I have a Discourse Docker container running on Ubuntu (created from DO template) with “Custom OAuth2” enabled. Works very well, expect it fails to update its Letsencrypt certificate. Tracking down the problem I can see from the logs that the update script is executed by Cron, but the challenge gets…

I’m not sure I see something obvious here, but honestly I would just put the setup behind a reverse proxy and terminate ssl there, then use DNS validation instead. (this is just a workaround, not a solution because problem is unknown)

More info on the issue: I can see the incoming acme-challenge request to http://community.site/.well-known/… It gets redirected to https://community.site/ and then redirected to /oauth_basic. The second redirect is very well expected, but not the first one. The incoming challenge request appears …

[afbeelding] Ostap1974: I found a /etc/nginx/conf.d/outlets/before-server/20-redirect-http-to-https.conf that seems always to return 301 https://community.site for any request to port 80. That issue has been fixed last August, letsencrypt updates: renew location for .well-known, add support f…

Interesting, I rebuilt the app on Nov 26th, so I would expect the fix included by then… Anyway, thank you all for help. Let’s close the topic and hope the issue will not return after next rebuild.

Ah, I see there was more to it, you can read about that here to the end of that topic and then you will see there was another fix on December 22. So that explains why you encountered it.

Looked the commit, I have it insalled. But I think there is a mistake there. return 301 https://${DISCOURSE_HOSTNAME}$request_uri; should be return 301 https://${DISCOURSE_HOSTNAME}\$request_uri; Please correct me if I am wrong.

That is exactly what the other fix I mentioned, fixes [image]

OAuth2 and Letsencrypt clash

Ondersteuning

RGJ (Richard - Communiteq) 28 januari 2026 om 14:37 4

That issue has been fixed last August, letsencrypt updates: renew location for .well-known, add support for … · discourse/discourse_docker@ae4887a · GitHub

Topic		Antwoorden	Weergaven
Let's Encrypt cert renewals (suddenly) failing Self-hosting	27	2973	27 januari 2022
Discourse failure to renew certificate Bug letsencrypt	25	766	27 december 2025
LetsEncrypt certificate not renewing Self-hosting letsencrypt	6	397	9 december 2024
Hit Let's encrypt renewal limit Self-hosting	7	2131	31 juli 2020
Letsencrypt not renewing Self-hosting	6	1527	8 juni 2024

OAuth2 and Letsencrypt clash

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