Or let me put it the other way. Below goes what I have figured out so
far.

1. Whenever I start my virtual machine (from a "Powered Off" state)
internet via proxy does not work.

  $ env | grep -i http_proxy
  HTTP_PROXY=http://localhost:48080/
  http_proxy=http://localhost:48080/

  $ systemctl status squid
  ● squid.service - LSB: Squid HTTP Proxy version 3.x
     Loaded: loaded (/etc/init.d/squid; generated; vendor preset: enabled)
     Active: active (running) since Fri 2018-02-16 13:11:38 CET; 7min ago
       Docs: man:systemd-sysv-generator(8)
    Process: 2081 ExecReload=/etc/init.d/squid reload (code=exited, 
status=0/SUCCESS)
    Process: 383 ExecStart=/etc/init.d/squid start (code=exited, 
status=0/SUCCESS)
      Tasks: 4 (limit: 4915)                                                    
                                                                                
                    
     CGroup: /system.slice/squid.service                                        
                                                                                
                    
             ├─ 539 /usr/sbin/squid -YC -f /etc/squid/squid.conf                
                                                                                
                    
             ├─ 541 (squid-1) -YC -f /etc/squid/squid.conf                      
                                                                                
                    
             ├─2095 (logfile-daemon) /var/log/squid/access.log                  
                                                                                
                    
             └─2285 (pinger)                                                    
                                                                                
                    
                                                                                
                                                                                
                    
  Feb 16 13:11:38 hatchling squid[539]: Squid Parent: will start 1 kids         
                                                                                
                    
  Feb 16 13:11:38 hatchling squid[539]: Squid Parent: (squid-1) process 541 
started
  Feb 16 13:11:49 hatchling systemd[1]: Reloading LSB: Squid HTTP Proxy version 
3.x.
  Feb 16 13:11:49 hatchling squid[904]:  * Reloading Squid HTTP Proxy 
configuration files
  Feb 16 13:11:49 hatchling squid[904]:    ...done.
  Feb 16 13:11:49 hatchling systemd[1]: Reloaded LSB: Squid HTTP Proxy version 
3.x.
  Feb 16 13:13:58 hatchling systemd[1]: Reloading LSB: Squid HTTP Proxy version 
3.x.
  Feb 16 13:13:58 hatchling squid[2081]:  * Reloading Squid HTTP Proxy 
configuration files
  Feb 16 13:13:58 hatchling squid[2081]:    ...done.
  Feb 16 13:13:58 hatchling systemd[1]: Reloaded LSB: Squid HTTP Proxy version 
3.x.

  $ sudo netstat -tulpn | grep 48080
  tcp6       0      0 :::48080                :::*                    LISTEN    
  541/(squid-1)

  $ wget google.com
  --2018-02-16 13:20:59--  http://google.com/
  Resolving localhost (localhost)... 127.0.0.1
  Connecting to localhost (localhost)|127.0.0.1|:48080... connected.
  Proxy request sent, awaiting response... 500 Internal Server Error
  2018-02-16 13:20:59 ERROR 500: Internal Server Error.

The curious thing is that squid listens to port 48080 (as stated in my
configuration). I.e. I assume it *has* read the configuration file.

2. Issuing `invoke-rc.d squid reload` manually does help:

  $ sudo invoke-rc.d squid reload
  $ systemctl status squid
  ● squid.service - LSB: Squid HTTP Proxy version 3.x
     Loaded: loaded (/etc/init.d/squid; generated; vendor preset: enabled)
     Active: active (running) since Fri 2018-02-16 13:11:38 CET; 11min ago
       Docs: man:systemd-sysv-generator(8)
    Process: 2674 ExecReload=/etc/init.d/squid reload (code=exited, 
status=0/SUCCESS)
    Process: 383 ExecStart=/etc/init.d/squid start (code=exited, 
status=0/SUCCESS)
      Tasks: 5 (limit: 4915)
     CGroup: /system.slice/squid.service
             ├─ 539 /usr/sbin/squid -YC -f /etc/squid/squid.conf
             ├─ 541 (squid-1) -YC -f /etc/squid/squid.conf
             ├─2285 (pinger)
             ├─2688 (logfile-daemon) /var/log/squid/access.log
             └─2689 (pinger)

  Feb 16 13:11:49 hatchling squid[904]:    ...done.
  Feb 16 13:11:49 hatchling systemd[1]: Reloaded LSB: Squid HTTP Proxy version 
3.x.
  Feb 16 13:13:58 hatchling systemd[1]: Reloading LSB: Squid HTTP Proxy version 
3.x.
  Feb 16 13:13:58 hatchling squid[2081]:  * Reloading Squid HTTP Proxy 
configuration files
  Feb 16 13:13:58 hatchling squid[2081]:    ...done.
  Feb 16 13:13:58 hatchling systemd[1]: Reloaded LSB: Squid HTTP Proxy version 
3.x.
  Feb 16 13:23:09 hatchling systemd[1]: Reloading LSB: Squid HTTP Proxy version 
3.x.
  Feb 16 13:23:09 hatchling squid[2674]:  * Reloading Squid HTTP Proxy 
configuration files
  Feb 16 13:23:09 hatchling squid[2674]:    ...done.
  Feb 16 13:23:09 hatchling systemd[1]: Reloaded LSB: Squid HTTP Proxy version 
3.x.

  $ wget google.com
  --2018-02-16 13:24:10--  http://google.com/
  Resolving localhost (localhost)... 127.0.0.1
  Connecting to localhost (localhost)|127.0.0.1|:48080... connected.
  Proxy request sent, awaiting response... 302 Found
  Location: http://www.google.pl/?gfe_rd=cr&dcr=0&ei=bM2GWp3vE6Li8Af6wZGwAQ 
[following]
  --2018-02-16 13:24:10--  
http://www.google.pl/?gfe_rd=cr&dcr=0&ei=bM2GWp3vE6Li8Af6wZGwAQ
  Reusing existing connection to localhost:48080.
  Proxy request sent, awaiting response... 200 OK
  Length: unspecified [text/html]
  Saving to: ‘index.html’

  index.html                                       [ <=>
]  12,79K  --.-KB/s    in 0,003s

  2018-02-16 13:24:10 (3,91 MB/s) - ‘index.html’ saved [13094]

3. However, if I replace `invoke-rc.d` with `systemctl` analog in
/etc/resolvconf/update-libc.d/squid the problem does not appear at all.
Squid just works since startup

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https://bugs.launchpad.net/bugs/1748471

Title:
  Automatic squid reload on resolv.conf update does not work

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