diff --git a/stapled/core/certfinder.py b/stapled/core/certfinder.py
index 474716d..842bf45 100644
--- a/stapled/core/certfinder.py
+++ b/stapled/core/certfinder.py
@@ -28,6 +28,7 @@
 import fnmatch
 import os
 import stapled
+import errno
 from stapled.core.excepthandler import stapled_except_handle
 from stapled.core.taskcontext import StapleTaskContext
 from stapled.core.certmodel import CertModel
@@ -165,13 +166,15 @@ def _find_new_certs(self, paths, cert_path=None):
                 dirs = []
                 try:
                     dirs = os.listdir(path)
-                except NotADirectoryError:
+                except (OSError, IOError) as exc:
                     # If a path is actually a file we can still use it..
-                    if os.path.isfile(path):
+                    if exc.errno == errno.ENOTDIR and os.path.isfile(path):
                         LOG.debug("%s may be a single file", path)
                         # This will allow us to use our usual iteration.
                         dirs = [os.path.basename(path)]
                         path = os.path.dirname(path)
+                    else:
+                        raise exc
                 for entry in dirs:
                     entry = os.path.join(path, entry)
                     if os.path.isdir(entry):
diff --git a/stapled/core/excepthandler.py b/stapled/core/excepthandler.py
index 47b4269..0120fe6 100755
--- a/stapled/core/excepthandler.py
+++ b/stapled/core/excepthandler.py
@@ -35,6 +35,7 @@
 import datetime
 import logging
 import os
+import errno
 import traceback
 import configargparse
 from stapled.core.exceptions import OCSPBadResponse
@@ -150,8 +151,17 @@ def stapled_except_handle(ctx=None):
             "entries",
             err_count, len_ocsp_urls
         )
-    except PermissionError as exc:
-        LOG.critical(exc)
+    except (IOError, OSError) as exc:
+        if exc.errno==errno.EPERM or exc.errno==errno.EACCES:
+            reason = "Permission error"
+        elif exc.errno==errno.ENOENT:
+            reason = "File not found error"
+        elif isinstance(exc, IOError):
+            reason = "I/O Error"
+        else:
+            reason = "OS Error"
+
+        LOG.critical("{}: {}".format(reason, str(exc)))
 
     # the show must go on..
     except Exception as exc:  # pylint: disable=broad-except