diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index 44a234daa6e2..50ec986aef12 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -291,7 +291,7 @@ jobs:
       - name: "Cargo test"
         working-directory: ${{ env.UV_WORKSPACE }}
         run: |
-          cargo nextest run --no-default-features --features python,pypi --workspace --status-level skip --failure-output immediate-final --no-fail-fast -j 20 --final-status-level slow
+          cargo nextest run --no-default-features --features python,pypi --workspace --status-level skip --failure-output immediate-final --no-fail-fast -j 20 --final-status-level slow tool_install_additional_entrypoints
 
       - name: "Smoke test"
         working-directory: ${{ env.UV_WORKSPACE }}
diff --git a/crates/uv-normalize/src/lib.rs b/crates/uv-normalize/src/lib.rs
index 0360a5a1a161..a28392883023 100644
--- a/crates/uv-normalize/src/lib.rs
+++ b/crates/uv-normalize/src/lib.rs
@@ -195,4 +195,13 @@ mod tests {
             assert!(is_normalized(input).is_err());
         }
     }
+
+    #[test]
+    fn sorting() {
+        let first = validate_and_normalize_ref("ansible").unwrap();
+        let second = validate_and_normalize_ref("ansible-core").unwrap();
+        assert_eq!(first, "ansible");
+        assert_eq!(second, "ansible-core");
+        assert!(first < second);
+    }
 }
diff --git a/crates/uv/src/commands/tool/common.rs b/crates/uv/src/commands/tool/common.rs
index 5077dbf30bc2..62578866922d 100644
--- a/crates/uv/src/commands/tool/common.rs
+++ b/crates/uv/src/commands/tool/common.rs
@@ -5,6 +5,7 @@ use std::{collections::BTreeSet, ffi::OsString};
 use anyhow::{bail, Context};
 use itertools::Itertools;
 use owo_colors::OwoColorize;
+use predicates::str;
 use tracing::{debug, warn};
 
 use distribution_types::{InstalledDist, Name};
@@ -62,6 +63,7 @@ pub(crate) fn remove_entrypoints(tool: &Tool) {
 }
 
 /// Installs tool executables for a given package and handles any conflicts.
+#[allow(clippy::cmp_owned)]
 pub(crate) fn install_executables(
     environment: &PythonEnvironment,
     tool_name: &PackageName,
@@ -92,6 +94,10 @@ pub(crate) fn install_executables(
         installed_dist.version(),
     )?;
 
+    // XXX
+    let _temp = entry_points.clone();
+    // XXX
+
     // Determine the entry points targets. Use a sorted collection for deterministic output.
     let target_entry_points = entry_points
         .into_iter()
@@ -106,6 +112,38 @@ pub(crate) fn install_executables(
         })
         .collect::<BTreeSet<_>>();
 
+    // XXX
+    #[cfg(windows)]
+    {
+        assert!("ansible".to_string() < "ansible-config".to_string());
+        let mut test = BTreeSet::new();
+        test.insert("ansible".to_string());
+        test.insert("ansible-config".to_string());
+        if name == &PackageName::new("ansible-core".to_string()).unwrap() {
+            dbg!(&target_entry_points);
+            let sorted: BTreeSet<_> = _temp.clone().into_iter().collect();
+            dbg!(&sorted);
+            let sorted2: BTreeSet<_> = _temp.into_iter().map(|(name, _)| name).collect();
+            dbg!(&sorted2);
+            let mut newset = BTreeSet::new();
+            let mut newset2 = BTreeSet::new();
+            let mut strbytes = vec![];
+            for entry in sorted2.clone() {
+                if entry == "ansible" || entry == "ansible-config" {
+                    newset2.insert(entry.clone());
+                }
+                newset.insert(entry.clone());
+                strbytes.push(entry.into_bytes());
+            }
+            dbg!(&newset);
+            assert_eq!(newset, sorted2);
+            dbg!(&newset2);
+            dbg!(&test);
+            dbg!(&strbytes);
+        }
+    }
+    // XXX
+
     if target_entry_points.is_empty() {
         writeln!(
             printer.stdout(),