Just got off the phone with Sky, a second level drobo support tech, and I asked her pointedly “Can I purchase drobocare anytime within the first year?” She said “Yes.”
Drobocare also runs from the date it is activated. I purchased my DroboS on March 31, 2011. I have until March 31, 2012 to purchase and activate drobocare. If I activate drobocare on March 31, 2012 then I have drobocare until March 31, 2013.
Drobocare has to be activated within 30 days of purchasing. From their site "You should purchase DroboCare BEFORE the standard warranty or active DroboCare contract expires, but no more than 30 days before expiration. Keep in mind that your DroboCare contract must be activated within 30 days of purchase.
This changes everything for me. I’ll probably buy drobocare next March for my DroboS.