Membership Status Pending Not Updating to Current (Scheduled Job)

We have several memberships for people that have a Member SInce date and a start date set at a later date. Initially this will set the status to PENDING(Because we have the NEW status disabled). Once the date start date has passed the membership should update to CURRENT(once the scheduled job runs). However, when I run the schedule to update membership status it does not change all the PENDING to CURRENT.

If I go into manually edit the membership for a contact then save it right away it will update the status to CURRENT. This means that my rules are correct.

For example the following membership data has the status set to PENDING and will not update when the scheduled job runs:
Member Since: 6/16/2016
Start Date: 7/1/2016
End Date: 1/1/2017
After further examination of the statuses I have found the behavior related to PENDING to be confusing. Given the following order for status rules:
Current - start/end
Grace - end/end
Expired - end
New - member since/member since
Pending - member since/member since

If I attempt to add a membership at a later date (than today) with NEW status enabled it will create the membership properly. If I disable NEW (so that PENDING will now be the status) and attempt to create the membership it will fail with the following errors:

There is no valid Membership Status available for selected membership dates.
Membership Status Error
Oops, it looks like there is no valid membership status available for the given membership dates. You can Configure Membership Status Rules. OR You can sign up by setting Status Override? to true.

This leads me to believe that there is something wrong with the built-in PENDING status.

*On a side note, the default order for status has NEW as the first rule. When this is the case I believe it never updates to any of the other statuses.