Hopefully I am the only one experiencing this, but just in case, I figured I would summarize what transpired.
tl;dr Almost a year ago, they gave me a free MAX membership for no real reason, set it to auto-renew, and are now planning to bill me for the renewal. And canceling took quite a bit of digging...with no indication it actually worked.
-I haven't purchased anything from KMart/Sears since 3/2017, and hadn't purchased using actual money (as opposed to points) since 12/2016
-Became a Shop Your Way MAX member on 8/30/2018.
Looking at my account, it shows "Annual Membership - FREE for VIP members." Ummm, ok. I had been VIP multiple times in the past, but hadn't bought one thing for actual money in over 18 months.
-Got email today from firstname.lastname@example.org
with headline "Expiring soon! Renew your Shop Your Way MAX membership"
Your Shop Your Way MAX® membership will be renewed on 08/30/19.
As a reminder, $39 (plus applicable taxes) will be charged to the card you
have on file. You've got another 12 months of amazing benefits, exclusive
offers and loads of savings coming your way!"
Here's the link I found to check your status and/or cancel renewal and/or membership.
Of course, nothing on the website actually changes when you Cancel, so who knows.