Public bug reported:

[Ubuntu server 18.04.1]
Yesterdays apt-get update && apt-get dist-upgrade broke wireguard on all 
systems. This is a little annoying if some of this systems are located 1600km 
away and the wireguard-vpn is used to reach them...

Packages relevant upgraded:
linux-image-5.0.0-37-generic -> linux-image-5.3.0-26-generic

The wireguard-dkms was rebuilded during this upgrade, and loads into the new 
kernel without problems:
[    5.038245] wireguard: loading out-of-tree module taints kernel.
[    5.038396] wireguard: module verification failed: signature and/or required 
key missing - tainting kernel
[    5.039066] wireguard: WireGuard 0.0.20191219 loaded. See www.wireguard.com 
for information.
[    5.039067] wireguard: Copyright (C) 2015-2019 Jason A. Donenfeld 
<ja...@zx2c4.com>. All Rights Reserved.

Wireguard is configured through systemd-networkd, the config has not
changed since months. There are no errors/warnings other signs of
problems regarding wireguard in any log. But Wireguard just don't
transfer any data, with TCP-Dump I can see that the wireguard-server
don't answer to any of the packets that are arriving from not affected
clients. And affected clients are not sending out any data to the
wireguard server.

One thing is eye-catching, in the output of wg on the affected devices the 
peers are missing:
Affected device:
interface: wg0
  public key: xxx
  private key: (hidden)
  listening port: 443

Not affected device:
interface: wg0
  public key: xxx
  private key: (hidden)
  listening port: 443

peer: xxx
  preshared key: (hidden)
  endpoint: xxx
  allowed ips: xxx
  transfer: 0 B received, 2.89 KiB sent
  persistent keepalive: every 25 seconds

Config of one device:
30-wg0.netdev:
[NetDev]
Name = wg0
Kind = wireguard
Description = Wireguard

[WireGuard]
PrivateKey = xxx
# PublicKey = xxx
ListenPort = xxx

[WireGuardPeer]
PublicKey = xxx
PresharedKey = xxx
AllowedIPs = xxx
Endpoint = xxx
PersistentKeepalive = 25

30-wg0.network:
[Match]
Name = wg0

[Link]
MTUBytes=1300

[Network]
DNS = xxx
DNS = xxx
Domains=xxx

[Address]
Address = xxx

[Address]
Address = xxx

[Route]
Gateway = xxx
Destination = xxx
Metric=50000

Full List of Packages updated:
Start-Date: 2020-01-17  14:40:50
Commandline: /usr/bin/apt-get -y -o Dpkg::Options::=--force-confold -o 
Dpkg::Options::=--force-confdef --force-yes dist-upgrade
Install: linux-image-5.3.0-26-generic:amd64 (5.3.0-26.28~18.04.1, automatic), 
linux-headers-5.3.0-26:amd64 (5.3.0-26.28~18.04.1, automatic), 
linux-headers-5.3.0-26-generic:amd64 (5.3.0-26.28~18.04.1, automatic), 
linux-modules-extra-5.3.0-26-generic:amd64 (5.3.0-26.28~18.04.1, automatic), 
linux-modules-5.3.0-26-generic:amd64 (5.3.0-26.28~18.04.1, automatic)
Upgrade: php7.2-bz2:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
php7.2-common:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
php7.2-cli:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
php7.2-fpm:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
php7.2-mysql:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
linux-headers-generic-hwe-18.04:amd64 (5.0.0.37.95, 5.3.0.26.95), 
php7.2-sqlite3:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
php7.2-json:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
php7.2-opcache:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
php7.2-curl:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
php7.2-xml:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
php7.2-intl:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
php7.2-zip:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
php7.2-mbstring:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
php7.2-readline:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
php7.2-gd:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
linux-image-generic-hwe-18.04:amd64 (5.0.0.37.95, 5.3.0.26.95), libdrm2:amd64 
(2.4.97-1ubuntu1~18.04.1, 2.4.99-1ubuntu1~18.04.1), 
linux-generic-hwe-18.04:amd64 (5.0.0.37.95, 5.3.0.26.95), php7.2-pgsql:amd64 
(7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), libdrm-common:amd64 
(2.4.97-1ubuntu1~18.04.1, 2.4.99-1ubuntu1~18.04.1)
End-Date: 2020-01-17  14:46:41

** Affects: wireguard-linux
     Importance: Undecided
         Status: New

** Affects: ubuntu
     Importance: Undecided
         Status: New

** Description changed:

- Yesterdays apt-get update && apt-get dist-upgrade broke wireguard on all
- systems. This is a little annoying if some of this systems are located
- 1600km away and the wireguard-vpn is used to reach them...
+ [Ubuntu server 18.04.1]
+ Yesterdays apt-get update && apt-get dist-upgrade broke wireguard on all 
systems. This is a little annoying if some of this systems are located 1600km 
away and the wireguard-vpn is used to reach them...
  
  Packages relevant upgraded:
  linux-image-5.0.0-37-generic -> linux-image-5.3.0-26-generic
  
  The wireguard-dkms was rebuilded during this upgrade, and loads into the new 
kernel without problems:
  [    5.038245] wireguard: loading out-of-tree module taints kernel.
  [    5.038396] wireguard: module verification failed: signature and/or 
required key missing - tainting kernel
  [    5.039066] wireguard: WireGuard 0.0.20191219 loaded. See 
www.wireguard.com for information.
  [    5.039067] wireguard: Copyright (C) 2015-2019 Jason A. Donenfeld 
<ja...@zx2c4.com>. All Rights Reserved.
  
  Wireguard is configured through systemd-networkd, the config has not
  changed since months. There are no errors/warnings other signs of
  problems regarding wireguard in any log. But Wireguard just don't
  transfer any data, with TCP-Dump I can see that the wireguard-server
  don't answer to any of the packets that are arriving from not affected
  clients. And affected clients are not sending out any data to the
  wireguard server.
  
  One thing is eye-catching, in the output of wg on the affected devices the 
peers are missing:
  Affected device:
  interface: wg0
-   public key: xxx
-   private key: (hidden)
-   listening port: 443
+   public key: xxx
+   private key: (hidden)
+   listening port: 443
  
  Not affected device:
  interface: wg0
-   public key: xxx
-   private key: (hidden)
-   listening port: 443
+   public key: xxx
+   private key: (hidden)
+   listening port: 443
  
  peer: xxx
-   preshared key: (hidden)
-   endpoint: xxx
-   allowed ips: xxx
-   transfer: 0 B received, 2.89 KiB sent
-   persistent keepalive: every 25 seconds
- 
+   preshared key: (hidden)
+   endpoint: xxx
+   allowed ips: xxx
+   transfer: 0 B received, 2.89 KiB sent
+   persistent keepalive: every 25 seconds
  
  Config of one device:
  30-wg0.netdev:
  [NetDev]
  Name = wg0
  Kind = wireguard
  Description = Wireguard
  
  [WireGuard]
  PrivateKey = xxx
  # PublicKey = xxx
  ListenPort = xxx
  
  [WireGuardPeer]
  PublicKey = xxx
  PresharedKey = xxx
  AllowedIPs = xxx
  Endpoint = xxx
  PersistentKeepalive = 25
  
  30-wg0.network:
  [Match]
  Name = wg0
  
  [Link]
  MTUBytes=1300
  
  [Network]
  DNS = xxx
  DNS = xxx
  Domains=xxx
  
  [Address]
  Address = xxx
  
  [Address]
  Address = xxx
  
  [Route]
  Gateway = xxx
  Destination = xxx
  Metric=50000
  
- 
  Full List of Packages updated:
  Start-Date: 2020-01-17  14:40:50
  Commandline: /usr/bin/apt-get -y -o Dpkg::Options::=--force-confold -o 
Dpkg::Options::=--force-confdef --force-yes dist-upgrade
  Install: linux-image-5.3.0-26-generic:amd64 (5.3.0-26.28~18.04.1, automatic), 
linux-headers-5.3.0-26:amd64 (5.3.0-26.28~18.04.1, automatic), 
linux-headers-5.3.0-26-generic:amd64 (5.3.0-26.28~18.04.1, automatic), 
linux-modules-extra-5.3.0-26-generic:amd64 (5.3.0-26.28~18.04.1, automatic), 
linux-modules-5.3.0-26-generic:amd64 (5.3.0-26.28~18.04.1, automatic)
  Upgrade: php7.2-bz2:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
php7.2-common:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
php7.2-cli:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
php7.2-fpm:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
php7.2-mysql:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
linux-headers-generic-hwe-18.04:amd64 (5.0.0.37.95, 5.3.0.26.95), 
php7.2-sqlite3:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
php7.2-json:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
php7.2-opcache:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
php7.2-curl:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
php7.2-xml:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
php7.2-intl:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
php7.2-zip:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
php7.2-mbstring:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
php7.2-readline:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
php7.2-gd:amd64 (7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), 
linux-image-generic-hwe-18.04:amd64 (5.0.0.37.95, 5.3.0.26.95), libdrm2:amd64 
(2.4.97-1ubuntu1~18.04.1, 2.4.99-1ubuntu1~18.04.1), 
linux-generic-hwe-18.04:amd64 (5.0.0.37.95, 5.3.0.26.95), php7.2-pgsql:amd64 
(7.2.24-0ubuntu0.18.04.1, 7.2.24-0ubuntu0.18.04.2), libdrm-common:amd64 
(2.4.97-1ubuntu1~18.04.1, 2.4.99-1ubuntu1~18.04.1)
  End-Date: 2020-01-17  14:46:41

** Also affects: wireguard-linux
   Importance: Undecided
       Status: New

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https://bugs.launchpad.net/bugs/1860206

Title:
  Wireguard is broken after yesterdays apt-get dist-upgrade

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