diff --git a/playground/package-lock.json b/playground/package-lock.json
index af4574264cad5..2d00c48165533 100644
--- a/playground/package-lock.json
+++ b/playground/package-lock.json
@@ -14,7 +14,8 @@
         "monaco-editor": "^0.51.0",
         "react": "^18.2.0",
         "react-dom": "^18.2.0",
-        "react-resizable-panels": "^2.0.0"
+        "react-resizable-panels": "^2.0.0",
+        "smol-toml": "^1.3.0"
       },
       "devDependencies": {
         "@types/react": "^18.0.26",
@@ -4560,6 +4561,18 @@
         "url": "https://github.com/sponsors/ljharb"
       }
     },
+    "node_modules/smol-toml": {
+      "version": "1.3.0",
+      "resolved": "https://registry.npmjs.org/smol-toml/-/smol-toml-1.3.0.tgz",
+      "integrity": "sha512-tWpi2TsODPScmi48b/OQZGi2lgUmBCHy6SZrhi/FdnnHiU1GwebbCfuQuxsC3nHaLwtYeJGPrDZDIeodDOc4pA==",
+      "license": "BSD-3-Clause",
+      "engines": {
+        "node": ">= 18"
+      },
+      "funding": {
+        "url": "https://github.com/sponsors/cyyynthia"
+      }
+    },
     "node_modules/source-map-js": {
       "version": "1.2.0",
       "resolved": "https://registry.npmjs.org/source-map-js/-/source-map-js-1.2.0.tgz",
diff --git a/playground/package.json b/playground/package.json
index 73f67503ef870..79b5580b93340 100644
--- a/playground/package.json
+++ b/playground/package.json
@@ -21,7 +21,8 @@
     "monaco-editor": "^0.51.0",
     "react": "^18.2.0",
     "react-dom": "^18.2.0",
-    "react-resizable-panels": "^2.0.0"
+    "react-resizable-panels": "^2.0.0",
+    "smol-toml": "^1.3.0"
   },
   "devDependencies": {
     "@types/react": "^18.0.26",
diff --git a/playground/src/Editor/SettingsEditor.tsx b/playground/src/Editor/SettingsEditor.tsx
index a8a5f5a72ec6c..d32ca7d13f3e4 100644
--- a/playground/src/Editor/SettingsEditor.tsx
+++ b/playground/src/Editor/SettingsEditor.tsx
@@ -2,10 +2,11 @@
  * Editor for the settings JSON.
  */
 
-import MonacoEditor, { useMonaco } from "@monaco-editor/react";
-import { useCallback, useEffect } from "react";
-import schema from "../../../ruff.schema.json";
+import { useCallback } from "react";
 import { Theme } from "./theme";
+import MonacoEditor from "@monaco-editor/react";
+import { editor } from "monaco-editor";
+import IStandaloneCodeEditor = editor.IStandaloneCodeEditor;
 
 export default function SettingsEditor({
   visible,
@@ -18,26 +19,86 @@ export default function SettingsEditor({
   theme: Theme;
   onChange: (source: string) => void;
 }) {
-  const monaco = useMonaco();
-
-  useEffect(() => {
-    monaco?.languages.json.jsonDefaults.setDiagnosticsOptions({
-      schemas: [
-        {
-          uri: "https://raw.githubusercontent.com/astral-sh/ruff/main/ruff.schema.json",
-          fileMatch: ["*"],
-          schema,
-        },
-      ],
-    });
-  }, [monaco]);
-
   const handleChange = useCallback(
     (value: string | undefined) => {
       onChange(value ?? "");
     },
     [onChange],
   );
+
+  const handleMount = useCallback((editor: IStandaloneCodeEditor) => {
+    editor.addAction({
+      id: "copyAsRuffToml",
+      label: "Copy as ruff.toml",
+      contextMenuGroupId: "9_cutcopypaste",
+      contextMenuOrder: 3,
+
+      async run(editor): Promise<undefined> {
+        const model = editor.getModel();
+
+        if (model == null) {
+          return;
+        }
+
+        const toml = await import("smol-toml");
+        const settings = model.getValue();
+        const tomlSettings = toml.stringify(JSON.parse(settings));
+
+        await navigator.clipboard.writeText(tomlSettings);
+      },
+    });
+
+    editor.addAction({
+      id: "copyAsPyproject.toml",
+      label: "Copy as pyproject.toml",
+      contextMenuGroupId: "9_cutcopypaste",
+      contextMenuOrder: 4,
+
+      async run(editor): Promise<undefined> {
+        const model = editor.getModel();
+
+        if (model == null) {
+          return;
+        }
+
+        const settings = model.getValue();
+        const toml = await import("smol-toml");
+        const tomlSettings = toml.stringify(
+          prefixWithRuffToml(JSON.parse(settings)),
+        );
+
+        await navigator.clipboard.writeText(tomlSettings);
+      },
+    });
+    editor.onDidPaste((event) => {
+      const model = editor.getModel();
+
+      if (model == null) {
+        return;
+      }
+
+      // Allow pasting a TOML settings configuration if it replaces the entire settings.
+      if (model.getFullModelRange().equalsRange(event.range)) {
+        const pasted = model.getValueInRange(event.range);
+
+        // Text starting with a `{` must be JSON. Don't even try to parse as TOML.
+        if (!pasted.trimStart().startsWith("{")) {
+          import("smol-toml").then((toml) => {
+            try {
+              const parsed = toml.parse(pasted);
+              const cleansed = stripToolRuff(parsed);
+
+              model.setValue(JSON.stringify(cleansed, null, 4));
+            } catch (e) {
+              // Turned out to not be TOML after all.
+              console.warn("Failed to parse settings as TOML", e);
+            }
+          });
+        }
+      }
+    });
+  }, []);
+
   return (
     <MonacoEditor
       options={{
@@ -46,13 +107,59 @@ export default function SettingsEditor({
         fontSize: 14,
         roundedSelection: false,
         scrollBeyondLastLine: false,
-        contextmenu: false,
+        contextmenu: true,
       }}
+      onMount={handleMount}
       wrapperProps={visible ? {} : { style: { display: "none" } }}
-      language={"json"}
+      language="json"
       value={source}
       theme={theme === "light" ? "Ayu-Light" : "Ayu-Dark"}
       onChange={handleChange}
     />
   );
 }
+
+function stripToolRuff(settings: object) {
+  const { tool, ...nonToolSettings } = settings as any;
+
+  // Flatten out `tool.ruff.x` to just `x`
+  if (typeof tool == "object" && !Array.isArray(tool)) {
+    if (tool.ruff != null) {
+      return { ...nonToolSettings, ...tool.ruff };
+    }
+  }
+
+  return Object.fromEntries(
+    Object.entries(settings).flatMap(([key, value]) => {
+      if (key.startsWith("tool.ruff")) {
+        const strippedKey = key.substring("tool.ruff".length);
+
+        if (strippedKey === "") {
+          return Object.entries(value);
+        }
+
+        return [[strippedKey.substring(1), value]];
+      }
+
+      return [[key, value]];
+    }),
+  );
+}
+
+function prefixWithRuffToml(settings: object) {
+  const subTableEntries = [];
+  const ruffTableEntries = [];
+
+  for (const [key, value] of Object.entries(settings)) {
+    if (typeof value === "object" && !Array.isArray(value)) {
+      subTableEntries.push([`tool.ruff.${key}`, value]);
+    } else {
+      ruffTableEntries.push([key, value]);
+    }
+  }
+
+  return {
+    ["tool.ruff"]: Object.fromEntries(ruffTableEntries),
+    ...Object.fromEntries(subTableEntries),
+  };
+}
diff --git a/playground/src/Editor/setupMonaco.tsx b/playground/src/Editor/setupMonaco.tsx
index 7bff263e07c66..9eaf2ccb44b8c 100644
--- a/playground/src/Editor/setupMonaco.tsx
+++ b/playground/src/Editor/setupMonaco.tsx
@@ -3,6 +3,7 @@
  */
 
 import { Monaco } from "@monaco-editor/react";
+import schema from "../../../ruff.schema.json";
 
 export const WHITE = "#ffffff";
 export const RADIATE = "#d7ff64";
@@ -31,6 +32,16 @@ export function setupMonaco(monaco: Monaco) {
   defineRustPythonTokensLanguage(monaco);
   defineRustPythonAstLanguage(monaco);
   defineCommentsLanguage(monaco);
+
+  monaco.languages.json.jsonDefaults.setDiagnosticsOptions({
+    schemas: [
+      {
+        uri: "https://raw.githubusercontent.com/astral-sh/ruff/main/ruff.schema.json",
+        fileMatch: ["*"],
+        schema,
+      },
+    ],
+  });
 }
 
 function defineAyuThemes(monaco: Monaco) {