diff --git a/Cargo.lock b/Cargo.lock
index 3573b01b00458..9fdd9f7ec6c10 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -276,15 +276,15 @@ dependencies = [
 
 [[package]]
 name = "astral-tokio-tar"
-version = "0.6.2"
+version = "0.6.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "cb50a7aae84a03bf55b067832bc376f4961b790c97e64d3eacee97d389b90277"
+checksum = "08648fef353ab39a9d26f909ad53fc4f071be4c91853b78523f5cc3d9e5ebffd"
 dependencies = [
- "filetime",
  "futures-core",
  "libc",
  "portable-atomic",
  "rustc-hash",
+ "rustix 0.38.44",
  "tokio",
  "tokio-stream",
  "xattr",
@@ -1464,7 +1464,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "39cab71617ae0d63f51a36d69f866391735b51691dbda63cf6f96d042b63efeb"
 dependencies = [
  "libc",
- "windows-sys 0.52.0",
+ "windows-sys 0.61.2",
 ]
 
 [[package]]
@@ -2334,7 +2334,7 @@ checksum = "3640c1c38b8e4e43584d8df18be5fc6b0aa314ce6ebf51b53313d4306cca8e46"
 dependencies = [
  "hermit-abi",
  "libc",
- "windows-sys 0.52.0",
+ "windows-sys 0.61.2",
 ]
 
 [[package]]
@@ -2576,6 +2576,12 @@ dependencies = [
  "libc",
 ]
 
+[[package]]
+name = "linux-raw-sys"
+version = "0.4.15"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "d26c52dbd32dccf2d10cac7725f8eae5296885fb5703b261f7d0a0739ec807ab"
+
 [[package]]
 name = "linux-raw-sys"
 version = "0.12.1"
@@ -3444,7 +3450,7 @@ dependencies = [
  "bitflags",
  "flate2",
  "procfs-core",
- "rustix",
+ "rustix 1.1.4",
 ]
 
 [[package]]
@@ -3736,7 +3742,7 @@ checksum = "13362233b147e57674c37b802d216b7c5e3dcccbed8967c84f0d8d223868ae27"
 dependencies = [
  "cfg-if",
  "libc",
- "rustix",
+ "rustix 1.1.4",
  "windows",
 ]
 
@@ -4128,6 +4134,19 @@ dependencies = [
  "nom",
 ]
 
+[[package]]
+name = "rustix"
+version = "0.38.44"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "fdb5bc1ae2baa591800df16c9ca78619bf65c0488b41b96ccec5d11220d8c154"
+dependencies = [
+ "bitflags",
+ "errno",
+ "libc",
+ "linux-raw-sys 0.4.15",
+ "windows-sys 0.52.0",
+]
+
 [[package]]
 name = "rustix"
 version = "1.1.4"
@@ -4137,8 +4156,8 @@ dependencies = [
  "bitflags",
  "errno",
  "libc",
- "linux-raw-sys",
- "windows-sys 0.52.0",
+ "linux-raw-sys 0.12.1",
+ "windows-sys 0.61.2",
 ]
 
 [[package]]
@@ -4195,7 +4214,7 @@ dependencies = [
  "security-framework",
  "security-framework-sys",
  "webpki-root-certs",
- "windows-sys 0.52.0",
+ "windows-sys 0.61.2",
 ]
 
 [[package]]
@@ -4400,7 +4419,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "5b55fb86dfd3a2f5f76ea78310a88f96c4ea21a3031f8d212443d56123fd0521"
 dependencies = [
  "libc",
- "windows-sys 0.52.0",
+ "windows-sys 0.61.2",
 ]
 
 [[package]]
@@ -4916,10 +4935,10 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "32497e9a4c7b38532efcdebeef879707aa9f794296a4f0244f6f69e9bc8574bd"
 dependencies = [
  "fastrand",
- "getrandom 0.3.3",
+ "getrandom 0.4.1",
  "once_cell",
- "rustix",
- "windows-sys 0.52.0",
+ "rustix 1.1.4",
+ "windows-sys 0.61.2",
 ]
 
 [[package]]
@@ -4928,7 +4947,7 @@ version = "0.4.4"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "230a1b821ccbd75b185820a1f1ff7b14d21da1e442e22c0863ea5f08771a8874"
 dependencies = [
- "rustix",
+ "rustix 1.1.4",
  "windows-sys 0.61.2",
 ]
 
@@ -6518,7 +6537,7 @@ dependencies = [
  "percent-encoding",
  "reflink-copy",
  "rustc-hash",
- "rustix",
+ "rustix 1.1.4",
  "same-file",
  "schemars",
  "self-replace",
@@ -6823,7 +6842,7 @@ dependencies = [
  "insta",
  "procfs",
  "regex",
- "rustix",
+ "rustix 1.1.4",
  "target-lexicon",
  "tempfile",
  "thiserror",
@@ -7754,7 +7773,7 @@ version = "0.1.11"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "c2a7b1c03c876122aa43f3020e6c3c3ee5c05081c9a00739faf7503aeba10d22"
 dependencies = [
- "windows-sys 0.52.0",
+ "windows-sys 0.61.2",
 ]
 
 [[package]]
@@ -8127,7 +8146,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "32e45ad4206f6d2479085147f02bc2ef834ac85886624a23575ae137c8aa8156"
 dependencies = [
  "libc",
- "rustix",
+ "rustix 1.1.4",
 ]
 
 [[package]]
@@ -8206,7 +8225,7 @@ dependencies = [
  "hex",
  "libc",
  "ordered-stream",
- "rustix",
+ "rustix 1.1.4",
  "serde",
  "serde_repr",
  "tokio",
diff --git a/Cargo.toml b/Cargo.toml
index 98ce7e6a9d21d..9a6514f5511ad 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -99,7 +99,7 @@ anstream = { version = "1.0.0" }
 anyhow = { version = "1.0.89" }
 arcstr = { version = "1.2.0" }
 arrayvec = { version = "0.7.6" }
-astral-tokio-tar = { version = "0.6.2" }
+astral-tokio-tar = { version = "0.6.3" }
 async-channel = { version = "2.3.1" }
 async-compression = { version = "0.4.12", features = [
   "bzip2",
diff --git a/crates/uv-client/src/registry_client.rs b/crates/uv-client/src/registry_client.rs
index ff039acaa3bc4..467bbcfa59278 100644
--- a/crates/uv-client/src/registry_client.rs
+++ b/crates/uv-client/src/registry_client.rs
@@ -1491,11 +1491,17 @@ impl SimpleDetailMetadata {
 
         // Group the distributions by version and kind
         for file in files {
-            let Some(filename) = DistFilename::try_from_filename(&file.filename, package_name)
-            else {
-                debug!("Skipping file for {package_name}: {}", file.filename);
-                continue;
-            };
+            let filename =
+                match DistFilename::try_from_filename_with_reason(&file.filename, package_name) {
+                    Ok(filename) => filename,
+                    Err(err) => {
+                        debug!(
+                            "Skipping file for {package_name}: {:?} ({err})",
+                            file.filename
+                        );
+                        continue;
+                    }
+                };
             let file = match File::try_from_pypi(file, &base) {
                 Ok(file) => file,
                 Err(err) => {
@@ -1551,11 +1557,17 @@ impl SimpleDetailMetadata {
                     continue;
                 }
             };
-            let Some(filename) = DistFilename::try_from_filename(&file.filename, package_name)
-            else {
-                debug!("Skipping file for {package_name}: {}", file.filename);
-                continue;
-            };
+            let filename =
+                match DistFilename::try_from_filename_with_reason(&file.filename, package_name) {
+                    Ok(filename) => filename,
+                    Err(err) => {
+                        debug!(
+                            "Skipping file for {package_name}: {:?} ({err})",
+                            file.filename
+                        );
+                        continue;
+                    }
+                };
             match version_map.entry(filename.version().clone()) {
                 std::collections::btree_map::Entry::Occupied(mut entry) => {
                     entry.get_mut().push(filename, file);
diff --git a/crates/uv-distribution-filename/src/lib.rs b/crates/uv-distribution-filename/src/lib.rs
index 41220d34c4fc8..9bfe955de8939 100644
--- a/crates/uv-distribution-filename/src/lib.rs
+++ b/crates/uv-distribution-filename/src/lib.rs
@@ -1,6 +1,7 @@
 use std::fmt::{Display, Formatter};
 use std::str::FromStr;
 
+use thiserror::Error;
 use uv_normalize::PackageName;
 use uv_pep440::Version;
 
@@ -29,20 +30,32 @@ pub enum DistFilename {
 impl DistFilename {
     /// Parse a filename as wheel or source dist name.
     pub fn try_from_filename(filename: &str, package_name: &PackageName) -> Option<Self> {
+        Self::try_from_filename_with_reason(filename, package_name).ok()
+    }
+
+    /// Parse a filename as wheel or source dist name, returning the reason the filename was
+    /// rejected when parsing fails.
+    ///
+    /// This is useful for surfacing actionable diagnostics when a registry returns entries that
+    /// do not look like distribution files (for example, devpi index entries like `+searchhelp`,
+    /// bare version directory links, or files with unrecognized extensions).
+    pub fn try_from_filename_with_reason(
+        filename: &str,
+        package_name: &PackageName,
+    ) -> Result<Self, DistFilenameError> {
         match DistExtension::from_path(filename) {
-            Ok(DistExtension::Wheel) => {
-                if let Ok(filename) = WheelFilename::from_str(filename) {
-                    return Some(Self::WheelFilename(filename));
-                }
-            }
+            Ok(DistExtension::Wheel) => match WheelFilename::from_str(filename) {
+                Ok(filename) => Ok(Self::WheelFilename(filename)),
+                Err(err) => Err(DistFilenameError::InvalidWheel(err)),
+            },
             Ok(DistExtension::Source(extension)) => {
-                if let Ok(filename) = SourceDistFilename::parse(filename, extension, package_name) {
-                    return Some(Self::SourceDistFilename(filename));
+                match SourceDistFilename::parse(filename, extension, package_name) {
+                    Ok(filename) => Ok(Self::SourceDistFilename(filename)),
+                    Err(err) => Err(DistFilenameError::InvalidSourceDist(err)),
                 }
             }
-            Err(_) => {}
+            Err(err) => Err(DistFilenameError::NoRecognizedExtension(err)),
         }
-        None
     }
 
     /// Like [`DistFilename::try_from_normalized_filename`], but without knowing the package name.
@@ -98,12 +111,83 @@ impl Display for DistFilename {
     }
 }
 
+/// The reason a registry entry could not be parsed as a wheel or source distribution filename.
+#[derive(Error, Debug)]
+pub enum DistFilenameError {
+    /// The filename does not have a recognized wheel or source distribution extension.
+    ///
+    /// This typically indicates the registry returned a non-distribution entry, such as a
+    /// directory listing link (e.g., a bare version like `0.1.0`) or an index management endpoint
+    /// (e.g., devpi's `+searchhelp`, `+status`).
+    #[error("not a wheel or source distribution archive (expected one of {0})")]
+    NoRecognizedExtension(#[source] ExtensionError),
+    /// The filename has a `.whl` extension but is otherwise an invalid wheel filename.
+    #[error(transparent)]
+    InvalidWheel(#[from] WheelFilenameError),
+    /// The filename has a source distribution extension but is otherwise invalid.
+    #[error(transparent)]
+    InvalidSourceDist(#[from] SourceDistFilenameError),
+}
+
 #[cfg(test)]
 mod tests {
-    use crate::WheelFilename;
+    use std::str::FromStr;
+
+    use uv_normalize::PackageName;
+
+    use crate::{DistFilename, DistFilenameError, WheelFilename};
 
     #[test]
     fn wheel_filename_size() {
         assert_eq!(size_of::<WheelFilename>(), 48);
     }
+
+    #[test]
+    fn try_from_filename_with_reason_no_extension() {
+        // A bare version string (the kind of entry devpi serves for its directory listings)
+        // is rejected because it has no recognized distribution extension.
+        let name = PackageName::from_str("my-package").unwrap();
+        let err = DistFilename::try_from_filename_with_reason("0.1.0", &name).unwrap_err();
+        assert!(
+            matches!(err, DistFilenameError::NoRecognizedExtension(_)),
+            "unexpected error variant: {err:?}"
+        );
+        let rendered = err.to_string();
+        assert!(
+            rendered.contains("not a wheel or source distribution archive"),
+            "unexpected error message: {rendered}"
+        );
+    }
+
+    #[test]
+    fn try_from_filename_with_reason_empty_filename() {
+        // An empty filename (which is what devpi reports for its top-level index entries) is
+        // similarly rejected with the no-extension reason rather than silently swallowing it.
+        let name = PackageName::from_str("my-package").unwrap();
+        let err = DistFilename::try_from_filename_with_reason("", &name).unwrap_err();
+        assert!(
+            matches!(err, DistFilenameError::NoRecognizedExtension(_)),
+            "unexpected error variant: {err:?}"
+        );
+    }
+
+    #[test]
+    fn try_from_filename_with_reason_invalid_wheel() {
+        // A file that looks like a wheel by extension but isn't a valid wheel name should bubble
+        // up the wheel parsing error rather than a generic extension error.
+        let name = PackageName::from_str("my-package").unwrap();
+        let err =
+            DistFilename::try_from_filename_with_reason("not-a-wheel.whl", &name).unwrap_err();
+        assert!(
+            matches!(err, DistFilenameError::InvalidWheel(_)),
+            "unexpected error variant: {err:?}"
+        );
+    }
+
+    #[test]
+    fn try_from_filename_accepts_valid_wheel() {
+        let name = PackageName::from_str("my-package").unwrap();
+        let parsed = DistFilename::try_from_filename("my_package-0.1.0-py3-none-any.whl", &name);
+        assert!(parsed.is_some(), "expected wheel to parse successfully");
+    }
 }