I know that this is how letsencrypt verifies that I own the server, however when I make the required file for this URL and navigate to it this is what OS X Server produces: Websites are turned off. An administrator can turn them on using the Server application. The website is on and working. Do…

I'm not sure, but I wonder if this prior issue is related to your problem: [image] [Solved] Apple server proxy blocks access to .well-known Server I…

Actually I found a solution to my problem just a few minutes ago here: https://github.com/letsencrypt/letsencrypt/issues/1782

Mac OS X Server "/.well-known/acme-challenge/KEY" Error

schoen March 24, 2016, 6:47pm 2

I'm not sure, but I wonder if this prior issue is related to your problem:

Topic		Replies	Views
[Solved] Apple server proxy blocks access to .well-known Server	17	10617	March 10, 2016
OSX / unauthorized & invalid response from Server	14	4172	December 2, 2016
'Failed authorization procedure' on macOS server - Web Root Server Not Correct Help	1	1111	May 21, 2017
Please make sure /.well-known alias is setup in WWW server Help	1	3740	June 2, 2017
404 error on <website>/.well-known/acme-challenge/ Help	7	12352	July 20, 2018