How about the Windows firewall?
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Not sure I'm fully tracking but if you go to foundry.koodgarma.com it does take you to my Foundry VTT server, just not via SSL I think
http://foundry.koodgarma.com/
Should that be?:
http://foundry.goodkarma.com/
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Which is it?
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it is foundry.koodgarma.com hehe it's a play on words
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OK.
I can play with words - LOL
Check your Windows wirefall settings.
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Roger that. I'm in Windows Defender Firewall with Advanced Security settings, not sure what to do next.
oh wait, just found this... Open TCP Port 80 in Windows Firewall [McNeel Wiki]
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Okay I set up a new rule for port 80 and then I tried to use portchecker.co but it still says port 80 is closed 
Well that's not exactly BAD news; As there is nothing listening on port 80 at the moment.
Let's retry:
certbot certonly --standalone -d foundry.koodgarma.com
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Just retried it and got the same error
Then your ISP might be blocking port 80.
OR
The router is eating port 80 requests.
"fixing" that requires a "visit" to your ISP's help pages and maybe their tech support
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Stupid COX and/or voracious router 
Is next logical course of action the DNS-01 route or one of the links at the site you shared earlier? ACME Client Implementations - Let's Encrypt
In the meantime, you could "try" your hand at manual DNS authentication.
That requires being able to create/modify TXT records at your DSP (GoDaddy?).
Login to the page where you created the A records and CNAME.
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Appears COX is blocking (hehe) port 80... Cox is blocking port 80 incoming, causing security certificates from installing! - Internet - Internet Forum - Cox Support Forums
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OK.
So, no easy route for you 
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Which is weird because I was able to get a secure cert using Certbot around May last year and I didn't run into this issue back then
Do you want to try your hand at DNS-01 auth?
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Heck ya and btw I really appreciate your help with all of this! I will be your Padawan!!
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Who would have expected that?
ROFLMAO
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