SQL Jobs logging only 2 days
You should either remove the checkbox to limit the size of the job history or increase it.  One of your maintenance steps should be to run the sp_purge_jobhistory MSDN command to remove job history older than your retention period.  

The "Remove Agent History" checkbox does this behind the scenes but is NOT an automated process that removes history older than the time period specified.  It's really badly named and placed.  

If you have lots of jobs or a few jobs that run very often then you will quickly use up 1000 logs of job executions.  As mentioned in the comments, another solution is to archive the contents of the sysjobhistory table.