diff --git a/test/cli/samples/wait-for-bundle-input/_config.js b/test/cli/samples/wait-for-bundle-input/_config.js
index 64f197395b4..e27820f5bb6 100644
--- a/test/cli/samples/wait-for-bundle-input/_config.js
+++ b/test/cli/samples/wait-for-bundle-input/_config.js
@@ -18,5 +18,7 @@ module.exports = {
 			// wait longer than one polling interval
 			setTimeout(() => atomicWriteFileSync(mainFile, 'export default 42;'), 600);
 		}
+		// We wait for a regular abort as we do not watch
+		return false;
 	}
 };
diff --git a/test/cli/samples/watch/bundle-error/_config.js b/test/cli/samples/watch/bundle-error/_config.js
index 2f38a2e2407..963497c1502 100644
--- a/test/cli/samples/watch/bundle-error/_config.js
+++ b/test/cli/samples/watch/bundle-error/_config.js
@@ -17,7 +17,7 @@ module.exports = {
 	},
 	abortOnStderr(data) {
 		if (data.includes('Error: Unexpected token')) {
-			setTimeout(() => atomicWriteFileSync(mainFile, 'export default 42;'), 500);
+			atomicWriteFileSync(mainFile, 'export default 42;');
 			return false;
 		}
 		if (data.includes('created _actual')) {
diff --git a/test/cli/samples/watch/no-config-file/_config.js b/test/cli/samples/watch/no-config-file/_config.js
index 7c7bb86caa3..af24c566137 100644
--- a/test/cli/samples/watch/no-config-file/_config.js
+++ b/test/cli/samples/watch/no-config-file/_config.js
@@ -1,8 +1,10 @@
+const path = require('path');
+
 module.exports = {
 	description: 'watches without a config file',
 	command: 'rollup main.js --watch --format es --file _actual/main.js',
 	abortOnStderr(data) {
-		if (data.includes('created _actual/main.js')) {
+		if (data.includes(`created _actual${path.sep}main.js`)) {
 			return true;
 		}
 	}
diff --git a/test/cli/samples/watch/node-config-file/_config.js b/test/cli/samples/watch/node-config-file/_config.js
index 10957e1893b..1181c599571 100644
--- a/test/cli/samples/watch/node-config-file/_config.js
+++ b/test/cli/samples/watch/node-config-file/_config.js
@@ -1,8 +1,10 @@
+const path = require('path');
+
 module.exports = {
 	description: 'watches using a node_modules config files',
 	command: 'rollup --watch --config node:custom',
 	abortOnStderr(data) {
-		if (data.includes('created _actual/main.js')) {
+		if (data.includes(`created _actual${path.sep}main.js`)) {
 			return true;
 		}
 	}
diff --git a/test/cli/samples/watch/watch-config-early-update/_config.js b/test/cli/samples/watch/watch-config-early-update/_config.js
index 550aa475729..1a230b7214b 100644
--- a/test/cli/samples/watch/watch-config-early-update/_config.js
+++ b/test/cli/samples/watch/watch-config-early-update/_config.js
@@ -2,7 +2,9 @@ const fs = require('fs');
 const path = require('path');
 const { writeAndSync } = require('../../../../utils');
 
-let configFile;
+const configFile = path.join(__dirname, 'rollup.config.js');
+let updateRetryTimeout;
+let retries = 0;
 
 module.exports = {
 	repeat: 100,
@@ -15,7 +17,6 @@ module.exports = {
 		// parsed. To do that, the first config hooks into process.stderr and looks for a log from the
 		// second config.
 		// That way, we simulate a complicated config file being changed while it is parsed.
-		configFile = path.join(__dirname, 'rollup.config.js');
 		fs.mkdirSync(path.join(__dirname, '_actual'));
 		writeAndSync(
 			configFile,
@@ -49,9 +50,25 @@ module.exports = {
 	},
 	abortOnStderr(data) {
 		if (data === 'initial\n') {
-			writeAndSync(
-				configFile,
-				`
+			retries = 0;
+			updateConfig();
+			return false;
+		}
+		if (data.includes(`created _actual${path.sep}output2.js`)) {
+			clearTimeout(updateRetryTimeout);
+			return true;
+		}
+	}
+};
+
+const updateConfig = () => {
+	if (retries > 0) {
+		console.error('RETRIED updateConfig', retries);
+	}
+	retries++;
+	writeAndSync(
+		configFile,
+		`
 				console.error('updated');
 		    export default {
           input: 'main.js',
@@ -60,11 +77,7 @@ module.exports = {
 		        format: "es"
 		      }
 		    };`
-			);
-			return false;
-		}
-		if (data.includes(`created _actual${path.sep}output2.js`)) {
-			return new Promise(resolve => setTimeout(() => resolve(true), 500));
-		}
-	}
+	);
+	// rarely, the watcher does not trigger on MacOS
+	updateRetryTimeout = setTimeout(updateConfig, 1000);
 };
diff --git a/test/cli/samples/watch/watch-config-error/_config.js b/test/cli/samples/watch/watch-config-error/_config.js
index 400b1953b88..b313c17851f 100644
--- a/test/cli/samples/watch/watch-config-error/_config.js
+++ b/test/cli/samples/watch/watch-config-error/_config.js
@@ -48,7 +48,7 @@ module.exports = {
 			return false;
 		}
 		if (data.includes(`created _actual${path.sep}main2.js`)) {
-			return new Promise(resolve => setTimeout(() => resolve(true), 600));
+			return true;
 		}
 	}
 };
diff --git a/test/cli/samples/watch/watch-config-no-update/_config.js b/test/cli/samples/watch/watch-config-no-update/_config.js
index 7bc29a79ab1..a90cb10e14a 100644
--- a/test/cli/samples/watch/watch-config-no-update/_config.js
+++ b/test/cli/samples/watch/watch-config-no-update/_config.js
@@ -23,9 +23,10 @@ module.exports = {
 		fs.unlinkSync(configFile);
 	},
 	abortOnStderr(data) {
-		if (data.includes('created _actual/main.js')) {
+		if (data.includes(`created _actual${path.sep}main.js`)) {
 			atomicWriteFileSync(configFile, configContent);
-			return new Promise(resolve => setTimeout(() => resolve(true), 500));
+			// wait some time for the watcher to trigger
+			return new Promise(resolve => setTimeout(() => resolve(true), 600));
 		}
 	},
 	stderr(stderr) {