diff --git a/README.md b/README.md
index 941a8885..d574287f 100644
--- a/README.md
+++ b/README.md
@@ -646,18 +646,21 @@ That'll post a line like follows to a preconfigured chatbot in Basecamp:
 [My App] [dhh] Rolled back to version d264c4e92470ad1bd18590f04466787262f605de
 ```
 
-### Using custom healthcheck path or port
+### Custom healthcheck
 
-MRSK defaults to checking the health of your application again `/up` on port 3000. You can tailor both with the `healthcheck` setting:
+MRSK defaults to checking the health of your application again `/up` on port 3000 up to 7 times. You can tailor the behaviour with the `healthcheck` setting:
 
 ```yaml
 healthcheck:
   path: /healthz
   port: 4000
+  max_attempts: 7
 ```
 
 This will ensure your application is configured with a traefik label for the healthcheck against `/healthz` and that the pre-deploy healthcheck that MRSK performs is done against the same path on port 4000.
 
+The healthcheck also allows for an optional `max_attempts` setting, which will attempt the healthcheck up to the specified number of times before failing the deploy. This is useful for applications that take a while to start up. The default is 7.
+
 ## Commands
 
 ### Running commands on servers
diff --git a/lib/mrsk/cli/healthcheck.rb b/lib/mrsk/cli/healthcheck.rb
index 3fda7754..5e9f42dc 100644
--- a/lib/mrsk/cli/healthcheck.rb
+++ b/lib/mrsk/cli/healthcheck.rb
@@ -1,5 +1,4 @@
 class Mrsk::Cli::Healthcheck < Mrsk::Cli::Base
-  MAX_ATTEMPTS = 7
 
   class HealthcheckError < StandardError; end
 
@@ -13,6 +12,7 @@ class Mrsk::Cli::Healthcheck < Mrsk::Cli::Base
 
         target = "Health check against #{MRSK.config.healthcheck["path"]}"
         attempt = 1
+        max_attempts = MRSK.config.healthcheck["max_attempts"]
 
         begin
           status = capture_with_info(*MRSK.healthcheck.curl)
@@ -23,8 +23,8 @@ class Mrsk::Cli::Healthcheck < Mrsk::Cli::Base
             raise HealthcheckError, "#{target} failed with status #{status}"
           end
         rescue SSHKit::Command::Failed
-          if attempt <= MAX_ATTEMPTS
-            info "#{target} failed to respond, retrying in #{attempt}s..."
+          if attempt <= max_attempts
+            info "#{target} failed to respond, retrying in #{attempt}s (attempt #{attempt}/#{max_attempts})..."
             sleep attempt
             attempt += 1
 
diff --git a/lib/mrsk/configuration.rb b/lib/mrsk/configuration.rb
index c8ac5a03..a2c2ecf1 100644
--- a/lib/mrsk/configuration.rb
+++ b/lib/mrsk/configuration.rb
@@ -158,7 +158,7 @@ class Mrsk::Configuration
   end
 
   def healthcheck
-    { "path" => "/up", "port" => 3000 }.merge(raw_config.healthcheck || {})
+    { "path" => "/up", "port" => 3000, "max_attempts" => 7 }.merge(raw_config.healthcheck || {})
   end
 
   def readiness_delay
diff --git a/test/cli/healthcheck_test.rb b/test/cli/healthcheck_test.rb
index 7a9df6eb..a3441a7e 100644
--- a/test/cli/healthcheck_test.rb
+++ b/test/cli/healthcheck_test.rb
@@ -23,8 +23,8 @@ class CliHealthcheckTest < CliTestCase
       .returns("200")
 
     run_command("perform").tap do |output|
-      assert_match "Health check against /up failed to respond, retrying in 1s...", output
-      assert_match "Health check against /up failed to respond, retrying in 2s...", output
+      assert_match "Health check against /up failed to respond, retrying in 1s (attempt 1/7)...", output
+      assert_match "Health check against /up failed to respond, retrying in 2s (attempt 2/7)...", output
       assert_match "Health check against /up succeeded with 200 OK!", output
     end
   end
diff --git a/test/configuration_test.rb b/test/configuration_test.rb
index ec65686d..2697673b 100644
--- a/test/configuration_test.rb
+++ b/test/configuration_test.rb
@@ -249,6 +249,6 @@ class ConfigurationTest < ActiveSupport::TestCase
   end
 
   test "to_h" do
-    assert_equal({ :roles=>["web"], :hosts=>["1.1.1.1", "1.1.1.2"], :primary_host=>"1.1.1.1", :version=>"missing", :repository=>"dhh/app", :absolute_image=>"dhh/app:missing", :service_with_version=>"app-missing", :env_args=>["-e", "REDIS_URL=\"redis://x/y\""], :ssh_options=>{:user=>"root", :auth_methods=>["publickey"]}, :volume_args=>["--volume", "/local/path:/container/path"], :logging=>["--log-opt", "max-size=\"10m\""], :healthcheck=>{"path"=>"/up", "port"=>3000 }}, @config.to_h)
+    assert_equal({ :roles=>["web"], :hosts=>["1.1.1.1", "1.1.1.2"], :primary_host=>"1.1.1.1", :version=>"missing", :repository=>"dhh/app", :absolute_image=>"dhh/app:missing", :service_with_version=>"app-missing", :env_args=>["-e", "REDIS_URL=\"redis://x/y\""], :ssh_options=>{:user=>"root", :auth_methods=>["publickey"]}, :volume_args=>["--volume", "/local/path:/container/path"], :logging=>["--log-opt", "max-size=\"10m\""], :healthcheck=>{"path"=>"/up", "port"=>3000, "max_attempts" => 7 }}, @config.to_h)
   end
 end