diff --git a/src/cli/serve/integration_tests/__snapshots__/reload_logging_config.test.js.snap b/src/cli/serve/integration_tests/__snapshots__/reload_logging_config.test.js.snap
index 04014e02fbb05..495ddab6aae6b 100644
--- a/src/cli/serve/integration_tests/__snapshots__/reload_logging_config.test.js.snap
+++ b/src/cli/serve/integration_tests/__snapshots__/reload_logging_config.test.js.snap
@@ -15,42 +15,13 @@ Object {
     },
     Object {
       "@timestamp": "## @timestamp ##",
-      "message": "starting server :tada:",
-      "pid": "## PID ##",
-      "tags": Array [
-        "info",
-        "server",
-      ],
-      "type": "log",
-    },
-    Object {
-      "@timestamp": "## @timestamp ##",
-      "message": "registering route handler for [/core]",
-      "pid": "## PID ##",
-      "tags": Array [
-        "info",
-        "http",
-      ],
-      "type": "log",
-    },
-    Object {
-      "@timestamp": "## @timestamp ##",
-      "message": "starting http server [localhost:8274]",
+      "message": "Server running at http://localhost:8274",
       "pid": "## PID ##",
       "tags": Array [
         "info",
         "http",
         "server",
-      ],
-      "type": "log",
-    },
-    Object {
-      "@timestamp": "## @timestamp ##",
-      "message": "Server running at http://localhost:8274",
-      "pid": "## PID ##",
-      "tags": Array [
         "listening",
-        "info",
       ],
       "type": "log",
     },
diff --git a/src/core/server/http/__tests__/__snapshots__/http_service.test.ts.snap b/src/core/server/http/__tests__/__snapshots__/http_service.test.ts.snap
index 86fce993d6da2..b6ee75c9a91ff 100644
--- a/src/core/server/http/__tests__/__snapshots__/http_service.test.ts.snap
+++ b/src/core/server/http/__tests__/__snapshots__/http_service.test.ts.snap
@@ -18,14 +18,14 @@ Object {
 
 exports[`register route handler 1`] = `
 Object {
-  "debug": Array [],
-  "error": Array [],
-  "fatal": Array [],
-  "info": Array [
+  "debug": Array [
     Array [
       "registering route handler for [/foo]",
     ],
   ],
+  "error": Array [],
+  "fatal": Array [],
+  "info": Array [],
   "log": Array [],
   "trace": Array [],
   "warn": Array [],
diff --git a/src/core/server/http/http_server.ts b/src/core/server/http/http_server.ts
index 7d51763968f96..c8e12ced3f4d5 100644
--- a/src/core/server/http/http_server.ts
+++ b/src/core/server/http/http_server.ts
@@ -83,9 +83,13 @@ export class HttpServer {
       });
     }
 
-    this.log.info(`starting http server [${config.host}:${config.port}]`);
-
     await this.server.start();
+
+    this.log.info(
+      `Server running at ${this.server.info.uri}${config.rewriteBasePath ? config.basePath : ''}`,
+      // The "legacy" Kibana will output log records with `listening` tag even if `quiet` logging mode is enabled.
+      { tags: ['listening'] }
+    );
   }
 
   public async stop() {
diff --git a/src/core/server/http/http_service.ts b/src/core/server/http/http_service.ts
index acede95f9c995..e6065d6c4b15d 100644
--- a/src/core/server/http/http_service.ts
+++ b/src/core/server/http/http_service.ts
@@ -85,7 +85,7 @@ export class HttpService implements CoreService {
           'Router will **not** be applied.'
       );
     } else {
-      this.log.info(`registering route handler for [${router.path}]`);
+      this.log.debug(`registering route handler for [${router.path}]`);
       this.httpServer.registerRouter(router);
     }
   }
diff --git a/src/core/server/index.ts b/src/core/server/index.ts
index 4ef90de03cebf..27d9a12081897 100644
--- a/src/core/server/index.ts
+++ b/src/core/server/index.ts
@@ -33,7 +33,7 @@ export class Server {
   }
 
   public async start() {
-    this.log.info('starting server :tada:');
+    this.log.debug('starting server :tada:');
 
     const router = new Router('/core');
     router.get({ path: '/', validate: false }, async (req, res) => res.ok({ version: '0.0.1' }));
diff --git a/src/core/server/legacy_compat/logging/appenders/__tests__/__snapshots__/legacy_appender.test.ts.snap b/src/core/server/legacy_compat/logging/appenders/__tests__/__snapshots__/legacy_appender.test.ts.snap
index 4a024fc806a13..c12ec9dc747b9 100644
--- a/src/core/server/legacy_compat/logging/appenders/__tests__/__snapshots__/legacy_appender.test.ts.snap
+++ b/src/core/server/legacy_compat/logging/appenders/__tests__/__snapshots__/legacy_appender.test.ts.snap
@@ -72,5 +72,25 @@ Array [
     "message-8-with-message",
     2012-02-01T11:22:33.044Z,
   ],
+  Array [
+    Array [
+      "info",
+      "context-9",
+      "sub-context-9",
+    ],
+    "message-9-with-message",
+    2012-02-01T11:22:33.044Z,
+  ],
+  Array [
+    Array [
+      "info",
+      "context-10",
+      "sub-context-10",
+      "tag1",
+      "tag2",
+    ],
+    "message-10-with-message",
+    2012-02-01T11:22:33.044Z,
+  ],
 ]
 `;
diff --git a/src/core/server/legacy_compat/logging/appenders/__tests__/legacy_appender.test.ts b/src/core/server/legacy_compat/logging/appenders/__tests__/legacy_appender.test.ts
index 25fe60b55c6d6..7bc600998891b 100644
--- a/src/core/server/legacy_compat/logging/appenders/__tests__/legacy_appender.test.ts
+++ b/src/core/server/legacy_compat/logging/appenders/__tests__/legacy_appender.test.ts
@@ -86,6 +86,20 @@ test('`append()` correctly pushes records to legacy platform.', () => {
       message: 'message-8-with-message',
       timestamp,
     },
+    {
+      context: 'context-9.sub-context-9',
+      level: LogLevel.Info,
+      message: 'message-9-with-message',
+      timestamp,
+      meta: { someValue: 3 },
+    },
+    {
+      context: 'context-10.sub-context-10',
+      level: LogLevel.Info,
+      message: 'message-10-with-message',
+      timestamp,
+      meta: { tags: ['tag1', 'tag2'] },
+    },
   ];
 
   const rawKbnServerMock = {
diff --git a/src/core/server/legacy_compat/logging/appenders/legacy_appender.ts b/src/core/server/legacy_compat/logging/appenders/legacy_appender.ts
index e2c7f996b8013..1a8d201276943 100644
--- a/src/core/server/legacy_compat/logging/appenders/legacy_appender.ts
+++ b/src/core/server/legacy_compat/logging/appenders/legacy_appender.ts
@@ -41,12 +41,10 @@ export class LegacyAppender implements DisposableAppender {
    * write record to the configured destination.
    * @param record `LogRecord` instance to forward to.
    */
-  public append(record: LogRecord) {
-    this.kbnServer.log(
-      [record.level.id.toLowerCase(), ...record.context.split('.')],
-      record.error || record.message,
-      record.timestamp
-    );
+  public append({ level, context, message, error, timestamp, meta = {} }: LogRecord) {
+    const tags = [level.id.toLowerCase(), ...context.split('.'), ...(meta.tags || [])];
+
+    this.kbnServer.log(tags, error || message, timestamp);
   }
 
   public async dispose() {
diff --git a/src/server/kbn_server.js b/src/server/kbn_server.js
index 7e9895d4a3afd..db4ddff754eab 100644
--- a/src/server/kbn_server.js
+++ b/src/server/kbn_server.js
@@ -140,10 +140,7 @@ export default class KbnServer {
    * @return undefined
    */
   async listen() {
-    const {
-      server,
-      config,
-    } = this;
+    const { server } = this;
 
     await this.ready();
     await fromNode(cb => server.start(cb));
@@ -153,11 +150,6 @@ export default class KbnServer {
       process.send(['WORKER_LISTENING']);
     }
 
-    server.log(['listening', 'info'], `Server running at ${server.info.uri}${
-      config.get('server.rewriteBasePath')
-        ? config.get('server.basePath')
-        : ''
-    }`);
     return server;
   }