diff --git a/core/src/main/scala/org/apache/spark/SparkConf.scala b/core/src/main/scala/org/apache/spark/SparkConf.scala
index c14764f773982..728c38f1a86b3 100644
--- a/core/src/main/scala/org/apache/spark/SparkConf.scala
+++ b/core/src/main/scala/org/apache/spark/SparkConf.scala
@@ -372,5 +372,5 @@ private[spark] object SparkConf {
   /**
    * Return whether the given config is a Spark port config.
    */
-  def isSparkPortConf(name: String): Boolean = name.startsWith("spark.") && name.endsWith(".port")
+  def isSparkPortConf(name: String): Boolean = name.startsWith("spark.") && name.contains(".port")
 }
diff --git a/core/src/main/scala/org/apache/spark/SparkContext.scala b/core/src/main/scala/org/apache/spark/SparkContext.scala
index 57bc3d4e4ae36..1b6411928db64 100644
--- a/core/src/main/scala/org/apache/spark/SparkContext.scala
+++ b/core/src/main/scala/org/apache/spark/SparkContext.scala
@@ -176,6 +176,10 @@ class SparkContext(config: SparkConf) extends Logging with ExecutorAllocationCli
   logInfo(s"Running Spark version $SPARK_VERSION")
   
   private[spark] val conf = config.clone()
+  val portRetriesConf = conf.getOption("spark.port.maxRetries")
+  if (portRetriesConf.isDefined) {
+    System.setProperty("spark.port.maxRetries", portRetriesConf.get)
+  }
   conf.validateSettings()
 
   /**
diff --git a/core/src/main/scala/org/apache/spark/util/Utils.scala b/core/src/main/scala/org/apache/spark/util/Utils.scala
index 0d771baaa6abc..f323870463b1c 100644
--- a/core/src/main/scala/org/apache/spark/util/Utils.scala
+++ b/core/src/main/scala/org/apache/spark/util/Utils.scala
@@ -1691,15 +1691,12 @@ private[spark] object Utils extends Logging {
   /**
    * Default maximum number of retries when binding to a port before giving up.
    */
-  val portMaxRetries: Int = {
+  lazy val portMaxRetries: Int = {
     if (sys.props.contains("spark.testing")) {
       // Set a higher number of retries for tests...
       sys.props.get("spark.port.maxRetries").map(_.toInt).getOrElse(100)
     } else {
-      Option(SparkEnv.get)
-        .flatMap(_.conf.getOption("spark.port.maxRetries"))
-        .map(_.toInt)
-        .getOrElse(16)
+      sys.props.get("spark.port.maxRetries").map(_.toInt).getOrElse(16)
     }
   }
 
@@ -1719,6 +1716,7 @@ private[spark] object Utils extends Logging {
       serviceName: String = "",
       maxRetries: Int = portMaxRetries): (T, Int) = {
     val serviceString = if (serviceName.isEmpty) "" else s" '$serviceName'"
+    logInfo(s"Starting service$serviceString on port $port with maximum $maxRetries retries. ")
     for (offset <- 0 to maxRetries) {
       // Do not increment port if startPort is 0, which is treated as a special port
       val tryPort = if (startPort == 0) {
diff --git a/yarn/src/main/scala/org/apache/spark/deploy/yarn/ExecutorRunnableUtil.scala b/yarn/src/main/scala/org/apache/spark/deploy/yarn/ExecutorRunnableUtil.scala
index 22d73ecf6d010..205c1e538fe83 100644
--- a/yarn/src/main/scala/org/apache/spark/deploy/yarn/ExecutorRunnableUtil.scala
+++ b/yarn/src/main/scala/org/apache/spark/deploy/yarn/ExecutorRunnableUtil.scala
@@ -76,7 +76,9 @@ trait ExecutorRunnableUtil extends Logging {
     // uses Akka to connect to the scheduler, the akka settings are needed as well as the
     // authentication settings.
     sparkConf.getAll.
-      filter { case (k, v) => k.startsWith("spark.auth") || k.startsWith("spark.akka") }.
+      filter { case (k, v) =>
+      k.startsWith("spark.auth") || k.startsWith("spark.akka") || k.equals("spark.port.maxRetries")
+      }.
       foreach { case (k, v) => javaOpts += YarnSparkHadoopUtil.escapeForShell(s"-D$k=$v") }
 
     sparkConf.getAkkaConf.