diff --git a/src/greaseweazle/image/image.py b/src/greaseweazle/image/image.py
index 31be5e16..62da19f0 100644
--- a/src/greaseweazle/image/image.py
+++ b/src/greaseweazle/image/image.py
@@ -23,6 +23,7 @@ class Image:
     ## Context manager for image objects created using .to_file()
 
     def __enter__(self):
+        os.makedirs(os.path.dirname(self.filename), exist_ok=True)
         self.file = open(self.filename, ('wb','xb')[self.noclobber])
         return self