diff --git a/lib/kubernetes-deploy/kubernetes_resource/deployment.rb b/lib/kubernetes-deploy/kubernetes_resource/deployment.rb
index 31d42d97f..fcdf34774 100644
--- a/lib/kubernetes-deploy/kubernetes_resource/deployment.rb
+++ b/lib/kubernetes-deploy/kubernetes_resource/deployment.rb
@@ -96,6 +96,16 @@ def validate_definition(_)
 
     private
 
+    def current_generation
+      return -2 unless exists? # different default than observed
+      @instance_data.dig('metadata', 'generation')
+    end
+
+    def observed_generation
+      return -1 unless exists? # different default than current
+      @instance_data.dig('status', 'observedGeneration')
+    end
+
     def desired_replicas
       return -1 unless exists?
       @instance_data["spec"]["replicas"].to_i
@@ -133,12 +143,13 @@ def deploy_failing_to_progress?
         # Deployments were being updated prematurely with incorrect progress information
         # https://github.com/kubernetes/kubernetes/issues/49637
         return false unless Time.now.utc - @deploy_started_at >= progress_deadline.to_i
-      else
-        return false unless deploy_started?
       end
 
-      progress_condition["status"] == 'False' &&
-      Time.parse(progress_condition["lastUpdateTime"]).to_i >= (@deploy_started_at - 5.seconds).to_i
+      # This assumes that when the controller bumps the observed generation, it also updates/clears all the status
+      # conditions. Specifically, it assumes the progress condition is immediately set to True if a rollout is starting.
+      deploy_started? &&
+      current_generation == observed_generation &&
+      progress_condition["status"] == 'False'
     end
 
     def find_latest_rs(mediator)
diff --git a/test/fixtures/for_unit_tests/deployment_test.yml b/test/fixtures/for_unit_tests/deployment_test.yml
index 05eec0dc6..115202557 100644
--- a/test/fixtures/for_unit_tests/deployment_test.yml
+++ b/test/fixtures/for_unit_tests/deployment_test.yml
@@ -4,6 +4,7 @@ kind: Deployment
 metadata:
   name: web
   uid: foobar
+  generation: 2
   annotations:
     "deployment.kubernetes.io/revision": "1"
   labels:
diff --git a/test/unit/kubernetes-deploy/kubernetes_resource/deployment_test.rb b/test/unit/kubernetes-deploy/kubernetes_resource/deployment_test.rb
index a9bc306b4..3b9eb34ea 100644
--- a/test/unit/kubernetes-deploy/kubernetes_resource/deployment_test.rb
+++ b/test/unit/kubernetes-deploy/kubernetes_resource/deployment_test.rb
@@ -267,33 +267,36 @@ def test_deploy_timed_out_based_on_progress_deadline
     Timecop.freeze do
       deployment_status = {
         "replicas" => 3,
+        "observedGeneration" => 2,
         "conditions" => [{
           "type" => "Progressing",
           "status" => 'False',
           "lastUpdateTime" => Time.now.utc - 10.seconds,
-          "reason" => "Failed to progress"
+          "reason" => "ProgressDeadlineExceeded"
         }]
       }
       deploy = build_synced_deployment(
         template: build_deployment_template(status: deployment_status),
         replica_sets: [build_rs_template(status: { "replica" => 1 })]
       )
-      deploy.deploy_started_at = Time.now.utc - 3.minutes
+      refute deploy.deploy_timed_out?, "Deploy not started shouldn't have timed out"
 
+      deploy.deploy_started_at = Time.now.utc - 3.minutes
       assert deploy.deploy_timed_out?
-      assert_equal "Timeout reason: Failed to progress\nLatest ReplicaSet: web-1", deploy.timeout_message.strip
+      assert_equal "Timeout reason: ProgressDeadlineExceeded\nLatest ReplicaSet: web-1", deploy.timeout_message.strip
     end
   end
 
-  def test_deploy_timed_out_based_on_progress_deadline_ignores_conditions_older_than_the_deploy
+  def test_deploy_timed_out_based_on_progress_deadline_ignores_statuses_for_older_generations
     Timecop.freeze do
       deployment_status = {
         "replicas" => 3,
+        "observedGeneration" => 1, # current generation is 2
         "conditions" => [{
           "type" => "Progressing",
           "status" => 'False',
           "lastUpdateTime" => Time.now.utc - 10.seconds,
-          "reason" => "Failed to progress"
+          "reason" => "ProgressDeadlineExceeded"
         }]
       }
       deploy = build_synced_deployment(
@@ -301,14 +304,8 @@ def test_deploy_timed_out_based_on_progress_deadline_ignores_conditions_older_th
         replica_sets: [build_rs_template(status: { "replica" => 1 })]
       )
 
-      deploy.deploy_started_at = nil # not started yet
+      deploy.deploy_started_at = Time.now.utc - 20.seconds
       refute deploy.deploy_timed_out?
-
-      deploy.deploy_started_at = Time.now.utc - 4.seconds # 10s ago is before deploy started
-      refute deploy.deploy_timed_out?
-
-      deploy.deploy_started_at = Time.now.utc - 5.seconds # 10s ago is "equal" to deploy time (fudge for clock skew)
-      assert deploy.deploy_timed_out?
     end
   end