diff --git a/lib/kamal/cli/app.rb b/lib/kamal/cli/app.rb
index 553ccbb2..d2f9c3f9 100644
--- a/lib/kamal/cli/app.rb
+++ b/lib/kamal/cli/app.rb
@@ -8,8 +8,10 @@ class Kamal::Cli::App < Kamal::Cli::Base
 
         # Assets are prepared in a separate step to ensure they are on all hosts before booting
         on(KAMAL.hosts) do
+          Kamal::Cli::App::ErrorPages.new(host, self).run
+
           KAMAL.roles_on(host).each do |role|
-            Kamal::Cli::App::PrepareAssets.new(host, role, self).run
+            Kamal::Cli::App::Assets.new(host, role, self).run
           end
         end
 
@@ -249,7 +251,37 @@ class Kamal::Cli::App < Kamal::Cli::Base
       stop
       remove_containers
       remove_images
-      remove_app_directory
+      remove_app_directories
+    end
+  end
+
+  desc "live", "Set the app to live mode"
+  def live
+    with_lock do
+      on(KAMAL.proxy_hosts) do |host|
+        roles = KAMAL.roles_on(host)
+
+        roles.each do |role|
+          execute *KAMAL.app(role: role, host: host).live if role.running_proxy?
+        end
+      end
+    end
+  end
+
+  desc "maintenance", "Set the app to maintenance mode"
+  option :drain_timeout, type: :numeric, desc: "How long to allow in-flight requests to complete (defaults to drain_timeout from config)"
+  option :message, type: :string, desc: "Message to display to clients while stopped"
+  def maintenance
+    maintenance_options = { drain_timeout: options[:drain_timeout] || KAMAL.config.drain_timeout, message: options[:message] }
+
+    with_lock do
+      on(KAMAL.proxy_hosts) do |host|
+        roles = KAMAL.roles_on(host)
+
+        roles.each do |role|
+          execute *KAMAL.app(role: role, host: host).maintenance(**maintenance_options) if role.running_proxy?
+        end
+      end
     end
   end
 
@@ -291,16 +323,19 @@ class Kamal::Cli::App < Kamal::Cli::Base
     end
   end
 
-  desc "remove_app_directory", "Remove the service directory from servers", hide: true
-  def remove_app_directory
+  desc "remove_app_directories", "Remove the app directories from servers", hide: true
+  def remove_app_directories
     with_lock do
       on(KAMAL.hosts) do |host|
         roles = KAMAL.roles_on(host)
 
         roles.each do |role|
-          execute *KAMAL.auditor.record("Removed #{KAMAL.config.app_directory} on all servers", role: role), verbosity: :debug
+          execute *KAMAL.auditor.record("Removed #{KAMAL.config.app_directory}", role: role), verbosity: :debug
           execute *KAMAL.server.remove_app_directory, raise_on_non_zero_exit: false
         end
+
+        execute *KAMAL.auditor.record("Removed #{KAMAL.config.app_directory}"), verbosity: :debug
+        execute *KAMAL.app.remove_proxy_app_directory, raise_on_non_zero_exit: false
       end
     end
   end
diff --git a/lib/kamal/cli/app/prepare_assets.rb b/lib/kamal/cli/app/assets.rb
similarity index 93%
rename from lib/kamal/cli/app/prepare_assets.rb
rename to lib/kamal/cli/app/assets.rb
index dd28fa41..2cab1423 100644
--- a/lib/kamal/cli/app/prepare_assets.rb
+++ b/lib/kamal/cli/app/assets.rb
@@ -1,4 +1,4 @@
-class Kamal::Cli::App::PrepareAssets
+class Kamal::Cli::App::Assets
   attr_reader :host, :role, :sshkit
   delegate :execute, :capture_with_info, :info, to: :sshkit
   delegate :assets?, to: :role
diff --git a/lib/kamal/cli/app/boot.rb b/lib/kamal/cli/app/boot.rb
index 8ddcaac3..a7eb1c1a 100644
--- a/lib/kamal/cli/app/boot.rb
+++ b/lib/kamal/cli/app/boot.rb
@@ -70,6 +70,7 @@ class Kamal::Cli::App::Boot
     def stop_old_version(version)
       execute *app.stop(version: version), raise_on_non_zero_exit: false
       execute *app.clean_up_assets if assets?
+      execute *app.clean_up_error_pages if KAMAL.config.error_pages_path
     end
 
     def release_barrier
diff --git a/lib/kamal/cli/app/error_pages.rb b/lib/kamal/cli/app/error_pages.rb
new file mode 100644
index 00000000..664f7eff
--- /dev/null
+++ b/lib/kamal/cli/app/error_pages.rb
@@ -0,0 +1,33 @@
+class Kamal::Cli::App::ErrorPages
+  ERROR_PAGES_GLOB = "{4??.html,5??.html}"
+
+  attr_reader :host, :sshkit
+  delegate :upload!, :execute, to: :sshkit
+
+  def initialize(host, sshkit)
+    @host = host
+    @sshkit = sshkit
+  end
+
+  def run
+    if KAMAL.config.error_pages_path
+      with_error_pages_tmpdir do |local_error_pages_dir|
+        execute *KAMAL.app.create_error_pages_directory
+        upload! local_error_pages_dir, KAMAL.config.proxy_error_pages_directory, mode: "0700", recursive: true
+      end
+    end
+  end
+
+  private
+    def with_error_pages_tmpdir
+      Dir.mktmpdir("kamal-error-pages") do |tmpdir|
+        error_pages_dir = File.join(tmpdir, KAMAL.config.version)
+        FileUtils.mkdir(error_pages_dir)
+
+        if (files = Dir[File.join(KAMAL.config.error_pages_path, ERROR_PAGES_GLOB)]).any?
+          FileUtils.cp(files, error_pages_dir)
+          yield error_pages_dir
+        end
+      end
+    end
+end
diff --git a/lib/kamal/commands/app.rb b/lib/kamal/commands/app.rb
index 6c4df0e4..d80684fb 100644
--- a/lib/kamal/commands/app.rb
+++ b/lib/kamal/commands/app.rb
@@ -1,5 +1,5 @@
 class Kamal::Commands::App < Kamal::Commands::Base
-  include Assets, Containers, Execution, Images, Logging, Proxy
+  include Assets, Containers, ErrorPages, Execution, Images, Logging, Proxy
 
   ACTIVE_DOCKER_STATUSES = [ :running, :restarting ]
 
diff --git a/lib/kamal/commands/app/error_pages.rb b/lib/kamal/commands/app/error_pages.rb
new file mode 100644
index 00000000..d51dba3f
--- /dev/null
+++ b/lib/kamal/commands/app/error_pages.rb
@@ -0,0 +1,9 @@
+module Kamal::Commands::App::ErrorPages
+  def create_error_pages_directory
+    make_directory(config.proxy_error_pages_directory)
+  end
+
+  def clean_up_error_pages
+    [ :find, config.proxy_error_pages_directory, "-mindepth", "1", "-maxdepth", "1", "!", "-name", KAMAL.config.version, "-exec", "rm", "-rf", "{} +" ]
+  end
+end
diff --git a/lib/kamal/commands/app/proxy.rb b/lib/kamal/commands/app/proxy.rb
index 777a4aaf..56d0ccea 100644
--- a/lib/kamal/commands/app/proxy.rb
+++ b/lib/kamal/commands/app/proxy.rb
@@ -9,6 +9,18 @@ module Kamal::Commands::App::Proxy
     proxy_exec :remove, role.container_prefix
   end
 
+  def live
+    proxy_exec :resume, role.container_prefix
+  end
+
+  def maintenance(**options)
+    proxy_exec :stop, role.container_prefix, *role.proxy.stop_command_args(**options)
+  end
+
+  def remove_proxy_app_directory
+    remove_directory config.proxy_app_directory
+  end
+
   private
     def proxy_exec(*command)
       docker :exec, proxy_container_name, "kamal-proxy", *command
diff --git a/lib/kamal/commands/proxy.rb b/lib/kamal/commands/proxy.rb
index c6b9929c..658252de 100644
--- a/lib/kamal/commands/proxy.rb
+++ b/lib/kamal/commands/proxy.rb
@@ -110,6 +110,6 @@ class Kamal::Commands::Proxy < Kamal::Commands::Base
         "--detach",
         "--restart", "unless-stopped",
         "--volume", "kamal-proxy-config:/home/kamal-proxy/.config/kamal-proxy",
-        *config.proxy_app_config_volume.docker_args
+        *config.proxy_apps_volume.docker_args
     end
 end
diff --git a/lib/kamal/configuration.rb b/lib/kamal/configuration.rb
index 7772985b..bd22178f 100644
--- a/lib/kamal/configuration.rb
+++ b/lib/kamal/configuration.rb
@@ -105,6 +105,10 @@ class Kamal::Configuration
     raw_config.minimum_version
   end
 
+  def service_and_destination
+    [ service, destination ].compact.join("-")
+  end
+
   def roles
     servers.roles
   end
@@ -210,7 +214,7 @@ class Kamal::Configuration
   end
 
   def app_directory
-    File.join apps_directory, [ service, destination ].compact.join("-")
+    File.join apps_directory, service_and_destination
   end
 
   def env_directory
@@ -229,6 +233,10 @@ class Kamal::Configuration
     raw_config.asset_path
   end
 
+  def error_pages_path
+    raw_config.error_pages_path
+  end
+
   def env_tags
     @env_tags ||= if (tags = raw_config.env["tags"])
       tags.collect { |name, config| Env::Tag.new(name, config: config, secrets: secrets) }
@@ -300,14 +308,34 @@ class Kamal::Configuration
     File.join proxy_directory, "image_version"
   end
 
-  def proxy_app_config_directory
-    File.join proxy_directory, "app-config"
+  def proxy_apps_directory
+    File.join proxy_directory, "apps-config"
   end
 
-  def proxy_app_config_volume
+  def proxy_apps_container_directory
+    "/home/kamal-proxy/.apps-config"
+  end
+
+  def proxy_apps_volume
     Volume.new \
-      host_path: proxy_app_config_directory,
-      container_path: "/home/kamal-proxy/.app-config"
+      host_path: proxy_apps_directory,
+      container_path: proxy_apps_container_directory
+  end
+
+  def proxy_app_directory
+    File.join proxy_apps_directory, service_and_destination
+  end
+
+  def proxy_app_container_directory
+    File.join proxy_apps_container_directory, service_and_destination
+  end
+
+  def proxy_error_pages_directory
+    File.join proxy_app_directory, "error_pages"
+  end
+
+  def proxy_error_pages_container_directory
+    File.join proxy_app_container_directory, "error_pages"
   end
 
   def to_h
diff --git a/lib/kamal/configuration/docs/configuration.yml b/lib/kamal/configuration/docs/configuration.yml
index 6b059346..76f57eae 100644
--- a/lib/kamal/configuration/docs/configuration.yml
+++ b/lib/kamal/configuration/docs/configuration.yml
@@ -82,6 +82,12 @@ asset_path: /path/to/assets
 # See https://kamal-deploy.org/docs/hooks for more information:
 hooks_path: /user_home/kamal/hooks
 
+# Error pages
+#
+# A directory relative to the app root to find error pages for the proxy to serve.
+# Any files in the format 4xx.html or 5xx.html will be copied to the hosts.
+error_pages_path: public
+
 # Require destinations
 #
 # Whether deployments require a destination to be specified, defaults to `false`:
diff --git a/lib/kamal/configuration/proxy.rb b/lib/kamal/configuration/proxy.rb
index a8272e88..19bc25f7 100644
--- a/lib/kamal/configuration/proxy.rb
+++ b/lib/kamal/configuration/proxy.rb
@@ -44,7 +44,8 @@ class Kamal::Configuration::Proxy
       "forward-headers": proxy_config.dig("forward_headers"),
       "tls-redirect": proxy_config.dig("ssl_redirect"),
       "log-request-header": proxy_config.dig("logging", "request_headers") || DEFAULT_LOG_REQUEST_HEADERS,
-      "log-response-header": proxy_config.dig("logging", "response_headers")
+      "log-response-header": proxy_config.dig("logging", "response_headers"),
+      "error-pages": error_pages
     }.compact
   end
 
@@ -52,6 +53,17 @@ class Kamal::Configuration::Proxy
     optionize ({ target: "#{target}:#{app_port}" }).merge(deploy_options), with: "="
   end
 
+  def stop_options(drain_timeout: nil, message: nil)
+    {
+      "drain-timeout": seconds_duration(drain_timeout),
+      message: message
+    }.compact
+  end
+
+  def stop_command_args(**options)
+    optionize stop_options(**options), with: "="
+  end
+
   def merge(other)
     self.class.new config: config, proxy_config: proxy_config.deep_merge(other.proxy_config)
   end
@@ -60,4 +72,8 @@ class Kamal::Configuration::Proxy
     def seconds_duration(value)
       value ? "#{value}s" : nil
     end
+
+    def error_pages
+      File.join config.proxy_error_pages_container_directory, config.version if config.error_pages_path
+    end
 end
diff --git a/test/cli/app_test.rb b/test/cli/app_test.rb
index 19190032..2ed00182 100644
--- a/test/cli/app_test.rb
+++ b/test/cli/app_test.rb
@@ -192,6 +192,19 @@ class CliAppTest < CliTestCase
     Thread.report_on_exception = true
   end
 
+  test "boot with error pages" do
+    with_error_pages(directory: "public") do
+      stub_running
+      run_command("boot", config: :with_error_pages).tap do |output|
+        assert_match /Uploading .*kamal-error-pages.*\/latest to \.kamal\/proxy\/apps-config\/app\/error_pages/, output
+        assert_match "docker tag dhh/app:latest dhh/app:latest", output
+        assert_match /docker run --detach --restart unless-stopped --name app-web-latest --network kamal --hostname 1.1.1.1-[0-9a-f]{12} /, output
+        assert_match "docker container ls --all --filter name=^app-web-123$ --quiet | xargs docker stop", output
+        assert_match "Running /usr/bin/env find .kamal/proxy/apps-config/app/error_pages -mindepth 1 -maxdepth 1 ! -name latest -exec rm -rf {} + on 1.1.1.1", output
+      end
+    end
+  end
+
   test "start" do
     SSHKit::Backend::Abstract.any_instance.stubs(:capture_with_info).returns("999") # old version
 
@@ -244,9 +257,11 @@ class CliAppTest < CliTestCase
 
   test "remove" do
     run_command("remove").tap do |output|
-      assert_match /#{Regexp.escape("sh -c 'docker ps --latest --quiet --filter label=service=app --filter label=destination= --filter label=role=web --filter status=running --filter status=restarting --filter ancestor=$(docker image ls --filter reference=dhh/app:latest --format '\\''{{.ID}}'\\'') ; docker ps --latest --quiet --filter label=service=app --filter label=destination= --filter label=role=web --filter status=running --filter status=restarting' | head -1 | xargs docker stop")}/, output
-      assert_match /#{Regexp.escape("docker container prune --force --filter label=service=app")}/, output
-      assert_match /#{Regexp.escape("docker image prune --all --force --filter label=service=app")}/, output
+      assert_match "sh -c 'docker ps --latest --quiet --filter label=service=app --filter label=destination= --filter label=role=web --filter status=running --filter status=restarting --filter ancestor=$(docker image ls --filter reference=dhh/app:latest --format '\\''{{.ID}}'\\'') ; docker ps --latest --quiet --filter label=service=app --filter label=destination= --filter label=role=web --filter status=running --filter status=restarting' | head -1 | xargs docker stop", output
+      assert_match "docker container prune --force --filter label=service=app", output
+      assert_match "docker image prune --all --force --filter label=service=app", output
+      assert_match "rm -r .kamal/apps/app on 1.1.1.1", output
+      assert_match "rm -r .kamal/proxy/apps-config/app on 1.1.1.1", output
     end
   end
 
@@ -268,6 +283,13 @@ class CliAppTest < CliTestCase
     end
   end
 
+  test "remove_app_directories" do
+    run_command("remove_app_directories").tap do |output|
+      assert_match "rm -r .kamal/apps/app on 1.1.1.1", output
+      assert_match "rm -r .kamal/proxy/apps-config/app on 1.1.1.1", output
+    end
+  end
+
   test "exec" do
     run_command("exec", "ruby -v").tap do |output|
       assert_match "docker run --rm --network kamal --env-file .kamal/apps/app/env/roles/web.env --log-opt max-size=\"10m\" dhh/app:latest ruby -v", output
@@ -437,6 +459,24 @@ class CliAppTest < CliTestCase
     end
   end
 
+  test "live" do
+    run_command("live").tap do |output|
+      assert_match "docker exec kamal-proxy kamal-proxy resume app-web on 1.1.1.1", output
+    end
+  end
+
+  test "maintenance" do
+    run_command("maintenance").tap do |output|
+      assert_match "docker exec kamal-proxy kamal-proxy stop app-web --drain-timeout=\"30s\" on 1.1.1.1", output
+    end
+  end
+
+  test "maintenance with options" do
+    run_command("maintenance", "--message", "Hello", "--drain_timeout", "10").tap do |output|
+      assert_match "docker exec kamal-proxy kamal-proxy stop app-web --drain-timeout=\"10s\" --message=\"Hello\" on 1.1.1.1", output
+    end
+  end
+
   private
     def run_command(*command, config: :with_accessories, host: "1.1.1.1", allow_execute_error: false)
       stdouted do
diff --git a/test/cli/proxy_test.rb b/test/cli/proxy_test.rb
index ae717f70..2ec4c726 100644
--- a/test/cli/proxy_test.rb
+++ b/test/cli/proxy_test.rb
@@ -56,12 +56,12 @@ class CliProxyTest < CliTestCase
     run_command("reboot", "-y").tap do |output|
       assert_match "docker container stop kamal-proxy on 1.1.1.1", output
       assert_match "docker container prune --force --filter label=org.opencontainers.image.title=kamal-proxy on 1.1.1.1", output
-      assert_match "echo $(cat .kamal/proxy/options 2> /dev/null || echo \"--publish 80:80 --publish 443:443 --log-opt max-size=10m\") $(cat .kamal/proxy/image 2> /dev/null || echo \"basecamp/kamal-proxy\"):$(cat .kamal/proxy/image_version 2> /dev/null || echo \"#{Kamal::Configuration::PROXY_MINIMUM_VERSION}\") | xargs docker run --name kamal-proxy --network kamal --detach --restart unless-stopped --volume kamal-proxy-config:/home/kamal-proxy/.config/kamal-proxy --volume $(pwd)/.kamal/proxy/app-config:/home/kamal-proxy/.app-config on 1.1.1.1", output
+      assert_match "echo $(cat .kamal/proxy/options 2> /dev/null || echo \"--publish 80:80 --publish 443:443 --log-opt max-size=10m\") $(cat .kamal/proxy/image 2> /dev/null || echo \"basecamp/kamal-proxy\"):$(cat .kamal/proxy/image_version 2> /dev/null || echo \"#{Kamal::Configuration::PROXY_MINIMUM_VERSION}\") | xargs docker run --name kamal-proxy --network kamal --detach --restart unless-stopped --volume kamal-proxy-config:/home/kamal-proxy/.config/kamal-proxy --volume $(pwd)/.kamal/proxy/apps-config:/home/kamal-proxy/.apps-config on 1.1.1.1", output
       assert_match "docker exec kamal-proxy kamal-proxy deploy app-web --target=\"abcdefabcdef:80\" --deploy-timeout=\"6s\" --drain-timeout=\"30s\" --buffer-requests --buffer-responses --log-request-header=\"Cache-Control\" --log-request-header=\"Last-Modified\" --log-request-header=\"User-Agent\" on 1.1.1.1", output
 
       assert_match "docker container stop kamal-proxy on 1.1.1.2", output
       assert_match "docker container prune --force --filter label=org.opencontainers.image.title=kamal-proxy on 1.1.1.2", output
-      assert_match "echo $(cat .kamal/proxy/options 2> /dev/null || echo \"--publish 80:80 --publish 443:443 --log-opt max-size=10m\") $(cat .kamal/proxy/image 2> /dev/null || echo \"basecamp/kamal-proxy\"):$(cat .kamal/proxy/image_version 2> /dev/null || echo \"#{Kamal::Configuration::PROXY_MINIMUM_VERSION}\") | xargs docker run --name kamal-proxy --network kamal --detach --restart unless-stopped --volume kamal-proxy-config:/home/kamal-proxy/.config/kamal-proxy --volume $(pwd)/.kamal/proxy/app-config:/home/kamal-proxy/.app-config on 1.1.1.2", output
+      assert_match "echo $(cat .kamal/proxy/options 2> /dev/null || echo \"--publish 80:80 --publish 443:443 --log-opt max-size=10m\") $(cat .kamal/proxy/image 2> /dev/null || echo \"basecamp/kamal-proxy\"):$(cat .kamal/proxy/image_version 2> /dev/null || echo \"#{Kamal::Configuration::PROXY_MINIMUM_VERSION}\") | xargs docker run --name kamal-proxy --network kamal --detach --restart unless-stopped --volume kamal-proxy-config:/home/kamal-proxy/.config/kamal-proxy --volume $(pwd)/.kamal/proxy/apps-config:/home/kamal-proxy/.apps-config on 1.1.1.2", output
       assert_match "docker exec kamal-proxy kamal-proxy deploy app-web --target=\"abcdefabcdef:80\" --deploy-timeout=\"6s\" --drain-timeout=\"30s\" --buffer-requests --buffer-responses --log-request-header=\"Cache-Control\" --log-request-header=\"Last-Modified\" --log-request-header=\"User-Agent\" on 1.1.1.2", output
     end
   end
diff --git a/test/commands/app_test.rb b/test/commands/app_test.rb
index 75241597..33418a00 100644
--- a/test/commands/app_test.rb
+++ b/test/commands/app_test.rb
@@ -497,6 +497,30 @@ class CommandsAppTest < ActiveSupport::TestCase
     ], new_command(asset_path: "/public/assets").clean_up_assets
   end
 
+  test "live" do
+    assert_equal \
+      "docker exec kamal-proxy kamal-proxy resume app-web",
+      new_command.live.join(" ")
+  end
+
+  test "maintenance" do
+    assert_equal \
+      "docker exec kamal-proxy kamal-proxy stop app-web",
+      new_command.maintenance.join(" ")
+  end
+
+  test "maintenance with options" do
+    assert_equal \
+      "docker exec kamal-proxy kamal-proxy stop app-web --drain-timeout=\"10s\" --message=\"Hi\"",
+      new_command.maintenance(drain_timeout: 10, message: "Hi").join(" ")
+  end
+
+  test "remove_proxy_app_directory" do
+    assert_equal \
+      "rm -r .kamal/proxy/apps-config/app",
+      new_command.remove_proxy_app_directory.join(" ")
+  end
+
   private
     def new_command(role: "web", host: "1.1.1.1", **additional_config)
       config = Kamal::Configuration.new(@config.merge(additional_config), destination: @destination, version: "999")
diff --git a/test/commands/proxy_test.rb b/test/commands/proxy_test.rb
index c55fbdeb..21863fc6 100644
--- a/test/commands/proxy_test.rb
+++ b/test/commands/proxy_test.rb
@@ -15,7 +15,7 @@ class CommandsProxyTest < ActiveSupport::TestCase
 
   test "run" do
     assert_equal \
-      "echo $(cat .kamal/proxy/options 2> /dev/null || echo \"--publish 80:80 --publish 443:443 --log-opt max-size=10m\") $(cat .kamal/proxy/image 2> /dev/null || echo \"basecamp/kamal-proxy\"):$(cat .kamal/proxy/image_version 2> /dev/null || echo \"#{Kamal::Configuration::PROXY_MINIMUM_VERSION}\") | xargs docker run --name kamal-proxy --network kamal --detach --restart unless-stopped --volume kamal-proxy-config:/home/kamal-proxy/.config/kamal-proxy --volume $(pwd)/.kamal/proxy/app-config:/home/kamal-proxy/.app-config",
+      "echo $(cat .kamal/proxy/options 2> /dev/null || echo \"--publish 80:80 --publish 443:443 --log-opt max-size=10m\") $(cat .kamal/proxy/image 2> /dev/null || echo \"basecamp/kamal-proxy\"):$(cat .kamal/proxy/image_version 2> /dev/null || echo \"#{Kamal::Configuration::PROXY_MINIMUM_VERSION}\") | xargs docker run --name kamal-proxy --network kamal --detach --restart unless-stopped --volume kamal-proxy-config:/home/kamal-proxy/.config/kamal-proxy --volume $(pwd)/.kamal/proxy/apps-config:/home/kamal-proxy/.apps-config",
       new_command.run.join(" ")
   end
 
@@ -23,7 +23,7 @@ class CommandsProxyTest < ActiveSupport::TestCase
     @config.delete(:proxy)
 
     assert_equal \
-      "echo $(cat .kamal/proxy/options 2> /dev/null || echo \"--publish 80:80 --publish 443:443 --log-opt max-size=10m\") $(cat .kamal/proxy/image 2> /dev/null || echo \"basecamp/kamal-proxy\"):$(cat .kamal/proxy/image_version 2> /dev/null || echo \"#{Kamal::Configuration::PROXY_MINIMUM_VERSION}\") | xargs docker run --name kamal-proxy --network kamal --detach --restart unless-stopped --volume kamal-proxy-config:/home/kamal-proxy/.config/kamal-proxy --volume $(pwd)/.kamal/proxy/app-config:/home/kamal-proxy/.app-config",
+      "echo $(cat .kamal/proxy/options 2> /dev/null || echo \"--publish 80:80 --publish 443:443 --log-opt max-size=10m\") $(cat .kamal/proxy/image 2> /dev/null || echo \"basecamp/kamal-proxy\"):$(cat .kamal/proxy/image_version 2> /dev/null || echo \"#{Kamal::Configuration::PROXY_MINIMUM_VERSION}\") | xargs docker run --name kamal-proxy --network kamal --detach --restart unless-stopped --volume kamal-proxy-config:/home/kamal-proxy/.config/kamal-proxy --volume $(pwd)/.kamal/proxy/apps-config:/home/kamal-proxy/.apps-config",
       new_command.run.join(" ")
   end
 
diff --git a/test/configuration_test.rb b/test/configuration_test.rb
index c1aaa697..04be59ea 100644
--- a/test/configuration_test.rb
+++ b/test/configuration_test.rb
@@ -395,4 +395,13 @@ class ConfigurationTest < ActiveSupport::TestCase
 
     assert_equal "Different roles can't share the same host for SSL: foo.example.com", exception.message
   end
+
+  test "proxy directories" do
+    assert_equal ".kamal/proxy/apps-config", @config.proxy_apps_directory
+    assert_equal "/home/kamal-proxy/.apps-config", @config.proxy_apps_container_directory
+    assert_equal ".kamal/proxy/apps-config/app", @config.proxy_app_directory
+    assert_equal "/home/kamal-proxy/.apps-config/app", @config.proxy_app_container_directory
+    assert_equal ".kamal/proxy/apps-config/app/error_pages", @config.proxy_error_pages_directory
+    assert_equal "/home/kamal-proxy/.apps-config/app/error_pages", @config.proxy_error_pages_container_directory
+  end
 end
diff --git a/test/fixtures/deploy_with_error_pages.yml b/test/fixtures/deploy_with_error_pages.yml
new file mode 100644
index 00000000..7806c54c
--- /dev/null
+++ b/test/fixtures/deploy_with_error_pages.yml
@@ -0,0 +1,11 @@
+service: app
+image: dhh/app
+servers:
+  - "1.1.1.1"
+  - "1.1.1.2"
+registry:
+  username: user
+  password: pw
+builder:
+  arch: amd64
+error_pages_path: public
diff --git a/test/integration/app_test.rb b/test/integration/app_test.rb
index f128054b..29d122f3 100644
--- a/test/integration/app_test.rb
+++ b/test/integration/app_test.rb
@@ -48,9 +48,36 @@ class AppTest < IntegrationTest
     assert_match "App Host: vm1", exec_output
     assert_match /1 root      0:\d\d nginx/, exec_output
 
+    kamal :app, :maintenance
+    assert_app_in_maintenance
+
+    kamal :app, :live
+    assert_app_is_up
+
     kamal :app, :remove
 
     assert_app_not_found
     assert_app_directory_removed
   end
+
+  test "custom error pages" do
+    @app = "app_with_roles"
+
+    kamal :deploy
+    assert_app_is_up
+
+    kamal :app, :maintenance
+    assert_app_in_maintenance message: "Custom Maintenance Page"
+
+    kamal :app, :live
+    kamal :app, :maintenance, "--message", "\"Testing Maintence Mode\""
+    assert_app_in_maintenance message: "Custom Maintenance Page: Testing Maintence Mode"
+
+    second_version = update_app_rev
+
+    kamal :redeploy
+
+    kamal :app, :maintenance
+    assert_app_in_maintenance message: "Custom Maintenance Page"
+  end
 end
diff --git a/test/integration/docker/deployer/app_with_roles/config/deploy.yml b/test/integration/docker/deployer/app_with_roles/config/deploy.yml
index 28449e0e..6c5ef9f4 100644
--- a/test/integration/docker/deployer/app_with_roles/config/deploy.yml
+++ b/test/integration/docker/deployer/app_with_roles/config/deploy.yml
@@ -37,6 +37,7 @@ proxy:
       - X-Request-Start
 
 asset_path: /usr/share/nginx/html/versions
+error_pages_path: error_pages
 
 registry:
   server: registry:4443
diff --git a/test/integration/docker/deployer/app_with_roles/error_pages/503.html b/test/integration/docker/deployer/app_with_roles/error_pages/503.html
new file mode 100644
index 00000000..3f844fb8
--- /dev/null
+++ b/test/integration/docker/deployer/app_with_roles/error_pages/503.html
@@ -0,0 +1,8 @@
+<html>
+  <head>
+    <title>503 Service Interrupted</title>
+  </head>
+  <body>
+    <p>Custom Maintenance Page: {{ .Message }}</p>
+  </body>
+</html>
diff --git a/test/integration/integration_test.rb b/test/integration/integration_test.rb
index e6e5520d..631d8fc4 100644
--- a/test/integration/integration_test.rb
+++ b/test/integration/integration_test.rb
@@ -45,15 +45,22 @@ class IntegrationTest < ActiveSupport::TestCase
     end
 
     def assert_app_is_down
-      response = app_response
-      debug_response_code(response, "502")
-      assert_equal "502", response.code
+      assert_app_error_code("502")
+    end
+
+    def assert_app_in_maintenance(message: nil)
+      assert_app_error_code("503", message: message)
     end
 
     def assert_app_not_found
+      assert_app_error_code("404")
+    end
+
+    def assert_app_error_code(code, message: nil)
       response = app_response
-      debug_response_code(response, "404")
-      assert_equal "404", response.code
+      debug_response_code(response, code)
+      assert_equal code, response.code
+      assert_match message, response.body.strip if message
     end
 
     def assert_app_is_up(version: nil, app: @app)
diff --git a/test/test_helper.rb b/test/test_helper.rb
index e77a0a8a..1704fa29 100644
--- a/test/test_helper.rb
+++ b/test/test_helper.rb
@@ -58,9 +58,7 @@ class ActiveSupport::TestCase
     def setup_test_secrets(**files)
       @original_pwd = Dir.pwd
       @secrets_tmpdir = Dir.mktmpdir
-      fixtures_dup = File.join(@secrets_tmpdir, "test")
-      FileUtils.mkdir_p(fixtures_dup)
-      FileUtils.cp_r("test/fixtures/", fixtures_dup)
+      copy_fixtures(@secrets_tmpdir)
 
       Dir.chdir(@secrets_tmpdir)
       FileUtils.mkdir_p(".kamal")
@@ -75,6 +73,30 @@ class ActiveSupport::TestCase
       Dir.chdir(@original_pwd)
       FileUtils.rm_rf(@secrets_tmpdir)
     end
+
+    def with_error_pages(directory:)
+      error_pages_tmpdir = Dir.mktmpdir
+
+      Dir.mktmpdir do |tmpdir|
+        copy_fixtures(tmpdir)
+
+        Dir.chdir(tmpdir) do
+          FileUtils.mkdir_p(directory)
+          Dir.chdir(directory) do
+            File.write("404.html", "404 page")
+            File.write("503.html", "503 page")
+          end
+
+          yield
+        end
+      end
+    end
+
+    def copy_fixtures(to_dir)
+      new_test_dir = File.join(to_dir, "test")
+      FileUtils.mkdir_p(new_test_dir)
+      FileUtils.cp_r("test/fixtures/", new_test_dir)
+    end
 end
 
 class SecretAdapterTestCase < ActiveSupport::TestCase