diff --git a/pipenv/cli.py b/pipenv/cli.py
index 06ab84b5..df2f7e7b 100644
--- a/pipenv/cli.py
+++ b/pipenv/cli.py
@@ -138,13 +138,11 @@ def add_to_path(p):
 @background.task
 def check_for_updates():
     """Background thread -- beautiful, isn't it?"""
-    if not need_update_check():
-        return
     try:
+        checked_for_updates()
         r = requests.get('https://pypi.python.org/pypi/pipenv/json', timeout=0.5)
         latest = max(map(semver.parse_version_info, r.json()['releases'].keys()))
         current = semver.parse_version_info(__version__)
-        checked_for_updates()
 
         if latest > current:
             click.echo('{0}: {1} is now available. You get bonus points for upgrading ($ {})!'.format(
@@ -158,6 +156,7 @@ def check_for_updates():
 
 def ensure_latest_self(user=False):
     """Updates Pipenv to latest version, cleverly."""
+    checked_for_updates()
     try:
         r = requests.get('https://pypi.python.org/pypi/pipenv/json', timeout=2)
     except requests.RequestException as e:
@@ -165,7 +164,6 @@ def ensure_latest_self(user=False):
         sys.exit(1)
     latest = max(map(semver.parse_version_info, r.json()['releases'].keys()))
     current = semver.parse_version_info(__version__)
-    checked_for_updates()
 
     if current < latest:
 
@@ -1624,7 +1622,7 @@ def cli(
         # Awesome sauce.
         click.echo(crayons.normal(xyzzy, bold=True))
 
-    if not update:
+    if not update and need_update_check():
         # Spun off in background thread, not unlike magic.
         check_for_updates()
     else:
diff --git a/pipenv/utils.py b/pipenv/utils.py
index b305effa..9f35c366 100644
--- a/pipenv/utils.py
+++ b/pipenv/utils.py
@@ -955,7 +955,7 @@ def need_update_check():
     if not os.path.exists(p):
         return True
     out_of_date_time = time() - (24 * 60 * 60)
-    if os.path.isfile(p) and os.stat(p).st_mtime <= out_of_date_time:
+    if os.path.isfile(p) and os.path.getmtime(p) <= out_of_date_time:
         return True
     else:
         return False
@@ -964,6 +964,9 @@ def need_update_check():
 def checked_for_updates():
     mkdir_p(PIPENV_CACHE_DIR)
     p = os.sep.join((PIPENV_CACHE_DIR, '.pipenv_update_check'))
-    with open(p, 'w') as fh:
-        fh.write('')
+    try:
+        os.utime(p)
+    except FileNotFoundError:
+        with open(p, 'w') as fh:
+            fh.write('')
     return True