diff --git a/crates/uv/src/commands/tool/install.rs b/crates/uv/src/commands/tool/install.rs
index cd1bfed0c8fa..97f9231c1d06 100644
--- a/crates/uv/src/commands/tool/install.rs
+++ b/crates/uv/src/commands/tool/install.rs
@@ -293,6 +293,16 @@ pub(crate) async fn install(
                         "Ignored existing environment for `{from}` due to stale Python interpreter",
                         from = from.name.cyan(),
                     );
+                    // XXX(lucab)
+                    #[cfg(target_os = "windows")]
+                    {
+                        let _ = writeln!(
+                            printer.stderr(),
+                            "Interpreter mismatch: old='{}' vs new='{}'",
+                            old_interpreter.display(),
+                            selected_interpreter.display(),
+                        );
+                    }
                 }
                 same_executable
             });
diff --git a/crates/uv/tests/tool_install.rs b/crates/uv/tests/tool_install.rs
index 6a3bb07ba8e3..0812d882860a 100644
--- a/crates/uv/tests/tool_install.rs
+++ b/crates/uv/tests/tool_install.rs
@@ -2215,6 +2215,65 @@ fn tool_install_python_params() {
     "###);
 }
 
+// XXX(lucab)
+#[test]
+fn tool_install_debug_windows_ci() {
+    let context = TestContext::new_with_versions(&["3.11", "3.12"])
+        .with_filtered_counts()
+        .with_filtered_exe_suffix();
+    let tool_dir = context.temp_dir.child("tools");
+    let bin_dir = context.temp_dir.child("bin");
+
+    // Install with managed Python 3.11.
+    uv_snapshot!(context.filters(), context.tool_install()
+        .arg("-p")
+        .arg("3.11")
+        .arg("--no-python-downloads")
+        .arg("--python-preference")
+        .arg("only-system")
+        .arg("black")
+        .env("UV_TOOL_DIR", tool_dir.as_os_str())
+        .env("XDG_BIN_HOME", bin_dir.as_os_str())
+        .env("PATH", bin_dir.as_os_str()), @r###"
+    success: true
+    exit_code: 0
+    ----- stdout -----
+
+    ----- stderr -----
+    Resolved [N] packages in [TIME]
+    Prepared [N] packages in [TIME]
+    Installed [N] packages in [TIME]
+     + black==24.3.0
+     + click==8.1.7
+     + mypy-extensions==1.0.0
+     + packaging==24.0
+     + pathspec==0.12.1
+     + platformdirs==4.2.0
+    Installed 2 executables: black, blackd
+    "###);
+
+    // Install with managed Python 3.11 (exact same command).
+    uv_snapshot!(context.filters(), context.tool_install()
+        .arg("-p")
+        .arg("3.11")
+        .arg("--no-python-downloads")
+        .arg("--python-preference")
+        // NOTE(lucab): test does NOT pass with 'managed' (the default)
+        // NOTE(lucab): test passes with 'only-managed'
+        .arg("only-system")
+        .arg("black")
+        .env("UV_TOOL_DIR", tool_dir.as_os_str())
+        .env("XDG_BIN_HOME", bin_dir.as_os_str())
+        .env("PATH", bin_dir.as_os_str()), @r###"
+    success: true
+    exit_code: 0
+    ----- stdout -----
+
+    ----- stderr -----
+    `black` is already installed
+    "###);
+}
+
 /// Test preserving a tool environment when new but incompatible requirements are requested.
 #[test]
 fn tool_install_preserve_environment() {