'A start job is running for wait for network to be configured'. optional:true skips this but breaks some docker containers

I have been running an Ubuntu Server for a while now. Recently, my router stopped "sending internet" to the devices connect via LAN, which includes my Ubuntu Server. The server is running on bare metal, it is not a VM.

I restarted the router and the connection fixed itself for other devices but now 'A start job is running for wait for network to be configured' appears during boot.

I have tried adding optional: true to /etc/netplan/00-installer-config.yaml. It did "work" but it caused my docker containers (*arr suite) to not spin up. Thus, after removing the optional: true, my containers can spin up just fine but there is the long boot time.

Furthermore, when I enter the server, it says "Failed to connect to https://changelogs.ubuntu.com/meta-release-lts. Check your Internet connection or proxy settings"

I have tried doing sudo apt update && sudo apt upgrade hoping that it fixes itself.

Here are some outputs:

OS

$ lsb_release -a
No LSB modules are available.
Distributor ID: Ubuntu
Description:    Ubuntu 22.04.2 LTS
Release:        22.04
Codename:       jammy

networkctl

$ networkctl -a status
● 2: eno1
                     Link File: /usr/lib/systemd/network/99-default.link
                  Network File: /run/systemd/network/10-netplan-eno1.network
                          Type: ether
                         State: routable (configuring)
                  Online state: online
             Alternative Names: enp0s31f6
                          Path: pci-0000:00:1f.6
                        Driver: e1000e
                        Vendor: Intel Corporation
                         Model: Ethernet Connection (7) I219-V
                    HW Address: XXX
                           MTU: 1500 (min: 68, max: 9000)
                         QDisc: fq_codel
  IPv6 Address Generation Mode: none
          Queue Length (Tx/Rx): 1/1
              Auto negotiation: yes
                         Speed: 1Gbps
                        Duplex: full
                          Port: tp
                       Address: 192.168.50.141 (DHCP4 via 192.168.50.1)
                       Gateway: 192.168.50.1
                           DNS: 1.1.1.1
                                8.8.8.8
                                8.8.4.4
                                192.168.50.1
             Activation Policy: up
           Required For Online: yes
               DHCP4 Client ID: IAID:0xb6220feb/DUID
                  Connected To: XXX on port XXX (eth4)

Jul 16 20:05:20 meowmeow-server systemd-networkd[775]: eno1: Link UP
Jul 16 20:05:23 meowmeow-server systemd-networkd[775]: eno1: Gained carrier
Jul 16 20:05:26 meowmeow-server systemd-networkd[775]: eno1: DHCPv4 address 192.168.50.141/24 via 192.168.50.1

syslog

$ cat /var/log/syslog | grep eno1
Jul 16 20:05:20 meowmeow-server systemd-networkd[775]: eno1: Link UP
Jul 16 20:05:20 meowmeow-server kernel: [    4.171127] e1000e 0000:00:1f.6 eno1: renamed from eth0
Jul 16 20:05:23 meowmeow-server systemd-networkd[775]: eno1: Gained carrier
Jul 16 20:05:23 meowmeow-server kernel: [   10.650222] e1000e 0000:00:1f.6 eno1: NIC Link is Up 1000 Mbps Full Duplex, Flow Control: Rx/Tx
Jul 16 20:05:23 meowmeow-server kernel: [   10.650276] IPv6: ADDRCONF(NETDEV_CHANGE): eno1: link becomes ready
Jul 16 20:05:26 meowmeow-server systemd-networkd[775]: eno1: DHCPv4 address 192.168.50.141/24 via 192.168.50.1

lshw -C network

$ sudo lshw -C network
  *-network
       description: Ethernet interface
       product: Ethernet Connection (7) I219-V
       vendor: Intel Corporation
       physical id: 1f.6
       bus info: pci@0000:00:1f.6
       logical name: eno1
       version: 10
       serial: XXX
       size: 1Gbit/s
       capacity: 1Gbit/s
       width: 32 bits
       clock: 33MHz
       capabilities: pm msi bus_master cap_list ethernet physical tp 10bt 10bt-fd 100bt 100bt-fd 1000bt-fd autonegotiation
       configuration: autonegotiation=on broadcast=yes driver=e1000e driverversion=5.15.0-76-generic duplex=full firmware=0.5-4 ip=192.168.50.141 latency=0 link=yes multicast=yes port=twisted pair speed=1Gbit/s
       resources: irq:126 memory:a3300000-a331ffff

ls /etc/netplan

00-installer-config.yaml

sudo netplan get

network:
  version: 2
  renderer: networkd
  ethernets:
    eno1:
      addresses:
      - "192.168.50.141/24"
      nameservers:
        addresses:
        - 1.1.1.1
        - 8.8.8.8
        - 8.8.4.4
        search: []
      dhcp4: true
      dhcp6: false
      routes:
      - scope: "link"
        from: "192.168.50.1"
        to: "0.0.0.0/0"
      link-local: []

If I don't put dhcp4: true, I won't get an inet 192.168.50.141 ... entry for ip addr show eno1

ls /etc/network

if-pre-up.d  if-up.d

ls /etc/systemd/network

EMPTY // NO OUTPUT

ip route

$ ip route show dev eno1
default via 192.168.50.1 proto dhcp src 192.168.50.141 metric 100
1.1.1.1 via 192.168.50.1 proto dhcp src 192.168.50.141 metric 100
192.168.50.0/24 proto kernel scope link src 192.168.50.141 metric 100
192.168.50.1 proto dhcp scope link src 192.168.50.141 metric 100

ip addr

$ ip addr show eno1
2: eno1: <BROADCAST,MULTICAST,UP,LOWER_UP> mtu 1500 qdisc fq_codel state UP group default qlen 1000
    link/ether XXX brd ff:ff:ff:ff:ff:ff
    altname enp0s31f6
    inet 192.168.50.141/24 metric 100 brd 192.168.50.255 scope global dynamic eno1
       valid_lft 85298sec preferred_lft 85298sec

You are getting an IP address via DHCP from a router, but you are not able to access the Internet from that IP. This is most likely a router configuration problem.

You should check your router's configuration and ensure that the IP address showing on your Ubuntu server is allowed to access the Internet.