diff --git a/pavelib/paver_tests/test_servers.py b/pavelib/paver_tests/test_servers.py
index 348c7089da..3016febb36 100644
--- a/pavelib/paver_tests/test_servers.py
+++ b/pavelib/paver_tests/test_servers.py
@@ -42,9 +42,9 @@ EXPECTED_INDEX_COURSE_COMMAND = (
     u"python manage.py {system} --settings={settings} reindex_course --setup"
 )
 EXPECTED_PRINT_SETTINGS_COMMAND = [
-    u"python manage.py lms --settings={settings} print_setting STATIC_ROOT 2>/dev/null",
-    u"python manage.py cms --settings={settings} print_setting STATIC_ROOT 2>/dev/null",
-    u"python manage.py lms --settings={settings} print_setting WEBPACK_CONFIG_PATH 2>/dev/null"
+    u"python manage.py lms --settings={settings} print_setting STATIC_ROOT 2>{log_file}",
+    u"python manage.py cms --settings={settings} print_setting STATIC_ROOT 2>{log_file}",
+    u"python manage.py lms --settings={settings} print_setting WEBPACK_CONFIG_PATH 2>{log_file}"
 ]
 EXPECTED_WEBPACK_COMMAND = (
     u"NODE_ENV={node_env} STATIC_ROOT_LMS={static_root_lms} STATIC_ROOT_CMS={static_root_cms} "
@@ -243,7 +243,8 @@ class TestPaverServerTasks(PaverTestCase):
             expected_messages.append(u"xmodule_assets common/static/xmodule")
             expected_messages.append(u"install npm_assets")
             expected_messages.extend(
-                [c.format(settings=expected_asset_settings) for c in EXPECTED_PRINT_SETTINGS_COMMAND]
+                [c.format(settings=expected_asset_settings,
+                          log_file=Env.PRINT_SETTINGS_LOG_FILE) for c in EXPECTED_PRINT_SETTINGS_COMMAND]
             )
             expected_messages.append(EXPECTED_WEBPACK_COMMAND.format(
                 node_env="production",
@@ -288,7 +289,8 @@ class TestPaverServerTasks(PaverTestCase):
             expected_messages.append(u"xmodule_assets common/static/xmodule")
             expected_messages.append(u"install npm_assets")
             expected_messages.extend(
-                [c.format(settings=expected_asset_settings) for c in EXPECTED_PRINT_SETTINGS_COMMAND]
+                [c.format(settings=expected_asset_settings,
+                          log_file=Env.PRINT_SETTINGS_LOG_FILE) for c in EXPECTED_PRINT_SETTINGS_COMMAND]
             )
             expected_messages.append(EXPECTED_WEBPACK_COMMAND.format(
                 node_env="production",
diff --git a/pavelib/utils/envs.py b/pavelib/utils/envs.py
index 639b92fbe5..817eee76bb 100644
--- a/pavelib/utils/envs.py
+++ b/pavelib/utils/envs.py
@@ -3,6 +3,7 @@ Helper functions for loading environment settings.
 """
 from __future__ import print_function
 
+import io
 import json
 import os
 import sys
@@ -11,7 +12,7 @@ from time import sleep
 import memcache
 from lazy import lazy
 from path import Path as path
-from paver.easy import sh
+from paver.easy import BuildFailure, sh
 from six.moves import configparser
 
 from pavelib.utils.cmd import django_cmd
@@ -95,6 +96,8 @@ class Env(object):
     # Directory that videos are served from
     VIDEO_SOURCE_DIR = REPO_ROOT / "test_root" / "data" / "video"
 
+    PRINT_SETTINGS_LOG_FILE = BOK_CHOY_LOG_DIR / "print_settings.log"
+
     # Detect if in a Docker container, and if so which one
     SERVER_HOST = os.environ.get('BOK_CHOY_HOSTNAME', '0.0.0.0')
     USING_DOCKER = SERVER_HOST != '0.0.0.0'
@@ -240,17 +243,27 @@ class Env(object):
         """
         if not settings:
             settings = os.environ.get("EDX_PLATFORM_SETTINGS", "aws")
-        value = sh(
-            django_cmd(
-                system,
-                settings,
-                "print_setting {django_setting} 2>/dev/null".format(
-                    django_setting=django_setting
-                )
-            ),
-            capture=True
-        )
-        return unicode(value).strip()
+        log_dir = os.path.dirname(cls.PRINT_SETTINGS_LOG_FILE)
+        if not os.path.exists(log_dir):
+            os.makedirs(log_dir)
+        try:
+            value = sh(
+                django_cmd(
+                    system,
+                    settings,
+                    "print_setting {django_setting} 2>{log_file}".format(
+                        django_setting=django_setting,
+                        log_file=cls.PRINT_SETTINGS_LOG_FILE
+                    )
+                ),
+                capture=True
+            )
+            return unicode(value).strip()
+        except BuildFailure:
+            print("Unable to print the value of the {} setting:".format(django_setting))
+            with io.open(cls.PRINT_SETTINGS_LOG_FILE, 'r') as f:
+                print(f.read())
+            sys.exit(1)
 
     @classmethod
     def covered_modules(cls):