diff --git a/resource-managers/kubernetes/core/src/test/scala/org/apache/spark/deploy/rest/kubernetes/ResourceStagingServerSuite.scala b/resource-managers/kubernetes/core/src/test/scala/org/apache/spark/deploy/rest/kubernetes/ResourceStagingServerSuite.scala
index 0c0908da20d89..1bcd85a611e00 100644
--- a/resource-managers/kubernetes/core/src/test/scala/org/apache/spark/deploy/rest/kubernetes/ResourceStagingServerSuite.scala
+++ b/resource-managers/kubernetes/core/src/test/scala/org/apache/spark/deploy/rest/kubernetes/ResourceStagingServerSuite.scala
@@ -23,12 +23,14 @@ import com.fasterxml.jackson.databind.ObjectMapper
 import com.fasterxml.jackson.module.scala.DefaultScalaModule
 import com.google.common.io.ByteStreams
 import okhttp3.{RequestBody, ResponseBody}
+import org.eclipse.jetty.server.Server
 import org.scalatest.BeforeAndAfter
 import org.scalatest.mock.MockitoSugar.mock
 import retrofit2.Call
 
 import org.apache.spark.{SparkFunSuite, SSLOptions}
 import org.apache.spark.deploy.kubernetes.SSLUtils
+import org.apache.spark.internal.Logging
 import org.apache.spark.util.Utils
 
 /**
@@ -40,30 +42,37 @@ import org.apache.spark.util.Utils
  * we've configured the Jetty server correctly and that the endpoints reached over HTTP can
  * receive streamed uploads and can stream downloads.
  */
-class ResourceStagingServerSuite extends SparkFunSuite with BeforeAndAfter {
+class ResourceStagingServerSuite extends SparkFunSuite with BeforeAndAfter with Logging {
+
+  private val MAX_SERVER_START_ATTEMPTS = 5
   private var serviceImpl: ResourceStagingService = _
   private var stagedResourcesCleaner: StagedResourcesCleaner = _
-  private var server: ResourceStagingServer = _
+  private var server: Option[ResourceStagingServer] = None
   private val OBJECT_MAPPER = new ObjectMapper().registerModule(new DefaultScalaModule)
 
-  private val serverPort = new ServerSocket(0).getLocalPort
-
   private val sslOptionsProvider = new SettableReferenceSslOptionsProvider()
 
   before {
     stagedResourcesCleaner = mock[StagedResourcesCleaner]
     serviceImpl = new ResourceStagingServiceImpl(
       new StagedResourcesStoreImpl(Utils.createTempDir()), stagedResourcesCleaner)
-    server = new ResourceStagingServer(serverPort, serviceImpl, sslOptionsProvider)
   }
 
   after {
-    server.stop()
+    server.foreach { s =>
+      try {
+        s.stop()
+      } catch {
+        case e: Throwable =>
+          log.warn("Failed to stop the resource staging server.", e)
+      }
+    }
+    server = None
   }
 
   test("Accept file and jar uploads and downloads") {
-    server.start()
-    runUploadAndDownload(SSLOptions())
+    val serverPort = startServer()
+    runUploadAndDownload(SSLOptions(), serverPort)
   }
 
   test("Enable SSL on the server") {
@@ -80,11 +89,11 @@ class ResourceStagingServerSuite extends SparkFunSuite with BeforeAndAfter {
       trustStore = Some(keyStoreAndTrustStore.trustStore),
       trustStorePassword = Some("trustStore"))
     sslOptionsProvider.setOptions(sslOptions)
-    server.start()
-    runUploadAndDownload(sslOptions)
+    val serverPort = startServer()
+    runUploadAndDownload(sslOptions, serverPort)
   }
 
-  private def runUploadAndDownload(sslOptions: SSLOptions): Unit = {
+  private def runUploadAndDownload(sslOptions: SSLOptions, serverPort: Int): Unit = {
     val scheme = if (sslOptions.enabled) "https" else "http"
     val retrofitService = RetrofitClientFactoryImpl.createRetrofitClient(
       s"$scheme://127.0.0.1:$serverPort/",
@@ -125,6 +134,44 @@ class ResourceStagingServerSuite extends SparkFunSuite with BeforeAndAfter {
     val downloadedBytes = ByteStreams.toByteArray(responseBody.byteStream())
     assert(downloadedBytes.toSeq === bytes)
   }
+
+  private def startServer(): Int = {
+    var currentAttempt = 0
+    var successfulStart = false
+    var latestServerPort = new ServerSocket(0).getLocalPort
+    while (currentAttempt < MAX_SERVER_START_ATTEMPTS && !successfulStart) {
+      val newServer = new ResourceStagingServer(latestServerPort, serviceImpl, sslOptionsProvider)
+      try {
+        newServer.start()
+        successfulStart = true
+        server = Some(newServer)
+      } catch {
+        case e: Throwable =>
+          try {
+            newServer.stop()
+          } catch {
+            case e1: Throwable =>
+              log.warn("Failed to stop a resource staging server that failed to start.", e1)
+          }
+
+          if (Utils.isBindCollision(e)) {
+            currentAttempt += 1
+            latestServerPort = latestServerPort + 1
+            if (currentAttempt == MAX_SERVER_START_ATTEMPTS) {
+              throw new RuntimeException(s"Failed to bind to a random port" +
+                s" $MAX_SERVER_START_ATTEMPTS times. Last attempted port: $latestServerPort", e)
+            } else {
+              logWarning(s"Attempt $currentAttempt/$MAX_SERVER_START_ATTEMPTS failed to start" +
+                s" server on port $latestServerPort.", e)
+            }
+          } else {
+            throw e
+          }
+      }
+    }
+    logInfo(s"Started resource staging server on port $latestServerPort.")
+    latestServerPort
+  }
 }
 
 private class SettableReferenceSslOptionsProvider extends ResourceStagingServerSslOptionsProvider {