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If I've got two vhosts for two different websites running off 8081 and 8082 (both SSL), do I need a wildcard cert? The hostnames resolve to the same IP but seeing as they are running off of different ports can I serve the correct cert? They are behind a reverse proxy.

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Nope, the port of your webserver is not relevant for SSL, only the hostname matters.

Thus: https://www.example.com:8443 and https://www.example.com:8444

can use the same SSL-Cert with e.g. CN=www.example.com

Your last sentence makes me wonder though: ...behind a reverse proxy... From where to where do you want to have your SSL-Connections? From the internet to the proxy (both ports) or from the proxy to the backend servers (different ports)?

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