diff --git a/notebook/services/contents/filemanager.py b/notebook/services/contents/filemanager.py
index d3f851910f..7b50809796 100644
--- a/notebook/services/contents/filemanager.py
+++ b/notebook/services/contents/filemanager.py
@@ -558,6 +558,10 @@ def rename_file(self, old_path, new_path):
         if new_path == old_path:
             return
 
+        # Perform path validation prior to converting to os-specific value since this
+        # is still relative to root_dir.
+        self._validate_path(new_path)
+
         new_os_path = self._get_os_path(new_path)
         old_os_path = self._get_os_path(old_path)
 
@@ -586,3 +590,23 @@ def get_kernel_path(self, path, model=None):
         else:
             parent_dir = ''
         return parent_dir
+
+    @staticmethod
+    def _validate_path(path):
+        """Checks if the path contains invalid characters relative to the current platform"""
+
+        if sys.platform == 'win32':
+            # On Windows systems, we MUST disallow colons otherwise an Alternative Data Stream will
+            # be created and confusion will reign! (See https://github.com/jupyter/notebook/issues/5190)
+            # Go ahead and add other invalid (and non-path-separator) characters here as well so there's
+            # consistent behavior - although all others will result in '[Errno 22]Invalid Argument' errors.
+            invalid_chars = '?:><*"|'
+        else:
+            # On non-windows systems, allow the underlying file creation to perform enforcement when appropriate
+            invalid_chars = ''
+
+        for char in invalid_chars:
+            if char in path:
+                raise web.HTTPError(400, "Path '{}' contains characters that are invalid for the filesystem. "
+                                         "Path names on this filesystem cannot contain any of the following "
+                                         "characters: {}".format(path, invalid_chars))
diff --git a/notebook/services/contents/tests/test_manager.py b/notebook/services/contents/tests/test_manager.py
index 0e6b0fb2b2..22ceda044c 100644
--- a/notebook/services/contents/tests/test_manager.py
+++ b/notebook/services/contents/tests/test_manager.py
@@ -522,6 +522,11 @@ def test_rename(self):
         # Fetching the notebook under the new name is successful
         assert isinstance(cm.get("changed_path"), dict)
 
+        # Test validation.  Currently, only Windows has a non-empty set of invalid characters
+        if sys.platform == 'win32' and isinstance(cm, FileContentsManager):
+            with self.assertRaisesHTTPError(400):
+                cm.rename("changed_path", "prevent: in name")
+
         # Ported tests on nested directory renaming from pgcontents
         all_dirs = ['foo', 'bar', 'foo/bar', 'foo/bar/foo', 'foo/bar/foo/bar']
         unchanged_dirs = all_dirs[:2]