Hi Zach Seeing that you have been waiting for over a year for an answer I'll do my best. https://www.wilderssecurity.com/threads/diskeeper-18.413283/#post-2808197 Diskeeper was introduced in its current iteration with DRAM caching in 2016. Since that time there has only been one upgrade, in 2018, to Diskeeper 18 (They skipped Diskeeper 17). Diskeeper 18 did not effect any of the basic functionality of the program for the home user. Diskeepr 18 added a revamped dashboard that shows the amount of I/O offloaded from storage and how much I/O processing time is saved, an Administartor management console allowing for endpoint deployment, and eliminated the need for reboot on installation. So it's a crap-shoot, i.e., it's been so long since a significant upgrade that one is overdue and Condusciv is close to a new release, or the fact that there has been no upgrade for so long means that Condusiv has decided to leave well enough alone and is not actively working on an upgrade. My gut tells me that the Upgrade Assurance is not necessary, but in view of the fact that if I tell you that, Condusiv will probably announce an upgrade tomorrow -- so I won't tell you that. Hope this helps.
I stopped using Diskeeper over 2 years ago as I didn't find it help with SSD's in any way but I would still recommend for HDD's.
I have tested recent proactive versions of Diskeeper, and haven't noticed any benefit whatsoever. In fact, after using the proactive type Diskeeper, you can analyze your disks with another traditional disk defragmenter and see that your disks are still fragmented. I still think a good traditional disk defragmenter gives better results. I have my preferred disk fragmenter, but I won't drag this thread down that road.