I am surprised no one has replied here.
I have seen exactly the same behaviour on the Meraki cloud authentication option to.
Where after the set time out the login splash does not appear for client to re-login.
Users have to forget the network and re-add it
The reason i have been told by Meraki is because - "The splash page is only generated when HTTP traffic is sent by the client"
Note the term HTTP and not HTTPS.
Dear Meraki I have had this out with your support team ... PLEASE find me a device that sends HTTP traffic by default for the splash page to re-appear after the set timeout. There isn't one !!!!
I have also been told by a Support manager there is no roadmap to change this behaviour.
Causing us a lot of pain to be honest.