diff --git a/src/calibre/srv/users.py b/src/calibre/srv/users.py
index 86e6b7a48f..42a3d57c36 100644
--- a/src/calibre/srv/users.py
+++ b/src/calibre/srv/users.py
@@ -76,8 +76,14 @@ def connect(path, exc_class=ValueError):
         pdir = os.path.dirname(path)
         if os.path.isdir(pdir):
             raise exc_class('Failed to open userdb database at {} with error: {}'.format(path, as_unicode(e)))
-        os.makedirs(pdir)
-        return apsw.Connection(path)
+        try:
+            os.makedirs(pdir)
+        except EnvironmentError as e:
+            raise exc_class('Failed to make directory for userdb database at {} with error: {}'.format(pdir, as_unicode(e)))
+        try:
+            return apsw.Connection(path)
+        except apsw.CantOpenError as e:
+            raise exc_class('Failed to open userdb database at {} with error: {}'.format(path, as_unicode(e)))
 
 
 class UserManager(object):