I'm interested in hearing about how various teams are tackling updating of packages? Do you do regular updates, do you carefully choose what packages you update etc? What's the reason behind your strategy? How does your automation for updating look like?

This is a very interesting reading on the topic, with quite clear position taken and I do pretty much agree with it (although several updates per week seem a bit of an overkill).

For example our product is quite a big solution (40+ projects) and we are referencing around 150 NuGet packages. You can imagine that updating all the dependencies is quite of a big task, especially if you do it once per year or so. So imagine braking changes in APIs, uncertainty with backwards incompatibilities etc.

Of course there is a mix of all sorts of packages - behemoths like ASP.NET MVC/WebApi stack, NHibernate and Xamarin.Forms as well as quite small ones where you wouldn't expect trouble.

The release cycle of our software is once per month, so I'm thinking to go into updating packages after every release, in order to avoid big-bang updates with lots of braking API changes (as now, when we did it every now and then, max twice per year). However on the other side this adds uncertainty part more frequently. Our automated tests coverage is far from 100%, so can't fully rely on these as well.