This morning I reported a deal to get one year of Shop Your Way Max for only $9.99: Sears / Kmart free shipping for one year, for only $9.99! YMMV.
I decided that it was worth extending my subscription by a year, so I tried purchasing the deal. During checkout, I clicked “apply my Shop Your Way coupons” and selected each one to see if any applied to this order.
Surprisingly, the system accepted the coupon titled “VIP excusive – For a limited time, enjoy a year of free 2-day shipping for only $19 (50% savings).”
And, in my cart, the system had zeroed out the price for Shop Your Way Max entirely. I wasn’t able to checkout with a zero cost so I added a $3 pickup in store item and checked out. My account now shows an extra year of SYW Max shipping eligibility!