Getting a grasp of how many people use my software

Question

We have a very small, specialized user base. No community. My boss wants to find out who is using it. And his approach is to simply make a hidden connection, maybe an auto update function, enabled by default WITHOUT notification when there is no update ... I don't really like the idea and try to come up with something different.

There is a registration, then you can download a free trial. No other limitations, but the time limit.

Sold licenses are usable across an ip-range - universities. So the registration and licensing itself is no indicator of usage. Not to speak of that the devs have no feedback about sold licenses whatsoever.

I would like to have some advice how you would, or better have actually, approached a problem like this.

Answer 1

"Simply call home" to notify you that someone is using your software is probably not a good idea, indeed : users don't tend to like that. And it can be bad for the reputation of your company/software.

A solution would be having some kind of good reason to "call home" ;-)

For instance, what about some kind of auto-update-mecanism ? That users could disable, of course, if they want (so not 100% percent efficient) ; but most won't disable it.
And it's really a good idea of reason to do a request to your server :-)

Just don't send anything that could identify the user ; some unique-id key, maybe (to make a distinction between users), but that cannot be used to identify a user ?

I don't like when software I use say to people "hello, this guy is using me!", but I really like the auto-update feature in Firefox, for instance... Event if it says I'm using the software ;-)