diff --git a/strix/tools/proxy/caido_api.py b/strix/tools/proxy/caido_api.py
index 525be944..c56db672 100644
--- a/strix/tools/proxy/caido_api.py
+++ b/strix/tools/proxy/caido_api.py
@@ -157,7 +157,7 @@ def build_raw_request(
     final_headers = {**headers}
     final_headers.setdefault("Host", parsed.netloc)
     final_headers.setdefault("User-Agent", "strix")
-    if body and "Content-Length" not in {k.title() for k in final_headers}:
+    if body is not None and "Content-Length" not in {k.title() for k in final_headers}:
         final_headers["Content-Length"] = str(len(body.encode("utf-8")))
 
     lines = [f"{method.upper()} {path} HTTP/1.1"]
diff --git a/tests/test_caido_api.py b/tests/test_caido_api.py
index e287f6de..ba577ea7 100644
--- a/tests/test_caido_api.py
+++ b/tests/test_caido_api.py
@@ -60,3 +60,20 @@ def test_build_raw_request_recomputes_content_length_after_replacement() -> None
     )
     head = raw.decode("utf-8").split("\r\n\r\n", 1)[0]
     assert f"Content-Length: {len(new_body.encode('utf-8'))}" in head
+
+
+def test_build_raw_request_sets_content_length_zero_for_empty_body() -> None:
+    components = _components(body="old")
+    modified = apply_modifications(
+        components,
+        {"body": ""},
+        "http://example.com/submit",
+    )
+    _, raw = build_raw_request(
+        method=modified["method"],
+        url=modified["url"],
+        headers=modified["headers"],
+        body=modified["body"],
+    )
+    head = raw.decode("utf-8").split("\r\n\r\n", 1)[0]
+    assert "Content-Length: 0" in head