diff --git a/llm/models.py b/llm/models.py
index 1c149127b..de66cf8de 100644
--- a/llm/models.py
+++ b/llm/models.py
@@ -91,7 +91,7 @@ def resolve_type(self):
         if self.path:
             return mimetype_from_path(self.path)
         if self.url:
-            response = httpx.head(self.url)
+            response = httpx.head(self.url, follow_redirects=True)
             response.raise_for_status()
             return response.headers.get("content-type")
         if self.content:
@@ -105,7 +105,7 @@ def content_bytes(self):
             if self.path:
                 content = Path(self.path).read_bytes()
             elif self.url:
-                response = httpx.get(self.url)
+                response = httpx.get(self.url, follow_redirects=True)
                 response.raise_for_status()
                 content = response.content
         return content
diff --git a/tests/test_attachments.py b/tests/test_attachments.py
index d523e4745..edcdb9321 100644
--- a/tests/test_attachments.py
+++ b/tests/test_attachments.py
@@ -97,3 +97,33 @@ def test_attachment_no_file_descriptor_leak(tmp_path):
 
     # File descriptor count should not have grown significantly
     assert _count_open_fds() <= baseline + 5
+
+
+def test_attachment_content_bytes_follows_redirects(httpx_mock):
+    httpx_mock.add_response(
+        url="https://example.com/redirected.png",
+        status_code=301,
+        headers={"Location": "https://example.com/actual.png"},
+    )
+    httpx_mock.add_response(
+        url="https://example.com/actual.png",
+        content=TINY_PNG,
+    )
+    attachment = llm.Attachment(url="https://example.com/redirected.png")
+    assert attachment.content_bytes() == TINY_PNG
+
+
+def test_attachment_resolve_type_follows_redirects(httpx_mock):
+    httpx_mock.add_response(
+        method="HEAD",
+        url="https://example.com/redirected.png",
+        status_code=301,
+        headers={"Location": "https://example.com/actual.png"},
+    )
+    httpx_mock.add_response(
+        method="HEAD",
+        url="https://example.com/actual.png",
+        headers={"content-type": "image/png"},
+    )
+    attachment = llm.Attachment(url="https://example.com/redirected.png")
+    assert attachment.resolve_type() == "image/png"