diff --git a/core/src/main/java/org/elasticsearch/common/settings/AddFileKeyStoreCommand.java b/core/src/main/java/org/elasticsearch/common/settings/AddFileKeyStoreCommand.java
index 5ccac9a2ac3..a488d238859 100644
--- a/core/src/main/java/org/elasticsearch/common/settings/AddFileKeyStoreCommand.java
+++ b/core/src/main/java/org/elasticsearch/common/settings/AddFileKeyStoreCommand.java
@@ -61,11 +61,18 @@ class AddFileKeyStoreCommand extends EnvironmentAwareCommand {
     protected void execute(Terminal terminal, OptionSet options, Environment env) throws Exception {
         KeyStoreWrapper keystore = KeyStoreWrapper.load(env.configFile());
         if (keystore == null) {
-            throw new UserException(ExitCodes.DATA_ERROR, "Elasticsearch keystore not found. Use 'create' command to create one.");
+            if (options.has(forceOption) == false &&
+                terminal.promptYesNo("The elasticsearch keystore does not exist. Do you want to create it?", false) == false) {
+                terminal.println("Exiting without creating keystore.");
+                return;
+            }
+            keystore = KeyStoreWrapper.create(new char[0] /* always use empty passphrase for auto created keystore */);
+            keystore.save(env.configFile());
+            terminal.println("Created elasticsearch keystore in " + env.configFile());
+        } else {
+            keystore.decrypt(new char[0] /* TODO: prompt for password when they are supported */);
         }
 
-        keystore.decrypt(new char[0] /* TODO: prompt for password when they are supported */);
-
         List<String> argumentValues = arguments.values(options);
         if (argumentValues.size() == 0) {
             throw new UserException(ExitCodes.USAGE, "Missing setting name");
diff --git a/core/src/main/java/org/elasticsearch/common/settings/AddStringKeyStoreCommand.java b/core/src/main/java/org/elasticsearch/common/settings/AddStringKeyStoreCommand.java
index 599fac8c376..69a76f0f18f 100644
--- a/core/src/main/java/org/elasticsearch/common/settings/AddStringKeyStoreCommand.java
+++ b/core/src/main/java/org/elasticsearch/common/settings/AddStringKeyStoreCommand.java
@@ -58,11 +58,18 @@ class AddStringKeyStoreCommand extends EnvironmentAwareCommand {
     protected void execute(Terminal terminal, OptionSet options, Environment env) throws Exception {
         KeyStoreWrapper keystore = KeyStoreWrapper.load(env.configFile());
         if (keystore == null) {
-            throw new UserException(ExitCodes.DATA_ERROR, "Elasticsearch keystore not found. Use 'create' command to create one.");
+            if (options.has(forceOption) == false &&
+                terminal.promptYesNo("The elasticsearch keystore does not exist. Do you want to create it?", false) == false) {
+                terminal.println("Exiting without creating keystore.");
+                return;
+            }
+            keystore = KeyStoreWrapper.create(new char[0] /* always use empty passphrase for auto created keystore */);
+            keystore.save(env.configFile());
+            terminal.println("Created elasticsearch keystore in " + env.configFile());
+        } else {
+            keystore.decrypt(new char[0] /* TODO: prompt for password when they are supported */);
         }
 
-        keystore.decrypt(new char[0] /* TODO: prompt for password when they are supported */);
-
         String setting = arguments.value(options);
         if (setting == null) {
             throw new UserException(ExitCodes.USAGE, "The setting name can not be null");
diff --git a/core/src/test/java/org/elasticsearch/common/settings/AddFileKeyStoreCommandTests.java b/core/src/test/java/org/elasticsearch/common/settings/AddFileKeyStoreCommandTests.java
index 91f08e8c0a0..071d394eb1e 100644
--- a/core/src/test/java/org/elasticsearch/common/settings/AddFileKeyStoreCommandTests.java
+++ b/core/src/test/java/org/elasticsearch/common/settings/AddFileKeyStoreCommandTests.java
@@ -59,10 +59,24 @@ public class AddFileKeyStoreCommandTests extends KeyStoreCommandTestCase {
         keystore.save(env.configFile());
     }
 
-    public void testMissing() throws Exception {
-        UserException e = expectThrows(UserException.class, this::execute);
-        assertEquals(ExitCodes.DATA_ERROR, e.exitCode);
-        assertThat(e.getMessage(), containsString("keystore not found"));
+    public void testMissingPromptCreate() throws Exception {
+        Path file1 = createRandomFile();
+        terminal.addTextInput("y");
+        execute("foo", file1.toString());
+        assertSecureFile("foo", file1);
+    }
+
+    public void testMissingForceCreate() throws Exception {
+        Path file1 = createRandomFile();
+        terminal.addSecretInput("bar");
+        execute("-f", "foo", file1.toString());
+        assertSecureFile("foo", file1);
+    }
+
+    public void testMissingNoCreate() throws Exception {
+        terminal.addTextInput("n"); // explicit no
+        execute("foo");
+        assertNull(KeyStoreWrapper.load(env.configFile()));
     }
 
     public void testOverwritePromptDefault() throws Exception {
diff --git a/core/src/test/java/org/elasticsearch/common/settings/AddStringKeyStoreCommandTests.java b/core/src/test/java/org/elasticsearch/common/settings/AddStringKeyStoreCommandTests.java
index a83349d28fa..d0d8fdb500d 100644
--- a/core/src/test/java/org/elasticsearch/common/settings/AddStringKeyStoreCommandTests.java
+++ b/core/src/test/java/org/elasticsearch/common/settings/AddStringKeyStoreCommandTests.java
@@ -49,10 +49,23 @@ public class AddStringKeyStoreCommandTests extends KeyStoreCommandTestCase {
         };
     }
 
-    public void testMissing() throws Exception {
-        UserException e = expectThrows(UserException.class, this::execute);
-        assertEquals(ExitCodes.DATA_ERROR, e.exitCode);
-        assertThat(e.getMessage(), containsString("keystore not found"));
+    public void testMissingPromptCreate() throws Exception {
+        terminal.addTextInput("y");
+        terminal.addSecretInput("bar");
+        execute("foo");
+        assertSecureString("foo", "bar");
+    }
+
+    public void testMissingForceCreate() throws Exception {
+        terminal.addSecretInput("bar");
+        execute("-f", "foo");
+        assertSecureString("foo", "bar");
+    }
+
+    public void testMissingNoCreate() throws Exception {
+        terminal.addTextInput("n"); // explicit no
+        execute("foo");
+        assertNull(KeyStoreWrapper.load(env.configFile()));
     }
 
     public void testOverwritePromptDefault() throws Exception {