diff --git a/crates/ruff/src/commands/show_settings.rs b/crates/ruff/src/commands/show_settings.rs
index a23f31a4967a2..12d275eb655e2 100644
--- a/crates/ruff/src/commands/show_settings.rs
+++ b/crates/ruff/src/commands/show_settings.rs
@@ -31,9 +31,9 @@ pub(crate) fn show_settings(
 
     let settings = resolver.resolve(&path);
 
-    writeln!(writer, "Resolved settings for: {path:?}")?;
+    writeln!(writer, "Resolved settings for: \"{}\"", path.display())?;
     if let Some(settings_path) = pyproject_config.path.as_ref() {
-        writeln!(writer, "Settings path: {settings_path:?}")?;
+        writeln!(writer, "Settings path: \"{}\"", settings_path.display())?;
     }
     write!(writer, "{settings}")?;
 
diff --git a/crates/ruff/tests/show_settings.rs b/crates/ruff/tests/show_settings.rs
index e2016e378542b..d418b77228f93 100644
--- a/crates/ruff/tests/show_settings.rs
+++ b/crates/ruff/tests/show_settings.rs
@@ -4,25 +4,29 @@ use std::process::Command;
 
 const BIN_NAME: &str = "ruff";
 
-#[cfg(not(target_os = "windows"))]
-const TEST_FILTERS: &[(&str, &str)] = &[
-    ("\"[^\\*\"]*/pyproject.toml", "\"[BASEPATH]/pyproject.toml"),
-    ("\".*/crates", "\"[BASEPATH]/crates"),
-    ("\".*/\\.ruff_cache", "\"[BASEPATH]/.ruff_cache"),
-    ("\".*/ruff\"", "\"[BASEPATH]\""),
-];
-#[cfg(target_os = "windows")]
-const TEST_FILTERS: &[(&str, &str)] = &[
-    (r#""[^\*"]*\\pyproject.toml"#, "\"[BASEPATH]/pyproject.toml"),
-    (r#"".*\\crates"#, "\"[BASEPATH]/crates"),
-    (r#"".*\\\.ruff_cache"#, "\"[BASEPATH]/.ruff_cache"),
-    (r#"".*\\ruff""#, "\"[BASEPATH]\""),
-    (r#"\\+(\w\w|\s|")"#, "/$1"),
-];
-
 #[test]
 fn display_default_settings() {
-    insta::with_settings!({ filters => TEST_FILTERS.to_vec() }, {
+    // Navigate from the crate directory to the workspace root.
+    let base_path = Path::new(env!("CARGO_MANIFEST_DIR"))
+        .parent()
+        .unwrap()
+        .parent()
+        .unwrap();
+    let base_path = base_path.to_string_lossy();
+
+    // Escape the backslashes for the regex.
+    let base_path = regex::escape(&base_path);
+
+    #[cfg(not(target_os = "windows"))]
+    let test_filters = &[(base_path.as_ref(), "[BASEPATH]")];
+
+    #[cfg(target_os = "windows")]
+    let test_filters = &[
+        (base_path.as_ref(), "[BASEPATH]"),
+        (r#"\\+(\w\w|\s|\.|")"#, "/$1"),
+    ];
+
+    insta::with_settings!({ filters => test_filters.to_vec() }, {
         assert_cmd_snapshot!(Command::new(get_cargo_bin(BIN_NAME))
             .args(["check", "--show-settings", "unformatted.py"]).current_dir(Path::new("./resources/test/fixtures")));
     });
diff --git a/crates/ruff/tests/snapshots/show_settings__display_default_settings.snap b/crates/ruff/tests/snapshots/show_settings__display_default_settings.snap
index 37b5699286474..f784ff99a0629 100644
--- a/crates/ruff/tests/snapshots/show_settings__display_default_settings.snap
+++ b/crates/ruff/tests/snapshots/show_settings__display_default_settings.snap
@@ -205,7 +205,9 @@ linter.external = []
 linter.ignore_init_module_imports = false
 linter.logger_objects = []
 linter.namespace_packages = []
-linter.src = ["[BASEPATH]"]
+linter.src = [
+	"[BASEPATH]",
+]
 linter.tab_size = 4
 linter.line_length = 88
 linter.task_tags = [
diff --git a/crates/ruff_linter/src/settings/mod.rs b/crates/ruff_linter/src/settings/mod.rs
index bd6289438eb96..53f41534195ea 100644
--- a/crates/ruff_linter/src/settings/mod.rs
+++ b/crates/ruff_linter/src/settings/mod.rs
@@ -123,6 +123,9 @@ macro_rules! display_settings {
     (@field $fmt:ident, $prefix:ident, $settings:ident.$field:ident | debug) => {
         writeln!($fmt, "{}{} = {:?}", $prefix, stringify!($field), $settings.$field)?;
     };
+    (@field $fmt:ident, $prefix:ident, $settings:ident.$field:ident | path) => {
+        writeln!($fmt, "{}{} = \"{}\"", $prefix, stringify!($field), $settings.$field.display())?;
+    };
     (@field $fmt:ident, $prefix:ident, $settings:ident.$field:ident | quoted) => {
         writeln!($fmt, "{}{} = \"{}\"", $prefix, stringify!($field), $settings.$field)?;
     };
@@ -152,6 +155,20 @@ macro_rules! display_settings {
             }
         }
     };
+    (@field $fmt:ident, $prefix:ident, $settings:ident.$field:ident | paths) => {
+        {
+            write!($fmt, "{}{} = ", $prefix, stringify!($field))?;
+            if $settings.$field.is_empty() {
+                writeln!($fmt, "[]")?;
+            } else {
+                writeln!($fmt, "[")?;
+                for elem in &$settings.$field {
+                    writeln!($fmt, "\t\"{}\",", elem.display())?;
+                }
+                writeln!($fmt, "]")?;
+            }
+        }
+    };
     (@field $fmt:ident, $prefix:ident, $settings:ident.$field:ident) => {
         writeln!($fmt, "{}{} = {}", $prefix, stringify!($field), $settings.$field)?;
     };
@@ -220,7 +237,7 @@ impl Display for LinterSettings {
             namespace = "linter",
             fields = [
                 self.exclude,
-                self.project_root | debug,
+                self.project_root | path,
 
                 self.rules | nested,
                 self.per_file_ignores,
@@ -238,7 +255,7 @@ impl Display for LinterSettings {
                 self.ignore_init_module_imports,
                 self.logger_objects | array,
                 self.namespace_packages | debug,
-                self.src | debug,
+                self.src | paths,
                 self.tab_size,
                 self.line_length,
                 self.task_tags | array,
diff --git a/crates/ruff_workspace/src/settings.rs b/crates/ruff_workspace/src/settings.rs
index f37dd3723b692..e24b0e9f28083 100644
--- a/crates/ruff_workspace/src/settings.rs
+++ b/crates/ruff_workspace/src/settings.rs
@@ -60,9 +60,7 @@ impl fmt::Display for Settings {
         display_settings! {
             formatter = f,
             fields = [
-                // We want the quotes and lossy UTF8 conversion for this path, so
-                // using PathBuf's `Debug` formatter suffices.
-                self.cache_dir     | debug,
+                self.cache_dir     | path,
                 self.fix,
                 self.fix_only,
                 self.output_format,
@@ -101,7 +99,7 @@ impl fmt::Display for FileResolverSettings {
                 self.include,
                 self.extend_include,
                 self.respect_gitignore,
-                self.project_root | debug,
+                self.project_root | path,
             ]
         }
         Ok(())