your network configuration:

*** [ DIAGNOSING ]: Networking
[✓] IPv4 address(es) bound to the ens3 interface:
   192.168.1.77/24 does not match the IP found in /etc/pihole/setupVars.conf 
   192.168.1.88/24 matches the IP found in /etc/pihole/setupVars.conf

[i] Default IPv4 gateway: 192.168.1.1
[✗] Gateway did not respond

*** [ DIAGNOSING ]: Ports in use
[53] is in use by pihole-FTL
[53] is in use by dnsmasq

*** [ DIAGNOSING ]: Name resolution (IPv4) using a random blocked domain and a known ad-serving domain
[✓] qpelznewstar.com is 0.0.0.0 via localhost (127.0.0.1)
[✗] Failed to resolve qpelznewstar.com via Pi-hole (192.168.1.88)
[✗] Failed to resolve doubleclick.com via a remote, public DNS server (8.8.8.8)

You seem to have assigned two IP addresses to the same network interface - is this by intention?
Note that your Pi-hole is only aware of one of them (.88), but fails to resolve hostnames via that one.

Also, it seems you are running an instance of dnsmasq in parallel to Pi-hole.
As this would lead to conflicts over port 53 and who's actually answering queries, you should disable it.

I think you just fixed my biggest headache.... I was constantly trying to avoid changing the DNS server on the router, by setting Pi-hole IP statically when configuring the installation. That was my issue. For whatever reason, it does not force the IP change of the VM, hence there were two IP addresses... DNSmasq is also disabled now. Thanks a million!

it stopped working again after the reboot of the VM...

Please can you take a look what is wrong now.. :frowning:

https://tricorder.pi-hole.net/4f809gh4lh

so it sometimes does not start at all, sometimes it is started and is looking okay but is not serving dns requests until the dns service is restarted. Mind boggling.

pihole-FTL is not running. What are the outputs of the following from the Pi command prompt:

sudo netstat -nltup | grep 'Proto\|:53 \|:5053 \|:5353 \|:5335 \|:8953 \|:67 \|:80 \|:471'

sudo service pihole-FTL status

new set of logs below. Upload fails so here's the lot.

This process collects information from your Pi-hole, and optionally uploads it to a unique and random directory on tricorder.pi-hole.net.

The intent of this script is to allow users to self-diagnose their installations.  This is accomplished by running tests against our software and providing the user with links to FAQ articles when a problem is detected.  Since we are a small team and Pi-hole has been growing steadily, it is our hope that this will help us spend more time on development.

NOTE: All log files auto-delete after 48 hours and ONLY the Pi-hole developers can access your data via the given token. We have taken these extra steps to secure your data and will work to further reduce any personal information gathered.

*** [ INITIALIZING ]
[i] 2020-06-17:10:09:24 debug log has been initialized.

*** [ INITIALIZING ] Sourcing setup variables
[i] Sourcing /etc/pihole/setupVars.conf...

*** [ DIAGNOSING ]: Core version
[i] Core: v5.0 (https://discourse.pi-hole.net/t/how-do-i-update-pi-hole/249)
[i] Branch: master
[i] Commit: v5.0-0-g4d25f69

*** [ DIAGNOSING ]: Web version
[i] Web: v5.0 (https://discourse.pi-hole.net/t/how-do-i-update-pi-hole/249)
[i] Branch: master
[i] Commit: v5.0-0-gb86e4a3

*** [ DIAGNOSING ]: FTL version
[✓] FTL: v5.0

*** [ DIAGNOSING ]: lighttpd version
[i] 1.4.35

*** [ DIAGNOSING ]: php version
[i] 7.0.33

*** [ DIAGNOSING ]: Operating system
[✓] Ubuntu 16.04.6 LTS

*** [ DIAGNOSING ]: SELinux
[i] SELinux not detected

*** [ DIAGNOSING ]: Processor
[i] x86_64

*** [ DIAGNOSING ]: Networking
[✓] IPv4 address(es) bound to the ens3 interface:
   192.168.1.88/24 matches the IP found in /etc/pihole/setupVars.conf

[✓] IPv6 address(es) bound to the ens3 interface:
   fe80::d0f3:2eff:b7c2:5f05 does not match the IP found in /etc/pihole/setupVars.conf (https://discourse.pi-hole.net/t/use-ipv6-ula-addresses-for-pi-hole/2127)

   ^ Please note that you may have more than one IP address listed.
   As long as one of them is green, and it matches what is in /etc/pihole/setupVars.conf, there is no need for concern.

   The link to the FAQ is for an issue that sometimes occurs when the IPv6 address changes, which is why we check for it.

[i] Default IPv4 gateway: 192.168.1.1
   * Pinging 192.168.1.1...
[✓] Gateway responded.

*** [ DIAGNOSING ]: Ports in use
[::1]:631 cupsd (IPv6)
127.0.0.1:631 cupsd (IPv4)
[53] is in use by pihole-FTL
[53] is in use by pihole-FTL
[53] is in use by pihole-FTL
[4711] is in use by pihole-FTL
[4711] is in use by pihole-FTL
[80] is in use by lighttpd
[80] is in use by lighttpd

*** [ DIAGNOSING ]: Name resolution (IPv4) using a random blocked domain and a known ad-serving domain
[✓] forrentarubacom.domainstel.org is 0.0.0.0 via localhost (127.0.0.1)
[✗] Failed to resolve forrentarubacom.domainstel.org via Pi-hole (192.168.1.88)
[✓] doubleclick.com is 216.58.204.78 via a remote, public DNS server (8.8.8.8)

*** [ DIAGNOSING ]: Pi-hole processes
[✓] lighttpd daemon is active
[✓] pihole-FTL daemon is active

*** [ DIAGNOSING ]: Setup variables
    PIHOLE_INTERFACE=ens3
    IPV4_ADDRESS=192.168.1.88/24
    IPV6_ADDRESS=
    PIHOLE_DNS_1=1.1.1.1
    PIHOLE_DNS_2=1.0.0.1
    QUERY_LOGGING=true
    INSTALL_WEB_SERVER=true
    INSTALL_WEB_INTERFACE=true
    LIGHTTPD_ENABLED=true
    BLOCKING_ENABLED=true

*** [ DIAGNOSING ]: Dashboard and block page
[✓] Block page X-Header: X-Pi-hole: A black hole for Internet advertisements.
[✓] Web interface X-Header: X-Pi-hole: The Pi-hole Web interface is working!

*** [ DIAGNOSING ]: Gravity List and Database
-rw-rw-r-- 1 pihole pihole 5227520 Jun 14 03:02 /etc/pihole/gravity.db

*** [ DIAGNOSING ]: Info table
   property              value                                   
   --------------------  ----------------------------------------
   version               12                                      
   updated               1592100129                              
   gravity_count         84609                                   
   Last gravity run finished at: Sun 14 Jun 03:02:09 BST 2020

   ----- First 10 Gravity Domains -----
   localhost.localdomain
   01mspmd5yalky8.com
   0byv9mgbn0.com
   analytics.247sports.com
   www.analytics.247sports.com
   2no.co
   www.2no.co
   logitechlogitechglobal.112.2o7.net
   www.logitechlogitechglobal.112.2o7.net
   30-day-change.com


*** [ DIAGNOSING ]: Groups
   id    enabled  name                                                date_added           date_modified        description                                       
   ----  -------  --------------------------------------------------  -------------------  -------------------  --------------------------------------------------
   0           1  Default                                             2020-06-12 16:55:34  2020-06-12 16:55:34  The default group                                 

*** [ DIAGNOSING ]: Domainlist (0/1 = exact white-/blacklist, 2/3 = regex white-/blacklist)

*** [ DIAGNOSING ]: Clients

*** [ DIAGNOSING ]: Adlists
   id    enabled  group_ids     address                                                                                               date_added           date_modified        comment                                           
   ----  -------  ------------  ----------------------------------------------------------------------------------------------------  -------------------  -------------------  --------------------------------------------------
   1           1  0             https://raw.githubusercontent.com/StevenBlack/hosts/master/hosts                                      2020-06-12 16:55:35  2020-06-12 16:55:35  Migrated from /etc/pihole/adlists.list            
   2           1  0             https://mirror1.malwaredomains.com/files/justdomains                                                  2020-06-12 16:55:35  2020-06-12 16:55:35  Migrated from /etc/pihole/adlists.list            
   3           1  0             https://s3.amazonaws.com/lists.disconnect.me/simple_tracking.txt                                      2020-06-12 16:55:35  2020-06-12 16:55:35  Migrated from /etc/pihole/adlists.list            
   4           1  0             https://s3.amazonaws.com/lists.disconnect.me/simple_ad.txt                                            2020-06-12 16:55:35  2020-06-12 16:55:35  Migrated from /etc/pihole/adlists.list            

*** [ DIAGNOSING ]: contents of /etc/pihole

-rw-r--r-- 1 root root 44 Jun 14 03:02 /etc/pihole/local.list
   192.168.1.88 Pi-hole16
   192.168.1.88 pi.hole

-rw-r--r-- 1 root root 238 Jun 12 16:55 /etc/pihole/logrotate
   /var/log/pihole.log {
   	su root syslog
   	daily
   	copytruncate
   	rotate 5
   	compress
   	delaycompress
   	notifempty
   	nomail
   }
   /var/log/pihole-FTL.log {
   	su root syslog
   	weekly
   	copytruncate
   	rotate 3
   	compress
   	delaycompress
   	notifempty
   	nomail
   }

*** [ DIAGNOSING ]: contents of /etc/dnsmasq.d

-rw-r--r-- 1 root root 1385 Jun 12 16:55 /etc/dnsmasq.d/01-pihole.conf
   addn-hosts=/etc/pihole/local.list
   addn-hosts=/etc/pihole/custom.list
   localise-queries
   no-resolv
   cache-size=10000
   log-queries
   log-facility=/var/log/pihole.log
   local-ttl=2
   log-async
   server=1.1.1.1
   server=1.0.0.1
   interface=ens3
   server=/use-application-dns.net/

*** [ DIAGNOSING ]: contents of /etc/lighttpd

-rw-r--r-- 1 root root 3499 Jun 12 16:55 /etc/lighttpd/lighttpd.conf
   server.modules = (
   	"mod_access",
   	"mod_accesslog",
   	"mod_auth",
   	"mod_expire",
   	"mod_compress",
   	"mod_redirect",
   	"mod_setenv",
   	"mod_rewrite"
   )
   server.document-root        = "/var/www/html"
   server.error-handler-404    = "/pihole/index.php"
   server.upload-dirs          = ( "/var/cache/lighttpd/uploads" )
   server.errorlog             = "/var/log/lighttpd/error.log"
   server.pid-file             = "/var/run/lighttpd.pid"
   server.username             = "www-data"
   server.groupname            = "www-data"
   server.port                 = 80
   accesslog.filename          = "/var/log/lighttpd/access.log"
   accesslog.format            = "%{%s}t|%V|%r|%s|%b"
   index-file.names            = ( "index.php", "index.html", "index.lighttpd.html" )
   url.access-deny             = ( "~", ".inc", ".md", ".yml", ".ini" )
   static-file.exclude-extensions = ( ".php", ".pl", ".fcgi" )
   compress.cache-dir          = "/var/cache/lighttpd/compress/"
   compress.filetype           = ( "application/javascript", "text/css", "text/html", "text/plain" )
   mimetype.assign   = ( ".png"  => "image/png",
                         ".jpg"  => "image/jpeg",
                         ".jpeg" => "image/jpeg",
                         ".html" => "text/html",
                         ".css" => "text/css; charset=utf-8",
                         ".js" => "application/javascript",
                         ".json" => "application/json",
                         ".txt"  => "text/plain",
                         ".svg"  => "image/svg+xml" )
   include_shell "/usr/share/lighttpd/use-ipv6.pl " + server.port
   include_shell "find /etc/lighttpd/conf-enabled -name '*.conf' -a ! -name 'letsencrypt.conf' -printf 'include \"%p\"
' 2>/dev/null"
   $HTTP["url"] =~ "^/admin/" {
       
       setenv.add-response-header = (
           "X-Pi-hole" => "The Pi-hole Web interface is working!",
           "X-Frame-Options" => "DENY"
       )
       $HTTP["url"] =~ ".ttf$" {
           
           setenv.add-response-header = ( "Access-Control-Allow-Origin" => "*" )
       }
   }
   $HTTP["url"] =~ "^/admin/\.(.*)" {
        url.access-deny = ("")
   }
   include_shell "cat external.conf 2>/dev/null"

*** [ DIAGNOSING ]: contents of /etc/cron.d

-rw-r--r-- 1 root root 1703 Jun 12 16:55 /etc/cron.d/pihole
   2 3   * * 7   root    PATH="$PATH:/usr/local/bin/" pihole updateGravity >/var/log/pihole_updateGravity.log || cat /var/log/pihole_updateGravity.log
   00 00   * * *   root    PATH="$PATH:/usr/local/bin/" pihole flush once quiet
   @reboot root /usr/sbin/logrotate /etc/pihole/logrotate
   */10 *  * * *   root    PATH="$PATH:/usr/local/bin/" pihole updatechecker local
   34 19  * * *   root    PATH="$PATH:/usr/local/bin/" pihole updatechecker remote
   @reboot root    PATH="$PATH:/usr/local/bin/" pihole updatechecker remote reboot

*** [ DIAGNOSING ]: contents of /var/log/lighttpd

-rw-r--r-- 1 www-data www-data 194 Jun 17  2020 /var/log/lighttpd/error.log
   2020-06-14 07:35:03: (server.c.1242) logfiles cycled UID = 0 PID = 1099 
   2020-06-17 08:36:43: (server.c.1558) server stopped by UID = 0 PID = 1 
   2020-06-17 10:36:06: (log.c.164) server started 

*** [ DIAGNOSING ]: contents of /var/log

-rw-r--r-- 1 pihole pihole 4943 Jun 17  2020 /var/log/pihole-FTL.log
   -----head of pihole-FTL.log------
   [2020-06-17 06:41:06.593 2583] Resizing "/FTL-strings" from 122880 to 126976
   [2020-06-17 06:41:08.396 2583] Resizing "/FTL-dns-cache" from 118784 to 122880
   [2020-06-17 08:36:43.925 2583] IPv4 telnet error: Interrupted system call (4)
   [2020-06-17 08:36:44.059 2583] Shutting down...
   [2020-06-17 08:36:45.791 2583] Finished final database update
   [2020-06-17 08:36:45.819 2583] ########## FTL terminated after 3.908172e+05 s! ##########
   [2020-06-17 10:36:02.755 816] Using log file /var/log/pihole-FTL.log
   [2020-06-17 10:36:03.096 816] ########## FTL started! ##########
   [2020-06-17 10:36:03.096 816] FTL branch: master
   [2020-06-17 10:36:03.096 816] FTL version: v5.0
   [2020-06-17 10:36:03.096 816] FTL commit: 3d7c095
   [2020-06-17 10:36:03.096 816] FTL date: 2020-05-10 18:58:38 +0100
   [2020-06-17 10:36:03.096 816] FTL user: pihole
   [2020-06-17 10:36:03.096 816] Compiled for x86_64 (compiled on CI) using gcc (Debian 6.3.0-18+deb9u1) 6.3.0 20170516
   [2020-06-17 10:36:03.096 816] Starting config file parsing (/etc/pihole/pihole-FTL.conf)
   [2020-06-17 10:36:03.097 816]    SOCKET_LISTENING: only local
   [2020-06-17 10:36:03.097 816]    AAAA_QUERY_ANALYSIS: Show AAAA queries
   [2020-06-17 10:36:03.097 816]    MAXDBDAYS: max age for stored queries is 365 days
   [2020-06-17 10:36:03.097 816]    RESOLVE_IPV6: Resolve IPv6 addresses
   [2020-06-17 10:36:03.097 816]    RESOLVE_IPV4: Resolve IPv4 addresses
   [2020-06-17 10:36:03.097 816]    DBINTERVAL: saving to DB file every minute
   [2020-06-17 10:36:03.097 816]    DBFILE: Using /etc/pihole/pihole-FTL.db
   [2020-06-17 10:36:03.097 816]    MAXLOGAGE: Importing up to 24.0 hours of log data
   [2020-06-17 10:36:03.097 816]    PRIVACYLEVEL: Set to 0
   [2020-06-17 10:36:03.097 816]    IGNORE_LOCALHOST: Show queries from localhost
   [2020-06-17 10:36:03.097 816]    BLOCKINGMODE: Null IPs for blocked domains
   [2020-06-17 10:36:03.098 816]    ANALYZE_ONLY_A_AND_AAAA: Disabled. Analyzing all queries
   [2020-06-17 10:36:03.098 816]    DBIMPORT: Importing history from database
   [2020-06-17 10:36:03.098 816]    PIDFILE: Using /var/run/pihole-FTL.pid
   [2020-06-17 10:36:03.098 816]    PORTFILE: Using /var/run/pihole-FTL.port
   [2020-06-17 10:36:03.098 816]    SOCKETFILE: Using /var/run/pihole/FTL.sock
   [2020-06-17 10:36:03.098 816]    SETUPVARSFILE: Using /etc/pihole/setupVars.conf
   [2020-06-17 10:36:03.098 816]    MACVENDORDB: Using /etc/pihole/macvendor.db
   [2020-06-17 10:36:03.098 816]    GRAVITYDB: Using /etc/pihole/gravity.db
   [2020-06-17 10:36:03.098 816]    PARSE_ARP_CACHE: Active

   -----tail of pihole-FTL.log------
   [2020-06-17 10:36:03.098 816]    DELAY_STARTUP: No delay requested.
   [2020-06-17 10:36:03.099 816]    BLOCK_ESNI: Enabled, blocking _esni.{blocked domain}
   [2020-06-17 10:36:03.099 816] Finished config file parsing
   [2020-06-17 10:36:03.557 816] Database version is 5
   [2020-06-17 10:36:03.558 816] Database successfully initialized
   [2020-06-17 10:36:03.652 816] New upstream server: 1.0.0.1 (0/128)
   [2020-06-17 10:36:03.654 816] New upstream server: 1.1.1.1 (1/128)
   [2020-06-17 10:36:03.822 816] Resizing "/FTL-strings" from 4096 to 8192
   [2020-06-17 10:36:03.877 816] Resizing "/FTL-strings" from 8192 to 12288
   [2020-06-17 10:36:03.964 816] Resizing "/FTL-strings" from 12288 to 16384
   [2020-06-17 10:36:04.095 816] Resizing "/FTL-queries" from 262144 to 524288
   [2020-06-17 10:36:04.124 816] Resizing "/FTL-strings" from 16384 to 20480
   [2020-06-17 10:36:04.134 816] Resizing "/FTL-strings" from 20480 to 24576
   [2020-06-17 10:36:04.168 816] Resizing "/FTL-strings" from 24576 to 28672
   [2020-06-17 10:36:04.214 816] Resizing "/FTL-queries" from 524288 to 786432
   [2020-06-17 10:36:04.503 816] Resizing "/FTL-strings" from 28672 to 32768
   [2020-06-17 10:36:04.520 816] Imported 11243 queries from the long-term database
   [2020-06-17 10:36:04.520 816]  -> Total DNS queries: 11243
   [2020-06-17 10:36:04.521 816]  -> Cached DNS queries: 923
   [2020-06-17 10:36:04.521 816]  -> Forwarded DNS queries: 8882
   [2020-06-17 10:36:04.521 816]  -> Blocked DNS queries: 1436
   [2020-06-17 10:36:04.521 816]  -> Unknown DNS queries: 2
   [2020-06-17 10:36:04.521 816]  -> Unique domains: 1328
   [2020-06-17 10:36:04.521 816]  -> Unique clients: 13
   [2020-06-17 10:36:04.521 816]  -> Known forward destinations: 2
   [2020-06-17 10:36:04.521 816] Successfully accessed setupVars.conf
   [2020-06-17 10:36:04.664 873] PID of FTL process: 873
   [2020-06-17 10:36:04.664 873] Listening on port 4711 for incoming IPv4 telnet connections
   [2020-06-17 10:36:04.664 873] Listening on port 4711 for incoming IPv6 telnet connections
   [2020-06-17 10:36:04.665 873] Listening on Unix socket
   [2020-06-17 10:36:05.018 873] Reloading DNS cache
   [2020-06-17 10:36:05.019 873] Blocking status is enabled
   [2020-06-17 10:36:05.045 873] INFO: No regex blacklist entries found
   [2020-06-17 10:36:05.053 873] INFO: No regex whitelist entries found
   [2020-06-17 10:36:05.063 873] Compiled 0 whitelist and 0 blacklist regex filters in 19.1 msec

*** [ DIAGNOSING ]: contents of /dev/shm
-rw------- 1 pihole pihole 20480 Jun 17  2020 /dev/shm/FTL-clients
-rw------- 1 pihole pihole 124 Jun 17  2020 /dev/shm/FTL-counters
-rw------- 1 pihole pihole 4096 Jun 17  2020 /dev/shm/FTL-dns-cache
-rw------- 1 pihole pihole 98304 Jun 17  2020 /dev/shm/FTL-domains
-rw------- 1 pihole pihole 48 Jun 17  2020 /dev/shm/FTL-lock
-rw------- 1 pihole pihole 12288 Jun 17  2020 /dev/shm/FTL-overTime
-rw------- 1 pihole pihole 4096 Jun 17  2020 /dev/shm/FTL-per-client-regex
-rw------- 1 pihole pihole 786432 Jun 17  2020 /dev/shm/FTL-queries
-rw------- 1 pihole pihole 12 Jun 17  2020 /dev/shm/FTL-settings
-rw------- 1 pihole pihole 32768 Jun 17  2020 /dev/shm/FTL-strings
-rw------- 1 pihole pihole 4096 Jun 17  2020 /dev/shm/FTL-upstreams
-rwx------ 1 lightdm lightdm 67108904 Jun 17  2020 /dev/shm/pulse-shm-1278890742
-rwx------ 1 volcano4life volcano4life 67108904 Jun 17 09:59 /dev/shm/pulse-shm-15440288
-rwx------ 1 volcano4life volcano4life 67108904 Jun 17 09:59 /dev/shm/pulse-shm-2495114010
-rwx------ 1 volcano4life volcano4life 67108904 Jun 17 09:59 /dev/shm/pulse-shm-2691536280
-rwx------ 1 lightdm lightdm 67108904 Jun 17  2020 /dev/shm/pulse-shm-3088634048
-rwx------ 1 volcano4life volcano4life 67108904 Jun 17 09:59 /dev/shm/pulse-shm-3667466219
-rwx------ 1 lightdm lightdm 67108904 Jun 17  2020 /dev/shm/pulse-shm-435658976
-rwx------ 1 volcano4life volcano4life 67108904 Jun 17 09:59 /dev/shm/pulse-shm-469181608

*** [ DIAGNOSING ]: Locale
    LANG=en_GB.UTF-8

*** [ DIAGNOSING ]: Pi-hole log
-rw-r--r-- 1 pihole pihole 1576588 Jun 17 10:09 /var/log/pihole.log
   -----head of pihole.log------
   Jun 17 00:00:06 dnsmasq[2583]: query[A] weather-data.apple.com from 192.168.1.64
   Jun 17 00:00:06 dnsmasq[2583]: forwarded weather-data.apple.com to 1.0.0.1
   Jun 17 00:00:06 dnsmasq[2583]: query[A] weather-edge.news.apple-dns.net from 192.168.1.64
   Jun 17 00:00:06 dnsmasq[2583]: forwarded weather-edge.news.apple-dns.net to 1.0.0.1
   Jun 17 00:00:06 dnsmasq[2583]: query[A] configuration.ls.apple.com from 192.168.1.64
   Jun 17 00:00:06 dnsmasq[2583]: forwarded configuration.ls.apple.com to 1.0.0.1
   Jun 17 00:00:06 dnsmasq[2583]: reply weather-data.apple.com is <CNAME>
   Jun 17 00:00:06 dnsmasq[2583]: reply weather-data.apple.com.akadns.net is <CNAME>
   Jun 17 00:00:06 dnsmasq[2583]: reply weather-data.apple.com.akamaized.net is <CNAME>
   Jun 17 00:00:06 dnsmasq[2583]: reply a2047.dscb.akamai.net is 2.21.75.59
   Jun 17 00:00:06 dnsmasq[2583]: reply a2047.dscb.akamai.net is 2.21.75.64
   Jun 17 00:00:06 dnsmasq[2583]: reply a2047.dscb.akamai.net is 2.21.75.65
   Jun 17 00:00:06 dnsmasq[2583]: reply a2047.dscb.akamai.net is 2.21.75.67
   Jun 17 00:00:06 dnsmasq[2583]: reply a2047.dscb.akamai.net is 2.21.75.57
   Jun 17 00:00:06 dnsmasq[2583]: reply a2047.dscb.akamai.net is 2.21.75.56
   Jun 17 00:00:06 dnsmasq[2583]: reply a2047.dscb.akamai.net is 2.21.75.72
   Jun 17 00:00:06 dnsmasq[2583]: reply a2047.dscb.akamai.net is 2.21.75.51
   Jun 17 00:00:06 dnsmasq[2583]: reply a2047.dscb.akamai.net is 2.21.75.58
   Jun 17 00:00:06 dnsmasq[2583]: reply weather-edge.news.apple-dns.net is 17.56.48.13
   Jun 17 00:00:06 dnsmasq[2583]: reply configuration.ls.apple.com is <CNAME>


********************************************
********************************************
[✓] ** FINISHED DEBUGGING! **

    * The debug log can be uploaded to tricorder.pi-hole.net for sharing with developers only.
    * For more information, see: https://pi-hole.net/2016/11/07/crack-our-medical-tricorder-win-a-raspberry-pi-3/
    * If available, we'll use openssl to upload the log, otherwise it will fall back to netcat.
[i] Debug script running in automated mode
    * Using curl for transmission.
[✗]  There was an error uploading your debug log.
   * Please try again or contact the Pi-hole team for assistance.
   * A local copy of the debug log can be found at: /var/log/pihole_debug.log

same issue btw. FTL seems to be running but still no DNS resolution. Well at least pi.hole does noty resolve, that makes me think it's not working properly.

I will try the above commands now and restart the dns resolver

another DNS resolver restart and issue fixed itself, until the next server reboot at least...

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