Hey! A few quick updates here, sorry itās a little late - busy couple of weeks 
Windows Server 2012 R2 EOL:
Unfortunately, I donāt have any further context around the EOL side of things. Ultimately itās a decision made by the Product Managers for the Agent, and it mostly revolves around prioritising support for currently in-date operating systems.
At a guess, and only a guess (this is not authoritative information), the work required to keep supporting Server 2012 R2 might have taken too much resources or perhaps could not have been completed prior to the OS ending general support from Microsoftās side.
Generally Iād suggest getting in touch with your Customer Success Manager if you want to dig deeper into this decision. I know a few customers have opted to go via this route, but I donāt know the outcomes there.
Agent updates on version 2.7.x:
As for the autoupdate issues with older Agent versions, Iāve got an answer on this. Operating System returns were introduces in bootstrap version 2.3.0.3, which shipped with Agent version 3.0.8. Prior to these versions, bootstrap doesnāt return the OS of the asset the Agent is running on.
Agent updates are handled via the bootstrap, in which our Platform pushes Agent updates in accordance with organisation settings and such. As part of this, we have a service that prevents updates to certain operating systems that are no longer supported on newer versions. This service requires there to be an OS return; if there is a null value, it wonāt push any updates to that bootstrap.
So, given that youāre running Agents below version 3.0.8 in which the OS return was introduced, the service would not push any updates out to them on account of no OS return.
From chatting to dev about this, thereās no great way of adjusting the service to allow for updates without causing further problems as we have no way of knowing which operating systems they run on from a bootstrap perspective.
As an example of why removing the rule is not ideal, if we did so then any Agents running on Windows Server 2008 or Windows 7 SPO1, with a last-supported version of 2.7.22, would update to 3.0.8 which would break the installation and the Agent would not function anymore.
Our approach currently is to prevent these situations, and we currently recommend customers manually upgrade Agents below 3.0.8 that are supported up to or above this version. Itās an ongoing discussion to see if we can find a way around the limitations here without unintentionally breaking things, but Iād go with manual updates as I donāt expect us to make any changes here in the foreseeable future given itās near the end of the year.
And for reference, the last supported versions for out-of-support operating systems are listed here: