diff --git a/crates/uv-tool/src/tool.rs b/crates/uv-tool/src/tool.rs
index 1b12910d0..4cbe4cb9c 100644
--- a/crates/uv-tool/src/tool.rs
+++ b/crates/uv-tool/src/tool.rs
@@ -1,3 +1,4 @@
+use std::fmt::{self, Display, Formatter};
 use std::path::PathBuf;
 
 use serde::Deserialize;
@@ -6,7 +7,7 @@ use toml_edit::Table;
 use toml_edit::Value;
 use toml_edit::{Array, Item};
 
-use uv_fs::PortablePath;
+use uv_fs::{PortablePath, Simplified};
 use uv_pypi_types::{Requirement, VerbatimParsedUrl};
 use uv_settings::ToolOptions;
 
@@ -98,6 +99,32 @@ pub struct ToolEntrypoint {
     pub install_path: PathBuf,
 }
 
+impl Display for ToolEntrypoint {
+    fn fmt(&self, f: &mut Formatter) -> fmt::Result {
+        #[cfg(windows)]
+        {
+            write!(
+                f,
+                "{} ({})",
+                self.name,
+                self.install_path
+                    .simplified_display()
+                    .to_string()
+                    .replace('/', "\\")
+            )
+        }
+        #[cfg(unix)]
+        {
+            write!(
+                f,
+                "{} ({})",
+                self.name,
+                self.install_path.simplified_display()
+            )
+        }
+    }
+}
+
 /// Format an array so that each element is on its own line and has a trailing comma.
 ///
 /// Example:
diff --git a/crates/uv/src/commands/tool/list.rs b/crates/uv/src/commands/tool/list.rs
index 721ed9de2..3af75ae5c 100644
--- a/crates/uv/src/commands/tool/list.rs
+++ b/crates/uv/src/commands/tool/list.rs
@@ -98,12 +98,7 @@ pub(crate) async fn list(
         // Output tool entrypoints
         for entrypoint in tool.entrypoints() {
             if show_paths {
-                writeln!(
-                    printer.stdout(),
-                    "- {} ({})",
-                    entrypoint.name,
-                    entrypoint.install_path.simplified_display().cyan()
-                )?;
+                writeln!(printer.stdout(), "- {}", entrypoint.to_string().cyan())?;
             } else {
                 writeln!(printer.stdout(), "- {}", entrypoint.name)?;
             }
diff --git a/crates/uv/tests/it/common/mod.rs b/crates/uv/tests/it/common/mod.rs
index f55a6e963..fb432c27c 100644
--- a/crates/uv/tests/it/common/mod.rs
+++ b/crates/uv/tests/it/common/mod.rs
@@ -250,6 +250,19 @@ impl TestContext {
         self
     }
 
+    /// Add a filter that ignores temporary directory in path.
+    pub fn with_filtered_windows_temp_dir(mut self) -> Self {
+        let pattern = regex::escape(
+            &self
+                .temp_dir
+                .simplified_display()
+                .to_string()
+                .replace('/', "\\"),
+        );
+        self.filters.push((pattern, "[TEMP_DIR]".to_string()));
+        self
+    }
+
     /// Add extra directories and configuration for managed Python installations.
     #[must_use]
     pub fn with_managed_python_dirs(mut self) -> Self {
@@ -267,6 +280,12 @@ impl TestContext {
         self
     }
 
+    /// Clear filters on `TestContext`.
+    pub fn clear_filters(mut self) -> Self {
+        self.filters.clear();
+        self
+    }
+
     /// Discover the path to the XDG state directory. We use this, rather than the OS-specific
     /// temporary directory, because on macOS (and Windows on GitHub Actions), they involve
     /// symlinks. (On macOS, the temporary directory is, like `/var/...`, which resolves to
@@ -988,6 +1007,14 @@ impl TestContext {
             .collect()
     }
 
+    /// Only the filters added to this test context.
+    pub fn filters_without_standard_filters(&self) -> Vec<(&str, &str)> {
+        self.filters
+            .iter()
+            .map(|(p, r)| (p.as_str(), r.as_str()))
+            .collect()
+    }
+
     /// For when we add pypy to the test suite.
     #[allow(clippy::unused_self)]
     pub fn python_kind(&self) -> &'static str {
diff --git a/crates/uv/tests/it/tool_list.rs b/crates/uv/tests/it/tool_list.rs
index d0b0d6b93..3326bb7be 100644
--- a/crates/uv/tests/it/tool_list.rs
+++ b/crates/uv/tests/it/tool_list.rs
@@ -64,6 +64,38 @@ fn tool_list_paths() {
     "###);
 }
 
+#[cfg(windows)]
+#[test]
+fn tool_list_paths_windows() {
+    let context = TestContext::new("3.12")
+        .clear_filters()
+        .with_filtered_windows_temp_dir();
+    let tool_dir = context.temp_dir.child("tools");
+    let bin_dir = context.temp_dir.child("bin");
+
+    // Install `black`
+    context
+        .tool_install()
+        .arg("black==24.2.0")
+        .env(EnvVars::UV_TOOL_DIR, tool_dir.as_os_str())
+        .env(EnvVars::XDG_BIN_HOME, bin_dir.as_os_str())
+        .assert()
+        .success();
+
+    uv_snapshot!(context.filters_without_standard_filters(), context.tool_list().arg("--show-paths")
+    .env(EnvVars::UV_TOOL_DIR, tool_dir.as_os_str())
+    .env(EnvVars::XDG_BIN_HOME, bin_dir.as_os_str()), @r###"
+    success: true
+    exit_code: 0
+    ----- stdout -----
+    black v24.2.0 ([TEMP_DIR]\tools\black)
+    - black.exe ([TEMP_DIR]\bin\black.exe)
+    - blackd.exe ([TEMP_DIR]\bin\blackd.exe)
+
+    ----- stderr -----
+    "###);
+}
+
 #[test]
 fn tool_list_empty() {
     let context = TestContext::new("3.12").with_filtered_exe_suffix();