diff --git a/lib/kamal/cli/app.rb b/lib/kamal/cli/app.rb
index 040ab360..523eb487 100644
--- a/lib/kamal/cli/app.rb
+++ b/lib/kamal/cli/app.rb
@@ -14,12 +14,16 @@ class Kamal::Cli::App < Kamal::Cli::Base
             end
           end
 
+          #  Primary hosts and roles are returned first, so they can open the barrier
+          barrier = Kamal::Cli::Healthcheck::Barrier.new if KAMAL.roles.many?
+
           on(KAMAL.hosts, **KAMAL.boot_strategy) do |host|
             KAMAL.roles_on(host).each do |role|
-              Kamal::Cli::App::Boot.new(host, role, version, self).run
+              Kamal::Cli::App::Boot.new(host, role, self, version, barrier).run
             end
           end
 
+          #  Tag once the app booted on all hosts
           on(KAMAL.hosts) do |host|
             execute *KAMAL.auditor.record("Tagging #{KAMAL.config.absolute_image} as the latest image"), verbosity: :debug
             execute *KAMAL.app.tag_latest_image
diff --git a/lib/kamal/cli/app/boot.rb b/lib/kamal/cli/app/boot.rb
index 78670104..c4125771 100644
--- a/lib/kamal/cli/app/boot.rb
+++ b/lib/kamal/cli/app/boot.rb
@@ -1,19 +1,30 @@
 class Kamal::Cli::App::Boot
-  attr_reader :host, :role, :version, :sshkit
-  delegate :execute, :capture_with_info, :info, to: :sshkit
-  delegate :uses_cord?, :assets?, to: :role
+  attr_reader :host, :role, :version, :barrier, :sshkit
+  delegate :execute, :capture_with_info, :capture_with_pretty_json, :info, :error, to: :sshkit
+  delegate :uses_cord?, :assets?, :running_traefik?, to: :role
 
-  def initialize(host, role, version, sshkit)
+  def initialize(host, role, sshkit, version, barrier)
     @host = host
     @role = role
     @version = version
+    @barrier = barrier
     @sshkit = sshkit
   end
 
   def run
     old_version = old_version_renamed_if_clashing
 
-    start_new_version
+    wait_at_barrier if queuer?
+
+    begin
+      start_new_version
+    rescue => e
+      close_barrier if gatekeeper?
+      stop_new_version
+      raise
+    end
+
+    release_barrier if gatekeeper?
 
     if old_version
       stop_old_version(old_version)
@@ -21,18 +32,6 @@ class Kamal::Cli::App::Boot
   end
 
   private
-    def app
-      @app ||= KAMAL.app(role: role, host: host)
-    end
-
-    def auditor
-      @auditor = KAMAL.auditor(role: role)
-    end
-
-    def audit(message)
-      execute *auditor.record(message), verbosity: :debug
-    end
-
     def old_version_renamed_if_clashing
       if capture_with_info(*app.container_id_for_version(version), raise_on_non_zero_exit: false).present?
         renamed_version = "#{version}_replaced_#{SecureRandom.hex(8)}"
@@ -46,12 +45,17 @@ class Kamal::Cli::App::Boot
 
     def start_new_version
       audit "Booted app version #{version}"
+
       execute *app.tie_cord(role.cord_host_file) if uses_cord?
       hostname = "#{host.to_s[0...51].gsub(/\.+$/, '')}-#{SecureRandom.hex(6)}"
       execute *app.run(hostname: hostname)
       Kamal::Cli::Healthcheck::Poller.wait_for_healthy(pause_after_ready: true) { capture_with_info(*app.status(version: version)) }
     end
 
+    def stop_new_version
+      execute *app.stop(version: version), raise_on_non_zero_exit: false
+    end
+
     def stop_old_version(version)
       if uses_cord?
         cord = capture_with_info(*app.cord(version: version), raise_on_non_zero_exit: false).strip
@@ -65,4 +69,51 @@ class Kamal::Cli::App::Boot
 
       execute *app.clean_up_assets if assets?
     end
+
+    def release_barrier
+      if barrier.open
+        info "First #{KAMAL.primary_role} container is healthy on #{host}, booting other roles"
+      end
+    end
+
+    def wait_at_barrier
+      info "Waiting for the first healthy #{KAMAL.primary_role} container before booting #{role} on #{host}..."
+      barrier.wait
+      info "First #{KAMAL.primary_role} container is healthy, booting #{role} on #{host}..."
+    rescue Kamal::Cli::Healthcheck::Error
+      info "First #{KAMAL.primary_role} container is unhealthy, not booting #{role} on #{host}"
+      raise
+    end
+
+    def close_barrier
+      if barrier.close
+        info "First #{KAMAL.primary_role} container is unhealthy on #{host}, not booting other roles"
+        error capture_with_info(*app.logs(version: version))
+        error capture_with_info(*app.container_health_log(version: version))
+      end
+    end
+
+    def barrier_role?
+      role == KAMAL.primary_role
+    end
+
+    def app
+      @app ||= KAMAL.app(role: role, host: host)
+    end
+
+    def auditor
+      @auditor = KAMAL.auditor(role: role)
+    end
+
+    def audit(message)
+      execute *auditor.record(message), verbosity: :debug
+    end
+
+    def gatekeeper?
+      barrier && barrier_role?
+    end
+
+    def queuer?
+      barrier && !barrier_role?
+    end
 end
diff --git a/lib/kamal/cli/healthcheck.rb b/lib/kamal/cli/healthcheck.rb
deleted file mode 100644
index b3dbf6bd..00000000
--- a/lib/kamal/cli/healthcheck.rb
+++ /dev/null
@@ -1,21 +0,0 @@
-class Kamal::Cli::Healthcheck < Kamal::Cli::Base
-  default_command :perform
-
-  desc "perform", "Health check current app version"
-  def perform
-    raise "The primary host is not configured to run Traefik" unless KAMAL.config.role(KAMAL.config.primary_role).running_traefik?
-    on(KAMAL.primary_host) do
-      begin
-        execute *KAMAL.healthcheck.run
-        Poller.wait_for_healthy { capture_with_info(*KAMAL.healthcheck.status) }
-      rescue Poller::HealthcheckError => e
-        error capture_with_info(*KAMAL.healthcheck.logs)
-        error capture_with_pretty_json(*KAMAL.healthcheck.container_health_log)
-        raise
-      ensure
-        execute *KAMAL.healthcheck.stop, raise_on_non_zero_exit: false
-        execute *KAMAL.healthcheck.remove, raise_on_non_zero_exit: false
-      end
-    end
-  end
-end
diff --git a/lib/kamal/cli/healthcheck/barrier.rb b/lib/kamal/cli/healthcheck/barrier.rb
new file mode 100644
index 00000000..0fbfb511
--- /dev/null
+++ b/lib/kamal/cli/healthcheck/barrier.rb
@@ -0,0 +1,31 @@
+class Kamal::Cli::Healthcheck::Barrier
+  def initialize
+    @ivar = Concurrent::IVar.new
+  end
+
+  def close
+    set(false)
+  end
+
+  def open
+    set(true)
+  end
+
+  def wait
+    unless opened?
+      raise Kamal::Cli::Healthcheck::Error.new("Halted at barrier")
+    end
+  end
+
+  private
+    def opened?
+      @ivar.value
+    end
+
+    def set(value)
+      @ivar.set(value)
+      true
+    rescue Concurrent::MultipleAssignmentError
+      false
+    end
+end
diff --git a/lib/kamal/cli/healthcheck/error.rb b/lib/kamal/cli/healthcheck/error.rb
new file mode 100644
index 00000000..8824a72e
--- /dev/null
+++ b/lib/kamal/cli/healthcheck/error.rb
@@ -0,0 +1,2 @@
+class Kamal::Cli::Healthcheck::Error < StandardError
+end
diff --git a/lib/kamal/cli/healthcheck/poller.rb b/lib/kamal/cli/healthcheck/poller.rb
index 9d91adfc..06898b1c 100644
--- a/lib/kamal/cli/healthcheck/poller.rb
+++ b/lib/kamal/cli/healthcheck/poller.rb
@@ -3,7 +3,6 @@ module Kamal::Cli::Healthcheck::Poller
 
   TRAEFIK_UPDATE_DELAY = 5
 
-  class HealthcheckError < StandardError; end
 
   def wait_for_healthy(pause_after_ready: false, &block)
     attempt = 1
@@ -16,9 +15,9 @@ module Kamal::Cli::Healthcheck::Poller
       when "running" # No health check configured
         sleep KAMAL.config.readiness_delay if pause_after_ready
       else
-        raise HealthcheckError, "container not ready (#{status})"
+        raise Kamal::Cli::Healthcheck::Error, "container not ready (#{status})"
       end
-    rescue HealthcheckError => e
+    rescue Kamal::Cli::Healthcheck::Error => e
       if attempt <= max_attempts
         info "#{e.message}, retrying in #{attempt}s (attempt #{attempt}/#{max_attempts})..."
         sleep attempt
@@ -41,9 +40,9 @@ module Kamal::Cli::Healthcheck::Poller
       when "unhealthy"
         sleep TRAEFIK_UPDATE_DELAY if pause_after_ready
       else
-        raise HealthcheckError, "container not unhealthy (#{status})"
+        raise Kamal::Cli::Healthcheck::Error, "container not unhealthy (#{status})"
       end
-    rescue HealthcheckError => e
+    rescue Kamal::Cli::Healthcheck::Error => e
       if attempt <= max_attempts
         info "#{e.message}, retrying in #{attempt}s (attempt #{attempt}/#{max_attempts})..."
         sleep attempt
diff --git a/lib/kamal/cli/main.rb b/lib/kamal/cli/main.rb
index a09724b6..f17fd6cd 100644
--- a/lib/kamal/cli/main.rb
+++ b/lib/kamal/cli/main.rb
@@ -41,11 +41,6 @@ class Kamal::Cli::Main < Kamal::Cli::Base
         say "Ensure Traefik is running...", :magenta
         invoke "kamal:cli:traefik:boot", [], invoke_options
 
-        if KAMAL.config.role(KAMAL.config.primary_role).running_traefik?
-          say "Ensure app can pass healthcheck...", :magenta
-          invoke "kamal:cli:healthcheck:perform", [], invoke_options
-        end
-
         say "Detect stale containers...", :magenta
         invoke "kamal:cli:app:stale_containers", [], invoke_options.merge(stop: true)
 
@@ -76,9 +71,6 @@ class Kamal::Cli::Main < Kamal::Cli::Base
 
         run_hook "pre-deploy"
 
-        say "Ensure app can pass healthcheck...", :magenta
-        invoke "kamal:cli:healthcheck:perform", [], invoke_options
-
         say "Detect stale containers...", :magenta
         invoke "kamal:cli:app:stale_containers", [], invoke_options.merge(stop: true)
 
@@ -227,9 +219,6 @@ class Kamal::Cli::Main < Kamal::Cli::Base
   desc "env", "Manage environment files"
   subcommand "env", Kamal::Cli::Env
 
-  desc "healthcheck", "Healthcheck application"
-  subcommand "healthcheck", Kamal::Cli::Healthcheck
-
   desc "lock", "Manage the deploy lock"
   subcommand "lock", Kamal::Cli::Lock
 
@@ -254,7 +243,7 @@ class Kamal::Cli::Main < Kamal::Cli::Base
             raise "Container not found" unless container_id.present?
           end
         end
-      rescue SSHKit::Runner::ExecuteError => e
+      rescue SSHKit::Runner::ExecuteError, SSHKit::Runner::MultipleExecuteError => e
         if e.message =~ /Container not found/
           say "Error looking for container version #{version}: #{e.message}"
           return false
diff --git a/lib/kamal/commands/app/containers.rb b/lib/kamal/commands/app/containers.rb
index a62d9a35..0bab388b 100644
--- a/lib/kamal/commands/app/containers.rb
+++ b/lib/kamal/commands/app/containers.rb
@@ -1,4 +1,6 @@
 module Kamal::Commands::App::Containers
+  DOCKER_HEALTH_LOG_FORMAT    = "'{{json .State.Health}}'"
+
   def list_containers
     docker :container, :ls, "--all", *filter_args
   end
@@ -20,4 +22,10 @@ module Kamal::Commands::App::Containers
   def remove_containers
     docker :container, :prune, "--force", *filter_args
   end
+
+  def container_health_log(version:)
+    pipe \
+      container_id_for(container_name: container_name(version)),
+      xargs(docker(:inspect, "--format", DOCKER_HEALTH_LOG_FORMAT))
+  end
 end
diff --git a/lib/kamal/commands/app/logging.rb b/lib/kamal/commands/app/logging.rb
index 7e760512..8acb49e9 100644
--- a/lib/kamal/commands/app/logging.rb
+++ b/lib/kamal/commands/app/logging.rb
@@ -1,7 +1,7 @@
 module Kamal::Commands::App::Logging
-  def logs(since: nil, lines: nil, grep: nil)
+  def logs(version: nil, since: nil, lines: nil, grep: nil)
     pipe \
-      current_running_container_id,
+      version ? container_id_for_version(version) : current_running_container_id,
       "xargs docker logs#{" --since #{since}" if since}#{" --tail #{lines}" if lines} 2>&1",
       ("grep '#{grep}'" if grep)
   end
diff --git a/lib/kamal/commands/base.rb b/lib/kamal/commands/base.rb
index a98d6330..2173d064 100644
--- a/lib/kamal/commands/base.rb
+++ b/lib/kamal/commands/base.rb
@@ -3,7 +3,6 @@ module Kamal::Commands
     delegate :sensitive, :argumentize, to: Kamal::Utils
 
     DOCKER_HEALTH_STATUS_FORMAT = "'{{if .State.Health}}{{.State.Health.Status}}{{else}}{{.State.Status}}{{end}}'"
-    DOCKER_HEALTH_LOG_FORMAT    = "'{{json .State.Health}}'"
 
     attr_accessor :config
 
diff --git a/lib/kamal/commands/healthcheck.rb b/lib/kamal/commands/healthcheck.rb
deleted file mode 100644
index 2517a5e2..00000000
--- a/lib/kamal/commands/healthcheck.rb
+++ /dev/null
@@ -1,59 +0,0 @@
-class Kamal::Commands::Healthcheck < Kamal::Commands::Base
-  def run
-    primary = config.role(config.primary_role)
-
-    docker :run,
-      "--detach",
-      "--name", container_name_with_version,
-      "--publish", "#{exposed_port}:#{config.healthcheck["port"]}",
-      "--label", "service=#{config.healthcheck_service}",
-      "-e", "KAMAL_CONTAINER_NAME=\"#{config.healthcheck_service}\"",
-      *primary.env_args(config.primary_host),
-      *primary.health_check_args(cord: false),
-      *config.volume_args,
-      *primary.option_args,
-      config.absolute_image,
-      primary.cmd
-  end
-
-  def status
-    pipe container_id, xargs(docker(:inspect, "--format", DOCKER_HEALTH_STATUS_FORMAT))
-  end
-
-  def container_health_log
-    pipe container_id, xargs(docker(:inspect, "--format", DOCKER_HEALTH_LOG_FORMAT))
-  end
-
-  def logs
-    pipe container_id, xargs(docker(:logs, "--tail", log_lines, "2>&1"))
-  end
-
-  def stop
-    pipe container_id, xargs(docker(:stop))
-  end
-
-  def remove
-    pipe container_id, xargs(docker(:container, :rm))
-  end
-
-  private
-    def container_name_with_version
-      "#{config.healthcheck_service}-#{config.version}"
-    end
-
-    def container_id
-      container_id_for(container_name: container_name_with_version)
-    end
-
-    def health_url
-      "http://localhost:#{exposed_port}#{config.healthcheck["path"]}"
-    end
-
-    def exposed_port
-      config.healthcheck["exposed_port"]
-    end
-
-    def log_lines
-      config.healthcheck["log_lines"]
-    end
-end
diff --git a/lib/kamal/configuration.rb b/lib/kamal/configuration.rb
index 4957be17..bed91cf6 100644
--- a/lib/kamal/configuration.rb
+++ b/lib/kamal/configuration.rb
@@ -188,7 +188,7 @@ class Kamal::Configuration
 
 
   def healthcheck
-    { "path" => "/up", "port" => 3000, "max_attempts" => 7, "exposed_port" => 3999, "cord" => "/tmp/kamal-cord", "log_lines" => 50 }.merge(raw_config.healthcheck || {})
+    { "path" => "/up", "port" => 3000, "max_attempts" => 7, "cord" => "/tmp/kamal-cord", "log_lines" => 50 }.merge(raw_config.healthcheck || {})
   end
 
   def healthcheck_service
diff --git a/lib/kamal/sshkit_with_ext.rb b/lib/kamal/sshkit_with_ext.rb
index e0c62c3a..2d0257a8 100644
--- a/lib/kamal/sshkit_with_ext.rb
+++ b/lib/kamal/sshkit_with_ext.rb
@@ -103,3 +103,39 @@ class SSHKit::Backend::Netssh
 
   prepend LimitConcurrentStartsInstance
 end
+
+class SSHKit::Runner::Parallel
+  # SSHKit joins the threads in sequence and fails on the first error it encounters, which means that we wait threads
+  # before the first failure to complete but not for ones after.
+  #
+  # We'll patch it to wait for them all to complete, and to record all the threads that errored so we can see when a
+  # problem occurs on multiple hosts.
+  module CompleteAll
+    def execute
+      threads = hosts.map do |host|
+        Thread.new(host) do |h|
+          backend(h, &block).run
+        rescue ::StandardError => e
+          e2 = SSHKit::Runner::ExecuteError.new e
+          raise e2, "Exception while executing #{host.user ? "as #{host.user}@" : "on host "}#{host}: #{e.message}"
+        end
+      end
+
+      exceptions = []
+      threads.each do |t|
+        begin
+          t.join
+        rescue SSHKit::Runner::ExecuteError => e
+          exceptions << e
+        end
+      end
+      if exceptions.one?
+        raise exceptions.first
+      elsif exceptions.many?
+        raise exceptions.first, [ "Exceptions on #{exceptions.count} hosts:", exceptions.map(&:message) ].join("\n")
+      end
+    end
+  end
+
+  prepend CompleteAll
+end
diff --git a/test/cli/app_test.rb b/test/cli/app_test.rb
index c75a86cc..7a2a266e 100644
--- a/test/cli/app_test.rb
+++ b/test/cli/app_test.rb
@@ -118,6 +118,56 @@ class CliAppTest < CliTestCase
     end
   end
 
+  test "boot with web barrier opened" do
+    Object.any_instance.stubs(:sleep)
+
+    SSHKit::Backend::Abstract.any_instance.stubs(:capture_with_info).returns("123") # old version
+
+    SSHKit::Backend::Abstract.any_instance.expects(:capture_with_info)
+      .with(:docker, :container, :ls, "--all", "--filter", "name=^app-web-latest$", "--quiet", "|", :xargs, :docker, :inspect, "--format", "'{{if .State.Health}}{{.State.Health.Status}}{{else}}{{.State.Status}}{{end}}'")
+      .returns("running").at_least_once # web health check passing
+
+    SSHKit::Backend::Abstract.any_instance.expects(:capture_with_info)
+      .with(:docker, :container, :ls, "--all", "--filter", "name=^app-web-123$", "--quiet", "|", :xargs, :docker, :inspect, "--format", "'{{if .State.Health}}{{.State.Health.Status}}{{else}}{{.State.Status}}{{end}}'")
+      .returns("unhealthy").at_least_once # web health check failing
+
+    SSHKit::Backend::Abstract.any_instance.expects(:capture_with_info)
+      .with(:docker, :container, :ls, "--all", "--filter", "name=^app-workers-latest$", "--quiet", "|", :xargs, :docker, :inspect, "--format", "'{{if .State.Health}}{{.State.Health.Status}}{{else}}{{.State.Status}}{{end}}'")
+      .returns("running").at_least_once # workers health check
+
+    run_command("boot", config: :with_roles, host: nil).tap do |output|
+      assert_match "Waiting for the first healthy web container before booting workers on 1.1.1.3...", output
+      assert_match "Waiting for the first healthy web container before booting workers on 1.1.1.4...", output
+      assert_match "First web container is healthy, booting workers on 1.1.1.3", output
+      assert_match "First web container is healthy, booting workers on 1.1.1.4", output
+  end
+  end
+
+  test "boot with web barrier closed" do
+    Thread.report_on_exception = false
+
+    Object.any_instance.stubs(:sleep)
+
+    SSHKit::Backend::Abstract.any_instance.stubs(:capture_with_info).returns("123") # old version
+
+    SSHKit::Backend::Abstract.any_instance.expects(:capture_with_info)
+      .with(:docker, :container, :ls, "--all", "--filter", "name=^app-web-latest$", "--quiet", "|", :xargs, :docker, :inspect, "--format", "'{{if .State.Health}}{{.State.Health.Status}}{{else}}{{.State.Status}}{{end}}'")
+      .returns("unhealthy").at_least_once # web health check failing
+
+    stderred do
+      run_command("boot", config: :with_roles, host: nil, allow_execute_error: true).tap do |output|
+        assert_match "Waiting for the first healthy web container before booting workers on 1.1.1.3...", output
+        assert_match "Waiting for the first healthy web container before booting workers on 1.1.1.4...", output
+        assert_match "First web container is unhealthy, not booting workers on 1.1.1.3", output
+        assert_match "First web container is unhealthy, not booting workers on 1.1.1.4", output
+        assert_match "Running docker container ls --all --filter name=^app-web-latest$ --quiet | xargs docker stop on 1.1.1.1", output
+        assert_match "Running docker container ls --all --filter name=^app-web-latest$ --quiet | xargs docker stop on 1.1.1.2", output
+      end
+    end
+  ensure
+    Thread.report_on_exception = true
+  end
+
   test "start" do
     run_command("start").tap do |output|
       assert_match "docker start app-web-999", output
@@ -283,8 +333,12 @@ class CliAppTest < CliTestCase
   end
 
   private
-    def run_command(*command, config: :with_accessories)
-      stdouted { Kamal::Cli::App.start([ *command, "-c", "test/fixtures/deploy_#{config}.yml", "--hosts", "1.1.1.1" ]) }
+    def run_command(*command, config: :with_accessories, host: "1.1.1.1", allow_execute_error: false)
+      stdouted do
+        Kamal::Cli::App.start([ *command, "-c", "test/fixtures/deploy_#{config}.yml", *([ "--hosts", host ] if host) ])
+      rescue SSHKit::Runner::ExecuteError => e
+        raise e unless allow_execute_error
+      end
     end
 
     def stub_running
diff --git a/test/cli/healthcheck_test.rb b/test/cli/healthcheck_test.rb
deleted file mode 100644
index e273bf2e..00000000
--- a/test/cli/healthcheck_test.rb
+++ /dev/null
@@ -1,82 +0,0 @@
-require_relative "cli_test_case"
-
-class CliHealthcheckTest < CliTestCase
-  test "perform" do
-    # Prevent expected failures from outputting to terminal
-    Thread.report_on_exception = false
-
-    Kamal::Cli::Healthcheck::Poller.stubs(:sleep) # No sleeping when retrying
-    Kamal::Configuration.any_instance.stubs(:run_id).returns("12345678901234567890123456789012")
-
-    SSHKit::Backend::Abstract.any_instance.stubs(:execute)
-      .with(:docker, :container, :ls, "--all", "--filter", "name=^healthcheck-app-999$", "--quiet", "|", :xargs, :docker, :stop, raise_on_non_zero_exit: false)
-    SSHKit::Backend::Abstract.any_instance.stubs(:execute)
-      .with(:docker, :run, "--detach", "--name", "healthcheck-app-999", "--publish", "3999:3000", "--label", "service=healthcheck-app", "-e", "KAMAL_CONTAINER_NAME=\"healthcheck-app\"", "--env-file", ".kamal/env/roles/app-web.env", "--health-cmd", "\"curl -f http://localhost:3000/up || exit 1\"", "--health-interval", "\"1s\"", "dhh/app:999")
-    SSHKit::Backend::Abstract.any_instance.stubs(:execute)
-      .with(:docker, :container, :ls, "--all", "--filter", "name=^healthcheck-app-999$", "--quiet", "|", :xargs, :docker, :container, :rm, raise_on_non_zero_exit: false)
-
-    # Fail twice to test retry logic
-    SSHKit::Backend::Abstract.any_instance.stubs(:capture_with_info)
-      .with(:docker, :container, :ls, "--all", "--filter", "name=^healthcheck-app-999$", "--quiet", "|", :xargs, :docker, :inspect, "--format", "'{{if .State.Health}}{{.State.Health.Status}}{{else}}{{.State.Status}}{{end}}'")
-      .returns("starting")
-      .then
-      .returns("unhealthy")
-      .then
-      .returns("healthy")
-
-    run_command("perform").tap do |output|
-      assert_match "container not ready (starting), retrying in 1s (attempt 1/7)...", output
-      assert_match "container not ready (unhealthy), retrying in 2s (attempt 2/7)...", output
-      assert_match "Container is healthy!", output
-    end
-  end
-
-  test "perform failing to become healthy" do
-    # Prevent expected failures from outputting to terminal
-    Thread.report_on_exception = false
-
-    Kamal::Cli::Healthcheck::Poller.stubs(:sleep) # No sleeping when retrying
-
-    SSHKit::Backend::Abstract.any_instance.stubs(:execute)
-      .with(:docker, :container, :ls, "--all", "--filter", "name=^healthcheck-app-999$", "--quiet", "|", :xargs, :docker, :stop, raise_on_non_zero_exit: false)
-    SSHKit::Backend::Abstract.any_instance.stubs(:execute)
-      .with(:docker, :run, "--detach", "--name", "healthcheck-app-999", "--publish", "3999:3000", "--label", "service=healthcheck-app", "-e", "KAMAL_CONTAINER_NAME=\"healthcheck-app\"", "--env-file", ".kamal/env/roles/app-web.env", "--health-cmd", "\"curl -f http://localhost:3000/up || exit 1\"", "--health-interval", "\"1s\"", "dhh/app:999")
-    SSHKit::Backend::Abstract.any_instance.stubs(:execute)
-      .with(:docker, :container, :ls, "--all", "--filter", "name=^healthcheck-app-999$", "--quiet", "|", :xargs, :docker, :container, :rm, raise_on_non_zero_exit: false)
-
-    # Continually report unhealthy
-    SSHKit::Backend::Abstract.any_instance.stubs(:capture_with_info)
-      .with(:docker, :container, :ls, "--all", "--filter", "name=^healthcheck-app-999$", "--quiet", "|", :xargs, :docker, :inspect, "--format", "'{{if .State.Health}}{{.State.Health.Status}}{{else}}{{.State.Status}}{{end}}'")
-      .returns("unhealthy")
-
-    # Capture logs when failing
-    SSHKit::Backend::Abstract.any_instance.stubs(:capture_with_info)
-      .with(:docker, :container, :ls, "--all", "--filter", "name=^healthcheck-app-999$", "--quiet", "|", :xargs, :docker, :logs, "--tail", 50, "2>&1")
-      .returns("some log output")
-
-    # Capture container health log when failing
-    SSHKit::Backend::Abstract.any_instance.stubs(:capture_with_pretty_json)
-      .with(:docker, :container, :ls, "--all", "--filter", "name=^healthcheck-app-999$", "--quiet", "|", :xargs, :docker, :inspect, "--format",  "'{{json .State.Health}}'")
-      .returns('{"Status":"unhealthy","Log":[{"ExitCode": 1,"Output": "/bin/sh: 1: curl: not found\n"}]}"')
-
-    exception = assert_raises do
-      run_command("perform")
-    end
-    assert_match "container not ready (unhealthy)", exception.message
-  end
-
-  test "raises an exception if primary does not have traefik" do
-    SSHKit::Backend::Abstract.any_instance.expects(:execute).never
-
-    exception = assert_raises do
-      run_command("perform", config_file: "test/fixtures/deploy_workers_only.yml")
-    end
-
-    assert_equal "The primary host is not configured to run Traefik", exception.message
-  end
-
-  private
-    def run_command(*command, config_file: "test/fixtures/deploy_with_accessories.yml")
-      stdouted { Kamal::Cli::Healthcheck.start([ *command, "-c", config_file ]) }
-    end
-end
diff --git a/test/cli/main_test.rb b/test/cli/main_test.rb
index 81d3eb4d..358a7394 100644
--- a/test/cli/main_test.rb
+++ b/test/cli/main_test.rb
@@ -25,7 +25,6 @@ class CliMainTest < CliTestCase
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:registry:login", [], invoke_options)
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:build:pull", [], invoke_options)
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:traefik:boot", [], invoke_options)
-    Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:healthcheck:perform", [], invoke_options)
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:app:stale_containers", [], invoke_options.merge(stop: true))
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:app:boot", [], invoke_options)
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:prune:all", [], invoke_options)
@@ -38,7 +37,6 @@ class CliMainTest < CliTestCase
       assert_match /Log into image registry/, output
       assert_match /Pull app image/, output
       assert_match /Ensure Traefik is running/, output
-      assert_match /Ensure app can pass healthcheck/, output
       assert_match /Detect stale containers/, output
       assert_match /Prune old containers and images/, output
       assert_match /Releasing the deploy lock/, output
@@ -51,7 +49,6 @@ class CliMainTest < CliTestCase
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:registry:login", [], invoke_options)
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:build:deliver", [], invoke_options)
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:traefik:boot", [], invoke_options)
-    Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:healthcheck:perform", [], invoke_options)
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:app:stale_containers", [], invoke_options.merge(stop: true))
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:app:boot", [], invoke_options)
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:prune:all", [], invoke_options)
@@ -65,7 +62,6 @@ class CliMainTest < CliTestCase
       assert_match /Build and push app image/, output
       assert_hook_ran "pre-deploy", output, **hook_variables
       assert_match /Ensure Traefik is running/, output
-      assert_match /Ensure app can pass healthcheck/, output
       assert_match /Detect stale containers/, output
       assert_match /Prune old containers and images/, output
       assert_hook_ran "post-deploy", output, **hook_variables, runtime: true
@@ -78,7 +74,6 @@ class CliMainTest < CliTestCase
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:registry:login", [], invoke_options)
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:build:pull", [], invoke_options)
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:traefik:boot", [], invoke_options)
-    Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:healthcheck:perform", [], invoke_options)
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:app:stale_containers", [], invoke_options.merge(stop: true))
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:app:boot", [], invoke_options)
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:prune:all", [], invoke_options)
@@ -88,7 +83,6 @@ class CliMainTest < CliTestCase
       assert_match /Log into image registry/, output
       assert_match /Pull app image/, output
       assert_match /Ensure Traefik is running/, output
-      assert_match /Ensure app can pass healthcheck/, output
       assert_match /Detect stale containers/, output
       assert_match /Prune old containers and images/, output
       assert_match /Releasing the deploy lock/, output
@@ -154,7 +148,6 @@ class CliMainTest < CliTestCase
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:registry:login", [], invoke_options)
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:build:deliver", [], invoke_options)
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:traefik:boot", [], invoke_options)
-    Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:healthcheck:perform", [], invoke_options)
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:app:stale_containers", [], invoke_options.merge(stop: true))
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:app:boot", [], invoke_options)
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:prune:all", [], invoke_options)
@@ -185,7 +178,6 @@ class CliMainTest < CliTestCase
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:registry:login", [], invoke_options)
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:build:deliver", [], invoke_options)
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:traefik:boot", [], invoke_options)
-    Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:healthcheck:perform", [], invoke_options)
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:app:stale_containers", [], invoke_options.merge(stop: true))
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:app:boot", [], invoke_options)
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:prune:all", [], invoke_options)
@@ -197,7 +189,6 @@ class CliMainTest < CliTestCase
     invoke_options = { "config_file" => "test/fixtures/deploy_simple.yml", "version" => "999", "skip_hooks" => false, "verbose" => true }
 
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:build:deliver", [], invoke_options)
-    Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:healthcheck:perform", [], invoke_options)
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:app:stale_containers", [], invoke_options.merge(stop: true))
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:app:boot", [], invoke_options)
 
@@ -210,7 +201,6 @@ class CliMainTest < CliTestCase
       assert_match /Build and push app image/, output
       assert_hook_ran "pre-deploy", output, **hook_variables
       assert_match /Running the pre-deploy hook.../, output
-      assert_match /Ensure app can pass healthcheck/, output
       assert_hook_ran "post-deploy", output, **hook_variables, runtime: true
     end
   end
@@ -219,13 +209,11 @@ class CliMainTest < CliTestCase
     invoke_options = { "config_file" => "test/fixtures/deploy_simple.yml", "version" => "999", "skip_hooks" => false }
 
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:build:pull", [], invoke_options)
-    Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:healthcheck:perform", [], invoke_options)
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:app:stale_containers", [], invoke_options.merge(stop: true))
     Kamal::Cli::Main.any_instance.expects(:invoke).with("kamal:cli:app:boot", [], invoke_options)
 
     run_command("redeploy", "--skip_push").tap do |output|
       assert_match /Pull app image/, output
-      assert_match /Ensure app can pass healthcheck/, output
     end
   end
 
diff --git a/test/commander_test.rb b/test/commander_test.rb
index 2bbdb479..6a7ec536 100644
--- a/test/commander_test.rb
+++ b/test/commander_test.rb
@@ -99,6 +99,11 @@ class CommanderTest < ActiveSupport::TestCase
     assert_equal [ "workers" ], @kamal.roles_on("1.1.1.3").map(&:name)
   end
 
+  test "roles_on web comes first" do
+    configure_with(:deploy_with_two_roles_one_host)
+    assert_equal [ "web", "workers" ], @kamal.roles_on("1.1.1.1").map(&:name)
+  end
+
   test "default group strategy" do
     assert_empty @kamal.boot_strategy
   end
diff --git a/test/commands/healthcheck_test.rb b/test/commands/healthcheck_test.rb
deleted file mode 100644
index 829aa0b2..00000000
--- a/test/commands/healthcheck_test.rb
+++ /dev/null
@@ -1,124 +0,0 @@
-require "test_helper"
-
-class CommandsHealthcheckTest < ActiveSupport::TestCase
-  setup do
-    @config = {
-      service: "app", image: "dhh/app", registry: { "username" => "dhh", "password" => "secret" }, servers: [ "1.1.1.1" ],
-      traefik: { "args" => { "accesslog.format" => "json", "metrics.prometheus.buckets" => "0.1,0.3,1.2,5.0" } }
-    }
-  end
-
-  test "run" do
-    assert_equal \
-      "docker run --detach --name healthcheck-app-123 --publish 3999:3000 --label service=healthcheck-app -e KAMAL_CONTAINER_NAME=\"healthcheck-app\" --env-file .kamal/env/roles/app-web.env --health-cmd \"curl -f http://localhost:3000/up || exit 1\" --health-interval \"1s\" dhh/app:123",
-      new_command.run.join(" ")
-  end
-
-  test "run with custom port" do
-    @config[:healthcheck] = { "port" => 3001 }
-
-    assert_equal \
-      "docker run --detach --name healthcheck-app-123 --publish 3999:3001 --label service=healthcheck-app -e KAMAL_CONTAINER_NAME=\"healthcheck-app\" --env-file .kamal/env/roles/app-web.env --health-cmd \"curl -f http://localhost:3001/up || exit 1\" --health-interval \"1s\" dhh/app:123",
-      new_command.run.join(" ")
-  end
-
-  test "run with destination" do
-    @destination = "staging"
-
-    assert_equal \
-      "docker run --detach --name healthcheck-app-staging-123 --publish 3999:3000 --label service=healthcheck-app-staging -e KAMAL_CONTAINER_NAME=\"healthcheck-app-staging\" --env-file .kamal/env/roles/app-web-staging.env --health-cmd \"curl -f http://localhost:3000/up || exit 1\" --health-interval \"1s\" dhh/app:123",
-      new_command.run.join(" ")
-  end
-
-  test "run with custom healthcheck" do
-    @config[:healthcheck] = { "cmd" => "/bin/up" }
-
-    assert_equal \
-      "docker run --detach --name healthcheck-app-123 --publish 3999:3000 --label service=healthcheck-app -e KAMAL_CONTAINER_NAME=\"healthcheck-app\" --env-file .kamal/env/roles/app-web.env --health-cmd \"/bin/up\" --health-interval \"1s\" dhh/app:123",
-      new_command.run.join(" ")
-  end
-
-  test "run with custom options" do
-    @config[:servers] = { "web" => { "hosts" => [ "1.1.1.1" ], "options" => { "mount" => "somewhere" } } }
-    @config[:healthcheck] = { "exposed_port" => 4999 }
-    assert_equal \
-      "docker run --detach --name healthcheck-app-123 --publish 4999:3000 --label service=healthcheck-app -e KAMAL_CONTAINER_NAME=\"healthcheck-app\" --env-file .kamal/env/roles/app-web.env --health-cmd \"curl -f http://localhost:3000/up || exit 1\" --health-interval \"1s\" --mount \"somewhere\" dhh/app:123",
-      new_command.run.join(" ")
-  end
-
-  test "run with tags" do
-    @config[:servers] = [ { "1.1.1.1" => "tag1" } ]
-    @config[:env] = {}
-    @config[:env]["tags"] = { "tag1" => { "ENV1" => "value1" } }
-
-    assert_equal \
-      "docker run --detach --name healthcheck-app-123 --publish 3999:3000 --label service=healthcheck-app -e KAMAL_CONTAINER_NAME=\"healthcheck-app\" --env-file .kamal/env/roles/app-web.env --env ENV1=\"value1\" --health-cmd \"curl -f http://localhost:3000/up || exit 1\" --health-interval \"1s\" dhh/app:123",
-      new_command.run.join(" ")
-  end
-
-  test "status" do
-    assert_equal \
-      "docker container ls --all --filter name=^healthcheck-app-123$ --quiet | xargs docker inspect --format '{{if .State.Health}}{{.State.Health.Status}}{{else}}{{.State.Status}}{{end}}'",
-      new_command.status.join(" ")
-  end
-
-  test "container_health_log" do
-    assert_equal \
-      "docker container ls --all --filter name=^healthcheck-app-123$ --quiet | xargs docker inspect --format '{{json .State.Health}}'",
-      new_command.container_health_log.join(" ")
-  end
-
-  test "stop" do
-    assert_equal \
-      "docker container ls --all --filter name=^healthcheck-app-123$ --quiet | xargs docker stop",
-      new_command.stop.join(" ")
-  end
-
-  test "stop with destination" do
-    @destination = "staging"
-
-    assert_equal \
-      "docker container ls --all --filter name=^healthcheck-app-staging-123$ --quiet | xargs docker stop",
-      new_command.stop.join(" ")
-  end
-
-  test "remove" do
-    assert_equal \
-      "docker container ls --all --filter name=^healthcheck-app-123$ --quiet | xargs docker container rm",
-      new_command.remove.join(" ")
-  end
-
-  test "remove with destination" do
-    @destination = "staging"
-
-    assert_equal \
-      "docker container ls --all --filter name=^healthcheck-app-staging-123$ --quiet | xargs docker container rm",
-      new_command.remove.join(" ")
-  end
-
-  test "logs" do
-    assert_equal \
-      "docker container ls --all --filter name=^healthcheck-app-123$ --quiet | xargs docker logs --tail 50 2>&1",
-      new_command.logs.join(" ")
-  end
-
-  test "logs with custom lines number" do
-    @config[:healthcheck] = { "log_lines" => 150 }
-    assert_equal \
-      "docker container ls --all --filter name=^healthcheck-app-123$ --quiet | xargs docker logs --tail 150 2>&1",
-      new_command.logs.join(" ")
-  end
-
-  test "logs with destination" do
-    @destination = "staging"
-
-    assert_equal \
-      "docker container ls --all --filter name=^healthcheck-app-staging-123$ --quiet | xargs docker logs --tail 50 2>&1",
-      new_command.logs.join(" ")
-  end
-
-  private
-    def new_command
-      Kamal::Commands::Healthcheck.new(Kamal::Configuration.new(@config, destination: @destination, version: "123"))
-    end
-end
diff --git a/test/configuration_test.rb b/test/configuration_test.rb
index 6a86b231..e7e7f151 100644
--- a/test/configuration_test.rb
+++ b/test/configuration_test.rb
@@ -272,7 +272,7 @@ class ConfigurationTest < ActiveSupport::TestCase
         volume_args: [ "--volume", "/local/path:/container/path" ],
         builder: {},
         logging: [ "--log-opt", "max-size=\"10m\"" ],
-        healthcheck: { "path"=>"/up", "port"=>3000, "max_attempts" => 7, "exposed_port" => 3999, "cord" => "/tmp/kamal-cord", "log_lines" => 50 } }
+        healthcheck: { "path"=>"/up", "port"=>3000, "max_attempts" => 7, "cord" => "/tmp/kamal-cord", "log_lines" => 50 } }
 
     assert_equal expected_config, @config.to_h
   end
diff --git a/test/fixtures/deploy_with_two_roles_one_host.yml b/test/fixtures/deploy_with_two_roles_one_host.yml
new file mode 100644
index 00000000..cae05469
--- /dev/null
+++ b/test/fixtures/deploy_with_two_roles_one_host.yml
@@ -0,0 +1,15 @@
+service: app
+image: dhh/app
+servers:
+  workers:
+    hosts:
+      - 1.1.1.1
+  web:
+    hosts:
+      - 1.1.1.1
+env:
+  REDIS_URL: redis://x/y
+registry:
+  server: registry.digitalocean.com
+  username: user
+  password: pw
diff --git a/test/integration/broken_deploy_test.rb b/test/integration/broken_deploy_test.rb
new file mode 100644
index 00000000..a3f74d45
--- /dev/null
+++ b/test/integration/broken_deploy_test.rb
@@ -0,0 +1,34 @@
+require_relative "integration_test"
+
+class BrokenDeployTest < IntegrationTest
+  test "deploying a bad image" do
+    @app = "app_with_roles"
+
+    kamal :envify
+
+    first_version = latest_app_version
+
+    kamal :deploy
+
+    assert_app_is_up version: first_version
+    assert_container_running host: :vm3, name: "app-workers-#{first_version}"
+
+    second_version = break_app
+
+    output = kamal :deploy, raise_on_error: false, capture: true
+
+    assert_failed_deploy output
+    assert_app_is_up version: first_version
+    assert_container_running host: :vm3, name: "app-workers-#{first_version}"
+    assert_container_not_running host: :vm3, name: "app-workers-#{second_version}"
+  end
+
+  private
+    def assert_failed_deploy(output)
+      assert_match "Waiting for the first healthy web container before booting workers on vm3...", output
+      assert_match /First web container is unhealthy on vm[12], not booting other roles/, output
+      assert_match "First web container is unhealthy, not booting workers on vm3", output
+      assert_match "nginx: [emerg] unexpected end of file, expecting \";\" or \"}\" in /etc/nginx/conf.d/default.conf:2", output
+      assert_match 'ERROR {"Status":"unhealthy","FailingStreak":0,"Log":[]}', output
+    end
+end
diff --git a/test/integration/docker/deployer/app/config/deploy.yml b/test/integration/docker/deployer/app/config/deploy.yml
index 38113737..397a49ca 100644
--- a/test/integration/docker/deployer/app/config/deploy.yml
+++ b/test/integration/docker/deployer/app/config/deploy.yml
@@ -28,6 +28,7 @@ builder:
     COMMIT_SHA: <%= `git rev-parse HEAD` %>
 healthcheck:
   cmd: wget -qO- http://localhost > /dev/null || exit 1
+  max_attempts: 3
 traefik:
   args:
     accesslog: true
@@ -41,3 +42,4 @@ accessories:
     roles:
       - web
 stop_wait_time: 1
+readiness_delay: 0
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 004ffb25..2cf362c6 100644
--- a/test/integration/docker/deployer/app_with_roles/config/deploy.yml
+++ b/test/integration/docker/deployer/app_with_roles/config/deploy.yml
@@ -22,6 +22,7 @@ builder:
     COMMIT_SHA: <%= `git rev-parse HEAD` %>
 healthcheck:
   cmd: wget -qO- http://localhost > /dev/null || exit 1
+  max_attempts: 3
 traefik:
   args:
     accesslog: true
@@ -35,3 +36,4 @@ accessories:
     roles:
       - web
 stop_wait_time: 1
+readiness_delay: 0
diff --git a/test/integration/docker/deployer/break_app.sh b/test/integration/docker/deployer/break_app.sh
new file mode 100755
index 00000000..e8b19044
--- /dev/null
+++ b/test/integration/docker/deployer/break_app.sh
@@ -0,0 +1,3 @@
+#!/bin/bash
+
+cd $1 && echo "bad nginx config" > default.conf && git commit -am 'Broken'
diff --git a/test/integration/integration_test.rb b/test/integration/integration_test.rb
index bd62c474..f8f54d42 100644
--- a/test/integration/integration_test.rb
+++ b/test/integration/integration_test.rb
@@ -78,6 +78,11 @@ class IntegrationTest < ActiveSupport::TestCase
       latest_app_version
     end
 
+    def break_app
+      deployer_exec "./break_app.sh #{@app}", workdir: "/"
+      latest_app_version
+    end
+
     def latest_app_version
       deployer_exec("git rev-parse HEAD", capture: true)
     end
@@ -131,4 +136,16 @@ class IntegrationTest < ActiveSupport::TestCase
         puts "Tried to get the response code again and got #{app_response.code}"
       end
     end
+
+    def assert_container_running(host:, name:)
+      assert container_running?(host: host, name: name)
+    end
+
+    def assert_container_not_running(host:, name:)
+      assert_not container_running?(host: host, name: name)
+    end
+
+    def container_running?(host:, name:)
+      docker_compose("exec #{host} docker ps --filter=name=#{name} | tail -n+2", capture: true).tap { |x| p [ x, x.strip, x.strip.present? ] }.strip.present?
+    end
 end
diff --git a/test/integration/main_test.rb b/test/integration/main_test.rb
index a2dc8a0c..62857d4a 100644
--- a/test/integration/main_test.rb
+++ b/test/integration/main_test.rb
@@ -56,6 +56,12 @@ class MainTest < IntegrationTest
     assert_app_is_up version: version
     assert_hooks_ran "pre-connect", "pre-build", "pre-deploy", "post-deploy"
     assert_container_running host: :vm3, name: "app-workers-#{version}"
+
+    second_version = update_app_rev
+
+    kamal :redeploy
+    assert_app_is_up version: second_version
+    assert_container_running host: :vm3, name: "app-workers-#{second_version}"
   end
 
   test "config" do
@@ -73,7 +79,7 @@ class MainTest < IntegrationTest
     assert_equal({ user: "root", port: 22, keepalive: true, keepalive_interval: 30, log_level: :fatal }, config[:ssh_options])
     assert_equal({ "multiarch" => false, "args" => { "COMMIT_SHA" => version } }, config[:builder])
     assert_equal [ "--log-opt", "max-size=\"10m\"" ], config[:logging]
-    assert_equal({ "path" => "/up", "port" => 3000, "max_attempts" => 7, "exposed_port" => 3999, "cord"=>"/tmp/kamal-cord", "log_lines" => 50, "cmd"=>"wget -qO- http://localhost > /dev/null || exit 1" }, config[:healthcheck])
+    assert_equal({ "path" => "/up", "port" => 3000, "max_attempts" => 3, "cord"=>"/tmp/kamal-cord", "log_lines" => 50, "cmd"=>"wget -qO- http://localhost > /dev/null || exit 1" }, config[:healthcheck])
   end
 
   test "setup and remove" do
@@ -157,8 +163,4 @@ class MainTest < IntegrationTest
       assert vm1_image_ids.any?
       assert vm1_container_ids.any?
     end
-
-    def assert_container_running(host:, name:)
-      assert docker_compose("exec #{host} docker ps --filter=name=#{name} -q", capture: true).strip.present?
-    end
 end