diff --git a/desktop/pkg/src/commands/init.ts b/desktop/pkg/src/commands/init.ts
index 45897003a..caad462d4 100644
--- a/desktop/pkg/src/commands/init.ts
+++ b/desktop/pkg/src/commands/init.ts
@@ -15,6 +15,8 @@ import {spawnSync} from 'child_process';
 import recursiveReaddirImport from 'recursive-readdir';
 import {promisify} from 'util';
 import inquirer from 'inquirer';
+import {homedir} from 'os';
+
 const recursiveReaddir = promisify<string, string[]>(recursiveReaddirImport);
 
 const templateDir = path.resolve(__dirname, '..', '..', 'templates', 'plugin');
@@ -38,6 +40,9 @@ export default class Init extends Command {
 
   public async run() {
     const {args} = this.parse(Init);
+    const pluginDirectory: string = path.resolve(process.cwd(), args.directory);
+    await verifyFlipperSearchPath(pluginDirectory);
+
     const idQuestion: inquirer.QuestionCollection = [
       {
         type: 'input',
@@ -55,7 +60,6 @@ export default class Init extends Command {
         default: id,
       },
     ];
-    const pluginDirectory: string = path.resolve(process.cwd(), args.directory);
     const title: string = (await inquirer.prompt(titleQuestion)).title;
     const packageName = getPackageNameFromId(id);
     const outputDirectory = path.join(pluginDirectory, packageName);
@@ -68,7 +72,7 @@ export default class Init extends Command {
       `⚙️  Initializing Flipper desktop template in ${outputDirectory}`,
     );
     await fs.ensureDir(outputDirectory);
-    initTemplate(id, title, outputDirectory);
+    await initTemplate(id, title, outputDirectory);
 
     console.log(`⚙️  Installing dependencies`);
     spawnSync('yarn', ['install'], {cwd: outputDirectory, stdio: [0, 1, 2]});
@@ -76,7 +80,9 @@ export default class Init extends Command {
     console.log(
       `✅  Plugin directory initialized. Package name: ${packageName}.`,
     );
-    console.log(`   Run 'cd ${packageName} && yarn watch' to get started!`);
+    console.log(
+      `   Run 'cd ${packageName} && yarn watch' to get started! You might need to restart Flipper before the new plugin is detected.`,
+    );
   }
 }
 
@@ -114,3 +120,48 @@ export async function initTemplate(
     }
   }
 }
+
+async function verifyFlipperSearchPath(pluginDirectory: string) {
+  const flipperConfigPath = path.join(homedir(), '.flipper', 'config.json');
+  if (!fs.existsSync(flipperConfigPath)) {
+    console.warn(
+      `It seems Flipper is not installed on your machine; failed to find ${flipperConfigPath}. Head to 'fbflipper.com' to download flipper`,
+    );
+  } else {
+    const config = JSON.parse(fs.readFileSync(flipperConfigPath, 'utf8'));
+    const pluginPaths: string[] = config.pluginPaths ?? [];
+    const isInSearchPath = pluginPaths.some(
+      (p) => pluginDirectory === path.resolve(p.replace(/^~/, homedir())),
+    );
+    if (!isInSearchPath) {
+      if (
+        (
+          await inquirer.prompt([
+            {
+              type: 'confirm',
+              name: 'addToPath',
+              message: `You are about to create a plugin in a directory that isn't watched by Flipper. Should we add ${pluginDirectory} to the Flipper search path? (Ctrl^C to abort)`,
+              default: true,
+            },
+          ])
+        ).addToPath
+      ) {
+        fs.writeFileSync(
+          flipperConfigPath,
+          JSON.stringify(
+            {
+              ...config,
+              pluginPaths: [...pluginPaths, pluginDirectory],
+            },
+            null,
+            2,
+          ),
+          'utf8',
+        );
+        console.log(
+          `⚙️  Added '${pluginDirectory}' to the search paths in '${flipperConfigPath}'`,
+        );
+      }
+    }
+  }
+}