It seems like your server is not directly on the internet

Do this:

In one terminal:

doas tcpdump -nettti pflog0 port 443
(This command will literally say BLOCKED or ALLOWED for traffic. It is the
absolute best feature of pf when I was using BSD).

In a separate window:

curl https://google.com

Now go back to your tcpdump - do you see the traffic show up as blocked?

If so, your local pf.conf is not allowing the HTTPS traffic outbound. You
need to create a rule to permit it.

Something like:

pass out log on em0 from em0 to any port 443

If it is being permitted, then it's something down the line, maybe the
gateway, maybe it's gateway. I have no idea what your network looks like.
But 100% of firewall concerns can be solved with that tcpdump command.

I don't check here often but hopefully it helps.

On Thu, Oct 17, 2024, 11:42 PM Aaron Mason <simplersolut...@gmail.com>
wrote:

> Do you get the same response when trying to connect to port 443 on the
> Windows machine? A standard config would block it if there isn't a
> service running on that port that was allowed, resulting in a
> connection timeout.
>
>

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