How to: Enable the “Connect to Outlook” grayed out/disabled button on SharePoint 2013 to synchronize your content
The short answer: just hit F5 (reload the page).
I had been terribly confused as to why the “Connect to Outlook” button on the SharePoint 2013 ribbon would be grayed out most of the time. The first time I loaded the site I was able to sync our corporate contacts with my Outlook 2013 but when I went around showing people how to do it they all had the grayed out button. That was kind of embarrassing, having it not work all of a sudden. You get the following message when you try to click it or hover over the grayed out button:
This control is currently disabled
You might not have the right permission level to use this, you might need to select an object or item, or the control might not work on this context.
Obviously that message does appear in other circumstances like as it indicates, you don’t have the right permissions etc. So I proceeded to check for all those things just to find a dead end. Finally I found a post on Microsoft that explains the reason why the button gets grayed out. SharePoint 2013 has a new feature called Minimal Download Strategy. You can probably guess where this is going by now: The way this new feature works allows in a few words for your page to load faster. Most people might be tempted to disable the Minimal download strategy but you will miss out on a lot of coolness. Yes, it is a pain to press F5 until Microsoft figures out how to resolve this but the benefits outweigh the pain of refreshing the page. If you disable that feature you will notice that button won’t be grayed out but also that your pages might take longer to load and your webserver might be more busy.
Anyway, just press F5 for the time being and enjoy SP2013!