I'm now getting the same message as of about a week or so.  Everytime
the server starts it tells me a new version is available and I click
"install Now" or something to that effect, but it never installs.
Running on an iMac OS 10.10.5.  Any idea why it wouldn't update?

Don't you even get to see the installer? Can you check the dock whether there is any activity going on? I've seen the installer being opened in the background before.

--

Michael
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