It means that Microsoft is providing information that they shouldn't.

And Canonical decided to take that data, search him on Linkedin and contact him. Seems reasonable to see that as a reason to loose respect for Canonical over.

Don't get me wrong, what Canonical has done here also isn't good. But what they've done shouldn't have been possible because Microsoft shouldn't have given Canonical the information in the first place.

The question I have is what's in it for Microsoft, why did they even bother to do this in the first place? I can't believe there would be that big of a cash incentive.

If this were Windows, I would expect Microsoft to pass it to an internal department that sells higher service contracts and then off to 3rd parties that provide the same for up to a week after you find the "don't share my data" checkbox.

That (enterprise support) is a very important side business. Whether they got cash from other OSes or just set it up the same to fight an eventual Anti-Trust Case is anyone's guess.

Again, the user's relationship was with Microsoft, not Canonical. Microsoft is the one who the user entrusted to protect their data, and they didn't.

The user chose Microsoft's Azure product to run Canonical's Ubuntu product. The user has relationships with both vendors.

how makes that Canonicals side of things better?

It doesn't.

Well, what should we be more angry about? That Canonicals sales rep is using data in their CMS, or that Microsoft is selling data to third parties. The root cause seems to be Microsoft, not Canonical and (at least in my eye) the conclusion is not "don't trust Ubuntu", but "don't trust Azure".

Someone giving you a gun doesn't absolve you of the crime of shooting someone with it or of keeping the gun.

edit: The data doesn't just magically show up in Canonical's CRM. They spent time and effort establish an integration with Microsoft and then building processes on top of that data.

As stated above, MS isn't selling this information. They are providing it for customer support purposes.

In the business world, having data marked "customer support only" is pretty common. There are quite a few laws acknowledging the difference. Importantly, the data is supposed to be kept separate and it sounds like Canonical screwed up here.

The takeaway is "don’t trust Ubuntu or Azure".

It’s like if you tell a friend that there's a key to your back door under the mat but to keep it a secret and instead of keeping the secret they tell a mutual friend about it and that mutual friend robs you since they know where the key is.

You shouldn’t trust the friend that told the your mutual friend where the key was and you shouldn’t trust the mutual friend who robbed you.

The friend who told your mutual friend may have done so for what they thought were useful reasons, like letting the mutual friend know so they could fix something for you while you’re out, but they still violated your trust non matter what their intent was.