diff --git a/jweb/context.py b/jweb/context.py
index 7e115a6..91b418c 100644
--- a/jweb/context.py
+++ b/jweb/context.py
@@ -105,6 +105,7 @@ class Context:
     def __write(self, content: Content) -> Path:
         relative_path = content.path.relative_to(self.__content_directory)
         output_path = self.__output_directory / relative_path
+        output_path.parent.mkdir(parents=True, exist_ok=True)
         with output_path.open("w") as output_file:
             output_file.write(content.data)
 
diff --git a/tests/test_context.py b/tests/test_context.py
index 4208402..bc6783d 100644
--- a/tests/test_context.py
+++ b/tests/test_context.py
@@ -49,8 +49,11 @@ def test_write(datadir: Path) -> None:
     with open(datadir / "build" / "content.txt", encoding="utf-8") as ouput_file:
         assert ouput_file.read() == "Otters\n"
 
+    with open(datadir / "build/subdir/content.txt", encoding="utf-8") as ouput_file:
+        assert ouput_file.read() == "Weasel\n"
+
     with open(datadir / "build" / "output.html", encoding="utf-8") as ouput_file:
-        assert ouput_file.read() == "/content.txt"
+        assert ouput_file.read() == "/content.txt\n/subdir/content.txt"
 
 
 def test_glob(datadir: Path) -> None:
diff --git a/tests/test_context/content/subdir/content.txt b/tests/test_context/content/subdir/content.txt
new file mode 100644
index 0000000..62214c4
--- /dev/null
+++ b/tests/test_context/content/subdir/content.txt
@@ -0,0 +1 @@
+Weasel
diff --git a/tests/test_context/src/test-write.html b/tests/test_context/src/test-write.html
index 6b1f13c..384fc5b 100644
--- a/tests/test_context/src/test-write.html
+++ b/tests/test_context/src/test-write.html
@@ -1 +1,2 @@
 {{ 'content.txt' | load | write }}
+{{ 'subdir/content.txt' | load | write }}