diff --git a/concourse-automation/src/main/java/com/cinchapi/concourse/automation/server/ManagedConcourseServer.java b/concourse-automation/src/main/java/com/cinchapi/concourse/automation/server/ManagedConcourseServer.java
index b0a52092f..9e652db31 100644
--- a/concourse-automation/src/main/java/com/cinchapi/concourse/automation/server/ManagedConcourseServer.java
+++ b/concourse-automation/src/main/java/com/cinchapi/concourse/automation/server/ManagedConcourseServer.java
@@ -690,22 +690,53 @@ public boolean hasWritesToTransport(String environment) {
     /**
      * Install the plugin(s) contained in the {@code bundle} on this
      * {@link ManagedConcourseServer}.
-     * 
+     *
      * @param bundle the path to the plugin bundle
      * @return {@code true} if the plugin(s) from the bundle is/are installed
      */
     public boolean installPlugin(Path bundle) {
         log.info("Attempting to install plugins from {}", bundle);
-        List<String> out = executeCli("plugin", "install", bundle.toString(),
-                "--username admin", "--password admin");
-        for (String line : out) {
-            if(line.contains("Successfully installed")) {
-                return true;
+        int maxAttempts = 10;
+        long waitMs = 500;
+        List<String> out = null;
+
+        for (int attempt = 1; attempt <= maxAttempts; attempt++) {
+            out = executeCli("plugin", "install", bundle.toString(),
+                    "--username admin", "--password admin");
+
+            boolean managementServerNotReady = false;
+            for (String line : out) {
+                if(line.contains("Successfully installed")) {
+                    return true;
+                }
+                if(line.contains(
+                        "Could not connect to the management server")) {
+                    managementServerNotReady = true;
+                }
+            }
+
+            if(managementServerNotReady && attempt < maxAttempts) {
+                log.debug(
+                        "Management server not ready, waiting {}ms before retry (attempt {}/{})",
+                        waitMs, attempt, maxAttempts);
+                try {
+                    Thread.sleep(waitMs);
+                    waitMs = Math.min(waitMs * 2, 5000); // exponential backoff,
+                                                         // max 5 seconds
+                }
+                catch (InterruptedException e) {
+                    Thread.currentThread().interrupt();
+                    break;
+                }
+                continue;
             }
+
+            // Not a management server issue, break and throw
+            break;
         }
+
         throw new RuntimeException(AnyStrings
                 .format("Unable to install plugin '{}': {}", bundle, out));
-
     }
 
     /**