Some details to think about... (I am not telling anyone what to do)
If Sears does file for Chapter 7, this will most likely end current COBRA benefits and health insurance for current employees.
For most companies, right now is the annual enrollment period. If you are fortunate enough to have a working spouse/domestic partner, you might want to consider jumping on their insurance so you have health insurance if the worst case scenario occurs. I am not sure what happens if Sears files for 7 in the next few months or early 2019 (regarding health insurance).
If you are currently using COBRA, you might want to consider applying for 'Obama-care' (healthcare.gov) during the enrollment period Nov 1 to Dec 15 to cover yourself in case Sears shuts down (chapter 7).
I am contacting my health insurance agent this week to mull over my options. I am supposed to be eligible for Sears retiree health insurance and COBRA but since this whole affair is so unstable it's best to think about an alternate plan.
Mentioning this because so many of us are looking for a job right now and details like this can fall thru the cracks. It can be devastating especially for families if your health coverage ends abruptly. Some health insurance companies have waiting periods so one could be without health insurance for a couple months if chapter 7 happens late this year or early next year.
Feel free to comment if you have any helpful advice or information about this topic.