diff --git a/crates/pep508-rs/src/lib.rs b/crates/pep508-rs/src/lib.rs
index 01d1e40b58b4c..799cceb38ed61 100644
--- a/crates/pep508-rs/src/lib.rs
+++ b/crates/pep508-rs/src/lib.rs
@@ -834,11 +834,19 @@ fn parse_extras_cursor<T: Pep508Url>(
 /// Parse a raw string for a URL requirement, which could be either a URL or a local path, and which
 /// could contain unexpanded environment variables.
 ///
+/// When parsing, we eat characters until we see any of the following:
+/// - A newline.
+/// - A semicolon (marker) or hash (comment), _preceded_ by a space. We parse the URL until the last
+///   non-whitespace character (inclusive).
+/// - A semicolon (marker) or hash (comment) _followed_ by a space. We treat this as an error, since
+///   the end of the URL is ambiguous.
+///
 /// For example:
 /// - `https://pypi.org/project/requests/...`
 /// - `file:///home/ferris/project/scripts/...`
 /// - `file:../editable/`
 /// - `../editable/`
+/// - `../path to editable/`
 /// - `https://download.pytorch.org/whl/torch_stable.html`
 fn parse_url<T: Pep508Url>(
     cursor: &mut Cursor,
@@ -847,7 +855,40 @@ fn parse_url<T: Pep508Url>(
     // wsp*
     cursor.eat_whitespace();
     // <URI_reference>
-    let (start, len) = cursor.take_while(|char| !char.is_whitespace());
+    let (start, len) = {
+        let start = cursor.pos();
+        let mut len = 0;
+        while let Some((_, c)) = cursor.next() {
+            // If we see a line break, we're done.
+            if matches!(c, '\r' | '\n') {
+                break;
+            }
+
+            // If we see top-level whitespace, check if it's followed by a semicolon or hash. If so,
+            // end the URL at the last non-whitespace character.
+            if c.is_whitespace() {
+                let mut cursor = cursor.clone();
+                cursor.eat_whitespace();
+                if matches!(cursor.peek_char(), None | Some(';' | '#')) {
+                    break;
+                }
+            }
+
+            len += c.len_utf8();
+
+            // If we see a top-level semicolon or hash followed by whitespace, we're done.
+            match c {
+                ';' if cursor.peek_char().is_some_and(char::is_whitespace) => {
+                    break;
+                }
+                '#' if cursor.peek_char().is_some_and(char::is_whitespace) => {
+                    break;
+                }
+                _ => {}
+            }
+        }
+        (start, len)
+    };
     let url = cursor.slice(start, len);
     if url.is_empty() {
         return Err(Pep508Error {
@@ -1087,16 +1128,21 @@ fn parse_pep508_requirement<T: Pep508Url>(
     // wsp*
     cursor.eat_whitespace();
     if let Some((pos, char)) = cursor.next() {
-        if let Some(VersionOrUrl::Url(url)) = requirement_kind {
-            if marker.is_none() && url.to_string().ends_with(';') {
-                return Err(Pep508Error {
-                    message: Pep508ErrorSource::String(
-                        "Missing space before ';', the end of the URL is ambiguous".to_string(),
-                    ),
-                    start: requirement_end - ';'.len_utf8(),
-                    len: ';'.len_utf8(),
-                    input: cursor.to_string(),
-                });
+        if marker.is_none() {
+            if let Some(VersionOrUrl::Url(url)) = requirement_kind {
+                let url = url.to_string();
+                for c in [';', '#'] {
+                    if url.ends_with(c) {
+                        return Err(Pep508Error {
+                            message: Pep508ErrorSource::String(format!(
+                                "Missing space before '{c}', the end of the URL is ambiguous"
+                            )),
+                            start: requirement_end - c.len_utf8(),
+                            len: c.len_utf8(),
+                            input: cursor.to_string(),
+                        });
+                    }
+                }
             }
         }
         let message = if marker.is_none() {
diff --git a/crates/pep508-rs/src/unnamed.rs b/crates/pep508-rs/src/unnamed.rs
index 06c4757438c33..1f97f50c198d8 100644
--- a/crates/pep508-rs/src/unnamed.rs
+++ b/crates/pep508-rs/src/unnamed.rs
@@ -175,16 +175,20 @@ fn parse_unnamed_requirement<Url: UnnamedRequirementUrl>(
     // wsp*
     cursor.eat_whitespace();
     if let Some((pos, char)) = cursor.next() {
-        if let Some(given) = url.given() {
-            if given.ends_with(';') && marker.is_none() {
-                return Err(Pep508Error {
-                    message: Pep508ErrorSource::String(
-                        "Missing space before ';', the end of the URL is ambiguous".to_string(),
-                    ),
-                    start: requirement_end - ';'.len_utf8(),
-                    len: ';'.len_utf8(),
-                    input: cursor.to_string(),
-                });
+        if marker.is_none() {
+            if let Some(given) = url.given() {
+                for c in [';', '#'] {
+                    if given.ends_with(c) {
+                        return Err(Pep508Error {
+                            message: Pep508ErrorSource::String(format!(
+                                "Missing space before '{c}', the end of the URL is ambiguous"
+                            )),
+                            start: requirement_end - c.len_utf8(),
+                            len: c.len_utf8(),
+                            input: cursor.to_string(),
+                        });
+                    }
+                }
             }
         }
         let message = if marker.is_none() {
@@ -349,9 +353,20 @@ fn preprocess_unnamed_url<Url: UnnamedRequirementUrl>(
 /// Like [`crate::parse_url`], but allows for extras to be present at the end of the URL, to comply
 /// with the non-PEP 508 extensions.
 ///
+/// When parsing, we eat characters until we see any of the following:
+/// - A newline.
+/// - A semicolon (marker) or hash (comment), _preceded_ by a space. We parse the URL until the last
+///   non-whitespace character (inclusive).
+/// - A semicolon (marker) or hash (comment) _followed_ by a space. We treat this as an error, since
+///   the end of the URL is ambiguous.
+///
+/// URLs can include extras at the end, enclosed in square brackets.
+///
 /// For example:
 /// - `https://download.pytorch.org/whl/torch_stable.html[dev]`
 /// - `../editable[dev]`
+/// - `https://download.pytorch.org/whl/torch_stable.html ; python_version > "3.8"`
+/// - `https://download.pytorch.org/whl/torch_stable.html # this is a comment`
 fn parse_unnamed_url<Url: UnnamedRequirementUrl>(
     cursor: &mut Cursor,
     working_dir: Option<&Path>,
@@ -363,30 +378,44 @@ fn parse_unnamed_url<Url: UnnamedRequirementUrl>(
     let (start, len) = {
         let start = cursor.pos();
         let mut len = 0;
-        let mut backslash = false;
         let mut depth = 0u32;
         while let Some((_, c)) = cursor.next() {
-            if backslash {
-                backslash = false;
-            } else if c == '\\' {
-                backslash = true;
-            } else if c == '[' {
+            // If we see a line break, we're done.
+            if matches!(c, '\r' | '\n') {
+                break;
+            }
+
+            // Track the depth of brackets.
+            if c == '[' {
                 depth = depth.saturating_add(1);
             } else if c == ']' {
                 depth = depth.saturating_sub(1);
             }
 
-            // If we see top-level whitespace, we're done.
+            // If we see top-level whitespace, check if it's followed by a semicolon or hash. If so,
+            // end the URL at the last non-whitespace character.
             if depth == 0 && c.is_whitespace() {
-                break;
-            }
-
-            // If we see a line break, we're done.
-            if matches!(c, '\r' | '\n') {
-                break;
+                let mut cursor = cursor.clone();
+                cursor.eat_whitespace();
+                if matches!(cursor.peek_char(), None | Some(';' | '#')) {
+                    break;
+                }
             }
 
             len += c.len_utf8();
+
+            // If we see a top-level semicolon or hash followed by whitespace, we're done.
+            if depth == 0 {
+                match c {
+                    ';' if cursor.peek_char().is_some_and(char::is_whitespace) => {
+                        break;
+                    }
+                    '#' if cursor.peek_char().is_some_and(char::is_whitespace) => {
+                        break;
+                    }
+                    _ => {}
+                }
+            }
         }
         (start, len)
     };
diff --git a/crates/requirements-txt/src/lib.rs b/crates/requirements-txt/src/lib.rs
index 5a7fd7cb377c8..93f71731db46c 100644
--- a/crates/requirements-txt/src/lib.rs
+++ b/crates/requirements-txt/src/lib.rs
@@ -1325,6 +1325,7 @@ mod test {
 
     #[cfg(unix)]
     #[test_case(Path::new("semicolon.txt"))]
+    #[test_case(Path::new("hash.txt"))]
     #[tokio::test]
     async fn parse_err(path: &Path) {
         let working_dir = workspace_test_data_dir().join("requirements-txt");
diff --git a/crates/requirements-txt/src/snapshots/requirements_txt__test__parse-unix-bare-url.txt.snap b/crates/requirements-txt/src/snapshots/requirements_txt__test__parse-unix-bare-url.txt.snap
index c74fdedd8fdf6..7689453b66baf 100644
--- a/crates/requirements-txt/src/snapshots/requirements_txt__test__parse-unix-bare-url.txt.snap
+++ b/crates/requirements-txt/src/snapshots/requirements_txt__test__parse-unix-bare-url.txt.snap
@@ -158,6 +158,156 @@ RequirementsTxt {
             ),
             hashes: [],
         },
+        RequirementEntry {
+            requirement: Unnamed(
+                UnnamedRequirement {
+                    url: VerbatimParsedUrl {
+                        parsed_url: Directory(
+                            ParsedDirectoryUrl {
+                                url: Url {
+                                    scheme: "file",
+                                    cannot_be_a_base: false,
+                                    username: "",
+                                    password: None,
+                                    host: None,
+                                    port: None,
+                                    path: "<REQUIREMENTS_DIR>/scripts/packages/black%20editable",
+                                    query: None,
+                                    fragment: None,
+                                },
+                                install_path: "<REQUIREMENTS_DIR>/scripts/packages/black editable",
+                                editable: false,
+                                virtual: false,
+                            },
+                        ),
+                        verbatim: VerbatimUrl {
+                            url: Url {
+                                scheme: "file",
+                                cannot_be_a_base: false,
+                                username: "",
+                                password: None,
+                                host: None,
+                                port: None,
+                                path: "<REQUIREMENTS_DIR>/scripts/packages/black%20editable",
+                                query: None,
+                                fragment: None,
+                            },
+                            given: Some(
+                                "./scripts/packages/black editable",
+                            ),
+                        },
+                    },
+                    extras: [],
+                    marker: true,
+                    origin: Some(
+                        File(
+                            "<REQUIREMENTS_DIR>/bare-url.txt",
+                        ),
+                    ),
+                },
+            ),
+            hashes: [],
+        },
+        RequirementEntry {
+            requirement: Unnamed(
+                UnnamedRequirement {
+                    url: VerbatimParsedUrl {
+                        parsed_url: Directory(
+                            ParsedDirectoryUrl {
+                                url: Url {
+                                    scheme: "file",
+                                    cannot_be_a_base: false,
+                                    username: "",
+                                    password: None,
+                                    host: None,
+                                    port: None,
+                                    path: "<REQUIREMENTS_DIR>/scripts/packages/black%20editable",
+                                    query: None,
+                                    fragment: None,
+                                },
+                                install_path: "<REQUIREMENTS_DIR>/scripts/packages/black editable",
+                                editable: false,
+                                virtual: false,
+                            },
+                        ),
+                        verbatim: VerbatimUrl {
+                            url: Url {
+                                scheme: "file",
+                                cannot_be_a_base: false,
+                                username: "",
+                                password: None,
+                                host: None,
+                                port: None,
+                                path: "<REQUIREMENTS_DIR>/scripts/packages/black%20editable",
+                                query: None,
+                                fragment: None,
+                            },
+                            given: Some(
+                                "./scripts/packages/black editable",
+                            ),
+                        },
+                    },
+                    extras: [],
+                    marker: python_full_version >= '3.9',
+                    origin: Some(
+                        File(
+                            "<REQUIREMENTS_DIR>/bare-url.txt",
+                        ),
+                    ),
+                },
+            ),
+            hashes: [],
+        },
+        RequirementEntry {
+            requirement: Unnamed(
+                UnnamedRequirement {
+                    url: VerbatimParsedUrl {
+                        parsed_url: Directory(
+                            ParsedDirectoryUrl {
+                                url: Url {
+                                    scheme: "file",
+                                    cannot_be_a_base: false,
+                                    username: "",
+                                    password: None,
+                                    host: None,
+                                    port: None,
+                                    path: "<REQUIREMENTS_DIR>/scripts/packages/black%20editable",
+                                    query: None,
+                                    fragment: None,
+                                },
+                                install_path: "<REQUIREMENTS_DIR>/scripts/packages/black editable",
+                                editable: false,
+                                virtual: false,
+                            },
+                        ),
+                        verbatim: VerbatimUrl {
+                            url: Url {
+                                scheme: "file",
+                                cannot_be_a_base: false,
+                                username: "",
+                                password: None,
+                                host: None,
+                                port: None,
+                                path: "<REQUIREMENTS_DIR>/scripts/packages/black%20editable",
+                                query: None,
+                                fragment: None,
+                            },
+                            given: Some(
+                                "./scripts/packages/black editable",
+                            ),
+                        },
+                    },
+                    extras: [],
+                    marker: true,
+                    origin: Some(
+                        File(
+                            "<REQUIREMENTS_DIR>/bare-url.txt",
+                        ),
+                    ),
+                },
+            ),
+            hashes: [],
+        },
     ],
     constraints: [],
     editables: [],
diff --git a/crates/requirements-txt/src/snapshots/requirements_txt__test__parse-unix-hash.txt.snap b/crates/requirements-txt/src/snapshots/requirements_txt__test__parse-unix-hash.txt.snap
new file mode 100644
index 0000000000000..c023fcaa804e0
--- /dev/null
+++ b/crates/requirements-txt/src/snapshots/requirements_txt__test__parse-unix-hash.txt.snap
@@ -0,0 +1,19 @@
+---
+source: crates/requirements-txt/src/lib.rs
+expression: actual
+---
+RequirementsTxtFileError {
+    file: "<REQUIREMENTS_DIR>/hash.txt",
+    error: Pep508 {
+        source: Pep508Error {
+            message: String(
+                "Missing space before '#', the end of the URL is ambiguous",
+            ),
+            start: 10,
+            len: 1,
+            input: "./editable# comment",
+        },
+        start: 49,
+        end: 68,
+    },
+}
diff --git a/crates/requirements-txt/src/snapshots/requirements_txt__test__parse-unix-semicolon.txt.snap b/crates/requirements-txt/src/snapshots/requirements_txt__test__parse-unix-semicolon.txt.snap
index 768f6fd9ff660..b35272fb749f8 100644
--- a/crates/requirements-txt/src/snapshots/requirements_txt__test__parse-unix-semicolon.txt.snap
+++ b/crates/requirements-txt/src/snapshots/requirements_txt__test__parse-unix-semicolon.txt.snap
@@ -9,7 +9,7 @@ RequirementsTxtFileError {
             message: String(
                 "Missing space before ';', the end of the URL is ambiguous",
             ),
-            start: 11,
+            start: 10,
             len: 1,
             input: "./editable; python_version >= \"3.9\" and os_name == \"posix\"",
         },
diff --git a/crates/requirements-txt/src/snapshots/requirements_txt__test__parse-windows-bare-url.txt.snap b/crates/requirements-txt/src/snapshots/requirements_txt__test__parse-windows-bare-url.txt.snap
index c53879e194b3b..087df70f72e9c 100644
--- a/crates/requirements-txt/src/snapshots/requirements_txt__test__parse-windows-bare-url.txt.snap
+++ b/crates/requirements-txt/src/snapshots/requirements_txt__test__parse-windows-bare-url.txt.snap
@@ -158,6 +158,106 @@ RequirementsTxt {
             ),
             hashes: [],
         },
+        RequirementEntry {
+            requirement: Unnamed(
+                UnnamedRequirement {
+                    url: VerbatimParsedUrl {
+                        parsed_url: Directory(
+                            ParsedDirectoryUrl {
+                                url: Url {
+                                    scheme: "file",
+                                    cannot_be_a_base: false,
+                                    username: "",
+                                    password: None,
+                                    host: None,
+                                    port: None,
+                                    path: "/<REQUIREMENTS_DIR>/scripts/packages/black%20editable",
+                                    query: None,
+                                    fragment: None,
+                                },
+                                install_path: "<REQUIREMENTS_DIR>/scripts/packages/black editable",
+                                editable: false,
+                                virtual: false,
+                            },
+                        ),
+                        verbatim: VerbatimUrl {
+                            url: Url {
+                                scheme: "file",
+                                cannot_be_a_base: false,
+                                username: "",
+                                password: None,
+                                host: None,
+                                port: None,
+                                path: "/<REQUIREMENTS_DIR>/scripts/packages/black%20editable",
+                                query: None,
+                                fragment: None,
+                            },
+                            given: Some(
+                                "./scripts/packages/black editable",
+                            ),
+                        },
+                    },
+                    extras: [],
+                    marker: true,
+                    origin: Some(
+                        File(
+                            "<REQUIREMENTS_DIR>/bare-url.txt",
+                        ),
+                    ),
+                },
+            ),
+            hashes: [],
+        },
+        RequirementEntry {
+            requirement: Unnamed(
+                UnnamedRequirement {
+                    url: VerbatimParsedUrl {
+                        parsed_url: Directory(
+                            ParsedDirectoryUrl {
+                                url: Url {
+                                    scheme: "file",
+                                    cannot_be_a_base: false,
+                                    username: "",
+                                    password: None,
+                                    host: None,
+                                    port: None,
+                                    path: "/<REQUIREMENTS_DIR>/scripts/packages/black%20editable",
+                                    query: None,
+                                    fragment: None,
+                                },
+                                install_path: "<REQUIREMENTS_DIR>/scripts/packages/black editable",
+                                editable: false,
+                                virtual: false,
+                            },
+                        ),
+                        verbatim: VerbatimUrl {
+                            url: Url {
+                                scheme: "file",
+                                cannot_be_a_base: false,
+                                username: "",
+                                password: None,
+                                host: None,
+                                port: None,
+                                path: "/<REQUIREMENTS_DIR>/scripts/packages/black%20editable",
+                                query: None,
+                                fragment: None,
+                            },
+                            given: Some(
+                                "./scripts/packages/black editable",
+                            ),
+                        },
+                    },
+                    extras: [],
+                    marker: true,
+                    origin: Some(
+                        File(
+                            "<REQUIREMENTS_DIR>/bare-url.txt",
+                        ),
+                    ),
+                },
+            ),
+            hashes: [],
+        },
     ],
     constraints: [],
     editables: [],
diff --git a/crates/requirements-txt/test-data/requirements-txt/bare-url.txt b/crates/requirements-txt/test-data/requirements-txt/bare-url.txt
index 080038a8c86db..2fef7fd16a89a 100644
--- a/crates/requirements-txt/test-data/requirements-txt/bare-url.txt
+++ b/crates/requirements-txt/test-data/requirements-txt/bare-url.txt
@@ -1,3 +1,6 @@
 ./scripts/packages/black_editable
 ./scripts/packages/black_editable[dev]
 file:///scripts/packages/black_editable
+./scripts/packages/black editable
+./scripts/packages/black editable ; python_version >= "3.9"
+./scripts/packages/black editable # comment
diff --git a/crates/requirements-txt/test-data/requirements-txt/hash.txt b/crates/requirements-txt/test-data/requirements-txt/hash.txt
new file mode 100644
index 0000000000000..d3d026f1be74a
--- /dev/null
+++ b/crates/requirements-txt/test-data/requirements-txt/hash.txt
@@ -0,0 +1,2 @@
+# Disallowed (missing whitespace before hash)
+-e ./editable# comment
diff --git a/crates/uv-fs/src/lib.rs b/crates/uv-fs/src/lib.rs
index 5c69e5a962b3f..f339e37c5ce6e 100644
--- a/crates/uv-fs/src/lib.rs
+++ b/crates/uv-fs/src/lib.rs
@@ -1,11 +1,7 @@
 use fs2::FileExt;
 use std::fmt::Display;
-use std::io;
 use std::path::{Path, PathBuf};
-use std::pin::Pin;
-use std::task::{Context, Poll};
 use tempfile::NamedTempFile;
-use tokio::io::{AsyncRead, ReadBuf};
 use tracing::{debug, error, info, trace, warn};
 
 pub use crate::path::*;
@@ -393,27 +389,32 @@ impl Drop for LockedFile {
 }
 
 /// An asynchronous reader that reports progress as bytes are read.
-pub struct ProgressReader<Reader: AsyncRead + Unpin, Callback: Fn(usize) + Unpin> {
+#[cfg(feature = "tokio")]
+pub struct ProgressReader<Reader: tokio::io::AsyncRead + Unpin, Callback: Fn(usize) + Unpin> {
     reader: Reader,
     callback: Callback,
 }
 
-impl<Reader: AsyncRead + Unpin, Callback: Fn(usize) + Unpin> ProgressReader<Reader, Callback> {
+#[cfg(feature = "tokio")]
+impl<Reader: tokio::io::AsyncRead + Unpin, Callback: Fn(usize) + Unpin>
+    ProgressReader<Reader, Callback>
+{
     /// Create a new [`ProgressReader`] that wraps another reader.
     pub fn new(reader: Reader, callback: Callback) -> Self {
         Self { reader, callback }
     }
 }
 
-impl<Reader: AsyncRead + Unpin, Callback: Fn(usize) + Unpin> AsyncRead
+#[cfg(feature = "tokio")]
+impl<Reader: tokio::io::AsyncRead + Unpin, Callback: Fn(usize) + Unpin> tokio::io::AsyncRead
     for ProgressReader<Reader, Callback>
 {
     fn poll_read(
-        mut self: Pin<&mut Self>,
-        cx: &mut Context<'_>,
-        buf: &mut ReadBuf<'_>,
-    ) -> Poll<io::Result<()>> {
-        Pin::new(&mut self.as_mut().reader)
+        mut self: std::pin::Pin<&mut Self>,
+        cx: &mut std::task::Context<'_>,
+        buf: &mut tokio::io::ReadBuf<'_>,
+    ) -> std::task::Poll<std::io::Result<()>> {
+        std::pin::Pin::new(&mut self.as_mut().reader)
             .poll_read(cx, buf)
             .map_ok(|()| {
                 (self.callback)(buf.filled().len());