After researching the logs further, I have found when the server which VisualCron is installed, is restarted, VisualCron will release handlers for triggers and then reactivate them when the server is back up.
Here is an example of this working properly:
Here is an alphabetical example of this not working:
There also seems to be incorrect details in the log message field, in the image where the trigger was not restored, notice the Accounting job has details regarding Careington inside of it, that is a completely different job and this seems to be occurring very often. Please let me know what next steps we need to take, hopefully avoiding an upgrade as upgrading VisualCron is often very troubling because of the bugs that I have encountered in the past. We are currently on version 8.2.4.