A common issue that comes up in Suppor tickets is that when creating a new Work Order, the Vehicle will have overdue services, but FleetWave will fail to prompt the end user to add those services to the Work Order being created.

User Error
In these cases, the first thing to rule out should be user error. You can check the Compliance tab on the Vehicle record in question to confirm that there is in fact a Vehicle Service Event created for that Vehicle, and that it is actually due at the time of Work Order creation:

It may also be worthwhile determining how the end user handles the creation of Vehicle Service Events, and if they don't use the Vehicle Service Event Tool, it may be pertinent to try and recreate the VSE using the tool to see if the issue still persists.
INI Codes
There are numerous INI Codes related to Work Orders and the overdue service popup. It is recommended that you check for any that may be affecting the functionality, however, these two INI Codes have a direct affect on how the functionality works:
Job Event Configuration
In a past ticket, the reason why some overdue services were not appearing in the pop-up window was due to how the Job Event itself was configured. On the JOB_EVENTS_FW table, if a Job Event does not have the "RAISE JOB DETAILS FOR THIS EVENT" flag enabled, then that job event will not appear in pop-ups for Vehicles that have an overdue service of that Job Event type.