diff --git a/lib/configuration.js b/lib/configuration.js
index 59638bce8..9ac2b57f2 100644
--- a/lib/configuration.js
+++ b/lib/configuration.js
@@ -1,5 +1,6 @@
 const clone = require('clone');
 const { EventEmitter } = require('events');
+const { format } = require('winston')
 
 const logger = require('./logger');
 const reporterOutputLogger = require('./reporters/reporterOutputLogger');
@@ -20,33 +21,87 @@ function coerceToBoolean(value) {
   return false;
 }
 
+function validateLogLevel(level, levels) {
+  if (!levels.includes(level)) {
+    throw new Error(`The logging level '${level}' is unsupported, `
+      + 'supported are: silent, error, warning, debug');
+  }
+
+  return true;
+}
+
+/**
+ * @returns {string}
+ */
+function getLogLevel(options) {
+  const supportedLogLevels = [
+    'silent',
+    'warning',
+    'warn',
+    'debug',
+    'error',
+  ];
+  const { loglevel } = options;
+  const defaultLogLevel = 'warn';
+
+  return loglevel && validateLogLevel(loglevel, supportedLogLevels)
+    ? loglevel
+    : defaultLogLevel;
+}
 
 function applyLoggingOptions(options) {
   if (options.color === false) {
-    logger.transports.console.colorize = false;
-    reporterOutputLogger.transports.console.colorize = false;
+    [logger, reporterOutputLogger].forEach((loggerInstance) => {
+      loggerInstance.configure({
+        format: format.colorize(false),
+      });
+    });
+    // logger.transports.console.colorize = false;
+    // reporterOutputLogger.transports.console.colorize = false;
   }
 
-  // Handling the 'loglevel' value
-  if (options.loglevel) {
-    const loglevel = options.loglevel.toLowerCase();
-    if (loglevel === 'silent') {
-      logger.transports.console.silent = true;
-    } else if (loglevel === 'warning') {
-      logger.transports.console.level = 'warn';
-    } else if (loglevel === 'debug') {
-      logger.transports.console.level = 'debug';
-      logger.transports.console.timestamp = true;
-    } else if (['warn', 'error'].includes(loglevel)) {
-      logger.transports.console.level = loglevel;
-    } else {
-      logger.transports.console.level = 'warn';
-      throw new Error(`The logging level '${loglevel}' is unsupported, `
-        + 'supported are: silent, error, warning, debug');
-    }
-  } else {
-    logger.transports.console.level = 'warn';
+  const loglevel = getLogLevel(options);
+
+  switch (loglevel) {
+    case 'silent':
+      logger.configure({ silent: true });
+      break;
+
+    case 'warning':
+      logger.configure({ level: 'warn' });
+      break;
+
+    case 'debug':
+      logger.configure({
+        level: loglevel,
+        format: format.timestamp(),
+      });
+      break;
+
+    default:
+      logger.configure({ level: loglevel });
   }
+
+  // Handling the 'loglevel' value
+  // if (logLevel) {
+  //   const loglevel = options.loglevel.toLowerCase();
+  //   if (loglevel === 'silent') {
+  //     logger.transports.console.silent = true;
+  //   } else if (loglevel === 'warning') {
+  //     logger.transports.console.level = 'warn';
+  //   } else if (loglevel === 'debug') {
+  //     logger.transports.console.level = 'debug';
+  //     logger.transports.console.timestamp = true;
+  //   } else if (['warn', 'error'].includes(loglevel)) {
+  //     logger.transports.console.level = loglevel;
+  //   } else {
+  //     logger.transports.console.level = 'warn';
+  //     throw new Error(`The logging level '${loglevel}' is unsupported, `
+  //       + 'supported are: silent, error, warning, debug');
+  //   }
+  // } else {
+  //   logger.transports.console.level = 'warn';
+  // }
 }
 
 
diff --git a/lib/logger.js b/lib/logger.js
index 97e27005d..850c1e58e 100644
--- a/lib/logger.js
+++ b/lib/logger.js
@@ -1,17 +1,19 @@
-const winston = require('winston');
+const { createLogger, transports, format } = require('winston');
 
-module.exports = new (winston.Logger)({
+module.exports = createLogger({
   transports: [
-    new (winston.transports.Console)({ colorize: true }),
+    new transports.Console({ colorize: true }),
   ],
   levels: {
     debug: 2,
     warn: 1,
     error: 0,
   },
-  colors: {
-    debug: 'cyan',
-    warn: 'yellow',
-    error: 'red',
-  },
+  format: format.colorize({
+    colors: {
+      debug: 'cyan',
+      warn: 'yellow',
+      error: 'red',
+    },
+  }),
 });
diff --git a/lib/reporters/reporterOutputLogger.js b/lib/reporters/reporterOutputLogger.js
index 93b8cf03c..6d7b37eb0 100644
--- a/lib/reporters/reporterOutputLogger.js
+++ b/lib/reporters/reporterOutputLogger.js
@@ -1,8 +1,8 @@
-const winston = require('winston');
+const { createLogger, transports, format } = require('winston');
 
-module.exports = new (winston.Logger)({
+module.exports = createLogger({
   transports: [
-    new (winston.transports.Console)({ colorize: true, level: 'info' }),
+    new transports.Console({ colorize: true, level: 'info' }),
   ],
   levels: {
     info: 10,
@@ -17,17 +17,19 @@ module.exports = new (winston.Logger)({
     skip: 1,
     error: 0,
   },
-  colors: {
-    info: 'blue',
-    test: 'yellow',
-    pass: 'green',
-    fail: 'red',
-    complete: 'green',
-    actual: 'red',
-    expected: 'red',
-    hook: 'green',
-    request: 'green',
-    skip: 'yellow',
-    error: 'red',
-  },
+  format: format.colorize({
+    colors: {
+      info: 'blue',
+      test: 'yellow',
+      pass: 'green',
+      fail: 'red',
+      complete: 'green',
+      actual: 'red',
+      expected: 'red',
+      hook: 'green',
+      request: 'green',
+      skip: 'yellow',
+      error: 'red',
+    },
+  }),
 });
diff --git a/package.json b/package.json
index 1193952fe..e3b642eb0 100644
--- a/package.json
+++ b/package.json
@@ -56,7 +56,7 @@
     "untildify": "3.0.3",
     "uuid": "3.3.2",
     "which": "1.3.1",
-    "winston": "2.4.0"
+    "winston": "3.2.1"
   },
   "devDependencies": {
     "@commitlint/cli": "7.5.2",
diff --git a/test/integration/helpers.js b/test/integration/helpers.js
index c9abe976b..2433dd11d 100644
--- a/test/integration/helpers.js
+++ b/test/integration/helpers.js
@@ -1,4 +1,5 @@
 const async = require('async');
+const sinon = require('sinon');
 const bodyParser = require('body-parser');
 const clone = require('clone');
 const express = require('express');
@@ -23,28 +24,44 @@ const DREDD_BIN = require.resolve('../../bin/dredd');
 //                  from the 'fn' function
 // - logging (string) - the recorded logging output
 function recordLogging(fn, callback) {
-  const loggerSilent = !!logger.transports.console.silent;
-  const reporterOutputLoggerSilent = !!reporterOutputLogger.transports.console.silent;
+  let logging = '';
+  const loggerSilent = !!logger.silent;
+  const reporterOutputLoggerSilent = !!reporterOutputLogger.silent;
 
   // Supress Dredd's console output (remove if debugging)
-  logger.transports.console.silent = true;
-  reporterOutputLogger.transports.console.silent = true;
+  [logger, reporterOutputLogger].forEach((loggerInstance) => {
+    loggerInstance.configure({ silent: true });
+
+    if (!loggerInstance.log.wrappedMethod) {
+      sinon.stub(loggerInstance, 'log').callsFake((level, message) => {
+        const nextLogging = `${level}: ${message}\n`;
+        console.log({nextLogging})
+        logging += nextLogging
+      });
+    }
+  });
 
-  let logging = '';
-  const record = (transport, level, message) => {
-    logging += `${level}: ${message}\n`;
-  };
+  // logger.transports.console.silent = true;
+  // reporterOutputLogger.transports.console.silent = true;
+
+  // const record = (transport, level, message) => {
+  //   logging += `${level}: ${message}\n`;
+  // };
 
-  logger.on('logging', record);
-  reporterOutputLogger.on('logging', record);
+  /**
+   * @todo "logging" is deprecated, replace.
+   */
+  // logger.on('logging', record);
+  // reporterOutputLogger.on('logging', record);
 
   fn((...args) => {
-    logger.removeListener('logging', record);
-    logger.transports.console.silent = loggerSilent;
+    // logger.removeListener('logging', record);
+    logger.configure({ silent: loggerSilent });
 
-    reporterOutputLogger.removeListener('logging', record);
-    reporterOutputLogger.transports.console.silent = reporterOutputLoggerSilent;
+    // reporterOutputLogger.removeListener('logging', record);
+    reporterOutputLogger.configure({ silent: reporterOutputLoggerSilent });
 
+    console.log('callbacking', logging)
     callback(null, args, logging);
   });
 }
diff --git a/test/integration/proxy-test.js b/test/integration/proxy-test.js
index a8010a24c..103312ea7 100644
--- a/test/integration/proxy-test.js
+++ b/test/integration/proxy-test.js
@@ -27,6 +27,7 @@ function createAndRunDredd(configuration, done) {
     dredd.configuration.http.strictSSL = false;
     next();
   }, (err, args, dreddInitLogging) => runDredd(dredd, (error, info) => {
+    console.log({dreddInitLogging, info})
     info.logging = `${dreddInitLogging}\n${info.logging}`;
     done(error, info);
   }));
diff --git a/test/unit/reporters/CLIReporter-test.js b/test/unit/reporters/CLIReporter-test.js
index 764d31cec..154e728fd 100644
--- a/test/unit/reporters/CLIReporter-test.js
+++ b/test/unit/reporters/CLIReporter-test.js
@@ -11,19 +11,10 @@ const CLIReporter = proxyquire('../../../lib/reporters/CLIReporter', {
   './reporterOutputLogger': reporterOutputLoggerStub,
 });
 
+
 describe('CLIReporter', () => {
   let test = {};
 
-  before(() => {
-    loggerStub.transports.console.silent = true;
-    reporterOutputLoggerStub.transports.console.silent = true;
-  });
-
-  after(() => {
-    loggerStub.transports.console.silent = false;
-    reporterOutputLoggerStub.transports.console.silent = false;
-  });
-
   describe('when starting', () => {
     beforeEach(() => sinon.spy(loggerStub, 'debug'));