diff --git a/lib/coffeescript/command.js b/lib/coffeescript/command.js
index 0f7ba90329..3526c5dda2 100644
--- a/lib/coffeescript/command.js
+++ b/lib/coffeescript/command.js
@@ -45,7 +45,7 @@
   BANNER = 'Usage: coffee [options] path/to/script.coffee [args]\n\nIf called without options, `coffee` will run your script.';
 
   // The list of all the valid option flags that `coffee` knows how to handle.
-  SWITCHES = [['-b', '--bare', 'compile without a top-level function wrapper'], ['-c', '--compile', 'compile to JavaScript and save as .js files'], ['-e', '--eval', 'pass a string from the command line as input'], ['-h', '--help', 'display this help message'], ['-i', '--interactive', 'run an interactive CoffeeScript REPL'], ['-j', '--join [FILE]', 'concatenate the source CoffeeScript before compiling'], ['-m', '--map', 'generate source map and save as .js.map files'], ['-M', '--inline-map', 'generate source map and include it directly in output'], ['-n', '--nodes', 'print out the parse tree that the parser produces'], ['--nodejs [ARGS]', 'pass options directly to the "node" binary'], ['--no-header', 'suppress the "Generated by" header'], ['-o', '--output [DIR]', 'set the output directory for compiled JavaScript'], ['-p', '--print', 'print out the compiled JavaScript'], ['-r', '--require [MODULE*]', 'require the given module before eval or REPL'], ['-s', '--stdio', 'listen for and compile scripts over stdio'], ['-l', '--literate', 'treat stdio as literate style coffeescript'], ['-t', '--tokens', 'print out the tokens that the lexer/rewriter produce'], ['-v', '--version', 'display the version number'], ['-w', '--watch', 'watch scripts for changes and rerun commands']];
+  SWITCHES = [['-b', '--bare', 'compile without a top-level function wrapper'], ['-c', '--compile', 'compile to JavaScript and save as .js files'], ['-e', '--eval', 'pass a string from the command line as input'], ['-h', '--help', 'display this help message'], ['-i', '--interactive', 'run an interactive CoffeeScript REPL'], ['-j', '--join [FILE]', 'concatenate the source CoffeeScript before compiling'], ['-m', '--map', 'generate source map and save as .js.map files'], ['-M', '--inline-map', 'generate source map and include it directly in output'], ['-n', '--nodes', 'print out the parse tree that the parser produces'], ['--nodejs [ARGS]', 'pass options directly to the "node" binary'], ['--no-header', 'suppress the "Generated by" header'], ['-o', '--output [PATH]', 'set the output path or path/filename for compiled JavaScript'], ['-p', '--print', 'print out the compiled JavaScript'], ['-r', '--require [MODULE*]', 'require the given module before eval or REPL'], ['-s', '--stdio', 'listen for and compile scripts over stdio'], ['-l', '--literate', 'treat stdio as literate style coffeescript'], ['-t', '--tokens', 'print out the tokens that the lexer/rewriter produce'], ['-v', '--version', 'display the version number'], ['-w', '--watch', 'watch scripts for changes and rerun commands']];
 
   // Top-level objects shared by all the functions.
   opts = {};
@@ -68,7 +68,7 @@
   // Many flags cause us to divert before compiling anything. Flags passed after
   // `--` will be passed verbatim to your script as arguments in `process.argv`
   exports.run = function() {
-    var err, i, len, literals, ref, replCliOpts, results, source;
+    var err, i, len, literals, outputBasename, ref, replCliOpts, results, source;
     optionParser = buildCSOptionParser();
     try {
       parseOptions();
@@ -117,7 +117,16 @@
     process.argv = process.argv.slice(0, 2).concat(literals);
     process.argv[0] = 'coffee';
     if (opts.output) {
-      opts.output = path.resolve(opts.output);
+      outputBasename = path.basename(opts.output);
+      if (indexOf.call(outputBasename, '.') >= 0 && (outputBasename !== '.' && outputBasename !== '..') && !helpers.ends(opts.output, path.sep)) {
+        // An output filename was specified, e.g. `/dist/scripts.js`.
+        opts.outputFilename = outputBasename;
+        opts.outputPath = path.resolve(path.dirname(opts.output));
+      } else {
+        // An output path was specified, e.g. `/dist`.
+        opts.outputFilename = null;
+        opts.outputPath = path.resolve(opts.output);
+      }
     }
     if (opts.join) {
       opts.join = path.resolve(opts.join);
@@ -235,43 +244,43 @@
   };
 
   // Compile a single source script, containing the given code, according to the
-  // requested options. If evaluating the script directly sets `__filename`,
+  // requested options. If evaluating the script directly, set `__filename`,
   // `__dirname` and `module.filename` to be correct relative to the script's path.
   compileScript = function(file, input, base = null) {
-    var compiled, err, message, o, options, t, task;
-    o = opts;
+    var compiled, err, message, options, saveTo, task;
     options = compileOptions(file, base);
     try {
-      t = task = {file, input, options};
+      task = {file, input, options};
       CoffeeScript.emit('compile', task);
-      if (o.tokens) {
-        return printTokens(CoffeeScript.tokens(t.input, t.options));
-      } else if (o.nodes) {
-        return printLine(CoffeeScript.nodes(t.input, t.options).toString().trim());
-      } else if (o.run) {
+      if (opts.tokens) {
+        return printTokens(CoffeeScript.tokens(task.input, task.options));
+      } else if (opts.nodes) {
+        return printLine(CoffeeScript.nodes(task.input, task.options).toString().trim());
+      } else if (opts.run) {
         CoffeeScript.register();
         if (opts.prelude) {
-          CoffeeScript.eval(opts.prelude, t.options);
+          CoffeeScript.eval(opts.prelude, task.options);
         }
-        return CoffeeScript.run(t.input, t.options);
-      } else if (o.join && t.file !== o.join) {
+        return CoffeeScript.run(task.input, task.options);
+      } else if (opts.join && task.file !== opts.join) {
         if (helpers.isLiterate(file)) {
-          t.input = helpers.invertLiterate(t.input);
+          task.input = helpers.invertLiterate(task.input);
         }
-        sourceCode[sources.indexOf(t.file)] = t.input;
+        sourceCode[sources.indexOf(task.file)] = task.input;
         return compileJoin();
       } else {
-        compiled = CoffeeScript.compile(t.input, t.options);
-        t.output = compiled;
-        if (o.map) {
-          t.output = compiled.js;
-          t.sourceMap = compiled.v3SourceMap;
+        compiled = CoffeeScript.compile(task.input, task.options);
+        task.output = compiled;
+        if (opts.map) {
+          task.output = compiled.js;
+          task.sourceMap = compiled.v3SourceMap;
         }
         CoffeeScript.emit('success', task);
-        if (o.print) {
-          return printLine(t.output.trim());
-        } else if (o.compile || o.map) {
-          return writeJs(base, t.file, t.output, options.jsPath, t.sourceMap);
+        if (opts.print) {
+          return printLine(task.output.trim());
+        } else if (opts.compile || opts.map) {
+          saveTo = opts.outputFilename && sources.length === 1 ? path.join(opts.outputPath, opts.outputFilename) : options.jsPath;
+          return writeJs(base, task.file, task.output, saveTo, task.sourceMap);
         }
       }
     } catch (error) {
@@ -281,7 +290,7 @@
         return;
       }
       message = (err != null ? err.stack : void 0) || `${err}`;
-      if (o.watch) {
+      if (opts.watch) {
         return printLine(message + '\x07');
       } else {
         printWarn(message);
@@ -486,13 +495,7 @@
     var basename, dir, srcDir;
     basename = helpers.baseFileName(source, true, useWinPathSep);
     srcDir = path.dirname(source);
-    if (!opts.output) {
-      dir = srcDir;
-    } else if (source === base) {
-      dir = opts.output;
-    } else {
-      dir = path.join(opts.output, path.relative(base, srcDir));
-    }
+    dir = !opts.outputPath ? srcDir : source === base ? opts.outputPath : path.join(opts.outputPath, path.relative(base, srcDir));
     return path.join(dir, basename + extension);
   };
 
diff --git a/src/command.coffee b/src/command.coffee
index fc0b318d42..d9e62627e5 100644
--- a/src/command.coffee
+++ b/src/command.coffee
@@ -32,25 +32,25 @@ BANNER = '''
 
 # The list of all the valid option flags that `coffee` knows how to handle.
 SWITCHES = [
-  ['-b', '--bare',            'compile without a top-level function wrapper']
-  ['-c', '--compile',         'compile to JavaScript and save as .js files']
-  ['-e', '--eval',            'pass a string from the command line as input']
-  ['-h', '--help',            'display this help message']
-  ['-i', '--interactive',     'run an interactive CoffeeScript REPL']
-  ['-j', '--join [FILE]',     'concatenate the source CoffeeScript before compiling']
-  ['-m', '--map',             'generate source map and save as .js.map files']
-  ['-M', '--inline-map',      'generate source map and include it directly in output']
-  ['-n', '--nodes',           'print out the parse tree that the parser produces']
-  [      '--nodejs [ARGS]',   'pass options directly to the "node" binary']
-  [      '--no-header',       'suppress the "Generated by" header']
-  ['-o', '--output [DIR]',    'set the output directory for compiled JavaScript']
-  ['-p', '--print',           'print out the compiled JavaScript']
+  ['-b', '--bare',              'compile without a top-level function wrapper']
+  ['-c', '--compile',           'compile to JavaScript and save as .js files']
+  ['-e', '--eval',              'pass a string from the command line as input']
+  ['-h', '--help',              'display this help message']
+  ['-i', '--interactive',       'run an interactive CoffeeScript REPL']
+  ['-j', '--join [FILE]',       'concatenate the source CoffeeScript before compiling']
+  ['-m', '--map',               'generate source map and save as .js.map files']
+  ['-M', '--inline-map',        'generate source map and include it directly in output']
+  ['-n', '--nodes',             'print out the parse tree that the parser produces']
+  [      '--nodejs [ARGS]',     'pass options directly to the "node" binary']
+  [      '--no-header',         'suppress the "Generated by" header']
+  ['-o', '--output [PATH]',     'set the output path or path/filename for compiled JavaScript']
+  ['-p', '--print',             'print out the compiled JavaScript']
   ['-r', '--require [MODULE*]', 'require the given module before eval or REPL']
-  ['-s', '--stdio',           'listen for and compile scripts over stdio']
-  ['-l', '--literate',        'treat stdio as literate style coffeescript']
-  ['-t', '--tokens',          'print out the tokens that the lexer/rewriter produce']
-  ['-v', '--version',         'display the version number']
-  ['-w', '--watch',           'watch scripts for changes and rerun commands']
+  ['-s', '--stdio',             'listen for and compile scripts over stdio']
+  ['-l', '--literate',          'treat stdio as literate style coffeescript']
+  ['-t', '--tokens',            'print out the tokens that the lexer/rewriter produce']
+  ['-v', '--version',           'display the version number']
+  ['-w', '--watch',             'watch scripts for changes and rerun commands']
 ]
 
 # Top-level objects shared by all the functions.
@@ -102,7 +102,19 @@ exports.run = ->
   process.argv = process.argv[0..1].concat literals
   process.argv[0] = 'coffee'
 
-  opts.output = path.resolve opts.output  if opts.output
+  if opts.output
+    outputBasename = path.basename opts.output
+    if '.' in outputBasename and
+       outputBasename not in ['.', '..'] and
+       not helpers.ends(opts.output, path.sep)
+      # An output filename was specified, e.g. `/dist/scripts.js`.
+      opts.outputFilename = outputBasename
+      opts.outputPath = path.resolve path.dirname opts.output
+    else
+      # An output path was specified, e.g. `/dist`.
+      opts.outputFilename = null
+      opts.outputPath = path.resolve opts.output
+
   if opts.join
     opts.join = path.resolve opts.join
     console.error '''
@@ -167,7 +179,7 @@ compilePath = (source, topLevel, base) ->
       code = fs.readFileSync source
     catch err
       if err.code is 'ENOENT' then return else throw err
-    compileScript(source, code.toString(), base)
+    compileScript source, code.toString(), base
   else
     notSources[source] = yes
 
@@ -182,43 +194,46 @@ findDirectoryIndex = (source) ->
   process.exit 1
 
 # Compile a single source script, containing the given code, according to the
-# requested options. If evaluating the script directly sets `__filename`,
+# requested options. If evaluating the script directly, set `__filename`,
 # `__dirname` and `module.filename` to be correct relative to the script's path.
 compileScript = (file, input, base = null) ->
-  o = opts
   options = compileOptions file, base
   try
-    t = task = {file, input, options}
+    task = {file, input, options}
     CoffeeScript.emit 'compile', task
-    if o.tokens
-      printTokens CoffeeScript.tokens t.input, t.options
-    else if o.nodes
-      printLine CoffeeScript.nodes(t.input, t.options).toString().trim()
-    else if o.run
+    if opts.tokens
+      printTokens CoffeeScript.tokens task.input, task.options
+    else if opts.nodes
+      printLine CoffeeScript.nodes(task.input, task.options).toString().trim()
+    else if opts.run
       CoffeeScript.register()
-      CoffeeScript.eval opts.prelude, t.options if opts.prelude
-      CoffeeScript.run t.input, t.options
-    else if o.join and t.file isnt o.join
-      t.input = helpers.invertLiterate t.input if helpers.isLiterate file
-      sourceCode[sources.indexOf(t.file)] = t.input
+      CoffeeScript.eval opts.prelude, task.options if opts.prelude
+      CoffeeScript.run task.input, task.options
+    else if opts.join and task.file isnt opts.join
+      task.input = helpers.invertLiterate task.input if helpers.isLiterate file
+      sourceCode[sources.indexOf(task.file)] = task.input
       compileJoin()
     else
-      compiled = CoffeeScript.compile t.input, t.options
-      t.output = compiled
-      if o.map
-        t.output = compiled.js
-        t.sourceMap = compiled.v3SourceMap
+      compiled = CoffeeScript.compile task.input, task.options
+      task.output = compiled
+      if opts.map
+        task.output = compiled.js
+        task.sourceMap = compiled.v3SourceMap
 
       CoffeeScript.emit 'success', task
-      if o.print
-        printLine t.output.trim()
-      else if o.compile or o.map
-        writeJs base, t.file, t.output, options.jsPath, t.sourceMap
+      if opts.print
+        printLine task.output.trim()
+      else if opts.compile or opts.map
+        saveTo = if opts.outputFilename and sources.length is 1
+          path.join opts.outputPath, opts.outputFilename
+        else
+          options.jsPath
+        writeJs base, task.file, task.output, saveTo, task.sourceMap
   catch err
     CoffeeScript.emit 'failure', err, task
     return if CoffeeScript.listeners('failure').length
     message = err?.stack or "#{err}"
-    if o.watch
+    if opts.watch
       printLine message + '\x07'
     else
       printWarn message
@@ -352,12 +367,12 @@ silentUnlink = (path) ->
 outputPath = (source, base, extension=".js") ->
   basename  = helpers.baseFileName source, yes, useWinPathSep
   srcDir    = path.dirname source
-  if not opts.output
-    dir = srcDir
+  dir = unless opts.outputPath
+    srcDir
   else if source is base
-    dir = opts.output
+    opts.outputPath
   else
-    dir = path.join opts.output, path.relative base, srcDir
+    path.join opts.outputPath, path.relative base, srcDir
   path.join dir, basename + extension
 
 # Recursively mkdir, like `mkdir -p`.
diff --git a/test/argument_parsing.coffee b/test/argument_parsing.coffee
index c82a3136e9..2ed4fdb8c7 100644
--- a/test/argument_parsing.coffee
+++ b/test/argument_parsing.coffee
@@ -130,7 +130,7 @@ If called without options, `coffee` will run your script.
   -n, --nodes        print out the parse tree that the parser produces
       --nodejs       pass options directly to the "node" binary
       --no-header    suppress the "Generated by" header
-  -o, --output       set the output directory for compiled JavaScript
+  -o, --output       set the output path or path/filename for compiled JavaScript
   -p, --print        print out the compiled JavaScript
   -r, --require      require the given module before eval or REPL
   -s, --stdio        listen for and compile scripts over stdio