Elapsed time on SLA's not working as expected.
Schedule defined incorrectly.
The behaviour seen is due to the configuration of the schedule entry.
Notice the When fields set here:
10/26/2018 and 10/26/2028
Generally, we will set a schedule over a period of a day, or a few days. However, I think part of the issue here is setting the end value to 2028. I think this should be set to match the same day:
10/26/2018 and 10/26/2018
Also, the 'Repeat until' field is set to a date in the past. Since this set to run only until 10/16/2018, the schedule will not run past that date.