diff --git a/fig/cli/command.py b/fig/cli/command.py
index c60020d750..abf087628a 100644
--- a/fig/cli/command.py
+++ b/fig/cli/command.py
@@ -11,7 +11,7 @@ import yaml
 from ..project import Project
 from .docopt_command import DocoptCommand
 from .formatter import Formatter
-from .utils import cached_property, docker_url
+from .utils import cached_property, docker_url, call_silently, is_mac, is_ubuntu
 from .errors import UserError
 
 log = logging.getLogger(__name__)
@@ -23,7 +23,29 @@ class Command(DocoptCommand):
         try:
             super(Command, self).dispatch(*args, **kwargs)
         except ConnectionError:
-            raise UserError("""
+            if call_silently(['which', 'docker']) != 0:
+                if is_mac():
+                    raise UserError("""
+Couldn't connect to Docker daemon. You might need to install docker-osx:
+
+https://github.com/noplay/docker-osx
+""")
+                elif is_ubuntu():
+                    raise UserError("""
+Couldn't connect to Docker daemon. You might need to install Docker:
+
+http://docs.docker.io/en/latest/installation/ubuntulinux/
+""")
+                else:
+                    raise UserError("""
+Couldn't connect to Docker daemon. You might need to install Docker:
+
+http://docs.docker.io/en/latest/installation/
+""")
+            elif call_silently(['which', 'docker-osx']) == 0:
+                raise UserError("Couldn't connect to Docker daemon - you might need to run `docker-osx shell`.")
+            else:
+                raise UserError("""
 Couldn't connect to Docker daemon at %s - is it running?
 
 If it's at a non-standard location, specify the URL with the DOCKER_HOST environment variable.
diff --git a/fig/cli/utils.py b/fig/cli/utils.py
index 3116df98bd..64b2ea383e 100644
--- a/fig/cli/utils.py
+++ b/fig/cli/utils.py
@@ -4,6 +4,8 @@ from __future__ import division
 import datetime
 import os
 import socket
+import subprocess
+import platform
 from .errors import UserError
 
 
@@ -108,3 +110,19 @@ def split_buffer(reader, separator):
 
     if len(buffered) > 0:
         yield buffered
+
+
+def call_silently(*args, **kwargs):
+    """
+    Like subprocess.call(), but redirects stdout and stderr to /dev/null.
+    """
+    with open(os.devnull, 'w') as shutup:
+        return subprocess.call(*args, stdout=shutup, stderr=shutup, **kwargs)
+
+
+def is_mac():
+    return platform.system() == 'Darwin'
+
+
+def is_ubuntu():
+    return platform.system() == 'Linux' and platform.linux_distribution()[0] == 'Ubuntu'