Public bug reported:

root@search-3 /run/systemd/network # for i in *; do echo $i; echo; cat $i; done 
; sudo service systemd-networkd stop; SYSTEMD_LOG_LEVEL=debug 
/lib/systemd/systemd-networkd
10-netplan-enp0s31f6.network

[Match]
Name=enp0s31f6

[Network]
LinkLocalAddressing=ipv6
Address=95.216.96.148/26
Gateway=95.216.96.129
DNS=8.8.8.8
DNS=1.1.1.1
Domains=148.96.216.95.clients.your-server.de
VLAN=vlan4000

[Route]
Destination=95.216.96.148/26
Gateway=95.216.96.129
GatewayOnlink=true
10-netplan-vlan4000.netdev

[NetDev]
Name=vlan4000
MTUBytes=1400
Kind=vlan

[VLAN]
Id=4000
10-netplan-vlan4000.network

[Match]
Name=vlan4000

[Network]
LinkLocalAddressing=ipv6
Address=10.0.2.3/24
ConfigureWithoutCarrier=yes
Failed to read $container of PID 1, ignoring: Permission denied
Found container virtualization none.
Bus n/a: changing state UNSET → OPENING
Bus n/a: changing state OPENING → AUTHENTICATING
Failed to open configuration file '/etc/systemd/networkd.conf': No such file or 
directory
timestamp of '/etc/systemd/network' changed
timestamp of '/run/systemd/network' changed
Ignoring /run/systemd/network/10-netplan-enp0s31f6.network, because it's not a 
regular file with suffix .netdev.
Ignoring /run/systemd/network/10-netplan-vlan4000.network, because it's not a 
regular file with suffix .netdev.
Ignoring /lib/systemd/network/99-default.link, because it's not a regular file 
with suffix .netdev.
Ignoring /lib/systemd/network/80-container-vz.network, because it's not a 
regular file with suffix .netdev.
Ignoring /lib/systemd/network/80-container-ve.network, because it's not a 
regular file with suffix .netdev.
Ignoring /lib/systemd/network/80-container-host0.network, because it's not a 
regular file with suffix .netdev.
vlan4000: loaded vlan
Ignoring /run/systemd/network/10-netplan-vlan4000.netdev, because it's not a 
regular file with suffix .network.
Ignoring /lib/systemd/network/99-default.link, because it's not a regular file 
with suffix .network.
tun0: MAC address not found for new device, continuing without
tun0: Flags change: +UP +LOWER_UP +RUNNING +MULTICAST +POINTOPOINT +NOARP
tun0: Link 12 added
tun0: udev initialized link
tun0: Saved original MTU: 1500
veth20a5a67: Flags change: +UP +LOWER_UP +RUNNING +MULTICAST +BROADCAST
veth20a5a67: Link 8 added
veth20a5a67: udev initialized link
veth20a5a67: Saved original MTU: 1500
vlan4000: Flags change: +UP +LOWER_UP +RUNNING +MULTICAST +BROADCAST
vlan4000: Link 6 added
vlan4000: udev initialized link
vlan4000: netdev has index 6
vlan4000: Saved original MTU: 1400
br-c7cc901345e8: Flags change: +UP +LOWER_UP +RUNNING +MULTICAST +BROADCAST
br-c7cc901345e8: Link 5 added
br-c7cc901345e8: udev initialized link
br-c7cc901345e8: Saved original MTU: 1500
docker0: Flags change: +UP +MULTICAST +BROADCAST
docker0: Link 3 added
docker0: udev initialized link
docker0: Saved original MTU: 1500
enp0s31f6: Flags change: +UP +LOWER_UP +RUNNING +MULTICAST +BROADCAST
enp0s31f6: Link 2 added
enp0s31f6: udev initialized link
enp0s31f6: Saved original MTU: 1500
lo: Flags change: +LOOPBACK +UP +LOWER_UP +RUNNING
lo: Link 1 added
lo: udev initialized link
lo: Saved original MTU: 0
vlan4000: Adding address: fe80::921b:eff:fe93:5015/64 (valid forever)
vlan4000: Gained IPv6LL
tun0: Adding address: 10.0.0.13/24 (valid forever)
vlan4000: Adding address: 10.0.2.3/24 (valid forever)
br-c7cc901345e8: Adding address: 172.18.0.1/16 (valid forever)
docker0: Adding address: 172.17.0.1/16 (valid forever)
enp0s31f6: Adding address: 95.216.96.148/26 (valid forever)
lo: Adding address: 127.0.0.1/8 (valid forever)
rtnl: received address with invalid family 129, ignoring
Enumeration completed
Bus n/a: changing state AUTHENTICATING → HELLO
Sent message type=method_call sender=n/a destination=org.freedesktop.DBus 
path=/org/freedesktop/DBus interface=org.freedesktop.DBus member=Hello cookie=1 
reply_cookie=0 signature=n/a error-name=n/a error-message=n/a
Sent message type=method_call sender=n/a destination=org.freedesktop.DBus 
path=/org/freedesktop/DBus interface=org.freedesktop.DBus member=RequestName 
cookie=2 reply_cookie=0 signature=su error-name=n/a error-message=n/a
Sent message type=method_call sender=n/a destination=org.freedesktop.DBus 
path=/org/freedesktop/DBus interface=org.freedesktop.DBus member=AddMatch 
cookie=3 reply_cookie=0 signature=s error-name=n/a error-message=n/a
Sent message type=signal sender=n/a destination=n/a 
path=/org/freedesktop/network1/link/_312 
interface=org.freedesktop.DBus.Properties member=PropertiesChanged cookie=4 
reply_cookie=0 signature=sa{sv}as error-name=n/a error-message=n/a
Sent message type=signal sender=n/a destination=n/a 
path=/org/freedesktop/network1/link/_38 
interface=org.freedesktop.DBus.Properties member=PropertiesChanged cookie=5 
reply_cookie=0 signature=sa{sv}as error-name=n/a error-message=n/a
Sent message type=signal sender=n/a destination=n/a 
path=/org/freedesktop/network1/link/_36 
interface=org.freedesktop.DBus.Properties member=PropertiesChanged cookie=6 
reply_cookie=0 signature=sa{sv}as error-name=n/a error-message=n/a
Sent message type=signal sender=n/a destination=n/a 
path=/org/freedesktop/network1/link/_35 
interface=org.freedesktop.DBus.Properties member=PropertiesChanged cookie=7 
reply_cookie=0 signature=sa{sv}as error-name=n/a error-message=n/a
Sent message type=signal sender=n/a destination=n/a 
path=/org/freedesktop/network1/link/_33 
interface=org.freedesktop.DBus.Properties member=PropertiesChanged cookie=8 
reply_cookie=0 signature=sa{sv}as error-name=n/a error-message=n/a
Sent message type=signal sender=n/a destination=n/a 
path=/org/freedesktop/network1/link/_32 
interface=org.freedesktop.DBus.Properties member=PropertiesChanged cookie=9 
reply_cookie=0 signature=sa{sv}as error-name=n/a error-message=n/a
Sent message type=signal sender=n/a destination=n/a 
path=/org/freedesktop/network1/link/_31 
interface=org.freedesktop.DBus.Properties member=PropertiesChanged cookie=10 
reply_cookie=0 signature=sa{sv}as error-name=n/a error-message=n/a
Sent message type=signal sender=n/a destination=n/a 
path=/org/freedesktop/network1/link/_36 
interface=org.freedesktop.DBus.Properties member=PropertiesChanged cookie=11 
reply_cookie=0 signature=sa{sv}as error-name=n/a error-message=n/a
Sent message type=signal sender=n/a destination=n/a 
path=/org/freedesktop/network1/link/_312 
interface=org.freedesktop.DBus.Properties member=PropertiesChanged cookie=12 
reply_cookie=0 signature=sa{sv}as error-name=n/a error-message=n/a
Sent message type=signal sender=n/a destination=n/a 
path=/org/freedesktop/network1/link/_36 
interface=org.freedesktop.DBus.Properties member=PropertiesChanged cookie=13 
reply_cookie=0 signature=sa{sv}as error-name=n/a error-message=n/a
Sent message type=signal sender=n/a destination=n/a 
path=/org/freedesktop/network1/link/_35 
interface=org.freedesktop.DBus.Properties member=PropertiesChanged cookie=14 
reply_cookie=0 signature=sa{sv}as error-name=n/a error-message=n/a
Sent message type=signal sender=n/a destination=n/a 
path=/org/freedesktop/network1/link/_32 
interface=org.freedesktop.DBus.Properties member=PropertiesChanged cookie=15 
reply_cookie=0 signature=sa{sv}as error-name=n/a error-message=n/a
Sent message type=signal sender=n/a destination=n/a 
path=/org/freedesktop/network1 interface=org.freedesktop.DBus.Properties 
member=PropertiesChanged cookie=16 reply_cookie=0 signature=sa{sv}as 
error-name=n/a error-message=n/a
tun0: Link state is up-to-date
No virtualization found in DMI
No virtualization found in CPUID
Virtualization XEN not found, /proc/xen does not exist
This platform does not support /proc/device-tree
No virtualization found in /proc/cpuinfo.
This platform does not support /proc/sysinfo
Found VM virtualization none
tun0: Unmanaged
Sent message type=signal sender=n/a destination=n/a 
path=/org/freedesktop/network1/link/_312 
interface=org.freedesktop.DBus.Properties member=PropertiesChanged cookie=17 
reply_cookie=0 signature=sa{sv}as error-name=n/a error-message=n/a
Got message type=method_return sender=org.freedesktop.DBus destination=:1.171 
path=n/a interface=n/a member=n/a cookie=1 reply_cookie=1 signature=s 
error-name=n/a error-message=n/a
Bus n/a: changing state HELLO → RUNNING
Got message type=signal sender=org.freedesktop.DBus.Local destination=n/a 
path=/org/freedesktop/DBus/Local interface=org.freedesktop.DBus.Local 
member=Connected cookie=4294967295 reply_cookie=0 signature=n/a error-name=n/a 
error-message=n/a
Got message type=signal sender=org.freedesktop.DBus destination=:1.171 
path=/org/freedesktop/DBus interface=org.freedesktop.DBus member=NameAcquired 
cookie=2 reply_cookie=0 signature=s error-name=n/a error-message=n/a
Got message type=signal sender=org.freedesktop.DBus destination=:1.171 
path=/org/freedesktop/DBus interface=org.freedesktop.DBus member=NameAcquired 
cookie=3 reply_cookie=0 signature=s error-name=n/a error-message=n/a
Got message type=method_return sender=org.freedesktop.DBus destination=:1.171 
path=n/a interface=n/a member=n/a cookie=4 reply_cookie=2 signature=u 
error-name=n/a error-message=n/a
Successfully acquired requested service name.
Got message type=method_return sender=org.freedesktop.DBus destination=:1.171 
path=n/a interface=n/a member=n/a cookie=5 reply_cookie=3 signature=n/a 
error-name=n/a error-message=n/a
Match 
type='signal',sender='org.freedesktop.login1',path='/org/freedesktop/login1',interface='org.freedesktop.login1.Manager',member='PrepareForSleep'
 successfully installed.
veth20a5a67: Link state is up-to-date
veth20a5a67: Unmanaged
Sent message type=signal sender=n/a destination=n/a 
path=/org/freedesktop/network1/link/_38 
interface=org.freedesktop.DBus.Properties member=PropertiesChanged cookie=18 
reply_cookie=0 signature=sa{sv}as error-name=n/a error-message=n/a
vlan4000: Link state is up-to-date
vlan4000: found matching network 
'/run/systemd/network/10-netplan-vlan4000.network'
tun0: Link is not managed by us
veth20a5a67: Link is not managed by us
br-c7cc901345e8: Link is not managed by us
docker0: Link is not managed by us
enp0s31f6: Link is not managed by us
lo: Link is not managed by us
LLDP: Started LLDP client
vlan4000: Started LLDP.
vlan4000: Discovering IPv6 routers
NDISC: Started IPv6 Router Solicitation client
Sent message type=signal sender=n/a destination=n/a 
path=/org/freedesktop/network1/link/_36 
interface=org.freedesktop.DBus.Properties member=PropertiesChanged cookie=19 
reply_cookie=0 signature=sa{sv}as error-name=n/a error-message=n/a
vlan4000: Setting addresses
NDISC: Sent Router Solicitation, next solicitation in 3s
br-c7cc901345e8: Link state is up-to-date
br-c7cc901345e8: Unmanaged
Sent message type=signal sender=n/a destination=n/a 
path=/org/freedesktop/network1/link/_35 
interface=org.freedesktop.DBus.Properties member=PropertiesChanged cookie=20 
reply_cookie=0 signature=sa{sv}as error-name=n/a error-message=n/a
docker0: Link state is up-to-date
docker0: Unmanaged
Sent message type=signal sender=n/a destination=n/a 
path=/org/freedesktop/network1/link/_33 
interface=org.freedesktop.DBus.Properties member=PropertiesChanged cookie=21 
reply_cookie=0 signature=sa{sv}as error-name=n/a error-message=n/a
enp0s31f6: Link state is up-to-date
enp0s31f6: found matching network 
'/run/systemd/network/10-netplan-enp0s31f6.network'
vlan4000: Link does not request DHCPv6 prefix delegation
tun0: Link is not managed by us
veth20a5a67: Link is not managed by us
br-c7cc901345e8: Link is not managed by us
docker0: Link is not managed by us
lo: Link is not managed by us
LLDP: Started LLDP client
enp0s31f6: Started LLDP.
Sent message type=signal sender=n/a destination=n/a 
path=/org/freedesktop/network1/link/_32 
interface=org.freedesktop.DBus.Properties member=PropertiesChanged cookie=22 
reply_cookie=0 signature=sa{sv}as error-name=n/a error-message=n/a
enp0s31f6: Setting addresses
lo: Link state is up-to-date
lo: Unmanaged
Sent message type=signal sender=n/a destination=n/a 
path=/org/freedesktop/network1/link/_31 
interface=org.freedesktop.DBus.Properties member=PropertiesChanged cookie=23 
reply_cookie=0 signature=sa{sv}as error-name=n/a error-message=n/a
vlan4000: Addresses set
vlan4000: Configured
Sent message type=signal sender=n/a destination=n/a 
path=/org/freedesktop/network1/link/_36 
interface=org.freedesktop.DBus.Properties member=PropertiesChanged cookie=24 
reply_cookie=0 signature=sa{sv}as error-name=n/a error-message=n/a
enp0s31f6: Addresses set
enp0s31f6: Setting routes
enp0s31f6: Could not set route: Invalid argument
enp0s31f6: Routes set
NDISC: Sent Router Solicitation, next solicitation in 7s
NDISC: Sent Router Solicitation, next solicitation in 15s
NDISC: No RA received before link confirmation timeout
NDISC: Invoking callback for 't'.
NDISC: Sent Router Solicitation, next solicitation in 30s
NDISC: Sent Router Solicitation, next solicitation in 59s
NDISC: Sent Router Solicitation, next solicitation in 2min 2s
NDISC: Sent Router Solicitation, next solicitation in 4min 9s
NDISC: Sent Router Solicitation, next solicitation in 8min 35s
^CBus n/a: changing state RUNNING → CLOSED


root@search-3 /run/systemd/network # ip route
default via 95.216.96.129 dev enp0s31f6 proto static
10.0.0.0/24 dev tun0 proto kernel scope link src 10.0.0.13
10.0.2.0/24 dev vlan4000 proto kernel scope link src 10.0.2.3
95.216.96.128/26 dev enp0s31f6 proto kernel scope link src 95.216.96.148
172.17.0.0/16 dev docker0 proto kernel scope link src 172.17.0.1 linkdown
172.18.0.0/16 dev br-c7cc901345e8 proto kernel scope link src 172.18.0.1

its missing to add

95.216.96.128/26 via 95.216.96.129 dev enp0s31f6

ProblemType: Bug
DistroRelease: Ubuntu 18.04
Package: systemd 237-3ubuntu10.21
ProcVersionSignature: Ubuntu 4.15.0-48.51-generic 4.15.18
Uname: Linux 4.15.0-48-generic x86_64
ApportVersion: 2.20.9-0ubuntu7.6
Architecture: amd64
Date: Thu Apr 25 20:41:40 2019
Lsusb:
 Bus 002 Device 002: ID 8564:1000 Transcend Information, Inc. JetFlash
 Bus 002 Device 001: ID 1d6b:0003 Linux Foundation 3.0 root hub
 Bus 001 Device 001: ID 1d6b:0002 Linux Foundation 2.0 root hub
MachineType: FUJITSU D3401-H1
ProcEnviron:
 TERM=xterm
 PATH=(custom, no user)
 XDG_RUNTIME_DIR=<set>
 LANG=en_US
 SHELL=/bin/bash
ProcKernelCmdLine: BOOT_IMAGE=/boot/vmlinuz-4.15.0-48-generic 
root=UUID=3b7af44e-1608-4ae6-8407-81831f3073c3 ro quiet splash 
crashkernel=384M-:128M vt.handoff=1
SourcePackage: systemd
UpgradeStatus: No upgrade log present (probably fresh install)
dmi.bios.date: 11/08/2018
dmi.bios.vendor: FUJITSU // American Megatrends Inc.
dmi.bios.version: V5.0.0.11 R1.27.0.SR.2 for D3401-H1x
dmi.board.name: D3401-H1
dmi.board.vendor: FUJITSU
dmi.board.version: S26361-D3401-H1
dmi.chassis.type: 3
dmi.chassis.vendor: FUJITSU
dmi.modalias: 
dmi:bvnFUJITSU//AmericanMegatrendsInc.:bvrV5.0.0.11R1.27.0.SR.2forD3401-H1x:bd11/08/2018:svnFUJITSU:pnD3401-H1:pvr:rvnFUJITSU:rnD3401-H1:rvrS26361-D3401-H1:cvnFUJITSU:ct3:cvr:
dmi.product.family: ESPRIMO-FTS
dmi.product.name: D3401-H1
dmi.sys.vendor: FUJITSU

** Affects: systemd (Ubuntu)
     Importance: Undecided
         Status: New


** Tags: amd64 apport-bug bionic

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https://bugs.launchpad.net/bugs/1826459

Title:
  systemd-networkd not installing GatewayOnlink=true

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