I'm trying to get letsencrypt/cert-manager running via this Helm chart. The K8s cluster is on Digital Ocean.

I successfully verified the installation as recommended and have created a ClusterIssuer for staging, and 1 for production. (letsencrypt-staging, letsencrypt-prod)

Problem: The acme challenge returns a 404 error.

$ k get challenge -o wide
NAME                                                      STATE     DOMAIN                 REASON                                                                               AGE
myapp-cert-2315925673-2905389610-1118496475   pending   myapp.example.com   Waiting for http-01 challenge propagation: wrong status code '404', expected '200'   7m55s

The Ingress works fine with port 80 when the tls block commented out. When I define tls however, requests on port 80 return a 404, which is probably why the challenge is failing.

Note: I get the same response when using my production ClusterIssuer.

apiVersion: extensions/v1beta1
kind: Ingress
metadata:
  name: myapp-ingress
  annotations:
    kubernetes.io/ingress.class: nginx
    cert-manager.io/cluster-issuer: letsencrypt-staging
  labels:
    app: myapp
spec:
  rules:
  - host: myapp.example.com
    http:
      paths:
      - backend:
          serviceName: myapp
          servicePort: 80
  tls:
  - hosts:
    - myapp.example.com
    secretName: myapp-cert

:: edited to add more configs ::

After adding more configs and logs as requested by @Tubc, it appears that Nginx is throwing an error when I update the ingress because the cert doesn't exist.

ClusterIssuer Manifests:

---
apiVersion: cert-manager.io/v1alpha2
kind: ClusterIssuer
metadata:
  name: letsencrypt-prod
spec:
  acme:
    server: https://acme-v02.api.letsencrypt.org/directory
    email: me@example.com
    privateKeySecretRef:
      name: letsencrypt-prod
    solvers:
    - http01:
        ingress:
          class: nginx
---
apiVersion: cert-manager.io/v1alpha2
kind: ClusterIssuer
metadata:
  name: letsencrypt-staging
spec:
  acme:
    server: https://acme-staging-v02.api.letsencrypt.org/directory
    email: me@example.com
    privateKeySecretRef:
      name: letsencrypt-staging
    solvers:
    - http01:
        ingress:
          class: nginx

Service Manifest:

---
apiVersion: v1
kind: Service
metadata:
  name: myapp
  labels:
    app: myapp
spec:
  ports:
    - port: 80
  selector:
    app: myapp
    tier: fe
  type: NodePort

Nginx log:

2019/12/08 14:45:44 [emerg] 62#62: cannot load certificate "/etc/nginx/secrets/default-myapp-cert": PEM_read_bio_X509_AUX() failed (SSL: error:0909006C:PEM routines:get_name:no start line:Expecting: TRUSTED CERTIFICATE) I1208 14:45:44.934644 1 event.go:209] Event(v1.ObjectReference{Kind:"Ingress", Namespace:"default", Name:"myapp-ingress", UID:"610c3304-0565-415d-8cde-0863bf9325ca", APIVersion:"extensions/v1beta1", ResourceVersion:"319124", FieldPath:""}): type: 'Warning' reason: 'AddedOrUpdatedWithError' Configuration for default/myapp-ingress was added or updated, but not applied: Error reloading NGINX for default/myapp-ingress: nginx reload failed: Command /usr/sbin/nginx -s reload stdout: "" stderr: "nginx: [emerg] cannot load certificate \"/etc/nginx/secrets/default-myapp-cert\": PEM_read_bio_X509_AUX() failed (SSL: error:0909006C:PEM routines:get_name:no start line:Expecting: TRUSTED CERTIFICATE)\n" finished with error: exit status 1