** Changed in: nginx (Ubuntu)
       Status: New => Incomplete

** Also affects: openssl (Ubuntu)
   Importance: Undecided
       Status: New

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https://bugs.launchpad.net/bugs/1835464

Title:
  nginx service fails after libssl update due to low entropy at boot

Status in nginx package in Ubuntu:
  Incomplete
Status in openssl package in Ubuntu:
  New

Bug description:
  After updating libssl and related packages, nginx will no longer
  autostart at system boot.

  Immediately after boot, nginx.service is in a failed state.

  # service nginx status
  ● nginx.service - A high performance web server and a reverse proxy server
     Loaded: loaded (/lib/systemd/system/nginx.service; enabled; vendor preset: 
enabled)
     Active: failed (Result: timeout) since Fri 2018-08-24 21:27:51 UTC; 32min 
ago
       Docs: man:nginx(8)

  systemd[1]: Starting A high performance web server and a reverse proxy 
server...
  systemd[1]: nginx.service: Start-pre operation timed out. Terminating.
  systemd[1]: nginx.service: Failed with result 'timeout'.
  systemd[1]: Failed to start A high performance web server and a reverse proxy 
server.

  
  The service can be manually started after boot.

  # service nginx start
  # service nginx status
  ● nginx.service - A high performance web server and a reverse proxy server
     Loaded: loaded (/lib/systemd/system/nginx.service; enabled; vendor preset: 
enabled)
     Active: active (running) since Fri 2018-08-24 22:02:06 UTC; 2s ago
       Docs: man:nginx(8)
    Process: 2704 ExecStart=/usr/sbin/nginx -g daemon on; master_process on; 
(code=exited, status=0/SUCCESS)
    Process: 2703 ExecStartPre=/usr/sbin/nginx -t -q -g daemon on; 
master_process on; (code=exited, status=0/SUCCESS)
   Main PID: 2705 (nginx)
     CGroup: /system.slice/nginx.service
             ├─2705 nginx: master process /usr/sbin/nginx -g daemon on; 
master_process on;
             └─2706 nginx: worker process

  systemd[1]: Starting A high performance web server and a reverse proxy 
server...
  systemd[1]: nginx.service: Failed to parse PID from file /run/nginx.pid: 
Invalid argument
  systemd[1]: Started A high performance web server and a reverse proxy server.

  
  This happens on an ARMHF based microcontroller running ubuntu 18.04.2 raspi 
server distribution with a stock kernel.org 4.9-181 kernel.

  Ubuntu repositories are not accessible from the device, so packages
  are copied to the device, and apt install is used to upgrade them:

  apt install --no-install-recommends $dir/updates/system/*.deb  |
  logger 2>&1

  
  The following is a list of packages that, when upgraded, cause the nginx 
systemd service to fail to autostart at boot.

  201,205c201,205
  < ii  libpython2.7:armhf              2.7.15-4ubuntu4~18.04             armhf 
       Shared Python runtime library (version 2.7)
  < ii  libpython2.7-minimal:armhf      2.7.15-4ubuntu4~18.04             armhf 
       Minimal subset of the Python language (version 2.7)
  < ii  libpython2.7-stdlib:armhf       2.7.15-4ubuntu4~18.04             armhf 
       Interactive high-level object-oriented language (standard library, 
version 2.7)
  < ii  libpython3.6-minimal:armhf      3.6.8-1~18.04.1                   armhf 
       Minimal subset of the Python language (version 3.6)
  < ii  libpython3.6-stdlib:armhf       3.6.8-1~18.04.1                   armhf 
       Interactive high-level object-oriented language (standard library, 
version 3.6)
  ---
  > ii  libpython2.7:armhf              2.7.15~rc1-1ubuntu0.1             armhf 
       Shared Python runtime library (version 2.7)
  > ii  libpython2.7-minimal:armhf      2.7.15~rc1-1ubuntu0.1             armhf 
       Minimal subset of the Python language (version 2.7)
  > ii  libpython2.7-stdlib:armhf       2.7.15~rc1-1ubuntu0.1             armhf 
       Interactive high-level object-oriented language (standard library, 
version 2.7)
  > ii  libpython3.6-minimal:armhf      3.6.7-1~18.04                     armhf 
       Minimal subset of the Python language (version 3.6)
  > ii  libpython3.6-stdlib:armhf       3.6.7-1~18.04                     armhf 
       Interactive high-level object-oriented language (standard library, 
version 3.6)
  225c225
  < ii  libssl1.1:armhf                 1.1.1-1ubuntu2.1~18.04.2          armhf 
       Secure Sockets Layer toolkit - shared libraries
  ---
  > ii  libssl1.1:armhf                 1.1.0g-2ubuntu4.3                 armhf 
       Secure Sockets Layer toolkit - shared libraries
  272c272
  < ii  openssl                         1.1.1-1ubuntu2.1~18.04.2          armhf 
       Secure Sockets Layer toolkit - cryptographic utility
  ---
  > ii  openssl                         1.1.0g-2ubuntu4.3                 armhf 
       Secure Sockets Layer toolkit - cryptographic utility
  282,283c282,283
  < ii  python3.6                       3.6.8-1~18.04.1                   armhf 
       Interactive high-level object-oriented language (version 3.6)
  < ii  python3.6-minimal               3.6.8-1~18.04.1                   armhf 
       Minimal subset of the Python language (version 3.6)
  ---
  > ii  python3.6                       3.6.7-1~18.04                     armhf 
       Interactive high-level object-oriented language (version 3.6)
  > ii  python3.6-minimal               3.6.7-1~18.04                     armhf 
       Minimal subset of the Python language (version 3.6)

  
  nginx is used primarily as an https front-end for web services on the device.

  libssl is the core dependency for all of the packages in the group
  that, when upgraded, causes nginx to fail.

  The nginx configuration includes the following SSL settings:

  
  http {
          ##
          # SSL Settings
          ##

          ssl_protocols TLSv1 TLSv1.1 TLSv1.2; # Dropping SSLv3, ref: POODLE
          ssl_prefer_server_ciphers on;
  }

  server {
    listen              443 ssl;
    ssl_certificate     /etc/certs/cert.crt;
    ssl_certificate_key /etc/certs/cert.key;
    ssl_protocols       TLSv1 TLSv1.1 TLSv1.2;
    ssl_ciphers         HIGH:!aNULL:!MD5;
  }

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