I've got a bit confused about the behavior of the system so I restarted
the process to check what's happening. Here the steps I performed:

1. Install clean image on SD card.
2. Block internet access of the RPI, so no updates to be installed on first 
boot. 
3. Reboot
4. Remove 50-cloud-init.yaml from /etc/netplan 
5. Create eth0-dhcp.yaml in /etc/netplan with the following content:

network:
    version: 2
    ethernets:
        eth0:
            dhcp4: true
            dhcp6: false
            optional: true

6. Create wlan0-dhcp.yaml in /etc/netplan with the following content:

network:
    version: 2
    wifis:
        wlan0:
            optional: true
            access-points:
                "SSID":
                    password: "PASS"
            dhcp4: true
            dhcp6: false

7. Execute "netplan try" and "netplan apply"
8. Reboot
9. At that point the kernel is "linux-image-5.3.0-1007-raspi2" and both 
adapters are connected, have their IPs and SSH is possible to both.
10. Remove ethernet cable from RPI.
11. SSH over wlan0 IP is possible.
12. Reboot
13. Check SSH over wlan0 IP - still possible.
14. Unblock internet access of the RPI and run "sudo apt-get update"
15. Install newest kernel "linux-image-5.3.0-1012-raspi2": sudo apt install 
linux-image-5.3.0-1012-raspi2
16. Reboot
17. SSH over wlan0 IP - NOT possible (connection time out)
18. Connect ethernet cable.
19. Check again SSH over wlan0 IP - NOT possible (connection time out)
20. Check SSH over eth0 IP - connection possible, but after 5-10 minutes of 
waiting. 
21. Install net tools: "sudo apt install net-tools"
22. ifconfig show that only eth0 is connected. wlan0 is up, but don't have IP.
23. Reboot
24. SSH possible over eth0 and wlan0. ifconfig confirm that both adapters have 
their IPs.
25. Remove ethernet cable from RPI.
26. SSH not possible to wlan0.
27. Connect ethernet cable - SSH still not possible to either eth0, nor wlan0.
28. Hard reset of the RPI to reboot it - remove power supply. 
29. SSH over eth0 possible. ifconfig show that wlan0 is up, but don't have IP. 


I performed the same steps with "linux-image-5.3.0-1013-raspi2" and the results 
are the same.

As a summaryI would say that "linux-image-5.3.0-1007-raspi2" have no
issues with plug-in, pulg-out  of the ethernet cable. wlan0 and eth0
seem to work independently and together without issues.

With kernels above the before mentioned, plug-in/pulg-out of the
ethernet cable disrupt wlan0 and without the cable, SSH (or ping) is not
possible to wlan0.

Tried to revert the kernel to 1007 (on another clean image) as you
suggested, but after reboot I no longer can establish SSH to RPI. And as
I'm running headless, I don't know if the RPI actually booted or it's a
connection issue.

-- 
You received this bug notification because you are a member of Kernel
Packages, which is subscribed to linux-raspi2 in Ubuntu.
https://bugs.launchpad.net/bugs/1853030

Title:
  No connection through SSH over WIfi after kernel update

Status in linux-raspi2 package in Ubuntu:
  Incomplete

Bug description:
  After updating from kernel "linux-image-5.3.0-1007-raspi2" to "linux-
  image-5.3.0-1012-raspi2" I no longer can establish SSH connection to
  Raspberry over Wifi.

  When it is on wired connection, SSH works and initial screen shows
  that both adapters (eth0 and wlan0) are connected and have their IPs.
  "ifconfig" confirms that both adapters are up and have their IPs.
  Establishing SSH session with both IPs is successful.

  When I disconnect the network cable, SSH is no longer possible
  (connection time out). In the same time the router is showing that the
  Raspberry is connected to the Wifi network.

  Plugging back the wire does not make the SSH possible. A restart of
  the Raspberry is required with plugged in network cable in order to
  establish SSH again.

  The system is Raspberry Pi 4, 4GB with Ubuntu server X64 image - clean
  install.

  Wifi was enabled by editing /etc/netplan/50-cloud-init.yaml and
  running "sudo netplan apply"

  Reference info for what is done so far:
  https://answers.launchpad.net/ubuntu/+question/685941

  Output of "ubuntu-bug linux":

  ProblemType: Bug
  ApportVersion: 2.20.11-0ubuntu8.2
  Architecture: arm64
  Date: Mon Nov 18 16:46:39 2019
  Dependencies:
   adduser 3.118ubuntu1
   apt 1.9.4
   apt-utils 1.9.4
   binutils 2.33-2ubuntu1
   binutils-aarch64-linux-gnu 2.33-2ubuntu1
   binutils-common 2.33-2ubuntu1
   busybox-initramfs 1:1.30.1-4ubuntu4
   ca-certificates 20190110
   coreutils 8.30-3ubuntu2
   cpio 2.12+dfsg-9ubuntu0.1
   debconf 1.5.73
   debconf-i18n 1.5.73
   device-tree-compiler 1.4.7-3ubuntu2
   devio 1.2-1.2
   dpkg 1.19.7ubuntu2
   e2fsprogs 1.45.3-4ubuntu2
   fdisk 2.34-0.1ubuntu2
   flash-kernel 3.98ubuntu5.1
   gcc-9-base 9.2.1-9ubuntu2
   gpgv 2.2.12-1ubuntu3
   initramfs-tools 0.133ubuntu10
   initramfs-tools-bin 0.133ubuntu10
   initramfs-tools-core 0.133ubuntu10
   klibc-utils 2.0.6-1ubuntu3
   kmod 26-1ubuntu1
   libacl1 2.2.53-4
   libapt-pkg5.90 1.9.4
   libattr1 1:2.4.48-4
   libaudit-common 1:2.8.5-2ubuntu1
   libaudit1 1:2.8.5-2ubuntu1
   libbinutils 2.33-2ubuntu1
   libblkid1 2.34-0.1ubuntu2
   libbz2-1.0 1.0.6-9.2
   libc6 2.30-0ubuntu2
   libcap-ng0 0.7.9-2
   libcom-err2 1.45.3-4ubuntu2
   libdb5.3 5.3.28+dfsg1-0.6ubuntu1
   libext2fs2 1.45.3-4ubuntu2
   libfdisk1 2.34-0.1ubuntu2
   libffi6 3.2.1-9
   libgcc1 1:9.2.1-9ubuntu2
   libgcrypt20 1.8.4-5ubuntu2
   libgmp10 2:6.1.2+dfsg-4
   libgnutls30 3.6.9-5ubuntu1
   libgpg-error0 1.36-7
   libgpm2 1.20.7-5
   libhogweed4 3.4.1-1
   libidn2-0 2.2.0-2
   libklibc 2.0.6-1ubuntu3
   libkmod2 26-1ubuntu1
   liblocale-gettext-perl 1.07-3build3
   liblz4-1 1.9.1-1
   liblzma5 5.2.4-1
   liblzo2-2 2.10-0.1
   libmount1 2.34-0.1ubuntu2
   libncursesw6 6.1+20190803-1ubuntu1
   libnettle6 3.4.1-1
   libp11-kit0 0.23.17-2
   libpam-modules 1.3.1-5ubuntu1
   libpam-modules-bin 1.3.1-5ubuntu1
   libpam-runtime 1.3.1-5ubuntu1
   libpam0g 1.3.1-5ubuntu1
   libpcre2-8-0 10.32-5
   libseccomp2 2.4.1-0ubuntu0.19.10.3
   libselinux1 2.9-2
   libsemanage-common 2.9-3
   libsemanage1 2.9-3
   libsepol1 2.9-2
   libsmartcols1 2.34-0.1ubuntu2
   libss2 1.45.3-4ubuntu2
   libssl1.1 1.1.1c-1ubuntu4
   libstdc++6 9.2.1-9ubuntu2
   libsystemd0 242-7ubuntu3
   libtasn1-6 4.14-3
   libtext-charwidth-perl 0.04-9
   libtext-iconv-perl 1.7-6
   libtext-wrapi18n-perl 0.06-9
   libtinfo6 6.1+20190803-1ubuntu1
   libudev1 242-7ubuntu3
   libunistring2 0.9.10-2
   libuuid1 2.34-0.1ubuntu2
   libzstd1 1.4.3+dfsg-1
   linux-base 4.5ubuntu2
   linux-modules-5.3.0-1012-raspi2 5.3.0-1012.14
   login 1:4.5-1.1ubuntu4
   logsave 1.45.3-4ubuntu2
   lsb-base 11.0.1ubuntu1
   lz4 1.9.1-1
   mtd-utils 1:2.0.1-1ubuntu3
   openssl 1.1.1c-1ubuntu4
   passwd 1:4.5-1.1ubuntu4
   perl-base 5.28.1-6build1
   sensible-utils 0.0.12
   tar 1.30+dfsg-6
   u-boot-tools 2019.07+dfsg-1ubuntu3
   ubuntu-keyring 2018.09.18.1
   ucf 3.0038+nmu1
   udev 242-7ubuntu3
   util-linux 2.34-0.1ubuntu2
   uuid-runtime 2.34-0.1ubuntu2
   zlib1g 1:1.2.11.dfsg-1ubuntu3
  DistroRelease: Ubuntu 19.10
  Package: linux-image-5.3.0-1012-raspi2 5.3.0-1012.14
  PackageArchitecture: arm64
  ProcCpuinfoMinimal:
   processor    : 3
   BogoMIPS     : 108.00
   Features     : fp asimd evtstrm crc32 cpuid
   CPU implementer      : 0x41
   CPU architecture: 8
   CPU variant  : 0x0
   CPU part     : 0xd08
   CPU revision : 3

   Hardware     : BCM2835
   Revision     : c03111
   Serial               : 10000000352e9f36
   Model                : Raspberry Pi 4 Model B Rev 1.1
  ProcEnviron:
   TERM=xterm
   PATH=(custom, no user)
   XDG_RUNTIME_DIR=<set>
   LANG=C.UTF-8
   SHELL=/bin/bash
  ProcVersionSignature: Ubuntu 5.3.0-1012.14-raspi2 5.3.7
  SourcePackage: linux-raspi2
  Tags:  eoan uec-images
  Uname: Linux 5.3.0-1012-raspi2 aarch64
  UpgradeStatus: No upgrade log present (probably fresh install)
  _MarkForUpload: True
  ---
  ProblemType: Bug
  AlsaDevices:
   total 0
   crw-rw---- 1 root audio 116,  1 Apr 11  2019 seq
   crw-rw---- 1 root audio 116, 33 Apr 11  2019 timer
  AlsaVersion: Advanced Linux Sound Architecture Driver Version 
k5.3.0-1012-raspi2.
  AplayDevices: Error: [Errno 2] No such file or directory: 'aplay': 'aplay'
  ApportVersion: 2.20.11-0ubuntu8.2
  Architecture: arm64
  ArecordDevices: Error: [Errno 2] No such file or directory: 'arecord': 
'arecord'
  AudioDevicesInUse: Error: command ['fuser', '-v', '/dev/snd/seq', 
'/dev/snd/timer'] failed with exit code 1:
  CRDA: N/A
  DistroRelease: Ubuntu 19.10
  Package: linux (not installed)
  PciMultimedia:

  ProcEnviron:
   TERM=xterm
   PATH=(custom, no user)
   LANG=C.UTF-8
   SHELL=/bin/bash
  ProcFB:

  ProcKernelCmdLine: coherent_pool=1M 8250.nr_uarts=1 cma=64M cma=256M  
smsc95xx.macaddr=DC:A6:32:1C:19:7B vc_mem.mem_base=0x3ec00000 
vc_mem.mem_size=0x40000000  net.ifnames=0 dwc_otg.lpm_enable=0 
console=ttyS0,115200 console=tty1 root=LABEL=writable rootfstype=ext4 
elevator=deadline rootwait
  ProcVersionSignature: Ubuntu 5.3.0-1012.14-raspi2 5.3.7
  RelatedPackageVersions:
   linux-restricted-modules-5.3.0-1012-raspi2 N/A
   linux-backports-modules-5.3.0-1012-raspi2  N/A
   linux-firmware                             1.183.2
  RfKill: Error: [Errno 2] No such file or directory: 'rfkill': 'rfkill'
  StagingDrivers: vc_sm_cma bcm2835_v4l2 bcm2835_mmal_vchiq
  Tags:  eoan uec-images staging
  Uname: Linux 5.3.0-1012-raspi2 aarch64
  UpgradeStatus: No upgrade log present (probably fresh install)
  UserGroups:

  _MarkForUpload: True

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