diff --git a/src/core_plugins/elasticsearch/lib/__tests__/ensure_allow_explicit_index.js b/src/core_plugins/elasticsearch/lib/__tests__/ensure_allow_explicit_index.js
new file mode 100644
index 0000000000000..ac86c4ec68ef0
--- /dev/null
+++ b/src/core_plugins/elasticsearch/lib/__tests__/ensure_allow_explicit_index.js
@@ -0,0 +1,75 @@
+import sinon from 'sinon';
+import expect from 'expect.js';
+
+import { ensureAllowExplicitIndex } from '../ensure_allow_explicit_index';
+
+const createStubCallWithInternal = responders => (
+  sinon.spy(async (params) => {
+    if (responders.length) {
+      return await responders.shift()(params);
+    }
+
+    throw new Error('Unexpected client.mget call');
+  })
+);
+
+const createStubConfig = () => ({
+  get: sinon.spy((key) => {
+    switch (key) {
+      case 'kibana.index': return '.kibana';
+      case 'pkg.version': return '0.0.0';
+      default: throw new Error(`Unexpected config.get('${key}') call`);
+    }
+  })
+});
+
+describe('ensureAllowExplicitIndex()', () => {
+  it('attempts an mget with index in request', async () => {
+    const config = createStubConfig();
+    const callWithInternalUser = createStubCallWithInternal([
+      () => ({ ok: true })
+    ]);
+
+    const resp = await ensureAllowExplicitIndex(callWithInternalUser, config);
+    expect(resp).to.be(true);
+  });
+
+  it(`reports "illegal_argument_exception" that mentions "explicit index"`, async () => {
+    const config = createStubConfig();
+    const callWithInternalUser = createStubCallWithInternal([
+      () => ({
+        error: {
+          type: 'illegal_argument_exception',
+          reason: 'explicit index not supported'
+        }
+      })
+    ]);
+
+    try {
+      await ensureAllowExplicitIndex(callWithInternalUser, config);
+      throw new Error('expected ensureAllowExplicitIndex() to throw error');
+    } catch (error) {
+      expect(error.message).to.contain('rest.action.multi.allow_explicit_index');
+    }
+  });
+
+  it('reports unexpected errors', async () => {
+    const config = createStubConfig();
+    const callWithInternalUser = createStubCallWithInternal([
+      () => ({
+        error: {
+          type: 'foo',
+          reason: 'bar'
+        }
+      })
+    ]);
+
+    try {
+      await ensureAllowExplicitIndex(callWithInternalUser, config);
+      throw new Error('expected ensureAllowExplicitIndex() to throw error');
+    } catch (error) {
+      expect(error.message).to.contain('[foo]');
+      expect(error.message).to.contain('bar');
+    }
+  });
+});
diff --git a/src/core_plugins/elasticsearch/lib/__tests__/health_check.js b/src/core_plugins/elasticsearch/lib/__tests__/health_check.js
index 016b22c164733..9bdde587f78e9 100644
--- a/src/core_plugins/elasticsearch/lib/__tests__/health_check.js
+++ b/src/core_plugins/elasticsearch/lib/__tests__/health_check.js
@@ -38,6 +38,7 @@ describe('plugins/elasticsearch', () => {
 
       cluster = { callWithInternalUser: sinon.stub() };
       cluster.callWithInternalUser.withArgs('index', sinon.match.any).returns(Promise.resolve());
+      cluster.callWithInternalUser.withArgs('mget', sinon.match.any).returns(Promise.resolve({ ok: true }));
       cluster.callWithInternalUser.withArgs('get', sinon.match.any).returns(Promise.resolve({ found: false }));
       cluster.callWithInternalUser.withArgs('search', sinon.match.any).returns(Promise.resolve({ hits: { hits: [] } }));
       cluster.callWithInternalUser.withArgs('nodes.info', sinon.match.any).returns(Promise.resolve({
diff --git a/src/core_plugins/elasticsearch/lib/ensure_allow_explicit_index.js b/src/core_plugins/elasticsearch/lib/ensure_allow_explicit_index.js
new file mode 100644
index 0000000000000..7444b6862721c
--- /dev/null
+++ b/src/core_plugins/elasticsearch/lib/ensure_allow_explicit_index.js
@@ -0,0 +1,36 @@
+export async function ensureAllowExplicitIndex(callWithInternalUser, config) {
+  const resp = await callWithInternalUser('mget', {
+    ignore: [400],
+    body: {
+      docs: [
+        {
+          _index: config.get('kibana.index'),
+          _type: 'config',
+          _id: config.get('pkg.version'),
+        },
+      ],
+    },
+  });
+
+  if (!resp.error) {
+    return true;
+  }
+
+  const error = resp.error || {};
+  const errorReason = error.reason || '';
+
+  const isArgError = error.type === 'illegal_argument_exception';
+  const isExplicitIndexException = isArgError && errorReason.includes('explicit index');
+
+  if (isExplicitIndexException) {
+    throw new Error(
+      'Kibana must be able to specify the index within Elasticsearch multi-requests ' +
+      '(rest.action.multi.allow_explicit_index=true).'
+    );
+  }
+
+  throw new Error(
+    'Unable to ensure that rest.action.multi.allow_explicit_index=true: ' +
+    `[${error.type}] ${errorReason}`
+  );
+}
diff --git a/src/core_plugins/elasticsearch/lib/health_check.js b/src/core_plugins/elasticsearch/lib/health_check.js
index 6b5e5f4085ea6..8bd4e877939fe 100644
--- a/src/core_plugins/elasticsearch/lib/health_check.js
+++ b/src/core_plugins/elasticsearch/lib/health_check.js
@@ -6,6 +6,7 @@ import createKibanaIndex from './create_kibana_index';
 import kibanaVersion from './kibana_version';
 import { ensureEsVersion } from './ensure_es_version';
 import { ensureNotTribe } from './ensure_not_tribe';
+import { ensureAllowExplicitIndex } from './ensure_allow_explicit_index';
 
 const NoConnections = elasticsearch.errors.NoConnections;
 import util from 'util';
@@ -94,7 +95,8 @@ module.exports = function (plugin, server) {
     const healthCheck =
       waitForPong(callAdminAsKibanaUser, config.get('elasticsearch.url'))
       .then(waitForEsVersion)
-      .then(ensureNotTribe.bind(this, callAdminAsKibanaUser))
+      .then(() => ensureNotTribe(callAdminAsKibanaUser))
+      .then(() => ensureAllowExplicitIndex(callAdminAsKibanaUser, config))
       .then(waitForShards)
       .then(_.partial(migrateConfig, server))
       .then(() => {