during recent testing of my raspbian-nspawn-64 image, I ran into a small race condition that I believe will probably also affect vanilla Raspbian installs.
Specifically, if the user boots the current (10 July 2019) Raspbian image, with no Ethernet connected, gets to the WiFi setup screen, specifies the desired connection and passphrase, and then immediately progresses to the "Update Software" stage, they are then in effect racing the automatic time sync. This can take up to between 30s -> 1m to correct the time (after a ping-capable wlan connection has been established) from the shipped 10th July, but if the user has clicked forward immediately they may get something like the following:

Not the end of the world, but some less experienced users may be confused by the error and not know to retry (since OK-ing the above error dialog takes them to the "Setup Complete" screen), leaving them running a (slightly) out-of-date (but still functional o/c) system.
This would be an easy corner case to address in piwiz (which otherwise works very nicely).
Apologies if I am in error, and this doesn't apply to standard Raspbian.
Best, sakaki