Usability improvement for the password bootstrap tool (reserved users) (elastic/x-pack-elasticsearch#2444)

Generate or prompt for passwords of the reserved users, validating strength
and typos, then issue change requests, keeping elastic user change request last.

Closes: elastic/x-pack-elasticsearch#2424

Original commit: elastic/x-pack-elasticsearch@1f827d393c

plugin/src/main/java/org/elasticsearch/xpack/security/authc/esnative/tool/CommandLineHttpClient.java

@@ -6,7 +6,8 @@
 package org.elasticsearch.xpack.security.authc.esnative.tool;
 
 import org.bouncycastle.util.io.Streams;
-import org.elasticsearch.common.Nullable;
+import org.elasticsearch.common.CheckedConsumer;
+import org.elasticsearch.common.CheckedSupplier;
 import org.elasticsearch.common.Strings;
 import org.elasticsearch.common.SuppressForbidden;
 import org.elasticsearch.common.lease.Releasables;
@@ -14,10 +15,8 @@ import org.elasticsearch.common.network.InetAddresses;
 import org.elasticsearch.common.network.NetworkService;
 import org.elasticsearch.common.settings.SecureString;
 import org.elasticsearch.common.settings.Settings;
-import org.elasticsearch.common.transport.PortsRange;
 import org.elasticsearch.common.xcontent.XContentType;
 import org.elasticsearch.env.Environment;
-import org.elasticsearch.http.HttpTransportSettings;
 import org.elasticsearch.xpack.XPackSettings;
 import org.elasticsearch.xpack.common.socket.SocketAccess;
 import org.elasticsearch.xpack.security.authc.support.UsernamePasswordToken;
@@ -30,7 +29,6 @@ import java.io.OutputStream;
 import java.io.UncheckedIOException;
 import java.net.HttpURLConnection;
 import java.net.InetAddress;
-import java.net.URI;
 import java.net.URL;
 import java.nio.charset.StandardCharsets;
 import java.security.AccessController;
@@ -57,16 +55,30 @@ public class CommandLineHttpClient {
         this.env = env;
     }
 
-    // We do not install the security manager when calling from the commandline.
+    /**
-    // However, doPrivileged blocks will be necessary for any test code that calls this.
+     * General purpose HTTP(S) call with JSON Content-Type and Authorization Header.
+     * SSL settings are read from the settings file, if any.
+     *
+     * @param user
+     *            user in the authorization header.
+     * @param password
+     *            password in the authorization header.
+     * @param requestBodySupplier
+     *            supplier for the JSON string body of the request.
+     * @param responseConsumer
+     *            consumer of the response Input Stream.
+     * @return HTTP protocol response code.
+     *
+     * @SuppressForbidden We do not install the security manager when calling from
+     *                    the commandline. However, doPrivileged blocks will be
+     *                    necessary for any test code that calls this.
+     */
     @SuppressForbidden(reason = "We call connect in doPrivileged and provide SocketPermission")
-    public String postURL(String method, String urlString, String user, SecureString password, @Nullable String bodyString)
+    public int postURL(String method, URL url, String user, SecureString password, CheckedSupplier<String, Exception> requestBodySupplier,
-            throws Exception {
+            CheckedConsumer<InputStream, Exception> responseConsumer) throws Exception {
-        URI uri = new URI(urlString);
-        URL url = uri.toURL();
         HttpURLConnection conn;
         // If using SSL, need a custom service because it's likely a self-signed certificate
-        if ("https".equalsIgnoreCase(uri.getScheme())) {
+        if ("https".equalsIgnoreCase(url.getProtocol())) {
             Settings sslSettings = settings.getByPrefix(setting("http.ssl."));
             final SSLService sslService = new SSLService(settings, env);
             final HttpsURLConnection httpsConn = (HttpsURLConnection) url.openConnection();
@@ -85,6 +97,7 @@ public class CommandLineHttpClient {
         String token = UsernamePasswordToken.basicAuthHeaderValue(user, password);
         conn.setRequestProperty("Authorization", token);
         conn.setRequestProperty("Content-Type", XContentType.JSON.mediaType());
+        String bodyString = requestBodySupplier.get();
         conn.setDoOutput(bodyString != null); // set true if we are sending a body
         SocketAccess.doPrivileged(conn::connect);
         if (bodyString != null) {
@@ -95,17 +108,19 @@ public class CommandLineHttpClient {
                 throw e;
             }
         }
+        // this throws IOException if there is a network problem
+        final int ans = conn.getResponseCode();
         try (InputStream inputStream = conn.getInputStream()) {
-            byte[] bytes = Streams.readAll(inputStream);
+            responseConsumer.accept(inputStream);
-            return new String(bytes, StandardCharsets.UTF_8);
         } catch (IOException e) {
+            // this IOException is if the HTTP response code is 'BAD' (>= 400)
             try (InputStream errorStream = conn.getErrorStream()) {
-                byte[] bytes = Streams.readAll(errorStream);
+                responseConsumer.accept(errorStream);
-                throw new IOException(new String(bytes, StandardCharsets.UTF_8), e);
             }
         } finally {
-            conn.disconnect();
+            Releasables.closeWhileHandlingException(conn::disconnect);
         }
+        return ans;
     }
 
     String getDefaultURL() {

plugin/src/main/java/org/elasticsearch/xpack/security/authc/esnative/tool/SetupPasswordTool.java

@@ -8,12 +8,16 @@ package org.elasticsearch.xpack.security.authc.esnative.tool;
 import joptsimple.OptionParser;
 import joptsimple.OptionSet;
 import joptsimple.OptionSpec;
+
+import org.bouncycastle.util.io.Streams;
 import org.elasticsearch.cli.EnvironmentAwareCommand;
 import org.elasticsearch.cli.ExitCodes;
 import org.elasticsearch.cli.MultiCommand;
 import org.elasticsearch.cli.Terminal;
+import org.elasticsearch.cli.Terminal.Verbosity;
 import org.elasticsearch.cli.UserException;
 import org.elasticsearch.common.Booleans;
+import org.elasticsearch.common.CheckedBiConsumer;
 import org.elasticsearch.common.CheckedFunction;
 import org.elasticsearch.common.settings.KeyStoreWrapper;
 import org.elasticsearch.common.settings.SecureString;
@@ -22,44 +26,52 @@ import org.elasticsearch.common.xcontent.XContentBuilder;
 import org.elasticsearch.common.xcontent.json.JsonXContent;
 import org.elasticsearch.env.Environment;
 import org.elasticsearch.xpack.security.authc.esnative.ReservedRealm;
+import org.elasticsearch.xpack.security.support.Validation;
 import org.elasticsearch.xpack.security.user.ElasticUser;
 import org.elasticsearch.xpack.security.user.KibanaUser;
 import org.elasticsearch.xpack.security.user.LogstashSystemUser;
 
 import java.io.IOException;
+import java.net.ConnectException;
+import java.net.HttpURLConnection;
+import java.net.URL;
+import java.nio.charset.StandardCharsets;
 import java.security.SecureRandom;
 import java.util.Arrays;
-import java.util.function.BiConsumer;
+import java.util.HashMap;
-import java.util.function.Function;
+import java.util.List;
+import java.util.Map;
 
 /**
- * A tool to set passwords of internal users. It first sets the elastic user password. After the elastic user
+ * A tool to set passwords of reserved users (elastic, kibana and
- * password is set, it will set the remaining user passwords. This tool will only work if the passwords have
+ * logstash_system). Can run in `interactive` or `auto` mode. In `auto` mode
- * not already been set by something else.
+ * generates random passwords and prints them on the console. In `interactive`
+ * mode prompts for each individual user's password. This tool only runs once,
+ * if successful. After the elastic user password is set you have to use the
+ * `security` API to manipulate passwords.
  */
 public class SetupPasswordTool extends MultiCommand {
 
-    private static final char[] CHARS = ("ABCDEFGHIJKLMNOPQRSTUVWXYZabcdefghijklmnopqrstuvwxyz0123456789" +
+    private static final char[] CHARS = ("ABCDEFGHIJKLMNOPQRSTUVWXYZabcdefghijklmnopqrstuvwxyz0123456789~!@#$%^&*-_=+?").toCharArray();
-            "~!@#$%^&*-_=+?").toCharArray();
+    public static final List<String> USERS = Arrays.asList(ElasticUser.NAME, KibanaUser.NAME, LogstashSystemUser.NAME);
-    private static final String[] USERS = new String[]{ElasticUser.NAME, KibanaUser.NAME, LogstashSystemUser.NAME};
 
-    private final Function<Environment, CommandLineHttpClient> clientFunction;
+    private final CheckedFunction<Environment, CommandLineHttpClient, Exception> clientFunction;
     private final CheckedFunction<Environment, KeyStoreWrapper, Exception> keyStoreFunction;
     private CommandLineHttpClient client;
 
     SetupPasswordTool() {
-        this((environment) -> new CommandLineHttpClient(environment.settings(), environment),
+        this((environment) -> new CommandLineHttpClient(environment.settings(), environment), (environment) -> {
-                (environment) -> {
+            KeyStoreWrapper keyStoreWrapper = KeyStoreWrapper.load(environment.configFile());
-                    KeyStoreWrapper keyStoreWrapper = KeyStoreWrapper.load(environment.configFile());
+            if (keyStoreWrapper == null) {
-                    if (keyStoreWrapper == null) {
+                throw new UserException(ExitCodes.CONFIG,
-                        throw new UserException(ExitCodes.CONFIG, "Keystore does not exist");
+                        "Elasticsearch keystore file is missing [" + KeyStoreWrapper.keystorePath(environment.configFile()) + "]");
-                    }
+            }
-                    return keyStoreWrapper;
+            return keyStoreWrapper;
-                });
+        });
     }
 
-    SetupPasswordTool(Function<Environment, CommandLineHttpClient> clientFunction,
+    SetupPasswordTool(CheckedFunction<Environment, CommandLineHttpClient, Exception> clientFunction,
-                      CheckedFunction<Environment, KeyStoreWrapper, Exception> keyStoreFunction) {
+            CheckedFunction<Environment, KeyStoreWrapper, Exception> keyStoreFunction) {
         super("Sets the passwords for reserved users");
         subcommands.put("auto", newAutoSetup());
         subcommands.put("interactive", newInteractiveSetup());
@@ -85,8 +97,8 @@ public class SetupPasswordTool extends MultiCommand {
     }
 
     /**
-     * This class sets the passwords using automatically generated random passwords. The passwords will be
+     * This class sets the passwords using automatically generated random passwords.
-     * printed to the console.
+     * The passwords will be printed to the console.
      */
     class AutoSetup extends SetupCommand {
 
@@ -97,9 +109,10 @@ public class SetupPasswordTool extends MultiCommand {
         @Override
         protected void execute(Terminal terminal, OptionSet options, Environment env) throws Exception {
             setupOptions(options, env);
+            checkElasticKeystorePasswordValid(terminal);
 
             if (shouldPrompt) {
-                terminal.println("Initiating the setup of reserved user " + Arrays.toString(USERS) + "  passwords.");
+                terminal.println("Initiating the setup of reserved user " + String.join(",", USERS) + "  passwords.");
                 terminal.println("The passwords will be randomly generated and printed to the console.");
                 boolean shouldContinue = terminal.promptYesNo("Please confirm that you would like to continue", false);
                 terminal.println("\n");
@@ -109,7 +122,7 @@ public class SetupPasswordTool extends MultiCommand {
             }
 
             SecureRandom secureRandom = new SecureRandom();
-            changePasswords(terminal, (user) -> generatePassword(secureRandom, user),
+            changePasswords((user) -> generatePassword(secureRandom, user),
                     (user, password) -> changedPasswordCallback(terminal, user, password));
         }
 
@@ -129,7 +142,7 @@ public class SetupPasswordTool extends MultiCommand {
     }
 
     /**
-     * This class sets the passwords using password entered manually by the user from the console.
+     * This class sets the passwords using input prompted on the console
      */
     class InteractiveSetup extends SetupCommand {
 
@@ -140,9 +153,10 @@ public class SetupPasswordTool extends MultiCommand {
         @Override
         protected void execute(Terminal terminal, OptionSet options, Environment env) throws Exception {
             setupOptions(options, env);
+            checkElasticKeystorePasswordValid(terminal);
 
             if (shouldPrompt) {
-                terminal.println("Initiating the setup of reserved user " + Arrays.toString(USERS) + "  passwords.");
+                terminal.println("Initiating the setup of reserved user " + String.join(",", USERS) + "  passwords.");
                 terminal.println("You will be prompted to enter passwords as the process progresses.");
                 boolean shouldContinue = terminal.promptYesNo("Please confirm that you would like to continue", false);
                 terminal.println("\n");
@@ -151,28 +165,41 @@ public class SetupPasswordTool extends MultiCommand {
                 }
             }
 
-            changePasswords(terminal, user -> promptForPassword(terminal, user),
+            changePasswords(user -> promptForPassword(terminal, user),
                     (user, password) -> changedPasswordCallback(terminal, user, password));
         }
 
         private SecureString promptForPassword(Terminal terminal, String user) throws UserException {
-            SecureString password1 = new SecureString(terminal.readSecret("Enter password for [" + user + "]: "));
+            // loop for two consecutive good passwords
-            try (SecureString password2 = new SecureString(terminal.readSecret("Reenter password for [" + user + "]: "))) {
+            while (true) {
-                if (password1.equals(password2) == false) {
+                SecureString password1 = new SecureString(terminal.readSecret("Enter password for [" + user + "]: "));
+                Validation.Error err = Validation.Users.validatePassword(password1.getChars());
+                if (err != null) {
+                    terminal.println(err.toString());
+                    terminal.println("Try again.");
                     password1.close();
-                    throw new UserException(ExitCodes.USAGE, "Passwords for user [" + user + "] do not match");
+                    continue;
                 }
+                try (SecureString password2 = new SecureString(terminal.readSecret("Reenter password for [" + user + "]: "))) {
+                    if (password1.equals(password2) == false) {
+                        terminal.println("Passwords do not match.");
+                        terminal.println("Try again.");
+                        password1.close();
+                        continue;
+                    }
+                }
+                return password1;
             }
-            return password1;
         }
 
         private void changedPasswordCallback(Terminal terminal, String user, SecureString password) {
-            terminal.println("Changed password for user " + user + "\n");
+            terminal.println("Changed password for user [" + user + "]");
         }
     }
 
     /**
-     * An abstract class that provides functionality common to both the auto and interactive setup modes.
+     * An abstract class that provides functionality common to both the auto and
+     * interactive setup modes.
      */
     private abstract class SetupCommand extends EnvironmentAwareCommand {
 
@@ -197,7 +224,7 @@ public class SetupPasswordTool extends MultiCommand {
                 url = providedUrl == null ? client.getDefaultURL() : providedUrl;
                 setShouldPrompt(options);
 
-                // TODO: We currently do  not support keystore passwords
+                // TODO: We currently do not support keystore passwords
                 keyStore.decrypt(new char[0]);
                 Settings build = Settings.builder().setSecureSettings(keyStore).build();
                 elasticUserPassword = ReservedRealm.BOOTSTRAP_ELASTIC_PASSWORD.get(build);
@@ -205,9 +232,9 @@ public class SetupPasswordTool extends MultiCommand {
         }
 
         private void setParser() {
-            urlOption = parser.acceptsAll(Arrays.asList("u", "url"), "The url for the change password request").withOptionalArg();
+            urlOption = parser.acceptsAll(Arrays.asList("u", "url"), "The url for the change password request.").withOptionalArg();
-            noPromptOption = parser.acceptsAll(Arrays.asList("b", "batch"), "Whether the user should be prompted to initiate the "
+            noPromptOption = parser.acceptsAll(Arrays.asList("b", "batch"),
-                    + "change password process").withOptionalArg();
+                    "If enabled, run the change password process without prompting the user.").withOptionalArg();
         }
 
         private void setShouldPrompt(OptionSet options) {
@@ -219,42 +246,98 @@ public class SetupPasswordTool extends MultiCommand {
             }
         }
 
-        void changePasswords(Terminal terminal, CheckedFunction<String, SecureString, UserException> passwordFn,
+        /**
-                             BiConsumer<String, SecureString> callback) throws Exception {
+         * Validates the bootstrap password from the local keystore by making an
-            for (String user : USERS) {
+         * '_authenticate' call. Returns silently if server is reachable and password is
-                changePassword(terminal, url, user, passwordFn, callback);
+         * valid. Throws {@link UserException} otherwise.
-            }
+         *
-        }
+         * @param terminal
-
+         *            where to write verbose info.
-        private void changePassword(Terminal terminal, String url, String user,
+         */
-                                    CheckedFunction<String, SecureString, UserException> passwordFn,
+        void checkElasticKeystorePasswordValid(Terminal terminal) throws Exception {
-                                    BiConsumer<String, SecureString> callback) throws Exception {
+            URL route = new URL(url + "/_xpack/security/_authenticate?pretty");
-            boolean isSuperUser = user.equals(elasticUser);
-            SecureString password = passwordFn.apply(user);
-
             try {
-                String route = url + "/_xpack/security/user/" + user + "/_password";
+                terminal.println(Verbosity.VERBOSE, "Testing if bootstrap password is valid for " + route.toString());
-                client.postURL("PUT", route, elasticUser, elasticUserPassword, buildPayload(password));
+                int httpCode = client.postURL("GET", route, elasticUser, elasticUserPassword, () -> null, is -> {
-                callback.accept(user, password);
+                    byte[] bytes = Streams.readAll(is);
-                if (isSuperUser) {
+                    terminal.println(Verbosity.VERBOSE, new String(bytes, StandardCharsets.UTF_8));
-                    elasticUserPassword = password;
+                });
-                }
+                // keystore password is not valid
-            } catch (Exception e) {
+                if (httpCode == HttpURLConnection.HTTP_UNAUTHORIZED) {
-                terminal.println("Exception making http rest request for user [" + user + "]");
+                    throw new UserException(ExitCodes.CONFIG, "Failed to verify bootstrap password.");
-                throw e;
-            } finally {
-                // We do not close the password if it is the super user as we are going to use the super user
-                // password in the followup requests to change other user passwords
-                if (isSuperUser == false) {
-                    password.close();
                 }
+            } catch (ConnectException e) {
+                throw new UserException(ExitCodes.CONFIG,
+                        "Failed to connect to elasticsearch at " + route.toString() + ". Is the URL correct and elasticsearch running?", e);
             }
         }
 
-        private String buildPayload(SecureString password) throws IOException {
+        /**
-            XContentBuilder xContentBuilder = JsonXContent.contentBuilder();
+         * Sets one user's password using the elastic superUser credentials.
-            xContentBuilder.startObject().field("password", password.toString()).endObject();
+         *
-            return xContentBuilder.string();
+         * @param user
+         *            The user who's password will change.
+         * @param password
+         *            the new password of the user.
+         */
+        private void changeUserPassword(String user, SecureString password) throws Exception {
+            URL route = new URL(url + "/_xpack/security/user/" + user + "/_password");
+            try {
+                // supplier should own his resources
+                SecureString supplierPassword = password.clone();
+                client.postURL("PUT", route, elasticUser, elasticUserPassword, () -> {
+                    try {
+                        XContentBuilder xContentBuilder = JsonXContent.contentBuilder();
+                        xContentBuilder.startObject().field("password", supplierPassword.toString()).endObject();
+                        return xContentBuilder.string();
+                    } finally {
+                        supplierPassword.close();
+                    }
+                }, is -> {
+                });
+            } catch (IOException e) {
+                throw new UserException(ExitCodes.TEMP_FAILURE, "Failed to set password for user [" + user + "].", e);
+            }
+        }
+
+        /**
+         * Collects passwords for all the users, then issues set requests. Fails on the
+         * first failed request. In this case rerun the tool to redo all the operations.
+         *
+         * @param passwordFn
+         *            Function to generate or prompt for each user's password.
+         * @param successCallback
+         *            Callback for each successful operation
+         */
+        void changePasswords(CheckedFunction<String, SecureString, UserException> passwordFn,
+                CheckedBiConsumer<String, SecureString, Exception> successCallback) throws Exception {
+            Map<String, SecureString> passwordsMap = new HashMap<>(USERS.size());
+            try {
+                for (String user : USERS) {
+                    passwordsMap.put(user, passwordFn.apply(user));
+                }
+                /*
+                 * Change elastic user last. This tool will not run after the elastic user
+                 * password is changed even if changing password for any subsequent user fails.
+                 * Stay safe and change elastic last.
+                 */
+                Map.Entry<String, SecureString> superUserEntry = null;
+                for (Map.Entry<String, SecureString> entry : passwordsMap.entrySet()) {
+                    if (entry.getKey().equals(elasticUser)) {
+                        superUserEntry = entry;
+                        continue;
+                    }
+                    changeUserPassword(entry.getKey(), entry.getValue());
+                    successCallback.accept(entry.getKey(), entry.getValue());
+                }
+                // change elastic superuser
+                if (superUserEntry != null) {
+                    changeUserPassword(superUserEntry.getKey(), superUserEntry.getValue());
+                    successCallback.accept(superUserEntry.getKey(), superUserEntry.getValue());
+                }
+            } finally {
+                passwordsMap.forEach((user, pass) -> pass.close());
+            }
         }
     }
 }

plugin/src/test/java/org/elasticsearch/xpack/security/authc/esnative/tool/SetupPasswordToolTests.java

@@ -10,6 +10,8 @@ import org.elasticsearch.cli.CommandTestCase;
 import org.elasticsearch.cli.ExitCodes;
 import org.elasticsearch.cli.Terminal;
 import org.elasticsearch.cli.UserException;
+import org.elasticsearch.common.CheckedConsumer;
+import org.elasticsearch.common.CheckedSupplier;
 import org.elasticsearch.common.settings.KeyStoreWrapper;
 import org.elasticsearch.common.settings.SecureString;
 import org.elasticsearch.common.settings.Settings;
@@ -18,47 +20,48 @@ import org.elasticsearch.common.xcontent.XContentParser;
 import org.elasticsearch.common.xcontent.json.JsonXContent;
 import org.elasticsearch.env.Environment;
 import org.elasticsearch.xpack.security.authc.esnative.ReservedRealm;
+import org.elasticsearch.xpack.security.support.Validation;
 import org.elasticsearch.xpack.security.user.ElasticUser;
-import org.elasticsearch.xpack.security.user.KibanaUser;
+import org.hamcrest.CoreMatchers;
-import org.elasticsearch.xpack.security.user.LogstashSystemUser;
 import org.junit.Before;
 import org.mockito.ArgumentCaptor;
 import org.mockito.InOrder;
 import org.mockito.Mockito;
 
 import java.io.IOException;
-import java.security.GeneralSecurityException;
+import java.net.HttpURLConnection;
+import java.net.URL;
+import java.util.ArrayList;
 import java.util.Arrays;
 import java.util.Collections;
 import java.util.HashSet;
+import java.util.List;
 import java.util.Map;
 
 import static org.mockito.Matchers.anyString;
-import static org.mockito.Matchers.contains;
 import static org.mockito.Matchers.eq;
+import static org.mockito.Matchers.any;
 import static org.mockito.Mockito.mock;
 import static org.mockito.Mockito.verify;
-import static org.mockito.Mockito.verifyZeroInteractions;
 import static org.mockito.Mockito.when;
 
 public class SetupPasswordToolTests extends CommandTestCase {
 
     private final String pathHomeParameter = "-Epath.home=" + createTempDir();
     private SecureString bootstrapPassword;
-    private final String ep = "elastic-password";
-    private final String kp = "kibana-password";
-    private final String lp = "logstash-password";
     private CommandLineHttpClient httpClient;
     private KeyStoreWrapper keyStore;
+    private List<String> usersInSetOrder;
 
     @Before
-    public void setSecretsAndKeyStore() throws GeneralSecurityException {
+    public void setSecretsAndKeyStore() throws Exception {
         // sometimes we fall back to the keystore seed as this is the default when a new node starts
         boolean useFallback = randomBoolean();
         bootstrapPassword = useFallback ?  new SecureString("0xCAFEBABE".toCharArray()) :
                 new SecureString("bootstrap-password".toCharArray());
         this.keyStore = mock(KeyStoreWrapper.class);
         this.httpClient = mock(CommandLineHttpClient.class);
+
         when(keyStore.isLoaded()).thenReturn(true);
         if (useFallback) {
             when(keyStore.getSettingNames()).thenReturn(new HashSet<>(Arrays.asList(ReservedRealm.BOOTSTRAP_ELASTIC_PASSWORD.getKey(),
@@ -68,14 +71,24 @@ public class SetupPasswordToolTests extends CommandTestCase {
             when(keyStore.getSettingNames()).thenReturn(Collections.singleton(KeyStoreWrapper.SEED_SETTING.getKey()));
             when(keyStore.getString(KeyStoreWrapper.SEED_SETTING.getKey())).thenReturn(bootstrapPassword);
         }
+
         when(httpClient.getDefaultURL()).thenReturn("http://localhost:9200");
 
-        terminal.addSecretInput(ep);
+        when(httpClient.postURL(anyString(), any(URL.class), anyString(), any(SecureString.class), any(CheckedSupplier.class),
-        terminal.addSecretInput(ep);
+                any(CheckedConsumer.class))).thenReturn(HttpURLConnection.HTTP_OK);
-        terminal.addSecretInput(kp);
+
-        terminal.addSecretInput(kp);
+        // elastic user is updated last
-        terminal.addSecretInput(lp);
+        usersInSetOrder = new ArrayList<>(SetupPasswordTool.USERS);
-        terminal.addSecretInput(lp);
+        for (int i = 0; i < usersInSetOrder.size() - 1; i++) {
+            if (ElasticUser.NAME.equals(usersInSetOrder.get(i))) {
+                Collections.swap(usersInSetOrder, i, i + 1);
+            }
+        }
+
+        for (String user : SetupPasswordTool.USERS) {
+            terminal.addSecretInput(user + "-password");
+            terminal.addSecretInput(user + "-password");
+        }
     }
 
     @Override
@@ -106,78 +119,110 @@ public class SetupPasswordToolTests extends CommandTestCase {
     }
 
     public void testAutoSetup() throws Exception {
+        String url = httpClient.getDefaultURL();
         execute("auto", pathHomeParameter, "-b", "true");
 
         verify(keyStore).decrypt(new char[0]);
 
-        ArgumentCaptor<String> passwordCaptor = ArgumentCaptor.forClass(String.class);
-
         InOrder inOrder = Mockito.inOrder(httpClient);
-        String elasticUrl = "http://localhost:9200/_xpack/security/user/elastic/_password";
-        inOrder.verify(httpClient).postURL(eq("PUT"), eq(elasticUrl), eq(ElasticUser.NAME), eq(bootstrapPassword),
-                passwordCaptor.capture());
 
-        String[] users = {KibanaUser.NAME, LogstashSystemUser.NAME};
+        URL checkUrl = new URL(url + "/_xpack/security/_authenticate?pretty");
-        SecureString newPassword = new SecureString(parsePassword(passwordCaptor.getValue()).toCharArray());
+        inOrder.verify(httpClient).postURL(eq("GET"), eq(checkUrl), eq(ElasticUser.NAME), eq(bootstrapPassword), any(CheckedSupplier.class),
-        for (String user : users) {
+                any(CheckedConsumer.class));
-            String urlWithRoute = "http://localhost:9200/_xpack/security/user/" + user + "/_password";
+        for (String user : usersInSetOrder) {
-            inOrder.verify(httpClient).postURL(eq("PUT"), eq(urlWithRoute), eq(ElasticUser.NAME), eq(newPassword), anyString());
+            URL urlWithRoute = new URL(url + "/_xpack/security/user/" + user + "/_password");
+            inOrder.verify(httpClient).postURL(eq("PUT"), eq(urlWithRoute), eq(ElasticUser.NAME), eq(bootstrapPassword),
+                    any(CheckedSupplier.class), any(CheckedConsumer.class));
         }
+
+    }
+
+    public void testAuthnFail() throws Exception {
+        URL authnURL = new URL(httpClient.getDefaultURL() + "/_xpack/security/_authenticate?pretty");
+        when(httpClient.postURL(eq("GET"), eq(authnURL), eq(ElasticUser.NAME), any(SecureString.class), any(CheckedSupplier.class),
+                any(CheckedConsumer.class))).thenReturn(HttpURLConnection.HTTP_UNAUTHORIZED);
+
+        try {
+            execute(randomBoolean() ? "auto" : "interactive", pathHomeParameter);
+            fail("Should have thrown exception");
+        } catch (UserException e) {
+            assertEquals(ExitCodes.CONFIG, e.exitCode);
+        }
+
     }
 
     public void testUrlOption() throws Exception {
         String url = "http://localhost:9202";
         execute("auto", pathHomeParameter, "-u", url, "-b");
 
-        ArgumentCaptor<String> passwordCaptor = ArgumentCaptor.forClass(String.class);
-
         InOrder inOrder = Mockito.inOrder(httpClient);
-        String elasticUrl = url + "/_xpack/security/user/elastic/_password";
-        inOrder.verify(httpClient).postURL(eq("PUT"), eq(elasticUrl), eq(ElasticUser.NAME), eq(bootstrapPassword),
-                passwordCaptor.capture());
 
-        String[] users = {KibanaUser.NAME, LogstashSystemUser.NAME};
+        URL checkUrl = new URL(url + "/_xpack/security/_authenticate?pretty");
-        SecureString newPassword = new SecureString(parsePassword(passwordCaptor.getValue()).toCharArray());
+        inOrder.verify(httpClient).postURL(eq("GET"), eq(checkUrl), eq(ElasticUser.NAME), eq(bootstrapPassword), any(CheckedSupplier.class),
-        for (String user : users) {
+                any(CheckedConsumer.class));
-            String urlWithRoute = url + "/_xpack/security/user/" + user + "/_password";
+        for (String user : usersInSetOrder) {
-            inOrder.verify(httpClient).postURL(eq("PUT"), eq(urlWithRoute), eq(ElasticUser.NAME), eq(newPassword), anyString());
+            URL urlWithRoute = new URL(url + "/_xpack/security/user/" + user + "/_password");
+            inOrder.verify(httpClient).postURL(eq("PUT"), eq(urlWithRoute), eq(ElasticUser.NAME), eq(bootstrapPassword),
+                    any(CheckedSupplier.class), any(CheckedConsumer.class));
         }
     }
 
     public void testInteractiveSetup() throws Exception {
+        String url = httpClient.getDefaultURL();
+
         terminal.addTextInput("Y");
+        execute("interactive", pathHomeParameter);
+
+        InOrder inOrder = Mockito.inOrder(httpClient);
+
+        URL checkUrl = new URL(url + "/_xpack/security/_authenticate?pretty");
+        inOrder.verify(httpClient).postURL(eq("GET"), eq(checkUrl), eq(ElasticUser.NAME), eq(bootstrapPassword), any(CheckedSupplier.class),
+                any(CheckedConsumer.class));
+        for (String user : usersInSetOrder) {
+            URL urlWithRoute = new URL(url + "/_xpack/security/user/" + user + "/_password");
+            ArgumentCaptor<CheckedSupplier<String, Exception>> passwordCaptor = ArgumentCaptor.forClass((Class) CheckedSupplier.class);
+            inOrder.verify(httpClient).postURL(eq("PUT"), eq(urlWithRoute), eq(ElasticUser.NAME), eq(bootstrapPassword),
+                    passwordCaptor.capture(), any(CheckedConsumer.class));
+            assertThat(passwordCaptor.getValue().get(), CoreMatchers.containsString(user + "-password"));
+        }
+    }
+
+    public void testInteractivePasswordsFatFingers() throws Exception {
+        String url = httpClient.getDefaultURL();
+
+        terminal.reset();
+        terminal.addTextInput("Y");
+        for (String user : SetupPasswordTool.USERS) {
+            // fail in strength and match
+            int failCount = randomIntBetween(3, 10);
+            while (failCount-- > 0) {
+                String password1 = randomAlphaOfLength(randomIntBetween(3, 10));
+                terminal.addSecretInput(password1);
+                Validation.Error err = Validation.Users.validatePassword(password1.toCharArray());
+                if (err == null) {
+                    // passes strength validation, fail by mismatch
+                    terminal.addSecretInput(password1 + "typo");
+                }
+            }
+            // two good passwords
+            terminal.addSecretInput(user + "-password");
+            terminal.addSecretInput(user + "-password");
+        }
 
         execute("interactive", pathHomeParameter);
 
         InOrder inOrder = Mockito.inOrder(httpClient);
-        String elasticUrl = "http://localhost:9200/_xpack/security/user/elastic/_password";
-        SecureString newPassword = new SecureString(ep.toCharArray());
-        inOrder.verify(httpClient).postURL(eq("PUT"), eq(elasticUrl), eq(ElasticUser.NAME), eq(bootstrapPassword), contains(ep));
 
-        String kibanaUrl = "http://localhost:9200/_xpack/security/user/" + KibanaUser.NAME + "/_password";
+        URL checkUrl = new URL(url + "/_xpack/security/_authenticate?pretty");
-        inOrder.verify(httpClient).postURL(eq("PUT"), eq(kibanaUrl), eq(ElasticUser.NAME), eq(newPassword), contains(kp));
+        inOrder.verify(httpClient).postURL(eq("GET"), eq(checkUrl), eq(ElasticUser.NAME), eq(bootstrapPassword), any(CheckedSupplier.class),
-        String logstashUrl = "http://localhost:9200/_xpack/security/user/" + LogstashSystemUser.NAME + "/_password";
+                any(CheckedConsumer.class));
-        inOrder.verify(httpClient).postURL(eq("PUT"), eq(logstashUrl), eq(ElasticUser.NAME), eq(newPassword), contains(lp));
+        for (String user : usersInSetOrder) {
-    }
+            URL urlWithRoute = new URL(url + "/_xpack/security/user/" + user + "/_password");
-
+            ArgumentCaptor<CheckedSupplier<String, Exception>> passwordCaptor = ArgumentCaptor.forClass((Class) CheckedSupplier.class);
-    public void testInteractivePasswordsNotMatching() throws Exception {
+            inOrder.verify(httpClient).postURL(eq("PUT"), eq(urlWithRoute), eq(ElasticUser.NAME), eq(bootstrapPassword),
-        String ep = "elastic-password";
+                    passwordCaptor.capture(), any(CheckedConsumer.class));
-
+            assertThat(passwordCaptor.getValue().get(), CoreMatchers.containsString(user + "-password"));
-        terminal.reset();
-        terminal.addTextInput("Y");
-        terminal.addSecretInput(ep);
-        terminal.addSecretInput(ep + "typo");
-        String url = "http://localhost:9200";
-
-        try {
-            execute("interactive", pathHomeParameter, "-u", url);
-            fail("Should have thrown exception");
-        } catch (UserException e) {
-            assertEquals(ExitCodes.USAGE, e.exitCode);
-            assertEquals("Passwords for user [elastic] do not match", e.getMessage());
         }
-
-        verifyZeroInteractions(httpClient);
     }
 
     private String parsePassword(String value) throws IOException {