Let's Encrypt Reissue Certificate failed cannot reassign certificate after it expiry .
I have tried [Click here]] but it wont resolve my issue
Could not issue an SSL/TLS certificate for example.com
Details
Could not issue a Let's Encrypt SSL/TLS certificate for example.com . Authorization for the domain failed.
The IP addresses your hostname resolves to are from CloudFlare. It's very weird that LE nor I nor SSLLabs can make a TLS connection to CloudFlare, but I'm not sure if there's anything we can do. I think this is something happening on CloudFlares end.
So at least your site is, except for the expired certificate, working again, so that's good.
There's a HTTP to HTTPS redirect in place for almost all requests to your site, but not for the ACME challenge on /.well-known/acme-challenge/, so it seems something knows about those validation requests and handles them differently, but apparently not good enough.
You said you've followed the steps in the link from Plesk provided with the error message. Did you also try the following part?
create a test.txt file in the \.well-known\acme-challenge\ folder (where Let's Encrypt stores its temporary files) and put some text into it. Then open this file in a web-browser at http://example.com/.well-known/acme-challenge/test.txt and make sure it is accessible from the Internet over HTTP without www prefix. If the file is not accessible, check website's configuration.
Because at the moment, a request for /.well-known/acme-challenge/test.txt fails..
How though does that relate to the Physical Path shown in the screenshot I referenced? Perhaps more importantly, what's the difference in file service location or options between http and https? Clearly file service works for https, so what is either preventing it from working for http or causing IIS to look elsewhere for http?
http://example.com/httpdocs/.well-known/... is not the path where certbot is looking. It expects the challenge folder containing the test file here: http://example.com/.well-known/acme-challenge/test.txt
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See the folder structure in the error message you received for the location of the token where the token was expected - no httpdocs folder is in the expected path.
Move the /.well-known folder out of the httpdocs folder and make it a first level folder directly below the domain. Then see if you can access/download the test file from the above URL.
It looks like IIS/Plesk/whatever is handeling the requests for /.well-known/acme-challenge/ in a whole different matter than "just" a physical place? If you look at the following line from the error message when you try to open the test.txt through HTTP: