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this post was submitted on 05 Nov 2023
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In general they wont. The way they usually find out with small businesses is disgruntled former employees snitching (some actually offer a reward for this).
I was once hired at a company to get them ISO compliant (8001, 27001 and various other certifications specific for data storage and handling for banks and healthcare).
First thing I did was run inventory on all hard and software and it was quickly clear they ran 50 something unlicensed Windows and Office copies, 3 unlicensed Windows Server copies, 2 unlicensed Exchange copies, a whole bunch of unlicensed Winzip copies and on and on and on.
The typical with small to mid sized businesses.
You absolutely need to get your licensing in order if you want to get those certifications, especially the banking and healthcare data ones.
I made them a list of everything we'd have to acquire to be in order with that part.
They refused. They refused to the point of telling me "it's not working out and we're letting you go".
So, yeah, that's how you get Microsoft to hear about a company running a couple hundred unlicensed products :)
They never got their ISO certs and downsized considerably a year or two later.