diff --git a/lib/coffee-script/repl.js b/lib/coffee-script/repl.js
index 977f4d42..b4e45629 100644
--- a/lib/coffee-script/repl.js
+++ b/lib/coffee-script/repl.js
@@ -1,6 +1,6 @@
 // Generated by CoffeeScript 1.5.0
 (function() {
-  var CoffeeScript, addMultilineHandler, merge, nodeREPL, replDefaults, vm;
+  var CoffeeScript, CompilerError, addMultilineHandler, merge, nodeREPL, replDefaults, vm;
 
   vm = require('vm');
 
@@ -8,24 +8,29 @@
 
   CoffeeScript = require('./coffee-script');
 
+  CompilerError = require('./error').CompilerError;
+
   merge = require('./helpers').merge;
 
   replDefaults = {
     prompt: 'coffee> ',
     "eval": function(input, context, filename, cb) {
-      var js;
+      var Assign, Block, Literal, Value, ast, js, _ref;
       input = input.replace(/\uFF00/g, '\n');
-      input = input.replace(/(^|[\r\n]+)(\s*)##?(?:[^#\r\n][^\r\n]*|)($|[\r\n])/, '$1$2$3');
-      if (/^\s*$/.test(input)) {
-        return cb(null);
-      }
+      input = input.replace(/^\(([\s\S]*)\n\)$/m, '$1');
+      _ref = require('./nodes'), Block = _ref.Block, Assign = _ref.Assign, Value = _ref.Value, Literal = _ref.Literal;
       try {
-        js = CoffeeScript.compile("_=(" + input + "\n)", {
-          filename: filename,
+        ast = CoffeeScript.nodes(input);
+        ast = new Block([new Assign(new Value(new Literal('_')), ast, '=')]);
+        js = ast.compile({
           bare: true
         });
       } catch (err) {
-        cb(err);
+        if (err instanceof CompilerError) {
+          console.log(err.prettyMessage(filename, input, true));
+        } else {
+          cb(err);
+        }
       }
       return cb(null, vm.runInContext(js, context, filename));
     }
diff --git a/src/repl.coffee b/src/repl.coffee
index c0855b43..fc2631e1 100644
--- a/src/repl.coffee
+++ b/src/repl.coffee
@@ -1,22 +1,35 @@
 vm = require 'vm'
 nodeREPL = require 'repl'
 CoffeeScript = require './coffee-script'
+{CompilerError} = require './error'
 {merge} = require './helpers'
 
 replDefaults =
   prompt: 'coffee> ',
   eval: (input, context, filename, cb) ->
-    # XXX: multiline hack
+    # XXX: multiline hack.
     input = input.replace /\uFF00/g, '\n'
-    # strip single-line comments
-    input = input.replace /(^|[\r\n]+)(\s*)##?(?:[^#\r\n][^\r\n]*|)($|[\r\n])/, '$1$2$3'
-    # empty command
-    return cb null if /^\s*$/.test input
+    # Node's REPL sends the input ending with a newline and then wrapped in
+    # parens. Unwrap all that.
+    input = input.replace /^\(([\s\S]*)\n\)$/m, '$1'
+
+    # Require AST nodes to do some AST manipulation.
+    {Block, Assign, Value, Literal} = require './nodes'
+
     # TODO: fix #1829: pass in-scope vars and avoid accidentally shadowing them by omitting those declarations
     try
-      js = CoffeeScript.compile "_=(#{input}\n)", {filename, bare: yes}
+      # Generate the AST of the clean input.
+      ast = CoffeeScript.nodes input
+      # Add assignment to `_` variable to force the input to be an expression.
+      ast = new Block [
+        new Assign (new Value new Literal '_'), ast, '='
+      ]
+      js = ast.compile bare: yes
     catch err
-      cb err
+      if err instanceof CompilerError
+        console.log err.prettyMessage filename, input, yes
+      else
+        cb err
     cb null, vm.runInContext(js, context, filename)
 
 addMultilineHandler = (repl) ->