You can do manual update with Drobo Dashboard by going to the Advance Controls menu > Tools tab > hold CTRL and click Check for Updates > Select the firmware you’ve downloaded and it will manual update the firmware.
As for “why Drobodash always tells me I have the latest version…”, I got the same message too, so I updated it manually. This issue has happend before with older drobo dashboard, so I just manually update ever since and didn’t trust the drobo dashboard software.
To tell the truth, I love the Drobo hardwares and it’s capabilities, but I’m not sure they are good at producing good software and drivers when compared with other high-end storage devices. I think some on this forum may agree with me on that as well. The Drobo Dashboard and the iSCSI driver can get glitchy at times and Datarobotics was fairly slow on producing fixes and updated versions of drivers. Even the new Drobo Dashboard 2.0 for the business units feels slow, glitchy, and simple (not as pro looking as highend server monitor software, for a pro unit you would think the software will provide more information like temperature info and etc.). I hope DR can slow down on dishing new hardware and take some time on the Drobo Dashboard / Drivers (especially iSCSI) and solve those “Drobo randomly disconnected for no reason” issues to build a strong driver foundation for future products.