diff --git a/crates/uv/tests/it/main.rs b/crates/uv/tests/it/main.rs
index 5daa56a3a..7835fa461 100644
--- a/crates/uv/tests/it/main.rs
+++ b/crates/uv/tests/it/main.rs
@@ -39,7 +39,7 @@ mod lock_conflict;
 
 mod lock_scenarios;
 
-mod version;
+mod network;
 
 #[cfg(all(feature = "python", feature = "pypi"))]
 mod pip_check;
@@ -120,6 +120,8 @@ mod tree;
 #[cfg(feature = "python")]
 mod venv;
 
+mod version;
+
 #[cfg(all(feature = "python", feature = "pypi"))]
 mod workflow;
 
diff --git a/crates/uv/tests/it/network.rs b/crates/uv/tests/it/network.rs
new file mode 100644
index 000000000..fba24afe1
--- /dev/null
+++ b/crates/uv/tests/it/network.rs
@@ -0,0 +1,154 @@
+use std::env;
+
+use assert_fs::fixture::{FileWriteStr, PathChild};
+use http::StatusCode;
+use serde_json::json;
+use wiremock::matchers::method;
+use wiremock::{Mock, MockServer, ResponseTemplate};
+
+use crate::common::{TestContext, uv_snapshot};
+
+/// Check the simple index error message when the server returns HTTP status 500, a retryable error.
+#[tokio::test]
+async fn simple_http_500() {
+    let context = TestContext::new("3.12");
+
+    let server = MockServer::start().await;
+    Mock::given(method("GET"))
+        .respond_with(ResponseTemplate::new(StatusCode::INTERNAL_SERVER_ERROR))
+        .mount(&server)
+        .await;
+    let mock_server_uri = server.uri();
+
+    let filters = vec![(mock_server_uri.as_str(), "[SERVER]")];
+    uv_snapshot!(filters, context
+        .pip_install()
+        .arg("tqdm")
+        .arg("--index-url")
+        .arg(server.uri()), @r"
+    success: false
+    exit_code: 2
+    ----- stdout -----
+
+    ----- stderr -----
+    error: Failed to fetch: `[SERVER]/tqdm/`
+      Caused by: HTTP status server error (500 Internal Server Error) for url ([SERVER]/tqdm/)
+    ");
+}
+
+/// Check the find links error message when the server returns HTTP status 500, a retryable error.
+#[tokio::test]
+async fn find_links_http_500() {
+    let context = TestContext::new("3.12");
+
+    let server = MockServer::start().await;
+    Mock::given(method("GET"))
+        .respond_with(ResponseTemplate::new(StatusCode::INTERNAL_SERVER_ERROR))
+        .mount(&server)
+        .await;
+    let mock_server_uri = server.uri();
+
+    let filters = vec![(mock_server_uri.as_str(), "[SERVER]")];
+    uv_snapshot!(filters, context
+        .pip_install()
+        .arg("tqdm")
+        .arg("--no-index")
+        .arg("--find-links")
+        .arg(server.uri()), @r"
+    success: false
+    exit_code: 2
+    ----- stdout -----
+
+    ----- stderr -----
+    error: Failed to read `--find-links` URL: [SERVER]/
+      Caused by: Failed to fetch: `[SERVER]/`
+      Caused by: HTTP status server error (500 Internal Server Error) for url ([SERVER]/)
+    ");
+}
+
+/// Check the direct package URL error message when the server returns HTTP status 500, a retryable
+/// error.
+#[tokio::test]
+async fn direct_url_http_500() {
+    let context = TestContext::new("3.12");
+
+    let server = MockServer::start().await;
+    Mock::given(method("GET"))
+        .respond_with(ResponseTemplate::new(StatusCode::INTERNAL_SERVER_ERROR))
+        .mount(&server)
+        .await;
+    let mock_server_uri = server.uri();
+
+    let tqdm_url = format!(
+        "{mock_server_uri}/packages/d0/30/dc54f88dd4a2b5dc8a0279bdd7270e735851848b762aeb1c1184ed1f6b14/tqdm-4.67.1-py3-none-any.whl"
+    );
+    let filters = vec![(mock_server_uri.as_str(), "[SERVER]")];
+    uv_snapshot!(filters, context
+        .pip_install()
+        .arg(format!("tqdm @ {tqdm_url}")), @r"
+    success: false
+    exit_code: 1
+    ----- stdout -----
+
+    ----- stderr -----
+      × Failed to download `tqdm @ [SERVER]/packages/d0/30/dc54f88dd4a2b5dc8a0279bdd7270e735851848b762aeb1c1184ed1f6b14/tqdm-4.67.1-py3-none-any.whl`
+      ├─▶ Failed to fetch: `[SERVER]/packages/d0/30/dc54f88dd4a2b5dc8a0279bdd7270e735851848b762aeb1c1184ed1f6b14/tqdm-4.67.1-py3-none-any.whl`
+      ╰─▶ HTTP status server error (500 Internal Server Error) for url ([SERVER]/packages/d0/30/dc54f88dd4a2b5dc8a0279bdd7270e735851848b762aeb1c1184ed1f6b14/tqdm-4.67.1-py3-none-any.whl)
+    ");
+}
+
+/// Check the Python install error message when the server returns HTTP status 500, a retryable
+/// error.
+#[tokio::test]
+async fn python_install_http_500() {
+    let context = TestContext::new("3.12")
+        .with_filtered_python_keys()
+        .with_filtered_exe_suffix()
+        .with_managed_python_dirs();
+
+    let server = MockServer::start().await;
+    Mock::given(method("GET"))
+        .respond_with(ResponseTemplate::new(StatusCode::INTERNAL_SERVER_ERROR))
+        .mount(&server)
+        .await;
+    let mock_server_uri = server.uri();
+
+    let python_downloads_json = context.temp_dir.child("python_downloads.json");
+    let interpreter = json!({
+        "cpython-3.10.0-darwin-aarch64-none": {
+            "arch": {
+                "family": "aarch64",
+                "variant": null
+            },
+            "libc": "none",
+            "major": 3,
+            "minor": 10,
+            "name": "cpython",
+            "os": "darwin",
+            "patch": 0,
+            "prerelease": "",
+            "sha256": null,
+            "url": format!("{mock_server_uri}/astral-sh/python-build-standalone/releases/download/20211017/cpython-3.10.0-aarch64-apple-darwin-pgo%2Blto-20211017T1616.tar.zst"),
+            "variant": null
+        }
+    });
+    python_downloads_json
+        .write_str(&serde_json::to_string(&interpreter).unwrap())
+        .unwrap();
+
+    let filters = vec![(mock_server_uri.as_str(), "[SERVER]")];
+    uv_snapshot!(filters, context
+        .python_install()
+        .arg("cpython-3.10.0-darwin-aarch64-none")
+        .arg("--python-downloads-json-url")
+        .arg(python_downloads_json.path()), @r"
+    success: false
+    exit_code: 1
+    ----- stdout -----
+
+    ----- stderr -----
+    error: Failed to install cpython-3.10.0-macos-aarch64-none
+      Caused by: Failed to download [SERVER]/astral-sh/python-build-standalone/releases/download/20211017/cpython-3.10.0-aarch64-apple-darwin-pgo%2Blto-20211017T1616.tar.zst
+      Caused by: HTTP status server error (500 Internal Server Error) for url ([SERVER]/astral-sh/python-build-standalone/releases/download/20211017/cpython-3.10.0-aarch64-apple-darwin-pgo%2Blto-20211017T1616.tar.zst)
+    ");
+}