diff --git a/gobblefile.js b/gobblefile.js
index bd87c2b..3acfd4a 100644
--- a/gobblefile.js
+++ b/gobblefile.js
@@ -9,6 +9,9 @@ module.exports = gobble('src').transform('babel', {
   ],
   plugins: [
     'syntax-decorators',
+    ['babel-plugin-transform-builtin-extend', {
+      globals: ['Error']
+    }],
     'transform-decorators-legacy',
     'transform-runtime',
     'add-module-exports'
diff --git a/package.json b/package.json
index c31ae25..e3e2774 100644
--- a/package.json
+++ b/package.json
@@ -54,6 +54,7 @@
     "babel": "6.5.2",
     "babel-plugin-add-module-exports": "0.1.2",
     "babel-plugin-syntax-decorators": "6.5.0",
+    "babel-plugin-transform-builtin-extend": "1.1.2",
     "babel-plugin-transform-decorators-legacy": "1.3.4",
     "babel-plugin-transform-runtime": "6.6.0",
     "babel-preset-es2015": "6.6.0",
diff --git a/src/defaults.js b/src/defaults.js
index e3e2943..d454bd5 100644
--- a/src/defaults.js
+++ b/src/defaults.js
@@ -10,6 +10,8 @@ export const portSecure = 443;
 
 export const reconnectInitialDelay = 1000;
 
+export const reconnectFailAfter = Infinity;
+
 export const reconnectMaxDelay = 15 * 1000;
 
 export const reconnectBackoffStrategy = 'fibonacci';
diff --git a/src/error.js b/src/error.js
index ae0d704..8efa22c 100644
--- a/src/error.js
+++ b/src/error.js
@@ -16,3 +16,9 @@ export class BadOptionsError extends LogentriesError {
     this.options = opts;
   }
 }
+
+export class ReconnectFailedError extends LogentriesError {
+  constructor(msg = 'Reconnect failed') {
+    super(msg);
+  }
+}
diff --git a/src/logger.js b/src/logger.js
index f5b5bcf..39f6d80 100644
--- a/src/logger.js
+++ b/src/logger.js
@@ -13,7 +13,8 @@ import text from './text';
 import build from './serialize';
 import {
     BadOptionsError,
-    LogentriesError
+    LogentriesError,
+    ReconnectFailedError,
 } from './error';
 import RingBuffer from './ringbuffer';
 import BunyanStream from './bunyanstream';
@@ -140,6 +141,8 @@ class Logger extends Writable {
     this.inactivityTimeout = opts.inactivityTimeout || defaults.inactivityTimeout;
     this.disableTimeout = opts.disableTimeout;
     this.token = opts.token;
+    this.reconnectFailed = false;
+    this.reconnectFailAfter = opts.reconnectFailAfter || defaults.reconnectFailAfter;
     this.reconnectInitialDelay = opts.reconnectInitialDelay || defaults.reconnectInitialDelay;
     this.reconnectMaxDelay = opts.reconnectMaxDelay || defaults.reconnectMaxDelay;
     this.reconnectBackoffStrategy =
@@ -187,6 +190,7 @@ class Logger extends Writable {
     this.on(bufferDrainEvent, () => {
       this.debugLogger.log('RingBuffer drained.');
       this.drained = true;
+      this.reconnectFailed = false;
     });
 
     this.on(timeoutEvent, () => {
@@ -211,6 +215,21 @@ class Logger extends Writable {
    */
   _write(ch, enc, cb) {
     this.drained = false;
+
+    if (this.reconnectFailed) {
+      this.ringBuffer.read();
+
+      if (this.ringBuffer.isEmpty()) {
+        this.emit(bufferDrainEvent);
+        // this event is DEPRECATED - will be removed in next major release.
+        // new users should use 'buffer drain' event instead.
+        this.emit('connection drain');
+      }
+
+      cb();
+      return;
+    }
+
     this.connection.then(conn => {
       const record = this.ringBuffer.read();
       if (record) {
@@ -233,8 +252,15 @@ class Logger extends Writable {
       }
       cb();
     }).catch(err => {
-      this.emit(errorEvent, err);
-      this.debugLogger.log(`Error: ${err}`);
+      if (err instanceof ReconnectFailedError) {
+        this.ringBuffer.read(); // this connection failed, shift the buffer
+        this.reconnectFailed = true;
+        this.debugLogger.log('Error: Reconnect failed');
+      } else {
+        this.emit(errorEvent, err);
+        this.debugLogger.log(`Error: ${err}`);
+      }
+
       cb();
     });
   }
@@ -413,12 +439,12 @@ class Logger extends Writable {
       initialDelay: this.reconnectInitialDelay,
       maxDelay: this.reconnectMaxDelay,
       strategy: this.reconnectBackoffStrategy,
-      failAfter: Infinity,
+      failAfter: this.reconnectFailAfter,
       randomisationFactor: 0,
       immediate: false
     });
 
-    this.connection = new Promise((resolve) => {
+    this.connection = new Promise((resolve, reject) => {
       const connOpts = {
         host: this.host,
         port: this.port
@@ -442,6 +468,10 @@ class Logger extends Writable {
         }
       });
 
+      this.reconnection.once('fail', () => {
+        reject(new ReconnectFailedError());
+      });
+
       this.reconnection.once('disconnect', () => {
         this.debugLogger.log('Socket was disconnected');
         this.connection = null;
@@ -579,6 +609,14 @@ class Logger extends Writable {
     this._json = val;
   }
 
+  get reconnectFailed() {
+    return this._reconnectFailed;
+  }
+
+  set reconnectFailed(val) {
+    this._reconnectFailed = val;
+  }
+
   get reconnectMaxDelay() {
     return this._reconnectMaxDelay;
   }
@@ -595,6 +633,14 @@ class Logger extends Writable {
     this._reconnectInitialDelay = val;
   }
 
+  get reconnectFailAfter() {
+    return this._reconnectFailAfter;
+  }
+
+  set reconnectFailAfter(val) {
+    this._reconnectFailAfter = val;
+  }
+
   get reconnectBackoffStrategy() {
     return this._reconnectBackoffStrategy;
   }
diff --git a/src/ringbuffer.js b/src/ringbuffer.js
index e2c467b..628a725 100644
--- a/src/ringbuffer.js
+++ b/src/ringbuffer.js
@@ -27,6 +27,11 @@ class RingBuffer extends EventEmitter {
     return this.records.shift();
   }
 
+  empty() {
+    this.bufferWasFull = false;
+    this.records = [];
+  }
+
   isEmpty() {
     return this.records.length === 0;
   }
diff --git a/test/test.js b/test/test.js
index 939b2ea..bcb2e36 100644
--- a/test/test.js
+++ b/test/test.js
@@ -3,6 +3,7 @@
 'use strict';
 
 const _ = require('lodash');
+const EventEmitter = require('events');
 const bunyan = require('bunyan');
 const defaults = require('../lib/defaults.js');
 const levels = require('../lib/levels.js');
@@ -660,6 +661,58 @@ tape('Socket is not closed after inactivity timeout when buffer is not empty.',
   logger.log(lvl, 'first log');
 });
 
+tape('Socket will not reconnect indefinitely when fail after is configured', function (t) {
+  t.plan(5);
+  t.timeoutAfter(1000);
+  const lvl = defaults.levels[3];
+  const tkn = x;
+  const logger = new Logger({ token: x, reconnectFailAfter: 3, reconnectInitialDelay: 100, reconnectMaxDelay: 101 });
+
+  const mock = new mitm();
+  let retryCounter = 0;
+
+  const origConnect = mock.connect;
+
+  const sendMoreLogs = () => {
+    mock.connect = origConnect;
+
+    mock.on('connection', (socket) => {
+      socket.once('data', (buffer) => {
+        const log = buffer.toString();
+        const expectedLog = [tkn, lvl, 'other log' + '\n'].join(' ');
+        t.equals(log, expectedLog, 'log received.');
+        mock.disable();
+      });
+    });
+
+    logger.log(lvl, 'other log');
+  };
+
+  logger.once('buffer drain', sendMoreLogs);
+
+  mock.connect = function() {
+    const emitter = new EventEmitter();
+
+    // mock properties
+    emitter.end = _.noop;
+    emitter.setTimeout = _.noop;
+    emitter.server = new EventEmitter();
+
+    t.true(retryCounter <= 3, `retry ${retryCounter}`);
+    retryCounter += 1;
+
+    setTimeout(() => {
+      emitter.emit('error', new Error('connection failed'))
+    }, 0);
+
+    return emitter;
+  };
+
+  mock.enable();
+
+  logger.log(lvl, 'test log 1');
+  logger.log(lvl, 'test log 2');
+});
 
 tape('RingBuffer buffers and shifts when it is full', function (t) {
   t.plan(5);