diff --git a/.gitignore b/.gitignore
index 07247a33c..8ccf60790 100644
--- a/.gitignore
+++ b/.gitignore
@@ -3,9 +3,10 @@
 
 # Generated by Cargo
 # will have compiled files and executables
+/vendor/
 debug/
-target/
 target-alpine/
+target/
 
 # Bootstrapped Python versions
 /bin/
diff --git a/Cargo.lock b/Cargo.lock
index 8e24c8ba9..264a17e55 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -933,7 +933,7 @@ dependencies = [
  "hashbrown 0.14.5",
  "lock_api",
  "once_cell",
- "parking_lot_core 0.9.10",
+ "parking_lot_core",
 ]
 
 [[package]]
@@ -1916,18 +1916,6 @@ dependencies = [
  "similar",
 ]
 
-[[package]]
-name = "instant"
-version = "0.1.13"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "e0242819d153cba4b4b05a5a8f2a7e9bbf97b6055b2a002b395c96b5ff3c0222"
-dependencies = [
- "cfg-if",
- "js-sys",
- "wasm-bindgen",
- "web-sys",
-]
-
 [[package]]
 name = "ipnet"
 version = "2.11.0"
@@ -2114,7 +2102,7 @@ checksum = "c0ff37bd590ca25063e35af745c343cb7a0271906fb7b37e4813e8f79f00268d"
 dependencies = [
  "bitflags 2.9.1",
  "libc",
- "redox_syscall 0.5.8",
+ "redox_syscall",
 ]
 
 [[package]]
@@ -2496,17 +2484,6 @@ version = "2.2.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "f38d5652c16fde515bb1ecef450ab0f6a219d619a7274976324d5e377f7dceba"
 
-[[package]]
-name = "parking_lot"
-version = "0.11.2"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "7d17b78036a60663b797adeaee46f5c9dfebb86948d1255007a1d6be0271ff99"
-dependencies = [
- "instant",
- "lock_api",
- "parking_lot_core 0.8.6",
-]
-
 [[package]]
 name = "parking_lot"
 version = "0.12.3"
@@ -2514,21 +2491,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "f1bf18183cf54e8d6059647fc3063646a1801cf30896933ec2311622cc4b9a27"
 dependencies = [
  "lock_api",
- "parking_lot_core 0.9.10",
-]
-
-[[package]]
-name = "parking_lot_core"
-version = "0.8.6"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "60a2cfe6f0ad2bfc16aefa463b497d5c7a5ecd44a23efa72aa342d90177356dc"
-dependencies = [
- "cfg-if",
- "instant",
- "libc",
- "redox_syscall 0.2.16",
- "smallvec",
- "winapi",
+ "parking_lot_core",
 ]
 
 [[package]]
@@ -2539,7 +2502,7 @@ checksum = "1e401f977ab385c9e4e3ab30627d6f26d00e2c73eef317493c4ec6d468726cf8"
 dependencies = [
  "cfg-if",
  "libc",
- "redox_syscall 0.5.8",
+ "redox_syscall",
  "smallvec",
  "windows-targets 0.52.6",
 ]
@@ -2969,15 +2932,6 @@ version = "0.5.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "3b42e27ef78c35d3998403c1d26f3efd9e135d3e5121b0a4845cc5cc27547f4f"
 
-[[package]]
-name = "redox_syscall"
-version = "0.2.16"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "fb5a58c1855b4b6819d59012155603f0b22ad30cad752600aadfcb695265519a"
-dependencies = [
- "bitflags 1.3.2",
-]
-
 [[package]]
 name = "redox_syscall"
 version = "0.5.8"
@@ -3137,8 +3091,7 @@ dependencies = [
 [[package]]
 name = "reqwest-middleware"
 version = "0.4.2"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "57f17d28a6e6acfe1733fe24bcd30774d13bffa4b8a22535b4c8c98423088d4e"
+source = "git+https://github.com/astral-sh/reqwest-middleware?rev=ad8b9d332d1773fde8b4cd008486de5973e0a3f8#ad8b9d332d1773fde8b4cd008486de5973e0a3f8"
 dependencies = [
  "anyhow",
  "async-trait",
@@ -3152,8 +3105,7 @@ dependencies = [
 [[package]]
 name = "reqwest-retry"
 version = "0.7.0"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "29c73e4195a6bfbcb174b790d9b3407ab90646976c55de58a6515da25d851178"
+source = "git+https://github.com/astral-sh/reqwest-middleware?rev=ad8b9d332d1773fde8b4cd008486de5973e0a3f8#ad8b9d332d1773fde8b4cd008486de5973e0a3f8"
 dependencies = [
  "anyhow",
  "async-trait",
@@ -3161,14 +3113,13 @@ dependencies = [
  "getrandom 0.2.15",
  "http",
  "hyper",
- "parking_lot 0.11.2",
  "reqwest",
  "reqwest-middleware",
  "retry-policies",
  "thiserror 1.0.69",
  "tokio",
  "tracing",
- "wasm-timer",
+ "wasmtimer",
 ]
 
 [[package]]
@@ -3916,7 +3867,7 @@ version = "0.3.6"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "96374855068f47402c3121c6eed88d29cb1de8f3ab27090e273e420bdabcf050"
 dependencies = [
- "parking_lot 0.12.3",
+ "parking_lot",
 ]
 
 [[package]]
@@ -4158,7 +4109,7 @@ dependencies = [
  "bytes",
  "libc",
  "mio",
- "parking_lot 0.12.3",
+ "parking_lot",
  "pin-project-lite",
  "signal-hook-registry",
  "socket2",
@@ -6183,18 +6134,17 @@ dependencies = [
 ]
 
 [[package]]
-name = "wasm-timer"
-version = "0.2.5"
+name = "wasmtimer"
+version = "0.4.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "be0ecb0db480561e9a7642b5d3e4187c128914e58aa84330b9493e3eb68c5e7f"
+checksum = "0048ad49a55b9deb3953841fa1fc5858f0efbcb7a18868c899a360269fac1b23"
 dependencies = [
  "futures",
  "js-sys",
- "parking_lot 0.11.2",
+ "parking_lot",
  "pin-utils",
+ "slab",
  "wasm-bindgen",
- "wasm-bindgen-futures",
- "web-sys",
 ]
 
 [[package]]
@@ -6250,7 +6200,7 @@ version = "1.6.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "6994d13118ab492c3c80c1f81928718159254c53c472bf9ce36f8dae4add02a7"
 dependencies = [
- "redox_syscall 0.5.8",
+ "redox_syscall",
  "wasite",
  "web-sys",
 ]
diff --git a/Cargo.toml b/Cargo.toml
index fa5ecad2f..479001ac8 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -143,8 +143,8 @@ reflink-copy = { version = "0.1.19" }
 regex = { version = "1.10.6" }
 regex-automata = { version = "0.4.8", default-features = false, features = ["dfa-build", "dfa-search", "perf", "std", "syntax"] }
 reqwest = { version = "=0.12.15", default-features = false, features = ["json", "gzip", "deflate", "zstd", "stream", "rustls-tls", "rustls-tls-native-roots", "socks", "multipart", "http2", "blocking"] }
-reqwest-middleware = { version = "0.4.0", features = ["multipart"] }
-reqwest-retry = { version = "0.7.0" }
+reqwest-middleware = { git = "https://github.com/astral-sh/reqwest-middleware", rev = "ad8b9d332d1773fde8b4cd008486de5973e0a3f8", features = ["multipart"] }
+reqwest-retry = { git = "https://github.com/astral-sh/reqwest-middleware", rev = "ad8b9d332d1773fde8b4cd008486de5973e0a3f8" }
 rkyv = { version = "0.8.8", features = ["bytecheck"] }
 rmp-serde = { version = "1.3.0" }
 rust-netrc = { version = "0.1.2" }
@@ -372,6 +372,10 @@ riscv64gc-unknown-linux-gnu = "2.31"
 "actions/download-artifact" = "d3f86a106a0bac45b974a628896c90dbdf5c8093" # v4.3.0
 "actions/attest-build-provenance" = "c074443f1aee8d4aeeae555aebba3282517141b2" #v2.2.3
 
+[patch.crates-io]
+reqwest-middleware = { git = "https://github.com/astral-sh/reqwest-middleware", rev = "ad8b9d332d1773fde8b4cd008486de5973e0a3f8" }
+reqwest-retry = { git = "https://github.com/astral-sh/reqwest-middleware", rev = "ad8b9d332d1773fde8b4cd008486de5973e0a3f8" }
+
 [workspace.metadata.dist.binaries]
 "*" = ["uv", "uvx"]
 # Add "uvw" binary for Windows targets
diff --git a/crates/uv-client/src/cached_client.rs b/crates/uv-client/src/cached_client.rs
index 5821fe9f3..d19f95ec7 100644
--- a/crates/uv-client/src/cached_client.rs
+++ b/crates/uv-client/src/cached_client.rs
@@ -1,4 +1,3 @@
-use std::fmt::{Debug, Display, Formatter};
 use std::time::{Duration, SystemTime};
 use std::{borrow::Cow, path::Path};
 
@@ -100,44 +99,62 @@ where
     }
 }
 
-/// Either a cached client error or a (user specified) error from the callback
+/// Dispatch type: Either a cached client error or a (user specified) error from the callback
 pub enum CachedClientError<CallbackError: std::error::Error + 'static> {
-    Client(Error),
-    Callback(CallbackError),
+    Client {
+        retries: Option<u32>,
+        err: Error,
+    },
+    Callback {
+        retries: Option<u32>,
+        err: CallbackError,
+    },
 }
 
-impl<CallbackError: std::error::Error + 'static> Display for CachedClientError<CallbackError> {
-    fn fmt(&self, f: &mut Formatter<'_>) -> std::fmt::Result {
+impl<CallbackError: std::error::Error + 'static> CachedClientError<CallbackError> {
+    /// Attach the number of retries to the error context.
+    ///
+    /// Adds to existing errors if any, in case different layers retried.
+    fn with_retries(self, retries: u32) -> Self {
         match self {
-            CachedClientError::Client(err) => write!(f, "{err}"),
-            CachedClientError::Callback(err) => write!(f, "{err}"),
+            CachedClientError::Client {
+                retries: existing_retries,
+                err,
+            } => CachedClientError::Client {
+                retries: Some(existing_retries.unwrap_or_default() + retries),
+                err,
+            },
+            CachedClientError::Callback {
+                retries: existing_retries,
+                err,
+            } => CachedClientError::Callback {
+                retries: Some(existing_retries.unwrap_or_default() + retries),
+                err,
+            },
         }
     }
-}
 
-impl<CallbackError: std::error::Error + 'static> Debug for CachedClientError<CallbackError> {
-    fn fmt(&self, f: &mut Formatter<'_>) -> std::fmt::Result {
+    fn retries(&self) -> Option<u32> {
         match self {
-            CachedClientError::Client(err) => write!(f, "{err:?}"),
-            CachedClientError::Callback(err) => write!(f, "{err:?}"),
+            CachedClientError::Client { retries, .. } => *retries,
+            CachedClientError::Callback { retries, .. } => *retries,
         }
     }
-}
 
-impl<CallbackError: std::error::Error + 'static> std::error::Error
-    for CachedClientError<CallbackError>
-{
-    fn source(&self) -> Option<&(dyn std::error::Error + 'static)> {
+    fn error(&self) -> &dyn std::error::Error {
         match self {
-            CachedClientError::Client(err) => Some(err),
-            CachedClientError::Callback(err) => Some(err),
+            CachedClientError::Client { err, .. } => err,
+            CachedClientError::Callback { err, .. } => err,
         }
     }
 }
 
 impl<CallbackError: std::error::Error + 'static> From<Error> for CachedClientError<CallbackError> {
     fn from(error: Error) -> Self {
-        Self::Client(error)
+        Self::Client {
+            retries: None,
+            err: error,
+        }
     }
 }
 
@@ -145,15 +162,35 @@ impl<CallbackError: std::error::Error + 'static> From<ErrorKind>
     for CachedClientError<CallbackError>
 {
     fn from(error: ErrorKind) -> Self {
-        Self::Client(error.into())
+        Self::Client {
+            retries: None,
+            err: error.into(),
+        }
     }
 }
 
 impl<E: Into<Self> + std::error::Error + 'static> From<CachedClientError<E>> for Error {
+    /// Attach retry error context, if there were retries.
     fn from(error: CachedClientError<E>) -> Self {
         match error {
-            CachedClientError::Client(error) => error,
-            CachedClientError::Callback(error) => error.into(),
+            CachedClientError::Client {
+                retries: Some(retries),
+                err,
+            } => ErrorKind::RequestWithRetries {
+                source: Box::new(err.into_kind()),
+                retries,
+            }
+            .into(),
+            CachedClientError::Client { retries: None, err } => err,
+            CachedClientError::Callback {
+                retries: Some(retries),
+                err,
+            } => ErrorKind::RequestWithRetries {
+                source: Box::new(err.into().into_kind()),
+                retries,
+            }
+            .into(),
+            CachedClientError::Callback { retries: None, err } => err.into(),
         }
     }
 }
@@ -385,7 +422,7 @@ impl CachedClient {
         let data = response_callback(response)
             .boxed_local()
             .await
-            .map_err(|err| CachedClientError::Callback(err))?;
+            .map_err(|err| CachedClientError::Callback { retries: None, err })?;
         let Some(cache_policy) = cache_policy else {
             return Ok(data.into_target());
         };
@@ -530,9 +567,21 @@ impl CachedClient {
             .for_host(&url)
             .execute(req)
             .await
-            .map_err(|err| ErrorKind::from_reqwest_middleware(url.clone(), err))?
-            .error_for_status()
-            .map_err(|err| ErrorKind::from_reqwest(url.clone(), err))?;
+            .map_err(|err| ErrorKind::from_reqwest_middleware(url.clone(), err))?;
+
+        let retry_count = response
+            .extensions()
+            .get::<reqwest_retry::RetryCount>()
+            .map(|retries| retries.value());
+
+        if let Err(status_error) = response.error_for_status_ref() {
+            return Err(CachedClientError::<Error>::Client {
+                retries: retry_count,
+                err: ErrorKind::from_reqwest(url, status_error).into(),
+            }
+            .into());
+        }
+
         let cache_policy = cache_policy_builder.build(&response);
         let cache_policy = if cache_policy.to_archived().is_storable() {
             Some(Box::new(cache_policy))
@@ -579,7 +628,7 @@ impl CachedClient {
         cache_control: CacheControl,
         response_callback: Callback,
     ) -> Result<Payload::Target, CachedClientError<CallBackError>> {
-        let mut n_past_retries = 0;
+        let mut past_retries = 0;
         let start_time = SystemTime::now();
         let retry_policy = self.uncached().retry_policy();
         loop {
@@ -587,11 +636,20 @@ impl CachedClient {
             let result = self
                 .get_cacheable(fresh_req, cache_entry, cache_control, &response_callback)
                 .await;
+
+            // Check if the middleware already performed retries
+            let middleware_retries = match &result {
+                Err(err) => err.retries().unwrap_or_default(),
+                Ok(_) => 0,
+            };
+
             if result
                 .as_ref()
-                .is_err_and(|err| is_extended_transient_error(err))
+                .is_err_and(|err| is_extended_transient_error(err.error()))
             {
-                let retry_decision = retry_policy.should_retry(start_time, n_past_retries);
+                // If middleware already retried, consider that in our retry budget
+                let total_retries = past_retries + middleware_retries;
+                let retry_decision = retry_policy.should_retry(start_time, total_retries);
                 if let reqwest_retry::RetryDecision::Retry { execute_after } = retry_decision {
                     debug!(
                         "Transient failure while handling response from {}; retrying...",
@@ -601,10 +659,15 @@ impl CachedClient {
                         .duration_since(SystemTime::now())
                         .unwrap_or_else(|_| Duration::default());
                     tokio::time::sleep(duration).await;
-                    n_past_retries += 1;
+                    past_retries += 1;
                     continue;
                 }
             }
+
+            if past_retries > 0 {
+                return result.map_err(|err| err.with_retries(past_retries));
+            }
+
             return result;
         }
     }
@@ -622,7 +685,7 @@ impl CachedClient {
         cache_entry: &CacheEntry,
         response_callback: Callback,
     ) -> Result<Payload, CachedClientError<CallBackError>> {
-        let mut n_past_retries = 0;
+        let mut past_retries = 0;
         let start_time = SystemTime::now();
         let retry_policy = self.uncached().retry_policy();
         loop {
@@ -630,12 +693,20 @@ impl CachedClient {
             let result = self
                 .skip_cache(fresh_req, cache_entry, &response_callback)
                 .await;
+
+            // Check if the middleware already performed retries
+            let middleware_retries = match &result {
+                Err(err) => err.retries().unwrap_or_default(),
+                _ => 0,
+            };
+
             if result
                 .as_ref()
                 .err()
-                .is_some_and(|err| is_extended_transient_error(err))
+                .is_some_and(|err| is_extended_transient_error(err.error()))
             {
-                let retry_decision = retry_policy.should_retry(start_time, n_past_retries);
+                let total_retries = past_retries + middleware_retries;
+                let retry_decision = retry_policy.should_retry(start_time, total_retries);
                 if let reqwest_retry::RetryDecision::Retry { execute_after } = retry_decision {
                     debug!(
                         "Transient failure while handling response from {}; retrying...",
@@ -645,10 +716,15 @@ impl CachedClient {
                         .duration_since(SystemTime::now())
                         .unwrap_or_else(|_| Duration::default());
                     tokio::time::sleep(duration).await;
-                    n_past_retries += 1;
+                    past_retries += 1;
                     continue;
                 }
             }
+
+            if past_retries > 0 {
+                return result.map_err(|err| err.with_retries(past_retries));
+            }
+
             return result;
         }
     }
diff --git a/crates/uv-client/src/error.rs b/crates/uv-client/src/error.rs
index 6629171e9..368e1ad33 100644
--- a/crates/uv-client/src/error.rs
+++ b/crates/uv-client/src/error.rs
@@ -197,6 +197,13 @@ pub enum ErrorKind {
     #[error("Failed to fetch: `{0}`")]
     WrappedReqwestError(DisplaySafeUrl, #[source] WrappedReqwestError),
 
+    /// Add the number of failed retries to the error.
+    #[error("Request failed after {retries} retries")]
+    RequestWithRetries {
+        source: Box<ErrorKind>,
+        retries: u32,
+    },
+
     #[error("Received some unexpected JSON from {}", url)]
     BadJson {
         source: serde_json::Error,
diff --git a/crates/uv-client/src/flat_index.rs b/crates/uv-client/src/flat_index.rs
index 0670fbe36..91668c5c4 100644
--- a/crates/uv-client/src/flat_index.rs
+++ b/crates/uv-client/src/flat_index.rs
@@ -246,7 +246,7 @@ impl<'a> FlatIndexClient<'a> {
                     .collect();
                 Ok(FlatIndexEntries::from_entries(files))
             }
-            Err(CachedClientError::Client(err)) if err.is_offline() => {
+            Err(CachedClientError::Client { err, .. }) if err.is_offline() => {
                 Ok(FlatIndexEntries::offline())
             }
             Err(err) => Err(err.into()),
diff --git a/crates/uv-client/src/registry_client.rs b/crates/uv-client/src/registry_client.rs
index 7dbdf7e49..6271b7d20 100644
--- a/crates/uv-client/src/registry_client.rs
+++ b/crates/uv-client/src/registry_client.rs
@@ -41,10 +41,7 @@ use crate::flat_index::FlatIndexEntry;
 use crate::html::SimpleHtml;
 use crate::remote_metadata::wheel_metadata_from_remote_zip;
 use crate::rkyvutil::OwnedArchive;
-use crate::{
-    BaseClient, CachedClient, CachedClientError, Error, ErrorKind, FlatIndexClient,
-    FlatIndexEntries,
-};
+use crate::{BaseClient, CachedClient, Error, ErrorKind, FlatIndexClient, FlatIndexEntries};
 
 /// A builder for an [`RegistryClient`].
 #[derive(Debug, Clone)]
@@ -607,18 +604,16 @@ impl RegistryClient {
             .boxed_local()
             .instrument(info_span!("parse_simple_api", package = %package_name))
         };
-        self.cached_client()
+        let simple = self
+            .cached_client()
             .get_cacheable_with_retry(
                 simple_request,
                 cache_entry,
                 cache_control,
                 parse_simple_response,
             )
-            .await
-            .map_err(|err| match err {
-                CachedClientError::Client(err) => err,
-                CachedClientError::Callback(err) => err,
-            })
+            .await?;
+        Ok(simple)
     }
 
     /// Fetch the [`SimpleMetadata`] from a local file, using a PEP 503-compatible directory
@@ -900,15 +895,13 @@ impl RegistryClient {
                     .map_err(|err| ErrorKind::AsyncHttpRangeReader(url.clone(), err))?;
                     trace!("Getting metadata for {filename} by range request");
                     let text = wheel_metadata_from_remote_zip(filename, url, &mut reader).await?;
-                    let metadata =
-                        ResolutionMetadata::parse_metadata(text.as_bytes()).map_err(|err| {
-                            Error::from(ErrorKind::MetadataParseError(
-                                filename.clone(),
-                                url.to_string(),
-                                Box::new(err),
-                            ))
-                        })?;
-                    Ok::<ResolutionMetadata, CachedClientError<Error>>(metadata)
+                    ResolutionMetadata::parse_metadata(text.as_bytes()).map_err(|err| {
+                        Error::from(ErrorKind::MetadataParseError(
+                            filename.clone(),
+                            url.to_string(),
+                            Box::new(err),
+                        ))
+                    })
                 }
                 .boxed_local()
                 .instrument(info_span!("read_metadata_range_request", wheel = %filename))
diff --git a/crates/uv-distribution/src/distribution_database.rs b/crates/uv-distribution/src/distribution_database.rs
index 0ecea36e6..dcb0a17e3 100644
--- a/crates/uv-distribution/src/distribution_database.rs
+++ b/crates/uv-distribution/src/distribution_database.rs
@@ -644,8 +644,8 @@ impl<'a, Context: BuildContext> DistributionDatabase<'a, Context> {
             })
             .await
             .map_err(|err| match err {
-                CachedClientError::Callback(err) => err,
-                CachedClientError::Client(err) => Error::Client(err),
+                CachedClientError::Callback { err, .. } => err,
+                CachedClientError::Client { err, .. } => Error::Client(err),
             })?;
 
         // If the archive is missing the required hashes, or has since been removed, force a refresh.
@@ -663,8 +663,8 @@ impl<'a, Context: BuildContext> DistributionDatabase<'a, Context> {
                         .skip_cache_with_retry(self.request(url)?, &http_entry, download)
                         .await
                         .map_err(|err| match err {
-                            CachedClientError::Callback(err) => err,
-                            CachedClientError::Client(err) => Error::Client(err),
+                            CachedClientError::Callback { err, .. } => err,
+                            CachedClientError::Client { err, .. } => Error::Client(err),
                         })
                 })
                 .await?
@@ -811,8 +811,8 @@ impl<'a, Context: BuildContext> DistributionDatabase<'a, Context> {
             })
             .await
             .map_err(|err| match err {
-                CachedClientError::Callback(err) => err,
-                CachedClientError::Client(err) => Error::Client(err),
+                CachedClientError::Callback { err, .. } => err,
+                CachedClientError::Client { err, .. } => Error::Client(err),
             })?;
 
         // If the archive is missing the required hashes, or has since been removed, force a refresh.
@@ -830,8 +830,8 @@ impl<'a, Context: BuildContext> DistributionDatabase<'a, Context> {
                         .skip_cache_with_retry(self.request(url)?, &http_entry, download)
                         .await
                         .map_err(|err| match err {
-                            CachedClientError::Callback(err) => err,
-                            CachedClientError::Client(err) => Error::Client(err),
+                            CachedClientError::Callback { err, .. } => err,
+                            CachedClientError::Client { err, .. } => Error::Client(err),
                         })
                 })
                 .await?
diff --git a/crates/uv-distribution/src/source/mod.rs b/crates/uv-distribution/src/source/mod.rs
index 7a92d700f..2cf148f2b 100644
--- a/crates/uv-distribution/src/source/mod.rs
+++ b/crates/uv-distribution/src/source/mod.rs
@@ -728,8 +728,8 @@ impl<'a, T: BuildContext> SourceDistributionBuilder<'a, T> {
             })
             .await
             .map_err(|err| match err {
-                CachedClientError::Callback(err) => err,
-                CachedClientError::Client(err) => Error::Client(err),
+                CachedClientError::Callback { err, .. } => err,
+                CachedClientError::Client { err, .. } => Error::Client(err),
             })?;
 
         // If the archive is missing the required hashes, force a refresh.
@@ -747,8 +747,8 @@ impl<'a, T: BuildContext> SourceDistributionBuilder<'a, T> {
                         )
                         .await
                         .map_err(|err| match err {
-                            CachedClientError::Callback(err) => err,
-                            CachedClientError::Client(err) => Error::Client(err),
+                            CachedClientError::Callback { err, .. } => err,
+                            CachedClientError::Client { err, .. } => Error::Client(err),
                         })
                 })
                 .await
@@ -2084,8 +2084,8 @@ impl<'a, T: BuildContext> SourceDistributionBuilder<'a, T> {
                     )
                     .await
                     .map_err(|err| match err {
-                        CachedClientError::Callback(err) => err,
-                        CachedClientError::Client(err) => Error::Client(err),
+                        CachedClientError::Callback { err, .. } => err,
+                        CachedClientError::Client { err, .. } => Error::Client(err),
                     })
             })
             .await
diff --git a/crates/uv-python/src/downloads.rs b/crates/uv-python/src/downloads.rs
index 0b7517960..fd3f6c417 100644
--- a/crates/uv-python/src/downloads.rs
+++ b/crates/uv-python/src/downloads.rs
@@ -53,6 +53,12 @@ pub enum Error {
     TooManyParts(String),
     #[error("Failed to download {0}")]
     NetworkError(DisplaySafeUrl, #[source] WrappedReqwestError),
+    #[error("Request failed after {retries} retries")]
+    NetworkErrorWithRetries {
+        #[source]
+        err: Box<Error>,
+        retries: u32,
+    },
     #[error("Failed to download {0}")]
     NetworkMiddlewareError(DisplaySafeUrl, #[source] anyhow::Error),
     #[error("Failed to extract archive: {0}")]
@@ -1143,8 +1149,20 @@ fn parse_json_downloads(
 }
 
 impl Error {
-    pub(crate) fn from_reqwest(url: DisplaySafeUrl, err: reqwest::Error) -> Self {
-        Self::NetworkError(url, WrappedReqwestError::from(err))
+    pub(crate) fn from_reqwest(
+        url: DisplaySafeUrl,
+        err: reqwest::Error,
+        retries: Option<u32>,
+    ) -> Self {
+        let err = Self::NetworkError(url, WrappedReqwestError::from(err));
+        if let Some(retries) = retries {
+            Self::NetworkErrorWithRetries {
+                err: Box::new(err),
+                retries,
+            }
+        } else {
+            err
+        }
     }
 
     pub(crate) fn from_reqwest_middleware(
@@ -1260,10 +1278,15 @@ async fn read_url(
             .await
             .map_err(|err| Error::from_reqwest_middleware(url.clone(), err))?;
 
-        // Ensure the request was successful.
-        response
-            .error_for_status_ref()
-            .map_err(|err| Error::from_reqwest(url, err))?;
+        let retry_count = response
+            .extensions()
+            .get::<reqwest_retry::RetryCount>()
+            .map(|retries| retries.value());
+
+        // Check the status code.
+        let response = response
+            .error_for_status()
+            .map_err(|err| Error::from_reqwest(url, err, retry_count))?;
 
         let size = response.content_length();
         let stream = response
diff --git a/crates/uv/tests/it/edit.rs b/crates/uv/tests/it/edit.rs
index 10c812473..a66cd2ed5 100644
--- a/crates/uv/tests/it/edit.rs
+++ b/crates/uv/tests/it/edit.rs
@@ -11477,7 +11477,8 @@ async fn add_unexpected_error_code() -> Result<()> {
     ----- stdout -----
 
     ----- stderr -----
-    error: Failed to fetch: `http://[LOCALHOST]/anyio/`
+    error: Request failed after 3 retries
+      Caused by: Failed to fetch: `http://[LOCALHOST]/anyio/`
       Caused by: HTTP status server error (503 Service Unavailable) for url (http://[LOCALHOST]/anyio/)
     "
     );
diff --git a/crates/uv/tests/it/network.rs b/crates/uv/tests/it/network.rs
index 8edbc63a2..1a5805970 100644
--- a/crates/uv/tests/it/network.rs
+++ b/crates/uv/tests/it/network.rs
@@ -54,7 +54,8 @@ async fn simple_http_500() {
     ----- stdout -----
 
     ----- stderr -----
-    error: Failed to fetch: `[SERVER]/tqdm/`
+    error: Request failed after 3 retries
+      Caused by: Failed to fetch: `[SERVER]/tqdm/`
       Caused by: HTTP status server error (500 Internal Server Error) for url ([SERVER]/tqdm/)
     ");
 }
@@ -105,6 +106,7 @@ async fn find_links_http_500() {
 
     ----- stderr -----
     error: Failed to read `--find-links` URL: [SERVER]/
+      Caused by: Request failed after 3 retries
       Caused by: Failed to fetch: `[SERVER]/`
       Caused by: HTTP status server error (500 Internal Server Error) for url ([SERVER]/)
     ");
@@ -159,6 +161,7 @@ async fn direct_url_http_500() {
 
     ----- stderr -----
       × Failed to download `tqdm @ [SERVER]/packages/d0/30/dc54f88dd4a2b5dc8a0279bdd7270e735851848b762aeb1c1184ed1f6b14/tqdm-4.67.1-py3-none-any.whl`
+      ├─▶ Request failed after 3 retries
       ├─▶ 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)
     ");
@@ -243,6 +246,7 @@ async fn python_install_http_500() {
 
     ----- stderr -----
     error: Failed to install cpython-3.10.0-macos-aarch64-none
+      Caused by: Request failed after 3 retries
       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)
     ");