diff --git a/qutebrowser/mainwindow/prompt.py b/qutebrowser/mainwindow/prompt.py
index ff676146d..2f833c3a3 100644
--- a/qutebrowser/mainwindow/prompt.py
+++ b/qutebrowser/mainwindow/prompt.py
@@ -665,6 +665,7 @@ class FilenamePrompt(_BasePrompt):
         return path
 
     def _show_error(self, msg):
+        log.prompt.error(msg)
         QToolTip.showText(self._lineedit.mapToGlobal(QPoint(0, 0)), msg)
 
     def accept(self, value=None):
diff --git a/tests/end2end/features/downloads.feature b/tests/end2end/features/downloads.feature
index 444cf8721..b47edf8d8 100644
--- a/tests/end2end/features/downloads.feature
+++ b/tests/end2end/features/downloads.feature
@@ -126,6 +126,20 @@ Feature: Downloading things from a website.
         Then the downloaded file ../foo should not exist
         And the downloaded file foo should exist
 
+    @windows
+    Scenario: Downloading a file to a reserved path
+        When I open data/downloads/download.bin
+        And I run :prompt-accept COM1
+        And I run :prompt-cancel
+        Then "Invalid filename" should be logged
+
+    @windows
+    Scenario: Downloading a file to a drive-relative working directory
+        When I open data/downloads/download.bin
+        And I run :prompt-accept C:foobar
+        And I run :prompt-cancel
+        Then "Invalid filename" should be logged
+
     ## :download-retry
 
     Scenario: Retrying a failed download