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They employ a lot of this strategy (the ads, the 'subscribe to Microsoft 365 today' 'your computer is at risk to ransomware because you aren't paying us for onedrive'). Except the "loss" part. In fact, I think it's rare nowadays to find a "loss" leader, they seem to have settled around at worst "barely profitable" in business. Too many loss leaders had pretty terrible business outcomes, so it seems to be an unpopular thing to expose your business the risk of going negative margin at any significant scale. Like this disaster: https://en.wikipedia.org/wiki/I-Opener
I must be behind. I've been under the impression that pulling people in on a minor loss meant greater margins. Perhaps COVID had a significant adverse impact on that as well.
Even before covid, I think companies got a bit skiddish about actually going negative. Probably still do on little things, but I think Microsoft at least makes Windows pay for itself while also using it as you would use a loss leader.