diff --git a/Cargo.lock b/Cargo.lock
index bb955e8ad..527e1273b 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -4530,6 +4530,7 @@ dependencies = [
  "hyper-util",
  "insta",
  "install-wheel-rs",
+ "itertools 0.13.0",
  "pep440_rs",
  "pep508_rs",
  "platform-tags",
diff --git a/crates/uv-client/Cargo.toml b/crates/uv-client/Cargo.toml
index fdadf59df..85a5fb6e0 100644
--- a/crates/uv-client/Cargo.toml
+++ b/crates/uv-client/Cargo.toml
@@ -29,6 +29,7 @@ fs-err = { workspace = true, features = ["tokio"] }
 futures = { workspace = true }
 html-escape = { workspace = true }
 http = { workspace = true }
+itertools = { workspace = true }
 reqwest = { workspace = true }
 reqwest-middleware = { workspace = true }
 reqwest-retry = { workspace = true }
diff --git a/crates/uv-client/src/base_client.rs b/crates/uv-client/src/base_client.rs
index 9994b2a97..7c1dcd678 100644
--- a/crates/uv-client/src/base_client.rs
+++ b/crates/uv-client/src/base_client.rs
@@ -1,14 +1,20 @@
-use pep508_rs::MarkerEnvironment;
-use platform_tags::Platform;
-use reqwest::{Client, ClientBuilder};
-use reqwest_middleware::ClientWithMiddleware;
-use reqwest_retry::policies::ExponentialBackoff;
-use reqwest_retry::RetryTransientMiddleware;
-use std::env;
+use std::error::Error;
 use std::fmt::Debug;
 use std::ops::Deref;
 use std::path::Path;
+use std::{env, iter};
+
+use itertools::Itertools;
+use reqwest::{Client, ClientBuilder, Response};
+use reqwest_middleware::ClientWithMiddleware;
+use reqwest_retry::policies::ExponentialBackoff;
+use reqwest_retry::{
+    DefaultRetryableStrategy, RetryTransientMiddleware, Retryable, RetryableStrategy,
+};
 use tracing::debug;
+
+use pep508_rs::MarkerEnvironment;
+use platform_tags::Platform;
 use uv_auth::AuthMiddleware;
 use uv_configuration::KeyringProviderType;
 use uv_fs::Simplified;
@@ -166,7 +172,10 @@ impl<'a> BaseClientBuilder<'a> {
                 // Initialize the retry strategy.
                 let retry_policy =
                     ExponentialBackoff::builder().build_with_max_retries(self.retries);
-                let retry_strategy = RetryTransientMiddleware::new_with_policy(retry_policy);
+                let retry_strategy = RetryTransientMiddleware::new_with_policy_and_strategy(
+                    retry_policy,
+                    LoggingRetryableStrategy,
+                );
                 let client = client.with(retry_strategy);
 
                 // Initialize the authentication middleware to set headers.
@@ -225,3 +234,30 @@ impl Deref for BaseClient {
         &self.client
     }
 }
+
+/// The same as [`DefaultRetryableStrategy`], but retry attempts on transient request failures are
+/// logged, so we can tell whether a request was retried before failing or not.
+struct LoggingRetryableStrategy;
+
+impl RetryableStrategy for LoggingRetryableStrategy {
+    fn handle(&self, res: &Result<Response, reqwest_middleware::Error>) -> Option<Retryable> {
+        let retryable = DefaultRetryableStrategy.handle(res);
+        if retryable == Some(Retryable::Transient) {
+            match res {
+                Ok(response) => {
+                    debug!("Transient request failure for: {}", response.url());
+                }
+                Err(err) => {
+                    let context = iter::successors(err.source(), |&err| err.source())
+                        .map(|err| format!("  Caused by: {err}"))
+                        .join("\n");
+                    debug!(
+                        "Transient request failure for {}, retrying: {err}\n{context}",
+                        err.url().map(|url| url.as_str()).unwrap_or("unknown URL")
+                    );
+                }
+            }
+        }
+        retryable
+    }
+}