Windows signing is a ripoff, $500/year you're getting nothing. Your certificate is not trusted. You have to "get reputation for it" before Windows Defender would stop giving users warnings. Also, renewing certificate is not a thing. Every time you have to get a new one, with same story of "reputation" again. [1] https://www.digicert.com/order/order-1.php
There's a backdoor that lets your bypass the SmartScreen reputation requirement: pay more money for an EV cert[1]. I don't agree with this industry practice. Reputation requirements either shouldn't have backdoors or shouldn't exist in the first place. 1. https://twitter.com/JosephRyanRies/status/951643158118567937
Arguably the Reputation requirement is more helpful than the information held in the certificate, since Reputation is hard to fake whereas that information is provided by the requestor and its validation depends on the CA's processes (which as I said varies wildly).
It is one of those "greater good" things. It does suck for FOSS however.