That they were able to successfully manually renew within LFDS makes me suspicious they're running an earlier version of LFDS 11 that still had this bug:

KB1014288: The Laserfiche Directory Server's primary license automatic renewal is not successful which was fixed in Laserfiche Directory Server 11 Update 2 (11.0.2204.1467) (and above).

Summary

The primary license autorenewal feature (based on expiration) fails. The Automatic Renewal Status always displays Unsuccessful. This issue exists in versions 10.4.4, 10.4.5, and 11, but patches are only available for 10.4.5 and 11. To work around this issue... manually renew the license.

Check the LFDS build version. If it's below 11.0.2204.1467 (Update 2), the cause is very likely this bug. Resolve by upgrading LFDS to the latest available Update, which includes the fix.

If it's at or above Update 2, please open a support case.

This is also a good example of why it's always helpful to provide the version/build number(s) when posting about an issue here. There are often many things that can quickly and easily be ruled out, or relevant bugs and patches identified when we know the software build on which the issue occurred.