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https://badssl.com/ is a nice website, it shows all the ways ssl can be misconfigured. So you can see how it affects connections.
Others have covered the what and why in this thread, but I just wanted to point out something a bit different - if you are able to, I would try giving certificate creation automation a try. There are things like Let's Encrypt and certbot that can make this process very smooth for Unix based systems and I think there are some Windows equivalents if you look out there. If you do depend on a certificate vendor like DigiCert I've heard some success of making changes to certbot to make them work but I can't guarantee anything. Just food for thought.
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