Basically I have been studying a bit Traefik, since it looks a bit more professional than the other reverse proxy I was using, and the only problem I am still facing is the generation of a certificate for ONLY my WILDCARD DuckDNS.

Example:
I want a single certificate generated for *.mydomain.duckdns.org, and that one certificate will be used by all selected services/containers. In my case, for studying purposes I have only Portainer and Traefik Whoami services, so their URLs are, respectively:

• portainer.mydomain.duckdns.org
• whoami.mydomain.duckdns.org

The current behavior is: Traefik is requesting one cert for the first URL and another cert for the second.

Goal: create just one wildcard cert and use it for both URLs.

I prefer doing all the configuration using the static and dynamic files instead of docker labels for now, as it seems easier to understand as a beginner, so here are my files:

# docker-compose.yml
networks:
  selfhost:
    external: true

services:
  portainer:
    image: portainer/portainer-ce:2.21.5
    container_name: portainer
    networks:
      - selfhost
    volumes:
      - ./portainer/data:/data:rw
      - /var/run/docker.sock:/var/run/docker.sock:ro
    restart: unless-stopped
    ports:
      - 9000:9000
  whoami:
    image: traefik/whoami
    container_name: whoami
    networks:
      - selfhost
    restart: unless-stopped
  traefik:
    image: traefik:v3.2
    container_name: traefik
    networks:
      - selfhost
    volumes:
      - ./traefik/traefik.yml:/etc/traefik/traefik.yml:ro
      - ./traefik/dynamic.yml:/config/dynamic.yml:ro
      - ./traefik/letsencrypt:/letsencrypt:rw
    restart: unless-stopped
    ports:
      - 8080:8080
      - 80:80
      - 443:443
    environment:
      DUCKDNS_TOKEN: duckdnstoken
  duckdns:
    image: linuxserver/duckdns:version-5046d23b
    container_name: duckdns
    networks:
      - selfhost
    restart: unless-stopped
    environment:
      PUID: 1000
      PGID: 1000
      TZ: America/Sao_Paulo
      SUBDOMAINS: mydomain
      TOKEN: duckdnstoken
      UPDATE_IP: ipv4

# traefik.yml
entryPoints:
  web:
    address: :80

  websecure:
    address: :443

certificatesResolvers:
  letsencrypt:
    acme:
      email: myemail
      storage: /letsencrypt/acme.json
      dnsChallenge:
        provider: duckdns
        disablePropagationCheck: true
        delayBeforeCheck: 60s
        resolvers:
          - "1.1.1.1:53"
          - "8.8.8.8:53"

api:
  insecure: true

providers:
  file:
    filename: /config/dynamic.yml
    watch: true

log:
  level: DEBUG

# dynamic.yml
http:
  routers:
    whoami:
      rule: Host(`whoami.mydomain.duckdns.org`)
      service: whoami
      entryPoints:
        - websecure
      tls:
        certResolver: letsencrypt

    portainer:
      rule: Host(`portainer.mydomain.duckdns.org`)
      service: portainer
      entryPoints:
        - websecure
      tls:
        certResolver: letsencrypt

  services:
    whoami:
      loadBalancer:
        servers:
          - url: http://whoami:80

    portainer:
      loadBalancer:
        servers:
          - url: http://portainer:9000

This is honestly what I could get so far… I have looked at so many topics and threads throughout the whole internet, such as Stack Overflow, Reddit, Discord communities, Traefik Community, but no configuration actually worked.

This setup I am using actually works SOMETIMES (this means that it works once in a while) for generating the certs for each URL, but having to use disablePropagationCheck and delayBeforeCheck seem so much more like a workaround than an actual feature in this case. Without them, I just get stuck with a single cert for whoami, while portainer cannot generate because the time limit for the ACME response exceeded. This current setup actually gives me that same error, but after a few minutes it kind of retries the request and successfully get a certificate for portainer…

You can see Traefik logs here, so that you can understand the “error”, and in this case, it could only get to another error, no success this time!: https://pastebin.com/Th9HDJLj