diff --git a/bin/ts-node-dev b/bin/ts-node-dev
old mode 100644
new mode 100755
diff --git a/lib/index.js b/lib/index.js
index ff1a995..d6596f2 100755
--- a/lib/index.js
+++ b/lib/index.js
@@ -8,6 +8,8 @@ var tsNodeVersion = require('ts-node').VERSION
 var tsVersion = require('typescript').version
 var kill = require('tree-kill')
 var readline = require('readline')
+var path = require('path')
+var chokidar = require('chokidar')
 
 module.exports = function(script, scriptArgs, nodeArgs, opts) {
   if (typeof script !== 'string' || script.length === 0) {
@@ -38,6 +40,7 @@ module.exports = function(script, scriptArgs, nodeArgs, opts) {
   // Run ./dedupe.js as preload script
   if (cfg.dedupe) process.env.NODE_DEV_PRELOAD = __dirname + '/dedupe'
 
+  var chokidarWatches = []
   var watcher = filewatcher({
     forcePolling: opts.poll,
     interval: parseInt(opts.interval),
@@ -150,7 +153,14 @@ module.exports = function(script, scriptArgs, nodeArgs, opts) {
 
     // Upon errors, display a notification and tell the child to exit.
     ipc.on(child, 'error', function(m) {
-      log.debug('Child error')
+      log.debug('Child error', m)
+      var lastRequire = m.lastRequire
+      if (m.code === 'MODULE_NOT_FOUND' && lastRequire && lastRequire.path.startsWith('.')) {
+        var pathNoExt = path.normalize(path.join(path.dirname(lastRequire.filename), lastRequire.path))
+        var watch = chokidar.watch([pathNoExt + '.ts', pathNoExt + '.tsx'])
+        watch.on('all', (arg, file) => restart(file, false))
+        chokidarWatches.push(watch)
+      }
       notify(m.error, m.message, 'error')
       stop(m.willTerminate)
     })
@@ -199,6 +209,8 @@ module.exports = function(script, scriptArgs, nodeArgs, opts) {
       return
     }
     log.debug('Removing all watchers from files')
+    chokidarWatches.forEach(nw => nw.close())
+    chokidarWatches = []
     watcher.removeAll()
     starting = true
     if (child) {
diff --git a/lib/wrap.js b/lib/wrap.js
index 486e40f..988efd2 100755
--- a/lib/wrap.js
+++ b/lib/wrap.js
@@ -1,3 +1,4 @@
+var Module = require('module')
 var path = require('path');
 var childProcess = require('child_process');
 var fork = childProcess.fork;
@@ -21,6 +22,15 @@ if (process.env.NODE_DEV_PRELOAD) {
   require(process.env.NODE_DEV_PRELOAD);
 }
 
+// We hook on the require call to keep track of the last required files in case there's a
+// MODULE_NOT_FOUND error for file watching
+var lastRequire = null;
+var origRequire = Module.prototype.require;
+Module.prototype.require = function (requirePath) {
+  lastRequire = { path: requirePath, filename: this.filename };
+  return origRequire.apply(this, arguments);
+};
+
 // Listen SIGTERM and exit unless there is another listener
 process.on('SIGTERM', function () {
   if (process.listeners('SIGTERM').length === 1) process.exit(0);
@@ -45,13 +55,16 @@ process.on('uncaughtException', function (err) {
   // If there's a custom uncaughtException handler expect it to terminate
   // the process.
   var hasCustomHandler = process.listeners('uncaughtException').length > 1;
-  var isTsError = err.message && /TypeScript/.test(err.message)
-  if (!hasCustomHandler &&  !isTsError) {
+  var isTsError = err.message && /TypeScript/.test(err.message);
+  if (!hasCustomHandler && !isTsError) {
     console.error(err.stack || err);
-  }    
+  }
+
   ipc.send({
     error: isTsError ? '' : err.name || 'Error',
     message: err.message,
+    code: err.code,
+    lastRequire: lastRequire,
     willTerminate: hasCustomHandler
   });
 });
diff --git a/package.json b/package.json
index 1b117e2..955e4d0 100644
--- a/package.json
+++ b/package.json
@@ -43,6 +43,7 @@
     "test-docker": "docker run --rm -v ${PWD}:/app mhart/alpine-node:8.7.0 sh -c 'cd app && node ./bin/ts-node-dev --cache-directory .ts-node test/ts/big'"
   },
   "dependencies": {
+    "chokidar": "^3.1.0",
     "dateformat": "~1.0.4-1.2.3",
     "dynamic-dedupe": "^0.3.0",
     "filewatcher": "~3.0.0",
@@ -50,7 +51,7 @@
     "mkdirp": "^0.5.1",
     "node-notifier": "^5.4.0",
     "resolve": "^1.0.0",
-    "rimraf": "^2.6.1",
+    "rimraf": "^2.7.1",
     "source-map-support": "^0.5.12",
     "tree-kill": "^1.2.1",
     "ts-node": "*",