diff --git a/actor/v7action/application.go b/actor/v7action/application.go
index f22bff8903f..2f8428d5921 100644
--- a/actor/v7action/application.go
+++ b/actor/v7action/application.go
@@ -311,6 +311,11 @@ func (actor Actor) PollStartForRolling(app resources.Application, deploymentGUID
 	for {
 		select {
 		case <-timeout:
+			warnings, err := actor.CancelDeployment(deploymentGUID)
+			allWarnings = append(allWarnings, warnings...)
+			if err != nil {
+				return allWarnings, err
+			}
 			return allWarnings, actionerror.StartupTimeoutError{Name: app.Name}
 		case <-timer.C():
 			if !isDeployed(deployment) {
diff --git a/actor/v7action/application_test.go b/actor/v7action/application_test.go
index 01bb6862d49..2b5748db286 100644
--- a/actor/v7action/application_test.go
+++ b/actor/v7action/application_test.go
@@ -1160,9 +1160,13 @@ var _ = Describe("Application Actions", func() {
 						ccv3.Warnings{"get-deployment-warning"},
 						nil,
 					)
+					fakeCloudControllerClient.CancelDeploymentReturns(
+						ccv3.Warnings{"cancel-deployment-warning"},
+						nil,
+					)
 				})
 
-				It("returns a timeout error and any warnings", func() {
+				It("returns a timeout error and any warnings and cancels the deployment", func() {
 					// initial tick
 					fakeClock.WaitForNWatchersAndIncrement(1*time.Millisecond, 2)
 
@@ -1171,12 +1175,43 @@ var _ = Describe("Application Actions", func() {
 					// timeout tick
 					fakeClock.Increment(1 * time.Millisecond)
 
+					Eventually(fakeCloudControllerClient.CancelDeploymentCallCount).Should(Equal(1))
+
 					// wait for func to finish
 					Eventually(done).Should(Receive(BeTrue()))
 
 					Expect(executeErr).To(MatchError(actionerror.StartupTimeoutError{}))
-					Expect(warnings).To(ConsistOf("get-deployment-warning"))
+					Expect(warnings).To(ConsistOf("get-deployment-warning", "cancel-deployment-warning"))
+				})
+
+				When("the cancel deployment fails", func() {
+					BeforeEach(func() {
+						fakeCloudControllerClient.CancelDeploymentReturns(
+							ccv3.Warnings{"cancel-deployment-warning"},
+							errors.New("cancel-deployment-error"),
+						)
+					})
+
+					It("returns a timeout error and any warnings and cancels the deployment", func() {
+						// initial tick
+						fakeClock.WaitForNWatchersAndIncrement(1*time.Millisecond, 2)
+
+						Eventually(fakeCloudControllerClient.GetDeploymentCallCount).Should(Equal(1))
+
+						// timeout tick
+						fakeClock.Increment(1 * time.Millisecond)
+
+						Eventually(fakeCloudControllerClient.CancelDeploymentCallCount).Should(Equal(1))
+
+						// wait for func to finish
+						Eventually(done).Should(Receive(BeTrue()))
+
+						Expect(executeErr).To(MatchError("cancel-deployment-error"))
+						Expect(warnings).To(ConsistOf("get-deployment-warning", "cancel-deployment-warning"))
+					})
+
 				})
+
 			})
 
 			When("the processes dont become healthy", func() {
diff --git a/integration/v7/push/rolling_push_test.go b/integration/v7/push/rolling_push_test.go
index d8bc9ec56ba..1b4739e507c 100644
--- a/integration/v7/push/rolling_push_test.go
+++ b/integration/v7/push/rolling_push_test.go
@@ -1,6 +1,8 @@
 package push
 
 import (
+	"fmt"
+
 	"code.cloudfoundry.org/cli/integration/helpers"
 	. "github.com/onsi/ginkgo"
 	. "github.com/onsi/gomega"
@@ -34,21 +36,21 @@ var _ = Describe("push with --strategy rolling", func() {
 					PushCommandName, appName, "--strategy", "rolling",
 				)
 
-				Eventually(session).Should(Say(`Pushing app %s to org %s / space %s as %s\.\.\.`, appName, organization, space, userName))
-				Eventually(session).Should(Say(`Packaging files to upload\.\.\.`))
-				Eventually(session).Should(Say(`Uploading files\.\.\.`))
-				Eventually(session).Should(Say(`100.00%`))
-				Eventually(session).Should(Say(`Waiting for API to complete processing files\.\.\.`))
-				Eventually(session).Should(Say(`Staging app and tracing logs\.\.\.`))
-				Eventually(session).Should(Say(`Starting deployment for app %s\.\.\.`, appName))
-				Eventually(session).Should(Say(`Waiting for app to deploy\.\.\.`))
-				Eventually(session).Should(Say(`name:\s+%s`, appName))
-				Eventually(session).Should(Say(`requested state:\s+started`))
-				Eventually(session).Should(Say(`routes:\s+%s.%s`, appName, helpers.DefaultSharedDomain()))
-				Eventually(session).Should(Say(`type:\s+web`))
-				Eventually(session).Should(Say(`start command:\s+%s`, helpers.StaticfileBuildpackStartCommand))
-				Eventually(session).Should(Say(`#0\s+running`))
 				Eventually(session).Should(Exit(0))
+				Expect(session).To(Say(`Pushing app %s to org %s / space %s as %s\.\.\.`, appName, organization, space, userName))
+				Expect(session).To(Say(`Packaging files to upload\.\.\.`))
+				Expect(session).To(Say(`Uploading files\.\.\.`))
+				Expect(session).To(Say(`100.00%`))
+				Expect(session).To(Say(`Waiting for API to complete processing files\.\.\.`))
+				Expect(session).To(Say(`Staging app and tracing logs\.\.\.`))
+				Expect(session).To(Say(`Starting deployment for app %s\.\.\.`, appName))
+				Expect(session).To(Say(`Waiting for app to deploy\.\.\.`))
+				Expect(session).To(Say(`name:\s+%s`, appName))
+				Expect(session).To(Say(`requested state:\s+started`))
+				Expect(session).To(Say(`routes:\s+%s.%s`, appName, helpers.DefaultSharedDomain()))
+				Expect(session).To(Say(`type:\s+web`))
+				Expect(session).To(Say(`start command:\s+%s`, helpers.StaticfileBuildpackStartCommand))
+				Expect(session).To(Say(`#0\s+running`))
 			})
 		})
 	})
@@ -100,19 +102,25 @@ var _ = Describe("push with --strategy rolling", func() {
 					WorkingDirectory: appDir,
 					EnvVars:          map[string]string{"CF_STARTUP_TIMEOUT": "0.1"},
 				}, PushCommandName, appName, "--strategy", "rolling")
-				Eventually(session).Should(Say(`Pushing app %s to org %s / space %s as %s\.\.\.`, appName, organization, space, userName))
-				Eventually(session).Should(Say(`Packaging files to upload\.\.\.`))
-				Eventually(session).Should(Say(`Uploading files\.\.\.`))
-				Eventually(session).Should(Say(`100.00%`))
-				Eventually(session).Should(Say(`Waiting for API to complete processing files\.\.\.`))
-				Eventually(session).Should(Say(`Staging app and tracing logs\.\.\.`))
-				Eventually(session).Should(Say(`Starting deployment for app %s\.\.\.`, appName))
-				Eventually(session).Should(Say(`Waiting for app to deploy\.\.\.`))
-				Eventually(session).Should(Say(`FAILED`))
-				Eventually(session.Err).Should(Say(`Start app timeout`))
-				Eventually(session.Err).Should(Say(`TIP: Application must be listening on the right port\. Instead of hard coding the port, use the \$PORT environment variable\.`))
-				Eventually(session.Err).Should(Say(`Use 'cf logs %s --recent' for more information`, appName))
 				Eventually(session).Should(Exit(1))
+				Expect(session).To(Say(`Pushing app %s to org %s / space %s as %s\.\.\.`, appName, organization, space, userName))
+				Expect(session).To(Say(`Packaging files to upload\.\.\.`))
+				Expect(session).To(Say(`Uploading files\.\.\.`))
+				Expect(session).To(Say(`100.00%`))
+				Expect(session).To(Say(`Waiting for API to complete processing files\.\.\.`))
+				Expect(session).To(Say(`Staging app and tracing logs\.\.\.`))
+				Expect(session).To(Say(`Starting deployment for app %s\.\.\.`, appName))
+				Expect(session).To(Say(`Waiting for app to deploy\.\.\.`))
+				Expect(session).To(Say(`FAILED`))
+				Expect(session.Err).To(Say(`Start app timeout`))
+				Expect(session.Err).To(Say(`TIP: Application must be listening on the right port\. Instead of hard coding the port, use the \$PORT environment variable\.`))
+				Expect(session.Err).To(Say(`Use 'cf logs %s --recent' for more information`, appName))
+				appGUID := helpers.AppGUID(appName)
+				Eventually(func() *Buffer {
+					session_deployment := helpers.CF("curl", fmt.Sprintf("/v3/deployments?app_guids=%s", appGUID))
+					Eventually(session_deployment).Should(Exit(0))
+					return session_deployment.Out
+				}).Should(Say(`"reason":\s*"CANCELED"`))
 			})
 		})
 	})