diff --git a/source/cli.ts b/source/cli.ts
index 20142ac7..ccf8ad0a 100644
--- a/source/cli.ts
+++ b/source/cli.ts
@@ -54,8 +54,11 @@ const cli = meow(`
 			throw new Error(formatter(diagnostics));
 		}
 	} catch (error: unknown) {
-		if (error && typeof (error as Error).message === 'string') {
-			console.error((error as Error).message);
+		const potentialError = error as Error | undefined;
+		const errorMessage = potentialError?.stack ?? potentialError?.message;
+
+		if (errorMessage) {
+			console.error(`Error running tsd: ${errorMessage}`);
 		}
 
 		process.exit(1);
diff --git a/source/test/cli.ts b/source/test/cli.ts
index 3806a5dd..32ef44f2 100644
--- a/source/test/cli.ts
+++ b/source/test/cli.ts
@@ -95,3 +95,13 @@ test('cli typings and files flags', async t => {
 	t.is(exitCode, 1);
 	t.true(stderr.includes('✖  5:19  Argument of type number is not assignable to parameter of type string.'));
 });
+
+test('tsd logs stacktrace on failure', async t => {
+	const {exitCode, stderr, stack} = await t.throwsAsync<ExecaError>(execa('../../../cli.js', {
+		cwd: path.join(__dirname, 'fixtures/empty-package-json')
+	}));
+
+	t.is(exitCode, 1);
+	t.true(stderr.includes('Error running tsd: JSONError: Unexpected end of JSON input while parsing empty string'));
+	t.truthy(stack);
+});
diff --git a/source/test/fixtures/empty-package-json/package.json b/source/test/fixtures/empty-package-json/package.json
new file mode 100644
index 00000000..e69de29b