I'm seeing the same problem on my Raspberry Pi 3b and Raspberry Pi 3b+. After a reboot, it sometimes successfully updates the time and sometimes it won't, so I'm thinking there's a race condition. "Wait for network = 60s" does not have any effect on this, nor setting the NTP servers.
systemctl status systemd-timesyncd prints this:
Code
Warning: The unit file, source configuration file or drop-ins of systemd-timesyncd.service changed on disk. Run 'systemctl daemon-reload'
● systemd-timesyncd.service - Network Time Synchronization
Loaded: loaded (/usr/lib/systemd/system/systemd-timesyncd.service; disabled; vendor preset: disabled)
Drop-In: /usr/lib/systemd/system/systemd-timesyncd.service.d
└─depend-on-kernel-ip-config.conf
Active: inactive (dead)
Condition: start condition failed at Thu 2019-04-11 19:28:37 EEST; 1 years 4 months ago
└─ ConditionPathExists=/dev/.kernel_ipconfig was not met
Docs: man:systemd-timesyncd.service(8)
Apr 11 19:28:37 raspberry systemd[1]: Condition check resulted in Network Time Synchronization being skipped.However, the same output is printed even if the time is set properly. Is systemd-timesyncd used for time sync?
EDIT: Also as a sidenote, systemctl daemon-reload won't make the warning disappear, I wonder why.