The endpoints are always going to show an expiration different from the license expiration shown in KAV. There are multiple licenses and timers in play that are integrated together to coordinate the Kaseya and Kaspersky licenses for the integrated KAV product. The Kaseya license (the license by which you are billed) expires 1 year after installation to the endpoint, and is noted in the KAV module as the license expiration date for the endpoint. At the end of that year, the number of expired licenses is increased by one, the agent ID is issued an unused license, and the unused license count is decreased by one. All of this is independent of anything happening on the endpoint.
On the endpoint, we apply an initial 90 day license file at installation. As that file nears expiration, 30 day extension license files are applied via the KServer during a maintenance process. As long as the endpoint is flagged on the KServer as having a valid KAV license, it will be issued an extended Kaspersky license.
Kaseya KAV license: 1 year, noted in KAV module
Kaspersky KAV license: initial 90 day, rolling 30 day extension on kserver checkin, noted on endpoint.
As long as the Kaseya KAV license is valid for the endpoint agent ID, the rolling 30 day license should be applied out automatically as the previous nears expiration. We have seen cases where the endpoint will display either a "License will expire in 'X' days" message or "License Expired" message. In these cases, open a support ticket, and a specialist will be able to investigate why the updated licenses are not being pushed to the endpoint.
An update is in the works to update how the License Status information is conveyed, which should clear up most of the confusion and issues created in the current licensing process.
Additional information is available at community.kaseya.com/.../877.aspx including updates to reflect current issues.