diff --git a/Gemfile.lock b/Gemfile.lock
index d22fc04c..17b41693 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -1,7 +1,7 @@
 PATH
   remote: .
   specs:
-    mrsk (0.7.2)
+    mrsk (0.8.0)
       activesupport (>= 7.0)
       dotenv (~> 2.8)
       sshkit (~> 1.21)
diff --git a/lib/mrsk/cli/build.rb b/lib/mrsk/cli/build.rb
index 5e493a56..3e8912d7 100644
--- a/lib/mrsk/cli/build.rb
+++ b/lib/mrsk/cli/build.rb
@@ -30,6 +30,7 @@ class Mrsk::Cli::Build < Mrsk::Cli::Base
   def pull
     on(MRSK.hosts) do
       execute *MRSK.auditor.record("Pulled image with version #{MRSK.version}"), verbosity: :debug
+      execute *MRSK.builder.clean, raise_on_non_zero_exit: false
       execute *MRSK.builder.pull
     end
   end
diff --git a/lib/mrsk/cli/healthcheck.rb b/lib/mrsk/cli/healthcheck.rb
index a9fcf803..ffb0805d 100644
--- a/lib/mrsk/cli/healthcheck.rb
+++ b/lib/mrsk/cli/healthcheck.rb
@@ -1,4 +1,6 @@
 class Mrsk::Cli::Healthcheck < Mrsk::Cli::Base
+  MAX_ATTEMPTS = 5
+
   default_command :perform
 
   desc "perform", "Health check current app version"
@@ -8,18 +10,31 @@ class Mrsk::Cli::Healthcheck < Mrsk::Cli::Base
         execute *MRSK.healthcheck.run
 
         target = "Health check against #{MRSK.config.healthcheck["path"]}"
+        attempt = 1
 
-        if capture_with_info(*MRSK.healthcheck.curl) == "200"
-          info "#{target} succeeded with 200 OK!"
-        else
-          # Catches 1xx, 2xx, 3xx
-          raise SSHKit::Command::Failed, "#{target} failed to return 200 OK!"
+        begin
+          status = capture_with_info(*MRSK.healthcheck.curl)
+
+          if status == "200"
+            info "#{target} succeeded with 200 OK!"
+          else
+            raise "#{target} failed with status #{status}"
+          end
+        rescue SSHKit::Command::Failed
+          if attempt <= MAX_ATTEMPTS
+            info "#{target} failed to respond, retrying in #{attempt}s..."
+            sleep attempt
+            attempt += 1
+
+            retry
+          else
+            raise
+          end
         end
       rescue SSHKit::Command::Failed => e
         error capture_with_info(*MRSK.healthcheck.logs)
 
         if e.message =~ /curl/
-          # Catches 4xx, 5xx
           raise SSHKit::Command::Failed, "#{target} failed to return 200 OK!"
         else
           raise
diff --git a/lib/mrsk/commands/builder.rb b/lib/mrsk/commands/builder.rb
index 70957afe..85dbce0a 100644
--- a/lib/mrsk/commands/builder.rb
+++ b/lib/mrsk/commands/builder.rb
@@ -1,5 +1,5 @@
 class Mrsk::Commands::Builder < Mrsk::Commands::Base
-  delegate :create, :remove, :push, :pull, :info, to: :target
+  delegate :create, :remove, :push, :clean, :pull, :info, to: :target
 
   def name
     target.class.to_s.remove("Mrsk::Commands::Builder::").underscore
diff --git a/lib/mrsk/commands/builder/base.rb b/lib/mrsk/commands/builder/base.rb
index 4f2a8dbe..d282fd01 100644
--- a/lib/mrsk/commands/builder/base.rb
+++ b/lib/mrsk/commands/builder/base.rb
@@ -1,6 +1,10 @@
 class Mrsk::Commands::Builder::Base < Mrsk::Commands::Base
   delegate :argumentize, to: Mrsk::Utils
 
+  def clean
+    docker :image, :rm, "--force", config.absolute_image
+  end
+
   def pull
     docker :pull, config.absolute_image
   end
diff --git a/lib/mrsk/commands/healthcheck.rb b/lib/mrsk/commands/healthcheck.rb
index feb35543..47626156 100644
--- a/lib/mrsk/commands/healthcheck.rb
+++ b/lib/mrsk/commands/healthcheck.rb
@@ -16,11 +16,11 @@ class Mrsk::Commands::Healthcheck < Mrsk::Commands::Base
   end
 
   def curl
-    [ :curl, "--silent", "--output", "/dev/null", "--write-out", "'%{http_code}'", "--retry-max-time", 10, "--retry", 5, health_url ]
+    [ :curl, "--silent", "--output", "/dev/null", "--write-out", "'%{http_code}'", "--max-time", "2", health_url ]
   end
 
   def logs
-    pipe container_id, xargs(docker(:logs, "2>&1"))
+    pipe container_id, xargs(docker(:logs, "--tail", 50, "2>&1"))
   end
 
   def stop
diff --git a/lib/mrsk/version.rb b/lib/mrsk/version.rb
index ecdce2cb..11d95f38 100644
--- a/lib/mrsk/version.rb
+++ b/lib/mrsk/version.rb
@@ -1,3 +1,3 @@
 module Mrsk
-  VERSION = "0.7.2"
+  VERSION = "0.8.0"
 end
diff --git a/test/cli/build_test.rb b/test/cli/build_test.rb
new file mode 100644
index 00000000..3d5f4431
--- /dev/null
+++ b/test/cli/build_test.rb
@@ -0,0 +1,15 @@
+require_relative "cli_test_case"
+
+class CliBuildTest < CliTestCase
+  test "pull" do
+    run_command("pull").tap do |output|
+      assert_match /docker image rm --force dhh\/app:999/, output
+      assert_match /docker pull dhh\/app:999/, output
+    end
+  end
+
+  private
+    def run_command(*command)
+      stdouted { Mrsk::Cli::Build.start([*command, "-c", "test/fixtures/deploy_with_accessories.yml"]) }
+    end
+end
diff --git a/test/commands/healthcheck_test.rb b/test/commands/healthcheck_test.rb
index c7438126..54580e61 100644
--- a/test/commands/healthcheck_test.rb
+++ b/test/commands/healthcheck_test.rb
@@ -24,7 +24,7 @@ class CommandsHealthcheckTest < ActiveSupport::TestCase
 
   test "curl" do
     assert_equal \
-      "curl --silent --output /dev/null --write-out '%{http_code}' --retry-max-time 10 --retry 5 http://localhost:3999/up",
+      "curl --silent --output /dev/null --write-out '%{http_code}' --max-time 2 http://localhost:3999/up",
       new_command.curl.join(" ")
   end
 
@@ -32,7 +32,7 @@ class CommandsHealthcheckTest < ActiveSupport::TestCase
     @config[:healthcheck] = { "path" => "/healthz" }
 
     assert_equal \
-      "curl --silent --output /dev/null --write-out '%{http_code}' --retry-max-time 10 --retry 5 http://localhost:3999/healthz",
+      "curl --silent --output /dev/null --write-out '%{http_code}' --max-time 2 http://localhost:3999/healthz",
       new_command.curl.join(" ")
   end