diff --git a/jobsupervisor/monit_job_supervisor_test.go b/jobsupervisor/monit_job_supervisor_test.go
index 063bb8173..140cdb570 100644
--- a/jobsupervisor/monit_job_supervisor_test.go
+++ b/jobsupervisor/monit_job_supervisor_test.go
@@ -353,7 +353,7 @@ var _ = Describe("monitJobSupervisor", func() {
 
 				failureMessage := "Timed out waiting for services 'foo' to no longer be pending after 5 minutes"
 
-				advanceTime(timeService, 10*time.Minute, 2)
+				timeService.WaitForNWatchersAndIncrement(10*time.Minute, 2)
 				Eventually(timeService.WatcherCount).Should(Equal(0))
 				Eventually(errchan).Should(Receive(Equal(errors.New(failureMessage))))
 				Expect(len(runner.RunCommands)).To(Equal(0)) // never called 'monit stop'
@@ -371,18 +371,16 @@ var _ = Describe("monitJobSupervisor", func() {
 					errchan <- monit.StopAndWait()
 				}()
 
-				Eventually(timeService.WatcherCount).Should(Equal(2)) // we hit the pending sleep
+				Eventually(timeService.WatcherCount).Should(Equal(2)) // wait for pending sleep
 
 				client.StatusStatus = fakemonit.FakeMonitStatus{
 					Services: []boshmonit.Service{
 						{Monitored: true, Name: "foo", Status: "unknown", Pending: false},
 					},
 				}
-				timeService.Increment(3 * time.Minute)
-
-				Eventually(timeService.WatcherCount).Should(Equal(2)) // we hit the stop sleep
 
 				timeService.Increment(3 * time.Minute)
+				timeService.WaitForNWatchersAndIncrement(3*time.Minute, 2) // wait for stop sleep, then advance
 
 				Eventually(errchan).Should(Receive(Equal(errors.New("Timed out waiting for services 'foo' to stop after 5 minutes"))))
 			})
@@ -555,7 +553,7 @@ var _ = Describe("monitJobSupervisor", func() {
 
 				failureMessage := "Timed out waiting for services 'unmonitored-start-pending, initializing, running, running-stop-pending, unmonitored-stop-pending, failing' to stop after 5 minutes"
 
-				advanceTime(timeService, 5*time.Minute, 2)
+				timeService.WaitForNWatchersAndIncrement(5*time.Minute, 2)
 				Eventually(timeService.WatcherCount).Should(Equal(0))
 				Eventually(errchan).Should(Receive(Equal(errors.New(failureMessage))))
 				Expect(statusRequests).To(Equal(3))
@@ -894,8 +892,3 @@ var _ = Describe("monitJobSupervisor", func() {
 		})
 	})
 })
-
-func advanceTime(timeService *fakeclock.FakeClock, duration time.Duration, watcherCount int) {
-	Eventually(timeService.WatcherCount).Should(Equal(watcherCount))
-	timeService.Increment(duration)
-}
diff --git a/jobsupervisor/windows_job_supervisor_test.go b/jobsupervisor/windows_job_supervisor_test.go
index 16cd3dede..00d2e09c9 100755
--- a/jobsupervisor/windows_job_supervisor_test.go
+++ b/jobsupervisor/windows_job_supervisor_test.go
@@ -64,8 +64,7 @@ var (
 )
 
 var _ = AfterSuite(func() {
-	err := os.RemoveAll(TempDir)
-	Expect(err).NotTo(HaveOccurred())
+	Eventually(func() error { return os.RemoveAll(TempDir) }, 2*time.Minute, time.Second).Should(Succeed())
 	gexec.CleanupBuildArtifacts()
 
 	match := func(s string) bool {
@@ -486,8 +485,11 @@ var _ = Describe("WindowsJobSupervisor", func() {
 		AfterEach(func() {
 			Expect(jobSupervisor.Stop()).To(Succeed())
 			Expect(jobSupervisor.RemoveAllJobs()).To(Succeed())
-			Eventually(func() error { return fs.RemoveAll(jobDir) }, 60*time.Second).Should(Succeed())
-			Expect(fs.RemoveAll(logDir)).To(Succeed())
+			// Windows releases file handles on the service wrapper exe and log
+			// files asynchronously after the SCM reports services as deleted.
+			// Use a long timeout with a slow poll to avoid spinning on busy CI.
+			Eventually(func() error { return fs.RemoveAll(jobDir) }, 2*time.Minute, time.Second).Should(Succeed())
+			Eventually(func() error { return fs.RemoveAll(logDir) }, 2*time.Minute, time.Second).Should(Succeed())
 		})
 
 		Describe("AddJob", func() {