summary refs log tree commit diff
path: root/nixos/tests/acme.nix
diff options
context:
space:
mode:
authorLucas Savva <lucas@m1cr0man.com>2021-11-28 17:03:31 +0000
committerLucas Savva <lucas@m1cr0man.com>2021-12-26 16:44:10 +0000
commit377c6bcefce8e8ccd471892a1b24621d5a909457 (patch)
tree4914c740b10fb82ff157ef2071929ba2c3f8822a /nixos/tests/acme.nix
parenta7f00013280416ce889d841e675526b8cb96a0ee (diff)
downloadnixpkgs-377c6bcefce8e8ccd471892a1b24621d5a909457.tar
nixpkgs-377c6bcefce8e8ccd471892a1b24621d5a909457.tar.gz
nixpkgs-377c6bcefce8e8ccd471892a1b24621d5a909457.tar.bz2
nixpkgs-377c6bcefce8e8ccd471892a1b24621d5a909457.tar.lz
nixpkgs-377c6bcefce8e8ccd471892a1b24621d5a909457.tar.xz
nixpkgs-377c6bcefce8e8ccd471892a1b24621d5a909457.tar.zst
nixpkgs-377c6bcefce8e8ccd471892a1b24621d5a909457.zip
nixos/acme: Add defaults and inheritDefaults option
Allows configuring many default settings for certificates,
all of which can still be overridden on a per-cert basis.
Some options have been moved into .defaults from security.acme,
namely email, server, validMinDays and renewInterval. These
changes will not break existing configurations thanks to
mkChangedOptionModule.

With this, it is also now possible to configure DNS-01 with
web servers whose virtualHosts utilise enableACME. The only
requirement is you set `acmeRoot = null` for each vhost.

The test suite has been revamped to cover these additions
and also to generally make it easier to maintain. Test config
for apache and nginx has been fully standardised, and it
is now much easier to add a new web server if it follows
the same configuration patterns as those two. I have also
optimised the use of switch-to-configuration which should
speed up testing.
Diffstat (limited to 'nixos/tests/acme.nix')
-rw-r--r--nixos/tests/acme.nix515
1 files changed, 285 insertions, 230 deletions
diff --git a/nixos/tests/acme.nix b/nixos/tests/acme.nix
index 80b85502d4e..549fa9e64ee 100644
--- a/nixos/tests/acme.nix
+++ b/nixos/tests/acme.nix
@@ -1,9 +1,9 @@
-let
+import ./make-test-python.nix ({ pkgs, lib, ... }: let
   commonConfig = ./common/acme/client;
 
   dnsServerIP = nodes: nodes.dnsserver.config.networking.primaryIPAddress;
 
-  dnsScript = {pkgs, nodes}: let
+  dnsScript = nodes: let
     dnsAddress = dnsServerIP nodes;
   in pkgs.writeShellScript "dns-hook.sh" ''
     set -euo pipefail
@@ -15,30 +15,137 @@ let
     fi
   '';
 
-  documentRoot = pkgs: pkgs.runCommand "docroot" {} ''
+  dnsConfig = nodes: {
+    dnsProvider = "exec";
+    dnsPropagationCheck = false;
+    credentialsFile = pkgs.writeText "wildcard.env" ''
+      EXEC_PATH=${dnsScript nodes}
+      EXEC_POLLING_INTERVAL=1
+      EXEC_PROPAGATION_TIMEOUT=1
+      EXEC_SEQUENCE_INTERVAL=1
+    '';
+  };
+
+  documentRoot = pkgs.runCommand "docroot" {} ''
     mkdir -p "$out"
     echo hello world > "$out/index.html"
   '';
 
-  vhostBase = pkgs: {
+  vhostBase = {
     forceSSL = true;
-    locations."/".root = documentRoot pkgs;
+    locations."/".root = documentRoot;
+  };
+
+  vhostBaseHttpd = {
+    forceSSL = true;
+    inherit documentRoot;
+  };
+
+  # Base specialisation config for testing general ACME features
+  webserverBasicConfig = {
+    services.nginx.enable = true;
+    services.nginx.virtualHosts."a.example.test" = vhostBase // {
+      enableACME = true;
+    };
+  };
+
+  # Generate specialisations for testing a web server
+  mkServerConfigs = { server, group, vhostBaseData, extraConfig ? {} }: let
+    baseConfig = { nodes, config, specialConfig ? {} }: lib.mkMerge [
+      {
+        security.acme = {
+          defaults = (dnsConfig nodes) // {
+            inherit group;
+          };
+          # One manual wildcard cert
+          certs."example.test" = {
+            domain = "*.example.test";
+          };
+        };
+
+        services."${server}" = {
+          enable = true;
+          virtualHosts = {
+            # Run-of-the-mill vhost using HTTP-01 validation
+            "${server}-http.example.test" = vhostBaseData // {
+              serverAliases = [ "${server}-http-alias.example.test" ];
+              enableACME = true;
+            };
+
+            # Another which inherits the DNS-01 config
+            "${server}-dns.example.test" = vhostBaseData // {
+              serverAliases = [ "${server}-dns-alias.example.test" ];
+              enableACME = true;
+              # Set acmeRoot to null instead of using the default of "/var/lib/acme/acme-challenge"
+              # webroot + dnsProvider are mutually exclusive.
+              acmeRoot = null;
+            };
+
+            # One using the wildcard certificate
+            "${server}-wildcard.example.test" = vhostBaseData // {
+              serverAliases = [ "${server}-wildcard-alias.example.test" ];
+              useACMEHost = "example.test";
+            };
+          };
+        };
+
+        # Used to determine if service reload was triggered
+        systemd.targets."test-renew-${server}" = {
+          wants = [ "acme-${server}-http.example.test.service" ];
+          after = [ "acme-${server}-http.example.test.service" "${server}-config-reload.service" ];
+        };
+      }
+      specialConfig
+      extraConfig
+    ];
+  in {
+    "${server}".configuration = { nodes, config, ... }: baseConfig {
+      inherit nodes config;
+    };
+
+    # Test that server reloads when an alias is removed (and subsequently test removal works in acme)
+    "${server}-remove-alias".configuration = { nodes, config, ... }: baseConfig {
+      inherit nodes config;
+      specialConfig = {
+        # Remove an alias, but create a standalone vhost in its place for testing.
+        # This configuration results in certificate errors as useACMEHost does not imply
+        # append extraDomains, and thus we can validate the SAN is removed.
+        services."${server}" = {
+          virtualHosts."${server}-http.example.test".serverAliases = lib.mkForce [];
+          virtualHosts."${server}-http-alias.example.test" = vhostBaseData // {
+            useACMEHost = "${server}-http.example.test";
+          };
+        };
+      };
+    };
+
+    # Test that the server reloads when only the acme configuration is changed.
+    "${server}-change-acme-conf".configuration = { nodes, config, ... }: baseConfig {
+      inherit nodes config;
+      specialConfig = {
+        security.acme.certs."${server}-http.example.test" = {
+          keyType = "ec384";
+          # Also test that postRun is exec'd as root
+          postRun = "id | grep root";
+        };
+      };
+    };
   };
 
-in import ./make-test-python.nix ({ lib, ... }: {
+in {
   name = "acme";
   meta.maintainers = lib.teams.acme.members;
 
   nodes = {
     # The fake ACME server which will respond to client requests
-    acme = { nodes, lib, ... }: {
+    acme = { nodes, ... }: {
       imports = [ ./common/acme/server ];
       networking.nameservers = lib.mkForce [ (dnsServerIP nodes) ];
     };
 
     # A fake DNS server which can be configured with records as desired
     # Used to test DNS-01 challenge
-    dnsserver = { nodes, pkgs, ... }: {
+    dnsserver = { nodes, ... }: {
       networking.firewall.allowedTCPPorts = [ 8055 53 ];
       networking.firewall.allowedUDPPorts = [ 53 ];
       systemd.services.pebble-challtestsrv = {
@@ -54,7 +161,7 @@ in import ./make-test-python.nix ({ lib, ... }: {
     };
 
     # A web server which will be the node requesting certs
-    webserver = { pkgs, nodes, lib, config, ... }: {
+    webserver = { nodes, config, ... }: {
       imports = [ commonConfig ];
       networking.nameservers = lib.mkForce [ (dnsServerIP nodes) ];
       networking.firewall.allowedTCPPorts = [ 80 443 ];
@@ -63,138 +170,88 @@ in import ./make-test-python.nix ({ lib, ... }: {
       environment.systemPackages = [ pkgs.openssl ];
 
       # Set log level to info so that we can see when the service is reloaded
-      services.nginx.enable = true;
       services.nginx.logError = "stderr info";
 
-      # First tests configure a basic cert and run a bunch of openssl checks
-      services.nginx.virtualHosts."a.example.test" = (vhostBase pkgs) // {
-        enableACME = true;
-      };
-
-      # Used to determine if service reload was triggered
-      systemd.targets.test-renew-nginx = {
-        wants = [ "acme-a.example.test.service" ];
-        after = [ "acme-a.example.test.service" "nginx-config-reload.service" ];
-      };
-
-      # Test that account creation is collated into one service
-      specialisation.account-creation.configuration = { nodes, pkgs, lib, ... }: let
-        email = "newhostmaster@example.test";
-        caDomain = nodes.acme.config.test-support.acme.caDomain;
-        # Exit 99 to make it easier to track if this is the reason a renew failed
-        testScript = ''
-          test -e accounts/${caDomain}/${email}/account.json || exit 99
-        '';
-      in {
-        security.acme.email = lib.mkForce email;
-        systemd.services."b.example.test".preStart = testScript;
-        systemd.services."c.example.test".preStart = testScript;
-
-        services.nginx.virtualHosts."b.example.test" = (vhostBase pkgs) // {
-          enableACME = true;
-        };
-        services.nginx.virtualHosts."c.example.test" = (vhostBase pkgs) // {
-          enableACME = true;
-        };
-      };
-
-      # Cert config changes will not cause the nginx configuration to change.
-      # This tests that the reload service is correctly triggered.
-      # It also tests that postRun is exec'd as root
-      specialisation.cert-change.configuration = { pkgs, ... }: {
-        security.acme.certs."a.example.test".keyType = "ec384";
-        security.acme.certs."a.example.test".postRun = ''
-          set -euo pipefail
-          touch /home/test
-          chown root:root /home/test
-          echo testing > /home/test
-        '';
-      };
-
-      # Now adding an alias to ensure that the certs are updated
-      specialisation.nginx-aliases.configuration = { pkgs, ... }: {
-        services.nginx.virtualHosts."a.example.test" = (vhostBase pkgs) // {
-          serverAliases = [ "b.example.test" ];
-        };
-      };
-
-      # Must be run after nginx-aliases
-      specialisation.remove-extra-domain.configuration = { pkgs, ... } : {
-        # This also validates that useACMEHost doesn't unexpectedly add the domain.
-        services.nginx.virtualHosts."b.example.test" = (vhostBase pkgs) // {
-          useACMEHost = "a.example.test";
-        };
-      };
-
-      # Test OCSP Stapling
-      specialisation.ocsp-stapling.configuration = { pkgs, ... }: {
-        security.acme.certs."a.example.test" = {
-          ocspMustStaple = true;
-        };
-        services.nginx.virtualHosts."a.example.com" = {
-          extraConfig = ''
-            ssl_stapling on;
-            ssl_stapling_verify on;
-          '';
-        };
-      };
-
-      # Test using Apache HTTPD
-      specialisation.httpd-aliases.configuration = { pkgs, config, lib, ... }: {
-        services.nginx.enable = lib.mkForce false;
-        services.httpd.enable = true;
-        services.httpd.adminAddr = config.security.acme.email;
-        services.httpd.virtualHosts."c.example.test" = {
-          serverAliases = [ "d.example.test" ];
-          forceSSL = true;
-          enableACME = true;
-          documentRoot = documentRoot pkgs;
-        };
-
-        # Used to determine if service reload was triggered
-        systemd.targets.test-renew-httpd = {
-          wants = [ "acme-c.example.test.service" ];
-          after = [ "acme-c.example.test.service" "httpd-config-reload.service" ];
-        };
-      };
-
-      # Validation via DNS-01 challenge
-      specialisation.dns-01.configuration = { pkgs, config, nodes, ... }: {
-        security.acme.certs."example.test" = {
-          domain = "*.example.test";
-          group = config.services.nginx.group;
-          dnsProvider = "exec";
-          dnsPropagationCheck = false;
-          credentialsFile = pkgs.writeText "wildcard.env" ''
-            EXEC_PATH=${dnsScript { inherit pkgs nodes; }}
+      specialisation = {
+        # First derivation used to test general ACME features
+        general.configuration = { ... }: let
+          caDomain = nodes.acme.config.test-support.acme.caDomain;
+          email = config.security.acme.defaults.email;
+          # Exit 99 to make it easier to track if this is the reason a renew failed
+          accountCreateTester = ''
+            test -e accounts/${caDomain}/${email}/account.json || exit 99
           '';
-        };
-
-        services.nginx.virtualHosts."dns.example.test" = (vhostBase pkgs) // {
-          useACMEHost = "example.test";
-        };
-      };
-
-      # Validate service relationships by adding a slow start service to nginx' wants.
-      # Reproducer for https://github.com/NixOS/nixpkgs/issues/81842
-      specialisation.slow-startup.configuration = { pkgs, config, nodes, lib, ... }: {
-        systemd.services.my-slow-service = {
-          wantedBy = [ "multi-user.target" "nginx.service" ];
-          before = [ "nginx.service" ];
-          preStart = "sleep 5";
-          script = "${pkgs.python3}/bin/python -m http.server";
-        };
-
-        services.nginx.virtualHosts."slow.example.com" = {
-          forceSSL = true;
-          enableACME = true;
-          locations."/".proxyPass = "http://localhost:8000";
-        };
-      };
+        in lib.mkMerge [
+          webserverBasicConfig
+          {
+            # Used to test that account creation is collated into one service.
+            # These should not run until after acme-finished-a.example.test.target
+            systemd.services."b.example.test".preStart = accountCreateTester;
+            systemd.services."c.example.test".preStart = accountCreateTester;
+
+            services.nginx.virtualHosts."b.example.test" = vhostBase // {
+              enableACME = true;
+            };
+            services.nginx.virtualHosts."c.example.test" = vhostBase // {
+              enableACME = true;
+            };
+          }
+        ];
+
+        # Test OCSP Stapling
+        ocsp-stapling.configuration = { ... }: lib.mkMerge [
+          webserverBasicConfig
+          {
+            security.acme.certs."a.example.test".ocspMustStaple = true;
+            services.nginx.virtualHosts."a.example.com" = {
+              extraConfig = ''
+                ssl_stapling on;
+                ssl_stapling_verify on;
+              '';
+            };
+          }
+        ];
+
+        # Validate service relationships by adding a slow start service to nginx' wants.
+        # Reproducer for https://github.com/NixOS/nixpkgs/issues/81842
+        slow-startup.configuration = { ... }: lib.mkMerge [
+          webserverBasicConfig
+          {
+            systemd.services.my-slow-service = {
+              wantedBy = [ "multi-user.target" "nginx.service" ];
+              before = [ "nginx.service" ];
+              preStart = "sleep 5";
+              script = "${pkgs.python3}/bin/python -m http.server";
+            };
+
+            services.nginx.virtualHosts."slow.example.com" = {
+              forceSSL = true;
+              enableACME = true;
+              locations."/".proxyPass = "http://localhost:8000";
+            };
+          }
+        ];
+
+      # Test compatibility with Nginx
+      } // (mkServerConfigs {
+          server = "nginx";
+          group = "nginx";
+          vhostBaseData = vhostBase;
+        })
+
+      # Test compatibility with Apache HTTPD
+        // (mkServerConfigs {
+          server = "httpd";
+          group = "wwwrun";
+          vhostBaseData = vhostBaseHttpd;
+          extraConfig = {
+            services.httpd.adminAddr = config.security.acme.defaults.email;
+          };
+        });
     };
 
     # The client will be used to curl the webserver to validate configuration
-    client = {nodes, lib, pkgs, ...}: {
+    client = { nodes, ... }: {
       imports = [ commonConfig ];
       networking.nameservers = lib.mkForce [ (dnsServerIP nodes) ];
 
@@ -203,7 +260,7 @@ in import ./make-test-python.nix ({ lib, ... }: {
     };
   };
 
-  testScript = {nodes, ...}:
+  testScript = { nodes, ... }:
     let
       caDomain = nodes.acme.config.test-support.acme.caDomain;
       newServerSystem = nodes.webserver.config.system.build.toplevel;
@@ -212,23 +269,26 @@ in import ./make-test-python.nix ({ lib, ... }: {
     # Note, wait_for_unit does not work for oneshot services that do not have RemainAfterExit=true,
     # this is because a oneshot goes from inactive => activating => inactive, and never
     # reaches the active state. Targets do not have this issue.
-
     ''
       import time
 
 
-      has_switched = False
+      def switch_to(node, name):
+          # On first switch, this will create a symlink to the current system so that we can
+          # quickly switch between derivations
+          root_specs = "/tmp/specialisation"
+          node.execute(
+            f"test -e {root_specs}"
+            f" || ln -s $(readlink /run/current-system)/specialisation {root_specs}"
+          )
 
+          switcher_path = f"/run/current-system/specialisation/{name}/bin/switch-to-configuration"
+          rc, _ = node.execute(f"test -e '{switcher_path}'")
+          if rc > 0:
+              switcher_path = f"/tmp/specialisation/{name}/bin/switch-to-configuration"
 
-      def switch_to(node, name):
-          global has_switched
-          if has_switched:
-              node.succeed(
-                  "${switchToNewServer}"
-              )
-          has_switched = True
           node.succeed(
-              f"/run/current-system/specialisation/{name}/bin/switch-to-configuration test"
+              f"{switcher_path} test"
           )
 
 
@@ -318,8 +378,7 @@ in import ./make-test-python.nix ({ lib, ... }: {
               return download_ca_certs(node, retries - 1)
 
 
-      client.start()
-      dnsserver.start()
+      start_all()
 
       dnsserver.wait_for_unit("pebble-challtestsrv.service")
       client.wait_for_unit("default.target")
@@ -328,19 +387,30 @@ in import ./make-test-python.nix ({ lib, ... }: {
           'curl --data \'{"host": "${caDomain}", "addresses": ["${nodes.acme.config.networking.primaryIPAddress}"]}\' http://${dnsServerIP nodes}:8055/add-a'
       )
 
-      acme.start()
-      webserver.start()
-
       acme.wait_for_unit("network-online.target")
       acme.wait_for_unit("pebble.service")
 
       download_ca_certs(client)
 
+      # Perform general tests first
+      switch_to(webserver, "general")
+
       with subtest("Can request certificate with HTTPS-01 challenge"):
           webserver.wait_for_unit("acme-finished-a.example.test.target")
+          check_fullchain(webserver, "a.example.test")
+          check_issuer(webserver, "a.example.test", "pebble")
+          webserver.wait_for_unit("nginx.service")
+          check_connection(client, "a.example.test")
+
+      with subtest("Runs 1 cert for account creation before others"):
+          webserver.wait_for_unit("acme-finished-b.example.test.target")
+          webserver.wait_for_unit("acme-finished-c.example.test.target")
+          check_connection(client, "b.example.test")
+          check_connection(client, "c.example.test")
 
       with subtest("Certificates and accounts have safe + valid permissions"):
-          group = "${nodes.webserver.config.security.acme.certs."a.example.test".group}"
+          # Nginx will set the group appropriately when enableACME is used
+          group = "nginx"
           webserver.succeed(
               f"test $(stat -L -c '%a %U %G' /var/lib/acme/a.example.test/*.pem | tee /dev/stderr | grep '640 acme {group}' | wc -l) -eq 5"
           )
@@ -354,12 +424,6 @@ in import ./make-test-python.nix ({ lib, ... }: {
               f"test $(find /var/lib/acme/accounts -type f -exec stat -L -c '%a %U %G' {{}} \\; | tee /dev/stderr | grep -v '600 acme {group}' | wc -l) -eq 0"
           )
 
-      with subtest("Certs are accepted by web server"):
-          webserver.succeed("systemctl start nginx.service")
-          check_fullchain(webserver, "a.example.test")
-          check_issuer(webserver, "a.example.test", "pebble")
-          check_connection(client, "a.example.test")
-
       # Selfsigned certs tests happen late so we aren't fighting the system init triggering cert renewal
       with subtest("Can generate valid selfsigned certs"):
           webserver.succeed("systemctl clean acme-a.example.test.service --what=state")
@@ -373,89 +437,80 @@ in import ./make-test-python.nix ({ lib, ... }: {
           # Will succeed if nginx can load the certs
           webserver.succeed("systemctl start nginx-config-reload.service")
 
-      with subtest("Can reload nginx when timer triggers renewal"):
-          webserver.succeed("systemctl start test-renew-nginx.target")
-          check_issuer(webserver, "a.example.test", "pebble")
-          check_connection(client, "a.example.test")
-
-      with subtest("Runs 1 cert for account creation before others"):
-          switch_to(webserver, "account-creation")
-          webserver.wait_for_unit("acme-finished-a.example.test.target")
-          check_connection(client, "a.example.test")
-          webserver.wait_for_unit("acme-finished-b.example.test.target")
-          webserver.wait_for_unit("acme-finished-c.example.test.target")
-          check_connection(client, "b.example.test")
-          check_connection(client, "c.example.test")
-
-      with subtest("Can reload web server when cert configuration changes"):
-          switch_to(webserver, "cert-change")
-          webserver.wait_for_unit("acme-finished-a.example.test.target")
-          check_connection_key_bits(client, "a.example.test", "384")
-          webserver.succeed("grep testing /home/test")
-          # Clean to remove the testing file (and anything else messy we did)
-          webserver.succeed("systemctl clean acme-a.example.test.service --what=state")
-
       with subtest("Correctly implements OCSP stapling"):
           switch_to(webserver, "ocsp-stapling")
           webserver.wait_for_unit("acme-finished-a.example.test.target")
           check_stapling(client, "a.example.test")
 
       with subtest("Can request certificate with HTTPS-01 when nginx startup is delayed"):
+          webserver.execute("systemctl stop nginx")
           switch_to(webserver, "slow-startup")
           webserver.wait_for_unit("acme-finished-slow.example.com.target")
           check_issuer(webserver, "slow.example.com", "pebble")
+          webserver.wait_for_unit("nginx.service")
           check_connection(client, "slow.example.com")
 
-      with subtest("Can request certificate for vhost + aliases (nginx)"):
-          # Check the key hash before and after adding an alias. It should not change.
-          # The previous test reverts the ed384 change
-          webserver.wait_for_unit("acme-finished-a.example.test.target")
-          switch_to(webserver, "nginx-aliases")
-          webserver.wait_for_unit("acme-finished-a.example.test.target")
-          check_issuer(webserver, "a.example.test", "pebble")
-          check_connection(client, "a.example.test")
-          check_connection(client, "b.example.test")
-
-      with subtest("Can remove extra domains from a cert"):
-          switch_to(webserver, "remove-extra-domain")
-          webserver.wait_for_unit("acme-finished-a.example.test.target")
-          webserver.wait_for_unit("nginx.service")
-          check_connection(client, "a.example.test")
-          rc, _ = client.execute(
-              "openssl s_client -CAfile /tmp/ca.crt -connect b.example.test:443"
-              " </dev/null 2>/dev/null | openssl x509 -noout -text"
-              " | grep DNS: | grep b.example.test"
-          )
-          assert rc > 0, "Removed extraDomainName was not removed from the cert"
-
-      with subtest("Can request certificates for vhost + aliases (apache-httpd)"):
-          try:
-              switch_to(webserver, "httpd-aliases")
-              webserver.wait_for_unit("acme-finished-c.example.test.target")
-          except Exception as err:
-              _, output = webserver.execute(
-                  "cat /var/log/httpd/*.log && ls -al /var/lib/acme/acme-challenge"
+      domains = ["http", "dns", "wildcard"]
+      for server, logsrc in [
+          ("nginx", "journalctl -n 30 -u nginx.service"),
+          ("httpd", "tail -n 30 /var/log/httpd/*.log"),
+      ]:
+          wait_for_server = lambda: webserver.wait_for_unit(f"{server}.service")
+          with subtest(f"Works with {server}"):
+              try:
+                  switch_to(webserver, server)
+                  # Skip wildcard domain for this check ([:-1])
+                  for domain in domains[:-1]:
+                      webserver.wait_for_unit(
+                          f"acme-finished-{server}-{domain}.example.test.target"
+                      )
+              except Exception as err:
+                  _, output = webserver.execute(
+                      f"{logsrc} && ls -al /var/lib/acme/acme-challenge"
+                  )
+                  print(output)
+                  raise err
+
+              wait_for_server()
+
+              for domain in domains[:-1]:
+                  check_issuer(webserver, f"{server}-{domain}.example.test", "pebble")
+              for domain in domains:
+                  check_connection(client, f"{server}-{domain}.example.test")
+                  check_connection(client, f"{server}-{domain}-alias.example.test")
+
+          test_domain = f"{server}-{domains[0]}.example.test"
+
+          with subtest(f"Can reload {server} when timer triggers renewal"):
+              # Switch to selfsigned first
+              webserver.succeed(f"systemctl clean acme-{test_domain}.service --what=state")
+              webserver.succeed(f"systemctl start acme-selfsigned-{test_domain}.service")
+              check_issuer(webserver, test_domain, "minica")
+              webserver.succeed(f"systemctl start {server}-config-reload.service")
+              webserver.succeed(f"systemctl start test-renew-{server}.target")
+              check_issuer(webserver, test_domain, "pebble")
+              check_connection(client, test_domain)
+
+          with subtest("Can remove an alias from a domain + cert is updated"):
+              test_alias = f"{server}-{domains[0]}-alias.example.test"
+              switch_to(webserver, f"{server}-remove-alias")
+              webserver.wait_for_unit(f"acme-finished-{test_domain}.target")
+              wait_for_server()
+              check_connection(client, test_domain)
+              rc, _ = client.execute(
+                  f"openssl s_client -CAfile /tmp/ca.crt -connect {test_alias}:443"
+                  " </dev/null 2>/dev/null | openssl x509 -noout -text"
+                  f" | grep DNS: | grep {test_alias}"
               )
-              print(output)
-              raise err
-          check_issuer(webserver, "c.example.test", "pebble")
-          check_connection(client, "c.example.test")
-          check_connection(client, "d.example.test")
-
-      with subtest("Can reload httpd when timer triggers renewal"):
-          # Switch to selfsigned first
-          webserver.succeed("systemctl clean acme-c.example.test.service --what=state")
-          webserver.succeed("systemctl start acme-selfsigned-c.example.test.service")
-          check_issuer(webserver, "c.example.test", "minica")
-          webserver.succeed("systemctl start httpd-config-reload.service")
-          webserver.succeed("systemctl start test-renew-httpd.target")
-          check_issuer(webserver, "c.example.test", "pebble")
-          check_connection(client, "c.example.test")
-
-      with subtest("Can request wildcard certificates using DNS-01 challenge"):
-          switch_to(webserver, "dns-01")
-          webserver.wait_for_unit("acme-finished-example.test.target")
-          check_issuer(webserver, "example.test", "pebble")
-          check_connection(client, "dns.example.test")
+              assert rc > 0, "Removed extraDomainName was not removed from the cert"
+
+          with subtest("security.acme changes reflect on web server"):
+              # Switch back to normal server config first, reset everything.
+              switch_to(webserver, server)
+              wait_for_server()
+              switch_to(webserver, f"{server}-change-acme-conf")
+              webserver.wait_for_unit(f"acme-finished-{test_domain}.target")
+              wait_for_server()
+              check_connection_key_bits(client, test_domain, "384")
     '';
 })