diff --git a/lib/kamal/commands/healthcheck.rb b/lib/kamal/commands/healthcheck.rb
index 5adc0244..05379ab6 100644
--- a/lib/kamal/commands/healthcheck.rb
+++ b/lib/kamal/commands/healthcheck.rb
@@ -1,7 +1,7 @@
 class Kamal::Commands::Healthcheck < Kamal::Commands::Base
 
   def run
-    web = config.role(:web)
+    web = config.role(config.primary_web_role)
 
     docker :run,
       "--detach",
diff --git a/lib/kamal/configuration.rb b/lib/kamal/configuration.rb
index fc881c06..64c74c63 100644
--- a/lib/kamal/configuration.rb
+++ b/lib/kamal/configuration.rb
@@ -90,14 +90,21 @@ class Kamal::Configuration
   end
 
   def primary_web_host
-    role(:web).primary_host
+    role(primary_web_role)&.primary_host
+  end
+
+  def traefik_roles
+    roles.select(&:running_traefik?)
+  end
+
+  def traefik_role_names
+    traefik_roles.flat_map(&:name)
   end
 
   def traefik_hosts
-    roles.select(&:running_traefik?).flat_map(&:hosts).uniq
+    traefik_roles.flat_map(&:hosts).uniq
   end
 
-
   def repository
     [ raw_config.registry["server"], image ].compact.join("/")
   end
@@ -199,6 +206,9 @@ class Kamal::Configuration
     raw_config.asset_path
   end
 
+  def primary_web_role
+    raw_config.primary_web_role || "web"
+  end
 
   def valid?
     ensure_destination_if_required && ensure_required_keys_present && ensure_valid_kamal_version
@@ -253,6 +263,10 @@ class Kamal::Configuration
         end
       end
 
+      unless traefik_role_names.include?(primary_web_role)
+        raise ArgumentError, "Role #{primary_web_role} needs to have traefik enabled"
+      end
+
       true
     end