diff --git a/core/src/main/java/org/elasticsearch/bootstrap/BootstrapCLIParser.java b/core/src/main/java/org/elasticsearch/bootstrap/BootstrapCLIParser.java
index 9ce2dba02b0..03ec082a285 100644
--- a/core/src/main/java/org/elasticsearch/bootstrap/BootstrapCLIParser.java
+++ b/core/src/main/java/org/elasticsearch/bootstrap/BootstrapCLIParser.java
@@ -128,7 +128,13 @@ final class BootstrapCLIParser extends CliTool {
             while (iterator.hasNext()) {
                 String arg = iterator.next();
                 if (!arg.startsWith("--")) {
-                    throw new IllegalArgumentException("Parameter [" + arg + "]does not start with --");
+                    if (arg.startsWith("-D") || arg.startsWith("-d") || arg.startsWith("-p")) {
+                        throw new IllegalArgumentException(
+                                "Parameter [" + arg + "] starting with \"-D\", \"-d\" or \"-p\" must be before any parameters starting with --"
+                        );
+                    } else {
+                        throw new IllegalArgumentException("Parameter [" + arg + "]does not start with --");
+                    }
                 }
                 // if there is no = sign, we have to get the next argu
                 arg = arg.replace("--", "");
diff --git a/core/src/test/java/org/elasticsearch/bootstrap/BootstrapCliParserTests.java b/core/src/test/java/org/elasticsearch/bootstrap/BootstrapCliParserTests.java
index da30874f584..a45c7221d04 100644
--- a/core/src/test/java/org/elasticsearch/bootstrap/BootstrapCliParserTests.java
+++ b/core/src/test/java/org/elasticsearch/bootstrap/BootstrapCliParserTests.java
@@ -220,6 +220,16 @@ public class BootstrapCliParserTests extends CliToolTestCase {
 
     }
 
+    public void testThatHelpfulErrorMessageIsGivenWhenParametersAreOutOfOrder() throws Exception {
+        BootstrapCLIParser parser = new BootstrapCLIParser(terminal);
+        try {
+            parser.parse("start", new String[]{"--foo=bar", "-Dbaz=qux"});
+            fail("expected IllegalArgumentException for out-of-order parameters");
+        } catch (IllegalArgumentException e) {
+            assertThat(e.getMessage(), containsString("must appear before any parameters starting with --"));
+        }
+    }
+
     private void registerProperties(String ... systemProperties) {
         propertiesToClear.addAll(Arrays.asList(systemProperties));
     }