diff --git a/lib/kubernetes-deploy/kubernetes_resource/custom_resource.rb b/lib/kubernetes-deploy/kubernetes_resource/custom_resource.rb
index db21e36a8..ca411297b 100644
--- a/lib/kubernetes-deploy/kubernetes_resource/custom_resource.rb
+++ b/lib/kubernetes-deploy/kubernetes_resource/custom_resource.rb
@@ -20,16 +20,21 @@ def timeout
     end
 
     def deploy_succeeded?
-      return false unless deploy_started?
-      unless @success_assumption_warning_shown
-        @logger.warn("Don't know how to monitor resources of type #{kind}. Assuming #{id} deployed successfully.")
-        @success_assumption_warning_shown = true
+      if monitor_rollout?
+        return false unless ready_status = @instance_data&.dig("status", "Conditions")&.find { |cond| cond["type"] == "Ready" }
+        ready_status["status"] == "True"
+      else
+        super
       end
-      true
     end
 
     def deploy_failed?
-      false
+      if monitor_rollout?
+        return false unless failed_status = @instance_data&.dig("status", "Conditions")&.find { |cond| cond["type"] == "Failed" }
+        failed_status["status"] == "True"
+      else
+        super
+      end
     end
 
     def id
@@ -45,5 +50,9 @@ def type
     def kind
       @definition["kind"]
     end
+
+    def monitor_rollout?
+      @crd.monitor_rollouts?
+    end
   end
 end
diff --git a/lib/kubernetes-deploy/kubernetes_resource/custom_resource_definition.rb b/lib/kubernetes-deploy/kubernetes_resource/custom_resource_definition.rb
index fff35a0b5..8c1ce2620 100644
--- a/lib/kubernetes-deploy/kubernetes_resource/custom_resource_definition.rb
+++ b/lib/kubernetes-deploy/kubernetes_resource/custom_resource_definition.rb
@@ -3,6 +3,7 @@ module KubernetesDeploy
   class CustomResourceDefinition < KubernetesResource
     TIMEOUT = 2.minutes
     CHILD_CR_TIMEOUT_ANNOTATION = "kubernetes-deploy.shopify.io/cr-timeout-override"
+    MONITOR_ROLLOUT_ANNOTATION = "kubernetes-deploy.shopify.io/monitor-rollout"
     GLOBAL = true
 
     def deploy_succeeded?
@@ -46,6 +47,10 @@ def timeout_for_children
       @definition.dig("metadata", "annotations", CHILD_CR_TIMEOUT_ANNOTATION)&.to_i
     end
 
+    def monitor_rollouts?
+      @definition.dig("metadata", "annotations", MONITOR_ROLLOUT_ANNOTATION) == "true"
+    end
+
     private
 
     def names_accepted_condition