diff --git a/crates/uv/src/commands/project/run.rs b/crates/uv/src/commands/project/run.rs
index cccac5591..29ca48300 100644
--- a/crates/uv/src/commands/project/run.rs
+++ b/crates/uv/src/commands/project/run.rs
@@ -1,6 +1,6 @@
 use std::borrow::Cow;
 use std::env::VarError;
-use std::ffi::OsString;
+use std::ffi::{OsStr, OsString};
 use std::fmt::Write;
 use std::io::Read;
 use std::path::{Path, PathBuf};
@@ -1116,6 +1116,58 @@ fn can_skip_ephemeral(
     }
 }
 
+#[derive(Debug)]
+enum WindowsScript {
+    /// `PowerShell` script (.ps1)
+    PowerShell,
+    /// Command Prompt NT script (.cmd)
+    Command,
+    /// Command Prompt script (.bat)
+    Batch,
+}
+
+impl WindowsScript {
+    /// Returns a list of all supported Windows script types.
+    fn all() -> &'static [Self] {
+        &[Self::PowerShell, Self::Command, Self::Batch]
+    }
+
+    /// Returns the script extension for a given Windows script type.
+    fn to_extension(&self) -> &'static str {
+        match self {
+            Self::PowerShell => "ps1",
+            Self::Command => "cmd",
+            Self::Batch => "bat",
+        }
+    }
+
+    /// Determines the script type from a given Windows file extension.
+    fn from_extension(ext: &str) -> Option<Self> {
+        match ext {
+            "ps1" => Some(Self::PowerShell),
+            "cmd" => Some(Self::Command),
+            "bat" => Some(Self::Batch),
+            _ => None,
+        }
+    }
+
+    /// Returns a [`Command`] to run the given script under the appropriate Windows command.
+    fn as_command(&self, script: &Path) -> Command {
+        match self {
+            Self::PowerShell => {
+                let mut cmd = Command::new("powershell");
+                cmd.arg("-NoLogo").arg("-File").arg(script);
+                cmd
+            }
+            Self::Command | Self::Batch => {
+                let mut cmd = Command::new("cmd");
+                cmd.arg("/q").arg("/c").arg(script);
+                cmd
+            }
+        }
+    }
+}
+
 #[derive(Debug)]
 pub(crate) enum RunCommand {
     /// Execute `python`.
@@ -1177,6 +1229,37 @@ impl RunCommand {
         }
     }
 
+    /// Handle legacy setuptools scripts for Windows.
+    ///
+    /// Returns [`Command`] that can be used to run `.ps1`, `.cmd`, or `.bat` scripts on Windows.
+    fn for_windows_script(interpreter: &Interpreter, executable: &OsStr) -> Command {
+        let script_path = interpreter.scripts().join(executable);
+
+        // Honor explicit extension if provided and recognized.
+        if let Some(script_type) = script_path
+            .extension()
+            .and_then(OsStr::to_str)
+            .and_then(WindowsScript::from_extension)
+            .filter(|_| script_path.is_file())
+        {
+            return script_type.as_command(&script_path);
+        }
+
+        // Guess the extension when an explicit one is not provided.
+        // We also add the extension when missing since for PowerShell it must be explicit.
+        WindowsScript::all()
+            .iter()
+            .map(|script_type| {
+                (
+                    script_type,
+                    script_path.with_extension(script_type.to_extension()),
+                )
+            })
+            .find(|(_, script_path)| script_path.is_file())
+            .map(|(script_type, script_path)| script_type.as_command(&script_path))
+            .unwrap_or_else(|| Command::new(executable))
+    }
+
     /// Convert a [`RunCommand`] into a [`Command`].
     fn as_command(&self, interpreter: &Interpreter) -> Command {
         match self {
@@ -1292,7 +1375,11 @@ impl RunCommand {
                 process
             }
             Self::External(executable, args) => {
-                let mut process = Command::new(executable);
+                let mut process = if cfg!(windows) {
+                    Self::for_windows_script(interpreter, executable)
+                } else {
+                    Command::new(executable)
+                };
                 process.args(args);
                 process
             }
diff --git a/crates/uv/tests/it/run.rs b/crates/uv/tests/it/run.rs
index 4c36be01e..9e458ce16 100644
--- a/crates/uv/tests/it/run.rs
+++ b/crates/uv/tests/it/run.rs
@@ -4372,3 +4372,234 @@ fn run_uv_variable() {
     ----- stderr -----
     "###);
 }
+
+/// Test legacy scripts <https://packaging.python.org/en/latest/guides/distributing-packages-using-setuptools/#scripts>.
+///
+/// This tests for execution and detection of legacy windows scripts with .bat, .cmd, and .ps1 extensions.
+#[cfg(windows)]
+#[test]
+fn run_windows_legacy_scripts() -> Result<()> {
+    let context = TestContext::new("3.12");
+
+    let pyproject_toml = context.temp_dir.child("pyproject.toml");
+
+    // Use `script-files` which enables legacy scripts packaging.
+    pyproject_toml.write_str(indoc! { r#"
+        [project]
+        name = "foo"
+        version = "1.0.0"
+        requires-python = ">=3.8"
+        dependencies = []
+
+        [tool.setuptools]
+        packages = []
+        script-files = [
+            "misc/custom_pydoc.bat",
+            "misc/custom_pydoc.cmd",
+            "misc/custom_pydoc.ps1"
+        ]
+
+        [build-system]
+        requires = ["setuptools>=42"]
+        build-backend = "setuptools.build_meta"
+        "#
+    })?;
+
+    let custom_pydoc_bat = context.temp_dir.child("misc").child("custom_pydoc.bat");
+    let custom_pydoc_cmd = context.temp_dir.child("misc").child("custom_pydoc.cmd");
+    let custom_pydoc_ps1 = context.temp_dir.child("misc").child("custom_pydoc.ps1");
+
+    custom_pydoc_bat.write_str("python.exe -m pydoc %*")?;
+    custom_pydoc_cmd.write_str("python.exe -m pydoc %*")?;
+    custom_pydoc_ps1.write_str("python.exe -m pydoc $args")?;
+
+    uv_snapshot!(context.filters(), context.run(), @r###"
+    success: false
+    exit_code: 2
+    ----- stdout -----
+    Provide a command or script to invoke with `uv run <command>` or `uv run <script>.py`.
+
+    The following commands are available in the environment:
+
+    - custom_pydoc.bat
+    - custom_pydoc.cmd
+    - custom_pydoc.ps1
+    - pydoc.bat
+    - python
+    - pythonw
+
+    See `uv run --help` for more information.
+
+    ----- stderr -----
+    Resolved 1 package in [TIME]
+    Prepared 1 package in [TIME]
+    Installed 1 package in [TIME]
+     + foo==1.0.0 (from file://[TEMP_DIR]/)
+    "###);
+
+    // Test with explicit .bat extension
+    uv_snapshot!(context.filters(), context.run().arg("custom_pydoc.bat"), @r###"
+    success: true
+    exit_code: 0
+    ----- stdout -----
+    pydoc - the Python documentation tool
+
+    pydoc <name> ...
+        Show text documentation on something.  <name> may be the name of a
+        Python keyword, topic, function, module, or package, or a dotted
+        reference to a class or function within a module or module in a
+        package.  If <name> contains a '\', it is used as the path to a
+        Python source file to document. If name is 'keywords', 'topics',
+        or 'modules', a listing of these things is displayed.
+
+    pydoc -k <keyword>
+        Search for a keyword in the synopsis lines of all available modules.
+
+    pydoc -n <hostname>
+        Start an HTTP server with the given hostname (default: localhost).
+
+    pydoc -p <port>
+        Start an HTTP server on the given port on the local machine.  Port
+        number 0 can be used to get an arbitrary unused port.
+
+    pydoc -b
+        Start an HTTP server on an arbitrary unused port and open a web browser
+        to interactively browse documentation.  This option can be used in
+        combination with -n and/or -p.
+
+    pydoc -w <name> ...
+        Write out the HTML documentation for a module to a file in the current
+        directory.  If <name> contains a '\', it is treated as a filename; if
+        it names a directory, documentation is written for all the contents.
+
+
+    ----- stderr -----
+    Resolved 1 package in [TIME]
+    Audited 1 package in [TIME]
+    "###);
+
+    // Test with explicit .cmd extension
+    uv_snapshot!(context.filters(), context.run().arg("custom_pydoc.cmd"), @r###"
+    success: true
+    exit_code: 0
+    ----- stdout -----
+    pydoc - the Python documentation tool
+
+    pydoc <name> ...
+        Show text documentation on something.  <name> may be the name of a
+        Python keyword, topic, function, module, or package, or a dotted
+        reference to a class or function within a module or module in a
+        package.  If <name> contains a '\', it is used as the path to a
+        Python source file to document. If name is 'keywords', 'topics',
+        or 'modules', a listing of these things is displayed.
+
+    pydoc -k <keyword>
+        Search for a keyword in the synopsis lines of all available modules.
+
+    pydoc -n <hostname>
+        Start an HTTP server with the given hostname (default: localhost).
+
+    pydoc -p <port>
+        Start an HTTP server on the given port on the local machine.  Port
+        number 0 can be used to get an arbitrary unused port.
+
+    pydoc -b
+        Start an HTTP server on an arbitrary unused port and open a web browser
+        to interactively browse documentation.  This option can be used in
+        combination with -n and/or -p.
+
+    pydoc -w <name> ...
+        Write out the HTML documentation for a module to a file in the current
+        directory.  If <name> contains a '\', it is treated as a filename; if
+        it names a directory, documentation is written for all the contents.
+
+
+    ----- stderr -----
+    Resolved 1 package in [TIME]
+    Audited 1 package in [TIME]
+    "###);
+
+    // Test with explicit .ps1 extension
+    uv_snapshot!(context.filters(), context.run().arg("custom_pydoc.ps1"), @r###"
+    success: true
+    exit_code: 0
+    ----- stdout -----
+    pydoc - the Python documentation tool
+
+    pydoc <name> ...
+        Show text documentation on something.  <name> may be the name of a
+        Python keyword, topic, function, module, or package, or a dotted
+        reference to a class or function within a module or module in a
+        package.  If <name> contains a '\', it is used as the path to a
+        Python source file to document. If name is 'keywords', 'topics',
+        or 'modules', a listing of these things is displayed.
+
+    pydoc -k <keyword>
+        Search for a keyword in the synopsis lines of all available modules.
+
+    pydoc -n <hostname>
+        Start an HTTP server with the given hostname (default: localhost).
+
+    pydoc -p <port>
+        Start an HTTP server on the given port on the local machine.  Port
+        number 0 can be used to get an arbitrary unused port.
+
+    pydoc -b
+        Start an HTTP server on an arbitrary unused port and open a web browser
+        to interactively browse documentation.  This option can be used in
+        combination with -n and/or -p.
+
+    pydoc -w <name> ...
+        Write out the HTML documentation for a module to a file in the current
+        directory.  If <name> contains a '\', it is treated as a filename; if
+        it names a directory, documentation is written for all the contents.
+
+
+    ----- stderr -----
+    Resolved 1 package in [TIME]
+    Audited 1 package in [TIME]
+    "###);
+
+    // Test without explicit extension (.ps1 should be used)
+    uv_snapshot!(context.filters(), context.run().arg("custom_pydoc"), @r###"
+    success: true
+    exit_code: 0
+    ----- stdout -----
+    pydoc - the Python documentation tool
+
+    pydoc <name> ...
+        Show text documentation on something.  <name> may be the name of a
+        Python keyword, topic, function, module, or package, or a dotted
+        reference to a class or function within a module or module in a
+        package.  If <name> contains a '\', it is used as the path to a
+        Python source file to document. If name is 'keywords', 'topics',
+        or 'modules', a listing of these things is displayed.
+
+    pydoc -k <keyword>
+        Search for a keyword in the synopsis lines of all available modules.
+
+    pydoc -n <hostname>
+        Start an HTTP server with the given hostname (default: localhost).
+
+    pydoc -p <port>
+        Start an HTTP server on the given port on the local machine.  Port
+        number 0 can be used to get an arbitrary unused port.
+
+    pydoc -b
+        Start an HTTP server on an arbitrary unused port and open a web browser
+        to interactively browse documentation.  This option can be used in
+        combination with -n and/or -p.
+
+    pydoc -w <name> ...
+        Write out the HTML documentation for a module to a file in the current
+        directory.  If <name> contains a '\', it is treated as a filename; if
+        it names a directory, documentation is written for all the contents.
+
+
+    ----- stderr -----
+    Resolved 1 package in [TIME]
+    Audited 1 package in [TIME]
+    "###);
+
+    Ok(())
+}