Reject ambiguously parsed URLs (#16622)

Co-authored-by: Zanie Blue <contact@zanie.dev>

Cargo.lock

@@ -5463,6 +5463,7 @@ dependencies = [
  "uv-extract",
  "uv-pep440",
  "uv-platform",
+ "uv-redacted",
 ]
 
 [[package]]
@@ -6437,6 +6438,7 @@ dependencies = [
  "ref-cast",
  "schemars",
  "serde",
+ "thiserror 2.0.17",
  "url",
 ]
 

crates/uv-auth/src/middleware.rs

@@ -502,7 +502,7 @@ impl AuthMiddleware {
             // Nothing to insert into the cache if we don't have credentials
             return next.run(request, extensions).await;
         };
-        let url = DisplaySafeUrl::from(request.url().clone());
+        let url = DisplaySafeUrl::from_url(request.url().clone());
         if matches!(auth_policy, AuthPolicy::Always) && credentials.password().is_none() {
             return Err(Error::Middleware(format_err!("Missing password for {url}")));
         }
@@ -801,7 +801,7 @@ impl AuthMiddleware {
 }
 
 fn tracing_url(request: &Request, credentials: Option<&Authentication>) -> DisplaySafeUrl {
-    let mut url = DisplaySafeUrl::from(request.url().clone());
+    let mut url = DisplaySafeUrl::from_url(request.url().clone());
     if let Some(Authentication::Credentials(creds)) = credentials {
         if let Some(username) = creds.username() {
             let _ = url.set_username(username);
@@ -1990,13 +1990,13 @@ mod tests {
         let base_url_2 = base_url.join("prefix_2")?;
         let indexes = Indexes::from_indexes(vec![
             Index {
-                url: DisplaySafeUrl::from(base_url_1.clone()),
+                url: DisplaySafeUrl::from_url(base_url_1.clone()),
-                root_url: DisplaySafeUrl::from(base_url_1.clone()),
+                root_url: DisplaySafeUrl::from_url(base_url_1.clone()),
                 auth_policy: AuthPolicy::Auto,
             },
             Index {
-                url: DisplaySafeUrl::from(base_url_2.clone()),
+                url: DisplaySafeUrl::from_url(base_url_2.clone()),
-                root_url: DisplaySafeUrl::from(base_url_2.clone()),
+                root_url: DisplaySafeUrl::from_url(base_url_2.clone()),
                 auth_policy: AuthPolicy::Auto,
             },
         ]);
@@ -2098,8 +2098,8 @@ mod tests {
         let base_url = Url::parse(&server.uri())?;
         let index_url = base_url.join("prefix_1")?;
         let indexes = Indexes::from_indexes(vec![Index {
-            url: DisplaySafeUrl::from(index_url.clone()),
+            url: DisplaySafeUrl::from_url(index_url.clone()),
-            root_url: DisplaySafeUrl::from(index_url.clone()),
+            root_url: DisplaySafeUrl::from_url(index_url.clone()),
             auth_policy: AuthPolicy::Auto,
         }]);
 
@@ -2153,7 +2153,7 @@ mod tests {
     }
 
     fn indexes_for(url: &Url, policy: AuthPolicy) -> Indexes {
-        let mut url = DisplaySafeUrl::from(url.clone());
+        let mut url = DisplaySafeUrl::from_url(url.clone());
         url.set_password(None).ok();
         url.set_username("").ok();
         Indexes::from_indexes(vec![Index {

crates/uv-auth/src/pyx.rs

@@ -10,7 +10,7 @@ use tracing::debug;
 use url::Url;
 
 use uv_cache_key::CanonicalUrl;
-use uv_redacted::DisplaySafeUrl;
+use uv_redacted::{DisplaySafeUrl, DisplaySafeUrlError};
 use uv_small_str::SmallString;
 use uv_state::{StateBucket, StateStore};
 use uv_static::EnvVars;
@@ -473,7 +473,7 @@ impl PyxTokenStore {
 #[derive(thiserror::Error, Debug)]
 pub enum TokenStoreError {
     #[error(transparent)]
-    Url(#[from] url::ParseError),
+    Url(#[from] DisplaySafeUrlError),
     #[error(transparent)]
     Io(#[from] io::Error),
     #[error(transparent)]

crates/uv-auth/src/service.rs

@@ -2,12 +2,12 @@ use serde::{Deserialize, Serialize};
 use std::str::FromStr;
 use thiserror::Error;
 use url::Url;
-use uv_redacted::DisplaySafeUrl;
+use uv_redacted::{DisplaySafeUrl, DisplaySafeUrlError};
 
 #[derive(Error, Debug)]
 pub enum ServiceParseError {
     #[error(transparent)]
-    InvalidUrl(#[from] url::ParseError),
+    InvalidUrl(#[from] DisplaySafeUrlError),
     #[error("Unsupported scheme: {0}")]
     UnsupportedScheme(String),
     #[error("HTTPS is required for non-local hosts")]
@@ -51,7 +51,7 @@ impl FromStr for Service {
         // First try parsing as-is
         let url = match DisplaySafeUrl::parse(s) {
             Ok(url) => url,
-            Err(url::ParseError::RelativeUrlWithoutBase) => {
+            Err(DisplaySafeUrlError::Url(url::ParseError::RelativeUrlWithoutBase)) => {
                 // If it's a relative URL, try prepending https://
                 let with_https = format!("https://{s}");
                 DisplaySafeUrl::parse(&with_https)?

crates/uv-bin-install/Cargo.toml

@@ -23,6 +23,7 @@ uv-distribution-filename = { workspace = true }
 uv-extract = { workspace = true }
 uv-pep440 = { workspace = true }
 uv-platform = { workspace = true }
+uv-redacted = { workspace = true }
 fs-err = { workspace = true, features = ["tokio"] }
 futures = { workspace = true }
 reqwest = { workspace = true }
@@ -34,4 +35,3 @@ tokio = { workspace = true }
 tokio-util = { workspace = true }
 tracing = { workspace = true }
 url = { workspace = true }
-

crates/uv-bin-install/src/lib.rs

@@ -24,6 +24,7 @@ use uv_client::{BaseClient, is_transient_network_error};
 use uv_extract::{Error as ExtractError, stream};
 use uv_pep440::Version;
 use uv_platform::Platform;
+use uv_redacted::DisplaySafeUrl;
 
 /// Binary tools that can be installed.
 #[derive(Debug, Clone, Copy, PartialEq, Eq, Hash)]
@@ -311,7 +312,7 @@ async fn download_and_unpack(
     let temp_dir = tempfile::tempdir_in(cache.bucket(CacheBucket::Binaries))?;
 
     let response = client
-        .for_host(&download_url.clone().into())
+        .for_host(&DisplaySafeUrl::from_url(download_url.clone()))
         .get(download_url.clone())
         .send()
         .await

crates/uv-cache-key/src/canonical_url.rs

@@ -4,7 +4,7 @@ use std::hash::{Hash, Hasher};
 use std::ops::Deref;
 
 use url::Url;
-use uv_redacted::DisplaySafeUrl;
+use uv_redacted::{DisplaySafeUrl, DisplaySafeUrlError};
 
 use crate::cache_key::{CacheKey, CacheKeyHasher};
 
@@ -98,7 +98,7 @@ impl CanonicalUrl {
         Self(url)
     }
 
-    pub fn parse(url: &str) -> Result<Self, url::ParseError> {
+    pub fn parse(url: &str) -> Result<Self, DisplaySafeUrlError> {
         Ok(Self::new(&DisplaySafeUrl::parse(url)?))
     }
 }
@@ -164,7 +164,7 @@ impl RepositoryUrl {
         Self(url)
     }
 
-    pub fn parse(url: &str) -> Result<Self, url::ParseError> {
+    pub fn parse(url: &str) -> Result<Self, DisplaySafeUrlError> {
         Ok(Self::new(&DisplaySafeUrl::parse(url)?))
     }
 }
@@ -204,7 +204,7 @@ mod tests {
     use super::*;
 
     #[test]
-    fn user_credential_does_not_affect_cache_key() -> Result<(), url::ParseError> {
+    fn user_credential_does_not_affect_cache_key() -> Result<(), DisplaySafeUrlError> {
         let mut hasher = CacheKeyHasher::new();
         CanonicalUrl::parse("https://example.com/pypa/sample-namespace-packages.git@2.0.0")?
             .cache_key(&mut hasher);
@@ -254,7 +254,7 @@ mod tests {
     }
 
     #[test]
-    fn canonical_url() -> Result<(), url::ParseError> {
+    fn canonical_url() -> Result<(), DisplaySafeUrlError> {
         // Two URLs should be considered equal regardless of the `.git` suffix.
         assert_eq!(
             CanonicalUrl::parse("git+https://github.com/pypa/sample-namespace-packages.git")?,
@@ -335,7 +335,7 @@ mod tests {
     }
 
     #[test]
-    fn repository_url() -> Result<(), url::ParseError> {
+    fn repository_url() -> Result<(), DisplaySafeUrlError> {
         // Two URLs should be considered equal regardless of the `.git` suffix.
         assert_eq!(
             RepositoryUrl::parse("git+https://github.com/pypa/sample-namespace-packages.git")?,

crates/uv-client/src/base_client.rs

@@ -35,6 +35,7 @@ use uv_pep508::MarkerEnvironment;
 use uv_platform_tags::Platform;
 use uv_preview::Preview;
 use uv_redacted::DisplaySafeUrl;
+use uv_redacted::DisplaySafeUrlError;
 use uv_static::EnvVars;
 use uv_version::version;
 use uv_warnings::warn_user_once;
@@ -577,7 +578,7 @@ impl BaseClient {
 
     /// Executes a request, applying redirect policy.
     pub async fn execute(&self, req: Request) -> reqwest_middleware::Result<Response> {
-        let client = self.for_host(&DisplaySafeUrl::from(req.url().clone()));
+        let client = self.for_host(&DisplaySafeUrl::from_url(req.url().clone()));
         client.execute(req).await
     }
 
@@ -707,7 +708,7 @@ fn request_into_redirect(
     res: &Response,
     cross_origin_credentials_policy: CrossOriginCredentialsPolicy,
 ) -> reqwest_middleware::Result<Option<Request>> {
-    let original_req_url = DisplaySafeUrl::from(req.url().clone());
+    let original_req_url = DisplaySafeUrl::from_url(req.url().clone());
     let status = res.status();
     let should_redirect = match status {
         StatusCode::MOVED_PERMANENTLY
@@ -760,7 +761,7 @@ fn request_into_redirect(
     let mut redirect_url = match DisplaySafeUrl::parse(location) {
         Ok(url) => url,
         // Per RFC 7231, URLs should be resolved against the request URL.
-        Err(ParseError::RelativeUrlWithoutBase) => original_req_url.join(location).map_err(|err| {
+        Err(DisplaySafeUrlError::Url(ParseError::RelativeUrlWithoutBase)) => original_req_url.join(location).map_err(|err| {
             reqwest_middleware::Error::Middleware(anyhow!(
                 "Invalid HTTP {status} 'Location' value `{location}` relative to `{original_req_url}`: {err}"
             ))

crates/uv-client/src/cached_client.rs

@@ -557,7 +557,7 @@ impl CachedClient {
         cached: DataWithCachePolicy,
         new_cache_policy_builder: CachePolicyBuilder,
     ) -> Result<CachedResponse, Error> {
-        let url = DisplaySafeUrl::from(req.url().clone());
+        let url = DisplaySafeUrl::from_url(req.url().clone());
         debug!("Sending revalidation request for: {url}");
         let mut response = self
             .0
@@ -627,7 +627,7 @@ impl CachedClient {
         req: Request,
         cache_control: CacheControl<'_>,
     ) -> Result<(Response, Option<Box<CachePolicy>>), Error> {
-        let url = DisplaySafeUrl::from(req.url().clone());
+        let url = DisplaySafeUrl::from_url(req.url().clone());
         trace!("Sending fresh {} request for {}", req.method(), url);
         let cache_policy_builder = CachePolicyBuilder::new(&req);
         let mut response = self

crates/uv-client/src/flat_index.rs

@@ -189,7 +189,7 @@ impl<'a> FlatIndexClient<'a> {
             async {
                 // Use the response URL, rather than the request URL, as the base for relative URLs.
                 // This ensures that we handle redirects and other URL transformations correctly.
-                let url = DisplaySafeUrl::from(response.url().clone());
+                let url = DisplaySafeUrl::from_url(response.url().clone());
 
                 let text = response
                     .text()

crates/uv-client/src/html.rs

@@ -8,7 +8,7 @@ use uv_normalize::PackageName;
 use uv_pep440::VersionSpecifiers;
 use uv_pypi_types::{BaseUrl, CoreMetadata, Hashes, PypiFile, Yanked};
 use uv_pypi_types::{HashError, LenientVersionSpecifiers};
-use uv_redacted::DisplaySafeUrl;
+use uv_redacted::{DisplaySafeUrl, DisplaySafeUrlError};
 
 /// A parsed structure from PyPI "HTML" index format for a single package.
 #[derive(Debug, Clone)]
@@ -285,7 +285,7 @@ pub enum Error {
     FromUtf8(#[from] std::string::FromUtf8Error),
 
     #[error("Failed to parse URL: {0}")]
-    UrlParse(String, #[source] url::ParseError),
+    UrlParse(String, #[source] DisplaySafeUrlError),
 
     #[error(transparent)]
     HtmlParse(#[from] tl::ParseError),

crates/uv-client/src/middleware.rs

@@ -43,7 +43,7 @@ impl Middleware for OfflineMiddleware {
     ) -> reqwest_middleware::Result<Response> {
         Err(reqwest_middleware::Error::Middleware(
             OfflineError {
-                url: DisplaySafeUrl::from(req.url().clone()),
+                url: DisplaySafeUrl::from_url(req.url().clone()),
             }
             .into(),
         ))

crates/uv-client/src/registry_client.rs

@@ -587,7 +587,7 @@ impl RegistryClient {
             async {
                 // Use the response URL, rather than the request URL, as the base for relative URLs.
                 // This ensures that we handle redirects and other URL transformations correctly.
-                let url = DisplaySafeUrl::from(response.url().clone());
+                let url = DisplaySafeUrl::from_url(response.url().clone());
 
                 let content_type = response
                     .headers()
@@ -766,7 +766,7 @@ impl RegistryClient {
             async {
                 // Use the response URL, rather than the request URL, as the base for relative URLs.
                 // This ensures that we handle redirects and other URL transformations correctly.
-                let url = DisplaySafeUrl::from(response.url().clone());
+                let url = DisplaySafeUrl::from_url(response.url().clone());
 
                 let content_type = response
                     .headers()

crates/uv-distribution-types/src/file.rs

@@ -8,7 +8,7 @@ use serde::{Deserialize, Serialize};
 use uv_pep440::{VersionSpecifiers, VersionSpecifiersParseError};
 use uv_pep508::split_scheme;
 use uv_pypi_types::{CoreMetadata, HashDigests, Yanked};
-use uv_redacted::DisplaySafeUrl;
+use uv_redacted::{DisplaySafeUrl, DisplaySafeUrlError};
 use uv_small_str::SmallString;
 
 /// Error converting [`uv_pypi_types::PypiFile`] to [`distribution_type::File`].
@@ -272,7 +272,7 @@ pub enum ToUrlError {
         base: String,
         /// The underlying URL parse error.
         #[source]
-        err: url::ParseError,
+        err: DisplaySafeUrlError,
     },
     /// An error that occurs when the base URL could not be joined with
     /// the relative path in a [`FileLocation::Relative`].
@@ -284,7 +284,7 @@ pub enum ToUrlError {
         path: String,
         /// The underlying URL parse error.
         #[source]
-        err: url::ParseError,
+        err: DisplaySafeUrlError,
     },
     /// An error that occurs when the absolute URL in [`FileLocation::Absolute`]
     /// could not be parsed as a valid URL.
@@ -294,7 +294,7 @@ pub enum ToUrlError {
         absolute: String,
         /// The underlying URL parse error.
         #[source]
-        err: url::ParseError,
+        err: DisplaySafeUrlError,
     },
 }
 

crates/uv-distribution-types/src/requirement.rs

@@ -13,7 +13,7 @@ use uv_pep440::VersionSpecifiers;
 use uv_pep508::{
     MarkerEnvironment, MarkerTree, RequirementOrigin, VerbatimUrl, VersionOrUrl, marker,
 };
-use uv_redacted::DisplaySafeUrl;
+use uv_redacted::{DisplaySafeUrl, DisplaySafeUrlError};
 
 use crate::{IndexMetadata, IndexUrl};
 
@@ -29,7 +29,7 @@ pub enum RequirementError {
     #[error(transparent)]
     ParsedUrlError(#[from] ParsedUrlError),
     #[error(transparent)]
-    UrlParseError(#[from] url::ParseError),
+    UrlParseError(#[from] DisplaySafeUrlError),
     #[error(transparent)]
     OidParseError(#[from] OidParseError),
     #[error(transparent)]

crates/uv-distribution/src/metadata/lowering.rs

@@ -14,7 +14,7 @@ use uv_normalize::{ExtraName, GroupName, PackageName};
 use uv_pep440::VersionSpecifiers;
 use uv_pep508::{MarkerTree, VerbatimUrl, VersionOrUrl, looks_like_git_repository};
 use uv_pypi_types::{ConflictItem, ParsedGitUrl, ParsedUrlError, VerbatimParsedUrl};
-use uv_redacted::DisplaySafeUrl;
+use uv_redacted::{DisplaySafeUrl, DisplaySafeUrlError};
 use uv_workspace::Workspace;
 use uv_workspace::pyproject::{PyProjectToml, Source, Sources};
 
@@ -527,7 +527,7 @@ pub enum LoweringError {
     #[error("Workspace members are not allowed in non-workspace contexts")]
     WorkspaceMember,
     #[error(transparent)]
-    InvalidUrl(#[from] url::ParseError),
+    InvalidUrl(#[from] DisplaySafeUrlError),
     #[error(transparent)]
     InvalidVerbatimUrl(#[from] uv_pep508::VerbatimUrlError),
     #[error("Fragments are not allowed in URLs: `{0}`")]

crates/uv-pep508/src/unnamed.rs

@@ -48,7 +48,7 @@ impl UnnamedRequirementUrl for VerbatimUrl {
     }
 
     fn parse_unnamed_url(given: impl AsRef<str>) -> Result<Self, Self::Err> {
-        Ok(Self::parse_url(given)?)
+        Self::parse_url(given)
     }
 
     fn with_given(self, given: impl AsRef<str>) -> Self {

crates/uv-pep508/src/verbatim_url.rs

@@ -9,12 +9,12 @@ use std::sync::LazyLock;
 use arcstr::ArcStr;
 use regex::Regex;
 use thiserror::Error;
-use url::{ParseError, Url};
+use url::Url;
 use uv_cache_key::{CacheKey, CacheKeyHasher};
 
 #[cfg_attr(not(feature = "non-pep508-extensions"), allow(unused_imports))]
 use uv_fs::{normalize_absolute_path, normalize_url_path};
-use uv_redacted::DisplaySafeUrl;
+use uv_redacted::{DisplaySafeUrl, DisplaySafeUrlError};
 
 use crate::Pep508Url;
 
@@ -57,8 +57,10 @@ impl VerbatimUrl {
     }
 
     /// Parse a URL from a string.
-    pub fn parse_url(given: impl AsRef<str>) -> Result<Self, ParseError> {
+    pub fn parse_url(given: impl AsRef<str>) -> Result<Self, VerbatimUrlError> {
-        let url = DisplaySafeUrl::parse(given.as_ref())?;
+        let given = given.as_ref();
+        let url = DisplaySafeUrl::parse(given)?;
+
         Ok(Self { url, given: None })
     }
 
@@ -251,7 +253,7 @@ impl std::str::FromStr for VerbatimUrl {
     type Err = VerbatimUrlError;
 
     fn from_str(s: &str) -> Result<Self, Self::Err> {
-        Ok(Self::parse_url(s).map(|url| url.with_given(s))?)
+        Self::parse_url(s).map(|url| url.with_given(s))
     }
 }
 
@@ -271,7 +273,7 @@ impl Deref for VerbatimUrl {
 
 impl From<Url> for VerbatimUrl {
     fn from(url: Url) -> Self {
-        Self::from_url(DisplaySafeUrl::from(url))
+        Self::from_url(DisplaySafeUrl::from_url(url))
     }
 }
 
@@ -390,7 +392,7 @@ impl Pep508Url for VerbatimUrl {
 pub enum VerbatimUrlError {
     /// Failed to parse a URL.
     #[error(transparent)]
-    Url(#[from] ParseError),
+    Url(#[from] DisplaySafeUrlError),
 
     /// Received a relative path, but no working directory was provided.
     #[error("relative path without a working directory: {0}")]
@@ -645,6 +647,8 @@ impl std::fmt::Display for Scheme {
 
 #[cfg(test)]
 mod tests {
+    use insta::assert_snapshot;
+
     use super::*;
 
     #[test]
@@ -749,4 +753,27 @@ mod tests {
         let url = Url::parse("https://github.com/pypa/pip/archive/1.3.1.zip#sha1=da9234ee9982d4bbb3c72346a6de940a148ea686").unwrap();
         assert!(!looks_like_git_repository(&url));
     }
+
+    #[test]
+    fn parse_url_ambiguous() {
+        assert_snapshot!(
+            VerbatimUrl::parse_url("https://user/name:password@domain/a/b/c").unwrap_err().to_string(),
+            @"ambiguous user/pass authority in URL (not percent-encoded?): https:***@domain/a/b/c"
+        );
+
+        assert_snapshot!(
+            VerbatimUrl::parse_url("https://user\\name:password@domain/a/b/c").unwrap_err().to_string(),
+            @"ambiguous user/pass authority in URL (not percent-encoded?): https:***@domain/a/b/c"
+        );
+
+        assert_snapshot!(
+            VerbatimUrl::parse_url("https://user#name:password@domain/a/b/c").unwrap_err().to_string(),
+            @"ambiguous user/pass authority in URL (not percent-encoded?): https:***@domain/a/b/c"
+        );
+
+        assert_snapshot!(
+            VerbatimUrl::parse_url("https://user.com/name:password@domain/a/b/c").unwrap_err().to_string(),
+            @"ambiguous user/pass authority in URL (not percent-encoded?): https:***@domain/a/b/c"
+        );
+    }
 }

crates/uv-publish/src/trusted_publishing.rs

@@ -10,13 +10,13 @@ use std::fmt::Display;
 use thiserror::Error;
 use tracing::{debug, trace};
 use url::Url;
-use uv_redacted::DisplaySafeUrl;
+use uv_redacted::{DisplaySafeUrl, DisplaySafeUrlError};
 use uv_static::EnvVars;
 
 #[derive(Debug, Error)]
 pub enum TrustedPublishingError {
     #[error(transparent)]
-    Url(#[from] url::ParseError),
+    Url(#[from] DisplaySafeUrlError),
     #[error("Failed to obtain OIDC token: is the `id-token: write` permission missing?")]
     GitHubPermissions(#[source] ambient_id::Error),
     /// A hard failure during OIDC token discovery.

crates/uv-pypi-types/src/direct_url.rs

@@ -2,7 +2,7 @@ use std::collections::BTreeMap;
 use std::path::Path;
 
 use serde::{Deserialize, Serialize};
-use uv_redacted::DisplaySafeUrl;
+use uv_redacted::{DisplaySafeUrl, DisplaySafeUrlError};
 
 /// Metadata for a distribution that was installed via a direct URL.
 ///
@@ -93,7 +93,7 @@ impl std::fmt::Display for VcsKind {
 }
 
 impl TryFrom<&DirectUrl> for DisplaySafeUrl {
-    type Error = url::ParseError;
+    type Error = DisplaySafeUrlError;
 
     fn try_from(value: &DirectUrl) -> Result<Self, Self::Error> {
         match value {

crates/uv-pypi-types/src/parsed_url.rs

@@ -2,7 +2,7 @@ use std::fmt::{Display, Formatter};
 use std::path::{Path, PathBuf};
 
 use thiserror::Error;
-use url::{ParseError, Url};
+use url::Url;
 use uv_cache_key::{CacheKey, CacheKeyHasher};
 
 use uv_distribution_filename::{DistExtension, ExtensionError};
@@ -10,7 +10,7 @@ use uv_git_types::{GitUrl, GitUrlParseError};
 use uv_pep508::{
     Pep508Url, UnnamedRequirementUrl, VerbatimUrl, VerbatimUrlError, looks_like_git_repository,
 };
-use uv_redacted::DisplaySafeUrl;
+use uv_redacted::{DisplaySafeUrl, DisplaySafeUrlError};
 
 use crate::{ArchiveInfo, DirInfo, DirectUrl, VcsInfo, VcsKind};
 
@@ -27,7 +27,7 @@ pub enum ParsedUrlError {
     #[error(transparent)]
     GitUrlParse(#[from] GitUrlParseError),
     #[error("Not a valid URL: `{0}`")]
-    UrlParse(String, #[source] ParseError),
+    UrlParse(String, #[source] DisplaySafeUrlError),
     #[error(transparent)]
     VerbatimUrl(#[from] VerbatimUrlError),
     #[error(

crates/uv-python/src/downloads.rs

@@ -28,7 +28,7 @@ use uv_extract::hash::Hasher;
 use uv_fs::{Simplified, rename_with_retry};
 use uv_platform::{self as platform, Arch, Libc, Os, Platform};
 use uv_pypi_types::{HashAlgorithm, HashDigest};
-use uv_redacted::DisplaySafeUrl;
+use uv_redacted::{DisplaySafeUrl, DisplaySafeUrlError};
 use uv_static::EnvVars;
 
 use crate::PythonVariant;
@@ -75,7 +75,7 @@ pub enum Error {
         actual: String,
     },
     #[error("Invalid download URL")]
-    InvalidUrl(#[from] url::ParseError),
+    InvalidUrl(#[from] DisplaySafeUrlError),
     #[error("Invalid download URL: {0}")]
     InvalidUrlFormat(DisplaySafeUrl),
     #[error("Invalid path in file URL: `{0}`")]

crates/uv-redacted/Cargo.toml

@@ -19,6 +19,7 @@ workspace = true
 ref-cast = { workspace = true }
 schemars = { workspace = true, optional = true }
 serde = { workspace = true }
+thiserror = { workspace = true }
 url = { workspace = true }
 
 [features]

crates/uv-redacted/src/lib.rs

@@ -4,8 +4,21 @@ use std::borrow::Cow;
 use std::fmt::{Debug, Display};
 use std::ops::{Deref, DerefMut};
 use std::str::FromStr;
+use thiserror::Error;
 use url::Url;
 
+#[derive(Error, Debug, Clone, PartialEq, Eq)]
+pub enum DisplaySafeUrlError {
+    /// Failed to parse a URL.
+    #[error(transparent)]
+    Url(#[from] url::ParseError),
+
+    /// We parsed a URL, but couldn't disambiguate its authority
+    /// component.
+    #[error("ambiguous user/pass authority in URL (not percent-encoded?): {0}")]
+    AmbiguousAuthority(String),
+}
+
 /// A [`Url`] wrapper that redacts credentials when displaying the URL.
 ///
 /// `DisplaySafeUrl` wraps the standard [`url::Url`] type, providing functionality to mask
@@ -47,8 +60,55 @@ pub struct DisplaySafeUrl(Url);
 
 impl DisplaySafeUrl {
     #[inline]
-    pub fn parse(input: &str) -> Result<Self, url::ParseError> {
+    pub fn parse(input: &str) -> Result<Self, DisplaySafeUrlError> {
-        Ok(Self(Url::parse(input)?))
+        let url = Url::parse(input)?;
+
+        // Reject some ambiguous cases, e.g., `https://user/name:password@domain/a/b/c`
+        //
+        // In this case the user *probably* meant to have a username of "user/name", but both RFC
+        // 3986 and WHATWG URL expect the userinfo (RFC 3986) or authority (WHATWG) to not contain a
+        // non-percent-encoded slash or other special character.
+        //
+        // This ends up being moderately annoying to detect, since the above gets parsed into a
+        // "valid" WHATWG URL where the host is `used` and the pathname is
+        // `/name:password@domain/a/b/c` rather than causing a parse error.
+        //
+        // To detect it, we use a heuristic: if the password component is missing but the path or
+        // fragment contain a `:` followed by a `@`, then we assume the URL is ambiguous.
+        if url.password().is_none()
+            && (url
+                .path()
+                .find(':')
+                .is_some_and(|pos| url.path()[pos..].contains('@'))
+                || url
+                    .fragment()
+                    .map(|fragment| {
+                        fragment
+                            .find(':')
+                            .is_some_and(|pos| fragment[pos..].contains('@'))
+                    })
+                    .unwrap_or(false))
+            // If the above is true, we should always expect to find these in the given URL
+            && let Some(col_pos) = input.find(':')
+            && let Some(at_pos) = input.rfind('@')
+        {
+            // Our ambiguous URL probably has credentials in it, so we don't want to blast it out in
+            // the error message. We somewhat aggressively replace everything between the scheme's
+            // ':' and the lastmost `@` with `***`.
+            let redacted_path = format!("{}***{}", &input[0..=col_pos], &input[at_pos..]);
+            return Err(DisplaySafeUrlError::AmbiguousAuthority(redacted_path));
+        }
+
+        Ok(Self(url))
+    }
+
+    /// Create a new [`DisplaySafeUrl`] from a [`Url`].
+    ///
+    /// Unlike [`Self::parse`], this doesn't perform any ambiguity checks.
+    /// That means that it's primarily useful for contexts where a human can't easily accidentally
+    /// introduce an ambiguous URL, such as URLs being read from a request.
+    pub fn from_url(url: Url) -> Self {
+        Self(url)
     }
 
     /// Cast a `&Url` to a `&DisplaySafeUrl` using ref-cast.
@@ -59,8 +119,8 @@ impl DisplaySafeUrl {
 
     /// Parse a string as an URL, with this URL as the base URL.
     #[inline]
-    pub fn join(&self, input: &str) -> Result<Self, url::ParseError> {
+    pub fn join(&self, input: &str) -> Result<Self, DisplaySafeUrlError> {
-        self.0.join(input).map(Self)
+        Ok(Self(self.0.join(input)?))
     }
 
     /// Serialize with Serde using the internal representation of the `Url` struct.
@@ -78,12 +138,12 @@ impl DisplaySafeUrl {
     where
         D: serde::Deserializer<'de>,
     {
-        Url::deserialize_internal(deserializer).map(Self)
+        Ok(Self(Url::deserialize_internal(deserializer)?))
     }
 
     #[allow(clippy::result_unit_err)]
     pub fn from_file_path<P: AsRef<std::path::Path>>(path: P) -> Result<Self, ()> {
-        Url::from_file_path(path).map(Self::from)
+        Ok(Self(Url::from_file_path(path)?))
     }
 
     /// Remove the credentials from a URL, allowing the generic `git` username (without a password)
@@ -175,12 +235,6 @@ impl Debug for DisplaySafeUrl {
     }
 }
 
-impl From<Url> for DisplaySafeUrl {
-    fn from(url: Url) -> Self {
-        Self(url)
-    }
-}
-
 impl From<DisplaySafeUrl> for Url {
     fn from(url: DisplaySafeUrl) -> Self {
         url.0
@@ -188,10 +242,10 @@ impl From<DisplaySafeUrl> for Url {
 }
 
 impl FromStr for DisplaySafeUrl {
-    type Err = url::ParseError;
+    type Err = DisplaySafeUrlError;
 
     fn from_str(input: &str) -> Result<Self, Self::Err> {
-        Ok(Self(Url::from_str(input)?))
+        Self::parse(input)
     }
 }
 
@@ -250,8 +304,8 @@ mod tests {
     #[test]
     fn from_url_no_credentials() {
         let url_str = "https://pypi-proxy.fly.dev/basic-auth/simple";
-        let url = DisplaySafeUrl::parse(url_str).unwrap();
+        let log_safe_url =
-        let log_safe_url = url;
+            DisplaySafeUrl::parse("https://pypi-proxy.fly.dev/basic-auth/simple").unwrap();
         assert_eq!(log_safe_url.username(), "");
         assert!(log_safe_url.password().is_none());
         assert_eq!(log_safe_url.to_string(), url_str);
@@ -259,9 +313,9 @@ mod tests {
 
     #[test]
     fn from_url_username_and_password() {
-        let url_str = "https://user:pass@pypi-proxy.fly.dev/basic-auth/simple";
+        let log_safe_url =
-        let url = DisplaySafeUrl::parse(url_str).unwrap();
+            DisplaySafeUrl::parse("https://user:pass@pypi-proxy.fly.dev/basic-auth/simple")
-        let log_safe_url = url;
+                .unwrap();
         assert_eq!(log_safe_url.username(), "user");
         assert!(log_safe_url.password().is_some_and(|p| p == "pass"));
         assert_eq!(
@@ -272,9 +326,8 @@ mod tests {
 
     #[test]
     fn from_url_just_password() {
-        let url_str = "https://:pass@pypi-proxy.fly.dev/basic-auth/simple";
+        let log_safe_url =
-        let url = DisplaySafeUrl::parse(url_str).unwrap();
+            DisplaySafeUrl::parse("https://:pass@pypi-proxy.fly.dev/basic-auth/simple").unwrap();
-        let log_safe_url = url;
         assert_eq!(log_safe_url.username(), "");
         assert!(log_safe_url.password().is_some_and(|p| p == "pass"));
         assert_eq!(
@@ -285,9 +338,8 @@ mod tests {
 
     #[test]
     fn from_url_just_username() {
-        let url_str = "https://user@pypi-proxy.fly.dev/basic-auth/simple";
+        let log_safe_url =
-        let url = DisplaySafeUrl::parse(url_str).unwrap();
+            DisplaySafeUrl::parse("https://user@pypi-proxy.fly.dev/basic-auth/simple").unwrap();
-        let log_safe_url = url;
         assert_eq!(log_safe_url.username(), "user");
         assert!(log_safe_url.password().is_none());
         assert_eq!(
@@ -383,4 +435,22 @@ mod tests {
             "https://user:****@pypi-proxy.fly.dev/basic-auth/simple"
         );
     }
+
+    #[test]
+    fn parse_url_ambiguous() {
+        for url in &[
+            "https://user/name:password@domain/a/b/c",
+            "https://user\\name:password@domain/a/b/c",
+            "https://user#name:password@domain/a/b/c",
+            "https://user.com/name:password@domain/a/b/c",
+        ] {
+            let err = DisplaySafeUrl::parse(url).unwrap_err();
+            match err {
+                DisplaySafeUrlError::AmbiguousAuthority(redacted) => {
+                    assert!(redacted.starts_with("https:***@domain/a/b/c"));
+                }
+                DisplaySafeUrlError::Url(_) => panic!("expected AmbiguousAuthority error"),
+            }
+        }
+    }
 }

crates/uv-requirements-txt/src/lib.rs

@@ -57,6 +57,7 @@ use uv_pep508::{Pep508Error, RequirementOrigin, VerbatimUrl, expand_env_vars};
 use uv_pypi_types::VerbatimParsedUrl;
 #[cfg(feature = "http")]
 use uv_redacted::DisplaySafeUrl;
+use uv_redacted::DisplaySafeUrlError;
 
 use crate::requirement::EditableError;
 pub use crate::requirement::RequirementsTxtRequirement;
@@ -282,7 +283,7 @@ impl RequirementsTxt {
                             requirements_txt.join(
                                 Url::parse(filename.as_ref())
                                     .map_err(|err| RequirementsTxtParserError::Url {
-                                        source: err,
+                                        source: DisplaySafeUrlError::Url(err).into(),
                                         url: filename.to_string(),
                                         start,
                                         end,
@@ -356,7 +357,7 @@ impl RequirementsTxt {
                             requirements_txt.join(
                                 Url::parse(filename.as_ref())
                                     .map_err(|err| RequirementsTxtParserError::Url {
-                                        source: err,
+                                        source: DisplaySafeUrlError::Url(err).into(),
                                         url: filename.to_string(),
                                         start,
                                         end,
@@ -1041,7 +1042,7 @@ pub struct RequirementsTxtFileError {
 pub enum RequirementsTxtParserError {
     Io(io::Error),
     Url {
-        source: url::ParseError,
+        source: uv_pep508::VerbatimUrlError,
         url: String,
         start: usize,
         end: usize,
@@ -1112,7 +1113,7 @@ pub enum RequirementsTxtParserError {
     #[cfg(feature = "http")]
     Reqwest(DisplaySafeUrl, reqwest_middleware::Error),
     #[cfg(feature = "http")]
-    InvalidUrl(String, url::ParseError),
+    InvalidUrl(String, DisplaySafeUrlError),
 }
 
 impl Display for RequirementsTxtParserError {
@@ -1184,7 +1185,15 @@ impl Display for RequirementsTxtParserError {
             }
             #[cfg(feature = "http")]
             Self::InvalidUrl(url, err) => {
-                write!(f, "Not a valid  URL, {err}: `{url}`")
+                match err {
+                    DisplaySafeUrlError::Url(err) => write!(f, "Not a valid URL, {err}: `{url}`"),
+                    DisplaySafeUrlError::AmbiguousAuthority(_) => {
+                        // Intentionally avoid leaking the URL here, since we suspect that the user
+                        // has given us an ambiguous URL that contains sensitive information.
+                        // The error's own Display will provide a redacted version of the URL.
+                        write!(f, "Invalid URL: {err}")
+                    }
+                }
             }
         }
     }
@@ -1343,9 +1352,15 @@ impl Display for RequirementsTxtFileError {
                 write!(f, "Error while accessing remote requirements file: `{url}`")
             }
             #[cfg(feature = "http")]
-            RequirementsTxtParserError::InvalidUrl(url, err) => {
+            RequirementsTxtParserError::InvalidUrl(url, err) => match err {
-                write!(f, "Not a valid URL, {err}: `{url}`")
+                DisplaySafeUrlError::Url(err) => write!(f, "Not a valid URL, {err}: `{url}`"),
-            }
+                DisplaySafeUrlError::AmbiguousAuthority(_) => {
+                    // Intentionally avoid leaking the URL here, since we suspect that the user
+                    // has given us an ambiguous URL that contains sensitive information.
+                    // The error's own Display will provide a redacted version of the URL.
+                    write!(f, "Invalid URL: {err}")
+                }
+            },
         }
     }
 }

crates/uv-requirements/src/source_tree.rs

@@ -178,7 +178,7 @@ impl<'a, Context: BuildContext> SourceTreeResolver<'a, Context> {
             }
         }
 
-        let Ok(url) = Url::from_directory_path(path).map(DisplaySafeUrl::from) else {
+        let Ok(url) = Url::from_directory_path(path).map(DisplaySafeUrl::from_url) else {
             return Err(anyhow::anyhow!("Failed to convert path to URL"));
         };
         let source = SourceUrl::Directory(DirectorySourceUrl {

crates/uv-resolver/src/lock/export/pylock_toml.rs

@@ -1420,7 +1420,7 @@ impl PylockTomlVcs {
             let mut url = if let Some(url) = self.url.as_ref() {
                 url.clone()
             } else if let Some(path) = self.path.as_ref() {
-                DisplaySafeUrl::from(
+                DisplaySafeUrl::from_url(
                     Url::from_directory_path(install_path.join(path))
                         .map_err(|()| PylockTomlErrorKind::PathToUrl)?,
                 )

crates/uv-resolver/src/lock/mod.rs

@@ -44,7 +44,7 @@ use uv_pypi_types::{
     ConflictKind, Conflicts, HashAlgorithm, HashDigest, HashDigests, Hashes, ParsedArchiveUrl,
     ParsedGitUrl, PyProjectToml,
 };
-use uv_redacted::DisplaySafeUrl;
+use uv_redacted::{DisplaySafeUrl, DisplaySafeUrlError};
 use uv_small_str::SmallString;
 use uv_types::{BuildContext, HashStrategy};
 use uv_workspace::{Editability, WorkspaceMember};
@@ -5975,7 +5975,7 @@ enum SourceParseError {
         given: String,
         /// The URL parse error.
         #[source]
-        err: url::ParseError,
+        err: DisplaySafeUrlError,
     },
     /// An error that occurs when a Git URL is missing a precise commit SHA.
     #[error("Missing SHA in source `{given}`")]

crates/uv-resolver/src/redirect.rs

@@ -84,13 +84,13 @@ fn apply_redirect(url: &VerbatimUrl, redirect: DisplaySafeUrl) -> VerbatimUrl {
 
 #[cfg(test)]
 mod tests {
-    use uv_pep508::VerbatimUrl;
+    use uv_pep508::{VerbatimUrl, VerbatimUrlError};
     use uv_redacted::DisplaySafeUrl;
 
     use crate::redirect::apply_redirect;
 
     #[test]
-    fn test_apply_redirect() -> Result<(), url::ParseError> {
+    fn test_apply_redirect() -> Result<(), VerbatimUrlError> {
         // If there's no `@` in the original representation, we can just append the precise suffix
         // to the given representation.
         let verbatim = VerbatimUrl::parse_url("https://github.com/flask.git")?

crates/uv/tests/it/sync.rs

@@ -14717,3 +14717,46 @@ fn sync_no_sources_editable_to_package_switch() -> Result<()> {
 
     Ok(())
 }
+
+#[test]
+fn sync_fails_ambiguous_url() -> Result<()> {
+    let context = TestContext::new("3.12");
+    let pyproject_toml = context.temp_dir.child("pyproject.toml");
+    pyproject_toml.write_str(
+        r#"
+        [project]
+        name = "project"
+        version = "0.1.0"
+        requires-python = ">=3.12"
+        dependencies = ["anyio==3.7.0"]
+
+        [[tool.uv.index]]
+        name = "bug"
+        url = "https://user/name:password@domain/a/b/c"
+        default = true
+        "#,
+    )?;
+
+    uv_snapshot!(context.filters(), context.sync(), @r#"
+    success: false
+    exit_code: 2
+    ----- stdout -----
+
+    ----- stderr -----
+    warning: Failed to parse `pyproject.toml` during settings discovery:
+      TOML parse error at line 10, column 15
+         |
+      10 |         url = "https://user/name:password@domain/a/b/c"
+         |               ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+      ambiguous user/pass authority in URL (not percent-encoded?): https:***@domain/a/b/c
+
+    error: Failed to parse: `pyproject.toml`
+      Caused by: TOML parse error at line 10, column 15
+       |
+    10 |         url = "https://user/name:password@domain/a/b/c"
+       |               ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+    ambiguous user/pass authority in URL (not percent-encoded?): https:***@domain/a/b/c
+    "#);
+
+    Ok(())
+}