diff --git a/packages/@aws-cdk-testing/framework-integ/test/aws-apigatewayv2-authorizers/test/http/integ.lambda.ts b/packages/@aws-cdk-testing/framework-integ/test/aws-apigatewayv2-authorizers/test/http/integ.lambda.ts
index 42bd3fd61c345..a184183d514f0 100644
--- a/packages/@aws-cdk-testing/framework-integ/test/aws-apigatewayv2-authorizers/test/http/integ.lambda.ts
+++ b/packages/@aws-cdk-testing/framework-integ/test/aws-apigatewayv2-authorizers/test/http/integ.lambda.ts
@@ -18,7 +18,7 @@ const stack = new Stack(app, 'AuthorizerInteg');
 const authHandler = new lambda.Function(stack, 'auth-function', {
   runtime: lambda.Runtime.NODEJS_18_X,
   handler: 'index.handler',
-  code: lambda.Code.fromAsset(path.join(__dirname, '../auth-handler')),
+  code: lambda.Code.fromAsset(path.join(__dirname, '..', 'auth-handler')),
 });
 
 const authorizer = new HttpLambdaAuthorizer('LambdaAuthorizer', authHandler, {
@@ -41,7 +41,7 @@ const httpApiWithDefaultAuthorizer = new HttpApi(stack, 'MyHttpApiWithDefaultAut
 const handler = new lambda.Function(stack, 'lambda', {
   runtime: lambda.Runtime.NODEJS_18_X,
   handler: 'index.handler',
-  code: lambda.AssetCode.fromAsset(path.join(__dirname, '../integ.lambda.handler')),
+  code: lambda.AssetCode.fromAsset(path.join(__dirname, '..', 'integ.lambda.handler')),
 });
 
 httpApi.addRoutes({
diff --git a/packages/@aws-cdk-testing/framework-integ/test/aws-apigatewayv2-authorizers/test/http/integ.user-pool.ts b/packages/@aws-cdk-testing/framework-integ/test/aws-apigatewayv2-authorizers/test/http/integ.user-pool.ts
index 45016d6d6e85e..0704a91dc893a 100644
--- a/packages/@aws-cdk-testing/framework-integ/test/aws-apigatewayv2-authorizers/test/http/integ.user-pool.ts
+++ b/packages/@aws-cdk-testing/framework-integ/test/aws-apigatewayv2-authorizers/test/http/integ.user-pool.ts
@@ -31,7 +31,7 @@ const httpApiWithDefaultAuthorizer = new HttpApi(stack, 'MyHttpApiWithDefaultAut
 const handler = new lambda.Function(stack, 'lambda', {
   runtime: lambda.Runtime.NODEJS_18_X,
   handler: 'index.handler',
-  code: lambda.AssetCode.fromAsset(path.join(__dirname, '../integ.user-pool.handler')),
+  code: lambda.AssetCode.fromAsset(path.join(__dirname, '..', 'integ.user-pool.handler')),
 });
 
 httpApi.addRoutes({
diff --git a/packages/@aws-cdk-testing/framework-integ/test/aws-appsync/test/integ.appsync-lambda.ts b/packages/@aws-cdk-testing/framework-integ/test/aws-appsync/test/integ.appsync-lambda.ts
index 106d73850eeb1..0ff2716d500c0 100644
--- a/packages/@aws-cdk-testing/framework-integ/test/aws-appsync/test/integ.appsync-lambda.ts
+++ b/packages/@aws-cdk-testing/framework-integ/test/aws-appsync/test/integ.appsync-lambda.ts
@@ -28,7 +28,7 @@ const api = new appsync.GraphqlApi(stack, 'LambdaAPI', {
 });
 
 const func = new lambda.Function(stack, 'func', {
-  code: lambda.Code.fromAsset(path.join(__dirname, 'verify/lambda-tutorial')),
+  code: lambda.Code.fromAsset(path.join(__dirname, 'verify', 'lambda-tutorial')),
   handler: 'lambda-tutorial.handler',
   runtime: STANDARD_NODEJS_RUNTIME,
 });
diff --git a/packages/@aws-cdk-testing/framework-integ/test/aws-appsync/test/integ.js-resolver.ts b/packages/@aws-cdk-testing/framework-integ/test/aws-appsync/test/integ.js-resolver.ts
index 8ba10b77e8f3b..be6d9b04bd317 100644
--- a/packages/@aws-cdk-testing/framework-integ/test/aws-appsync/test/integ.js-resolver.ts
+++ b/packages/@aws-cdk-testing/framework-integ/test/aws-appsync/test/integ.js-resolver.ts
@@ -58,7 +58,7 @@ const integ = new IntegTest(app, 'JsResolverIntegTest', { testCases: [stack] });
  * Handler that calls our api with an `addTest` Mutation
  */
 const invoke = new lambda.Function(stack, 'InvokeApi', {
-  code: lambda.Code.fromAsset(path.join(__dirname, 'integ-assets/js-resolver-assertion')),
+  code: lambda.Code.fromAsset(path.join(__dirname, 'integ-assets', 'js-resolver-assertion')),
   handler: 'index.handler',
   runtime: lambda.Runtime.NODEJS_18_X,
 });
diff --git a/packages/@aws-cdk-testing/framework-integ/test/aws-appsync/test/integ.lambda-auth.ts b/packages/@aws-cdk-testing/framework-integ/test/aws-appsync/test/integ.lambda-auth.ts
index aa39097be802c..ed955f56520f5 100644
--- a/packages/@aws-cdk-testing/framework-integ/test/aws-appsync/test/integ.lambda-auth.ts
+++ b/packages/@aws-cdk-testing/framework-integ/test/aws-appsync/test/integ.lambda-auth.ts
@@ -12,7 +12,7 @@ class GraphQLApiLambdaAuthStack extends cdk.Stack {
 
     const func = new lambda.Function(this, 'func', {
       code: lambda.Code.fromAsset(
-        path.join(__dirname, 'verify/lambda-tutorial'),
+        path.join(__dirname, 'verify', 'lambda-tutorial'),
       ),
       handler: 'lambda-tutorial.handler',
       runtime: STANDARD_NODEJS_RUNTIME,
diff --git a/packages/@aws-cdk-testing/framework-integ/test/aws-codepipeline-actions/test/integ.pipeline-elastic-beanstalk-deploy.ts b/packages/@aws-cdk-testing/framework-integ/test/aws-codepipeline-actions/test/integ.pipeline-elastic-beanstalk-deploy.ts
index 559e98fe4942c..32b44ba03f8d3 100644
--- a/packages/@aws-cdk-testing/framework-integ/test/aws-codepipeline-actions/test/integ.pipeline-elastic-beanstalk-deploy.ts
+++ b/packages/@aws-cdk-testing/framework-integ/test/aws-codepipeline-actions/test/integ.pipeline-elastic-beanstalk-deploy.ts
@@ -32,7 +32,7 @@ const bucket = new s3.Bucket(stack, 'PipelineBucket', {
 });
 
 const artifact = new deploy.BucketDeployment(stack, 'DeployApp', {
-  sources: [deploy.Source.asset(path.join(__dirname, 'assets/nodejs.zip'))],
+  sources: [deploy.Source.asset(path.join(__dirname, 'assets', 'nodejs.zip'))],
   destinationBucket: bucket,
   extract: false,
 });
diff --git a/packages/@aws-cdk-testing/framework-integ/test/aws-ecs/test/ec2/integ.environment-file.ts b/packages/@aws-cdk-testing/framework-integ/test/aws-ecs/test/ec2/integ.environment-file.ts
index dc5a0448a65ed..2a862f4de6c19 100644
--- a/packages/@aws-cdk-testing/framework-integ/test/aws-ecs/test/ec2/integ.environment-file.ts
+++ b/packages/@aws-cdk-testing/framework-integ/test/aws-ecs/test/ec2/integ.environment-file.ts
@@ -49,13 +49,13 @@ const taskDefinition = new ecs.Ec2TaskDefinition(stack, 'TaskDefinition', {
 // deploy an envfile to S3 and delete when the bucket is deleted
 const envFileDeployment = new s3deployment.BucketDeployment(stack, 'EnvFileDeployment', {
   destinationBucket: bucket,
-  sources: [s3deployment.Source.asset(path.join(__dirname, '../demo-envfiles'))],
+  sources: [s3deployment.Source.asset(path.join(__dirname, '..', 'demo-envfiles'))],
 });
 
 // define container with envfiles - one from local disk and another from S3
 const containerDefinition = new ecs.ContainerDefinition(stack, 'Container', {
   environmentFiles: [
-    ecs.EnvironmentFile.fromAsset(path.join(__dirname, '../demo-envfiles/test-envfile.env')),
+    ecs.EnvironmentFile.fromAsset(path.join(__dirname, '..', 'demo-envfiles', 'test-envfile.env')),
     ecs.EnvironmentFile.fromBucket(bucket, 'test-envfile.env'),
   ],
   image: ecs.ContainerImage.fromRegistry('amazon/amazon-ecs-sample'),
diff --git a/packages/@aws-cdk-testing/framework-integ/test/aws-servicecatalog/test/integ.two-products.ts b/packages/@aws-cdk-testing/framework-integ/test/aws-servicecatalog/test/integ.two-products.ts
index f66f6b6060301..6c4902fcd2073 100644
--- a/packages/@aws-cdk-testing/framework-integ/test/aws-servicecatalog/test/integ.two-products.ts
+++ b/packages/@aws-cdk-testing/framework-integ/test/aws-servicecatalog/test/integ.two-products.ts
@@ -64,7 +64,7 @@ class TestAssetProductStack1 extends servicecatalog.ProductStack {
 
     new lambda.Function(this, 'HelloHandler', {
       runtime: lambda.Runtime.PYTHON_3_9,
-      code: lambda.Code.fromAsset(path.join(__dirname, './assets')),
+      code: lambda.Code.fromAsset(path.join(__dirname, 'assets')),
       handler: 'index.handler',
     });
   }
@@ -76,7 +76,7 @@ class TestAssetProductStack2 extends servicecatalog.ProductStack {
 
     new lambda.Function(this, 'HelloHandler2', {
       runtime: lambda.Runtime.PYTHON_3_9,
-      code: lambda.Code.fromAsset(path.join(__dirname, './assetsv2')),
+      code: lambda.Code.fromAsset(path.join(__dirname, 'assetsv2')),
       handler: 'index.handler',
     });
   }
diff --git a/packages/@aws-cdk/app-staging-synthesizer-alpha/README.md b/packages/@aws-cdk/app-staging-synthesizer-alpha/README.md
index 6b430868f9865..8664303213f26 100644
--- a/packages/@aws-cdk/app-staging-synthesizer-alpha/README.md
+++ b/packages/@aws-cdk/app-staging-synthesizer-alpha/README.md
@@ -213,7 +213,7 @@ import { Asset } from 'aws-cdk-lib/aws-s3-assets';
 declare const stack: Stack;
 const asset = new Asset(stack, 'deploy-time-asset', {
   deployTime: true,
-  path: path.join(__dirname, './deploy-time-asset'),
+  path: path.join(__dirname, 'deploy-time-asset'),
 });
 ```
 
diff --git a/packages/@aws-cdk/aws-amplify-alpha/test/branch.test.ts b/packages/@aws-cdk/aws-amplify-alpha/test/branch.test.ts
index c4b7a6ac2f4e3..a0146ed84474a 100644
--- a/packages/@aws-cdk/aws-amplify-alpha/test/branch.test.ts
+++ b/packages/@aws-cdk/aws-amplify-alpha/test/branch.test.ts
@@ -105,7 +105,7 @@ test('with env vars', () => {
 test('with asset deployment', () => {
   // WHEN
   const asset = new Asset(app, 'SampleAsset', {
-    path: path.join(__dirname, './test-asset'),
+    path: path.join(__dirname, 'test-asset'),
   });
   app.addBranch('dev', { asset });
 
diff --git a/packages/@aws-cdk/aws-amplify-alpha/test/integ.app-asset-deployment.ts b/packages/@aws-cdk/aws-amplify-alpha/test/integ.app-asset-deployment.ts
index 73d2923233e4b..90043ad124051 100644
--- a/packages/@aws-cdk/aws-amplify-alpha/test/integ.app-asset-deployment.ts
+++ b/packages/@aws-cdk/aws-amplify-alpha/test/integ.app-asset-deployment.ts
@@ -10,7 +10,7 @@ class TestStack extends Stack {
     super(scope, id, props);
 
     const asset = new Asset(this, 'SampleAsset', {
-      path: path.join(__dirname, './test-asset'),
+      path: path.join(__dirname, 'test-asset'),
     });
 
     const amplifyApp = new amplify.App(this, 'App', {});
diff --git a/packages/@aws-cdk/aws-apprunner-alpha/README.md b/packages/@aws-cdk/aws-apprunner-alpha/README.md
index 2e85bb3730cd5..1cc9363c8c139 100644
--- a/packages/@aws-cdk/aws-apprunner-alpha/README.md
+++ b/packages/@aws-cdk/aws-apprunner-alpha/README.md
@@ -74,7 +74,7 @@ You can specify whether to enable continuous integration from the source reposit
 import * as assets from 'aws-cdk-lib/aws-ecr-assets';
 
 const imageAsset = new assets.DockerImageAsset(this, 'ImageAssets', {
-  directory: path.join(__dirname, './docker.assets'),
+  directory: path.join(__dirname, 'docker.assets'),
 });
 new apprunner.Service(this, 'Service', {
   source: apprunner.Source.fromAsset({
diff --git a/packages/@aws-cdk/aws-apprunner-alpha/test/integ.service-ecr.ts b/packages/@aws-cdk/aws-apprunner-alpha/test/integ.service-ecr.ts
index d6e7d10b692ac..012132a75e2e0 100644
--- a/packages/@aws-cdk/aws-apprunner-alpha/test/integ.service-ecr.ts
+++ b/packages/@aws-cdk/aws-apprunner-alpha/test/integ.service-ecr.ts
@@ -9,7 +9,7 @@ const stack = new cdk.Stack(app, 'integ-apprunner');
 
 // Scenario 3: Create the service from local code assets
 const imageAsset = new assets.DockerImageAsset(stack, 'ImageAssets', {
-  directory: path.join(__dirname, './docker.assets'),
+  directory: path.join(__dirname, 'docker.assets'),
 });
 const service3 = new Service(stack, 'Service3', {
   source: Source.fromAsset({
diff --git a/packages/@aws-cdk/aws-apprunner-alpha/test/service.test.ts b/packages/@aws-cdk/aws-apprunner-alpha/test/service.test.ts
index d73b9cf0d7a16..d4ef80d552bd1 100644
--- a/packages/@aws-cdk/aws-apprunner-alpha/test/service.test.ts
+++ b/packages/@aws-cdk/aws-apprunner-alpha/test/service.test.ts
@@ -574,7 +574,7 @@ test('create a service with local assets(image repository type: ECR)', () => {
   const stack = new cdk.Stack(app, 'demo-stack');
   // WHEN
   const dockerAsset = new ecr_assets.DockerImageAsset(stack, 'Assets', {
-    directory: path.join(__dirname, './docker.assets'),
+    directory: path.join(__dirname, 'docker.assets'),
   });
   new apprunner.Service(stack, 'DemoService', {
     source: apprunner.Source.fromAsset({
@@ -864,7 +864,7 @@ test('custom IAM access role and instance role are allowed', () => {
   const stack = new cdk.Stack(app, 'demo-stack');
   // WHEN
   const dockerAsset = new ecr_assets.DockerImageAsset(stack, 'Assets', {
-    directory: path.join(__dirname, './docker.assets'),
+    directory: path.join(__dirname, 'docker.assets'),
   });
   new apprunner.Service(stack, 'DemoService', {
     source: apprunner.Source.fromAsset({
@@ -1177,7 +1177,7 @@ test('autoDeploymentsEnabled flag is set true', () => {
   const stack = new cdk.Stack(app, 'demo-stack');
   // WHEN
   const dockerAsset = new ecr_assets.DockerImageAsset(stack, 'Assets', {
-    directory: path.join(__dirname, './docker.assets'),
+    directory: path.join(__dirname, 'docker.assets'),
   });
   new apprunner.Service(stack, 'DemoService', {
     source: apprunner.Source.fromAsset({
diff --git a/packages/@aws-cdk/aws-gamelift-alpha/README.md b/packages/@aws-cdk/aws-gamelift-alpha/README.md
index 64aa5ae057532..8dcccd6d4c5aa 100644
--- a/packages/@aws-cdk/aws-gamelift-alpha/README.md
+++ b/packages/@aws-cdk/aws-gamelift-alpha/README.md
@@ -99,7 +99,7 @@ match is made after 30 seconds, gradually relax the skill requirements.
 ```ts
 new gamelift.MatchmakingRuleSet(this, 'RuleSet', {
   matchmakingRuleSetName: 'my-test-ruleset',
-  content: gamelift.RuleSetContent.fromJsonFile(path.join(__dirname, 'my-ruleset/ruleset.json')),
+  content: gamelift.RuleSetContent.fromJsonFile(path.join(__dirname, 'my-ruleset', 'ruleset.json')),
 });
 ```
 
diff --git a/packages/@aws-cdk/aws-gamelift-alpha/test/integ.matchmaking-ruleset.ts b/packages/@aws-cdk/aws-gamelift-alpha/test/integ.matchmaking-ruleset.ts
index e2f2ffb723f18..f28c51db2e553 100644
--- a/packages/@aws-cdk/aws-gamelift-alpha/test/integ.matchmaking-ruleset.ts
+++ b/packages/@aws-cdk/aws-gamelift-alpha/test/integ.matchmaking-ruleset.ts
@@ -11,7 +11,7 @@ class TestStack extends cdk.Stack {
 
     const ruleSet = new gamelift.MatchmakingRuleSet(this, 'MatchmakingRuleSet', {
       matchmakingRuleSetName: 'my-test-ruleset',
-      content: gamelift.RuleSetContent.fromJsonFile(path.join(__dirname, 'my-ruleset/ruleset.json')),
+      content: gamelift.RuleSetContent.fromJsonFile(path.join(__dirname, 'my-ruleset', 'ruleset.json')),
     });
 
     new CfnOutput(this, 'MatchmakingRuleSetArn', { value: ruleSet.matchmakingRuleSetArn });
diff --git a/packages/@aws-cdk/aws-gamelift-alpha/test/integ.queued-matchmaking-configuration.ts b/packages/@aws-cdk/aws-gamelift-alpha/test/integ.queued-matchmaking-configuration.ts
index 696137c0c14d2..2d2b8310bb23c 100644
--- a/packages/@aws-cdk/aws-gamelift-alpha/test/integ.queued-matchmaking-configuration.ts
+++ b/packages/@aws-cdk/aws-gamelift-alpha/test/integ.queued-matchmaking-configuration.ts
@@ -12,7 +12,7 @@ class TestStack extends cdk.Stack {
 
     const ruleSet = new gamelift.MatchmakingRuleSet(this, 'QueuedMatchmakingConfiguration', {
       matchmakingRuleSetName: 'my-test-ruleset',
-      content: gamelift.RuleSetContent.fromJsonFile(path.join(__dirname, 'my-ruleset/ruleset.json')),
+      content: gamelift.RuleSetContent.fromJsonFile(path.join(__dirname, 'my-ruleset', 'ruleset.json')),
     });
 
     const build = new gamelift.Build(this, 'Build', {
diff --git a/packages/@aws-cdk/aws-gamelift-alpha/test/integ.standalone-matchmaking-configuration.ts b/packages/@aws-cdk/aws-gamelift-alpha/test/integ.standalone-matchmaking-configuration.ts
index ffe775515c306..96664d2f5b197 100644
--- a/packages/@aws-cdk/aws-gamelift-alpha/test/integ.standalone-matchmaking-configuration.ts
+++ b/packages/@aws-cdk/aws-gamelift-alpha/test/integ.standalone-matchmaking-configuration.ts
@@ -11,7 +11,7 @@ class TestStack extends cdk.Stack {
 
     const ruleSet = new gamelift.MatchmakingRuleSet(this, 'StandaloneMatchmakingConfiguration', {
       matchmakingRuleSetName: 'my-test-ruleset',
-      content: gamelift.RuleSetContent.fromJsonFile(path.join(__dirname, 'my-ruleset/ruleset.json')),
+      content: gamelift.RuleSetContent.fromJsonFile(path.join(__dirname, 'my-ruleset', 'ruleset.json')),
     });
 
     const matchmakingConfiguration = new gamelift.StandaloneMatchmakingConfiguration(this, 'MyStandaloneMatchmakingConfiguration', {
diff --git a/packages/@aws-cdk/aws-gamelift-alpha/test/matchmaking-ruleset-body.test.ts b/packages/@aws-cdk/aws-gamelift-alpha/test/matchmaking-ruleset-body.test.ts
index f0603ad324ac3..16e53ee71053d 100644
--- a/packages/@aws-cdk/aws-gamelift-alpha/test/matchmaking-ruleset-body.test.ts
+++ b/packages/@aws-cdk/aws-gamelift-alpha/test/matchmaking-ruleset-body.test.ts
@@ -35,14 +35,14 @@ describe('MatchmakingRuleSetBody', () => {
 
   describe('gamelift.MatchmakingRuleSetBody.fromJsonFile', () => {
     test('new RuleSetBody from Json file', () => {
-      const ruleSet = gamelift.RuleSetContent.fromJsonFile(path.join(__dirname, 'my-ruleset/ruleset.json'));
+      const ruleSet = gamelift.RuleSetContent.fromJsonFile(path.join(__dirname, 'my-ruleset', 'ruleset.json'));
       const content = ruleSet.bind(stack);
-      const result = JSON.parse(fs.readFileSync(path.join(__dirname, 'my-ruleset/ruleset.json')).toString());
+      const result = JSON.parse(fs.readFileSync(path.join(__dirname, 'my-ruleset', 'ruleset.json')).toString());
       expect(content.ruleSetBody).toEqual(JSON.stringify(result));
     });
 
     test('fails if file not exist', () => {
-      const content = path.join(__dirname, 'my-ruleset/file-not-exist.json');
+      const content = path.join(__dirname, 'my-ruleset', 'file-not-exist.json');
       expect(() => gamelift.RuleSetContent.fromJsonFile(content))
         .toThrow(`RuleSet path does not exist, please verify it, actual ${content}`);
     });
diff --git a/packages/@aws-cdk/aws-glue-alpha/README.md b/packages/@aws-cdk/aws-glue-alpha/README.md
index 67018d6559724..051044a74c8ff 100644
--- a/packages/@aws-cdk/aws-glue-alpha/README.md
+++ b/packages/@aws-cdk/aws-glue-alpha/README.md
@@ -60,7 +60,7 @@ new glue.Job(this, 'PythonSparkStreamingJob', {
   executable: glue.JobExecutable.pythonStreaming({
     glueVersion: glue.GlueVersion.V4_0,
     pythonVersion: glue.PythonVersion.THREE,
-    script: glue.Code.fromAsset(path.join(__dirname, 'job-script/hello_world.py')),
+    script: glue.Code.fromAsset(path.join(__dirname, 'job-script', 'hello_world.py')),
   }),
   description: 'an example Python Streaming job',
 });
@@ -97,7 +97,7 @@ new glue.Job(this, 'RayJob', {
     glueVersion: glue.GlueVersion.V4_0,
     pythonVersion: glue.PythonVersion.THREE_NINE,
     runtime: glue.Runtime.RAY_TWO_FOUR,
-    script: glue.Code.fromAsset(path.join(__dirname, 'job-script/hello_world.py')),
+    script: glue.Code.fromAsset(path.join(__dirname, 'job-script', 'hello_world.py')),
   }),
   workerType: glue.WorkerType.Z_2X,
   workerCount: 2,
@@ -118,7 +118,7 @@ new glue.Job(this, 'EnableSparkUI', {
   executable: glue.JobExecutable.pythonEtl({
     glueVersion: glue.GlueVersion.V3_0,
     pythonVersion: glue.PythonVersion.THREE,
-    script: glue.Code.fromAsset(path.join(__dirname, 'job-script/hello_world.py')),
+    script: glue.Code.fromAsset(path.join(__dirname, 'job-script', 'hello_world.py')),
   }),
 });
 ```
diff --git a/packages/@aws-cdk/aws-glue-alpha/test/code.test.ts b/packages/@aws-cdk/aws-glue-alpha/test/code.test.ts
index f67d6f71526b4..9b213cd891134 100644
--- a/packages/@aws-cdk/aws-glue-alpha/test/code.test.ts
+++ b/packages/@aws-cdk/aws-glue-alpha/test/code.test.ts
@@ -85,7 +85,7 @@ describe('Code', () => {
   });
 
   describe('.fromAsset()', () => {
-    const filePath = path.join(__dirname, 'job-script/hello_world.py');
+    const filePath = path.join(__dirname, 'job-script', 'hello_world.py');
     const directoryPath = path.join(__dirname, 'job-script');
 
     beforeEach(() => {
diff --git a/packages/@aws-cdk/aws-glue-alpha/test/integ.job-python-shell.ts b/packages/@aws-cdk/aws-glue-alpha/test/integ.job-python-shell.ts
index 4e283327f0ad4..a08a19713b9a7 100644
--- a/packages/@aws-cdk/aws-glue-alpha/test/integ.job-python-shell.ts
+++ b/packages/@aws-cdk/aws-glue-alpha/test/integ.job-python-shell.ts
@@ -22,7 +22,7 @@ const app = new cdk.App();
 
 const stack = new cdk.Stack(app, 'aws-glue-job-python-shell');
 
-const script = glue.Code.fromAsset(path.join(__dirname, 'job-script/hello_world.py'));
+const script = glue.Code.fromAsset(path.join(__dirname, 'job-script', 'hello_world.py'));
 
 new glue.Job(stack, 'ShellJob', {
   jobName: 'ShellJob',
diff --git a/packages/@aws-cdk/aws-glue-alpha/test/integ.job.ts b/packages/@aws-cdk/aws-glue-alpha/test/integ.job.ts
index aa420c52eccf4..c16b5f9691ae1 100644
--- a/packages/@aws-cdk/aws-glue-alpha/test/integ.job.ts
+++ b/packages/@aws-cdk/aws-glue-alpha/test/integ.job.ts
@@ -21,7 +21,7 @@ const app = new cdk.App();
 
 const stack = new cdk.Stack(app, 'aws-glue-job');
 
-const script = glue.Code.fromAsset(path.join(__dirname, 'job-script/hello_world.py'));
+const script = glue.Code.fromAsset(path.join(__dirname, 'job-script', 'hello_world.py'));
 
 [glue.GlueVersion.V2_0, glue.GlueVersion.V3_0, glue.GlueVersion.V4_0].forEach((glueVersion) => {
   const etlJob = new glue.Job(stack, 'EtlJob' + glueVersion.name, {
diff --git a/packages/@aws-cdk/aws-lambda-go-alpha/lib/bundling.ts b/packages/@aws-cdk/aws-lambda-go-alpha/lib/bundling.ts
index de91e04bb360d..303b12f8b76d3 100644
--- a/packages/@aws-cdk/aws-lambda-go-alpha/lib/bundling.ts
+++ b/packages/@aws-cdk/aws-lambda-go-alpha/lib/bundling.ts
@@ -143,7 +143,7 @@ export class Bundling implements cdk.BundlingOptions {
     // Docker bundling
     const shouldBuildImage = props.forcedDockerBundling || !Bundling.runsLocally;
     this.image = shouldBuildImage
-      ? props.dockerImage ?? cdk.DockerImage.fromBuild(path.join(__dirname, '../lib'), {
+      ? props.dockerImage ?? cdk.DockerImage.fromBuild(path.join(__dirname, '..', 'lib'), {
         buildArgs: {
           ...props.buildArgs ?? {},
           IMAGE: Runtime.GO_1_X.bundlingImage.image, // always use the GO_1_X build image
diff --git a/packages/@aws-cdk/aws-lambda-go-alpha/test/docker.test.ts b/packages/@aws-cdk/aws-lambda-go-alpha/test/docker.test.ts
index c67b2feac5ca7..9f25c23da4651 100644
--- a/packages/@aws-cdk/aws-lambda-go-alpha/test/docker.test.ts
+++ b/packages/@aws-cdk/aws-lambda-go-alpha/test/docker.test.ts
@@ -3,7 +3,7 @@ import * as path from 'path';
 
 const docker = process.env.CDK_DOCKER ?? 'docker';
 beforeAll(() => {
-  spawnSync(docker, ['build', '-t', 'golang', path.join(__dirname, '../lib')]);
+  spawnSync(docker, ['build', '-t', 'golang', path.join(__dirname, '..', 'lib')]);
 });
 
 test('golang is available', async () => {
diff --git a/packages/@aws-cdk/aws-lambda-go-alpha/test/function.test.ts b/packages/@aws-cdk/aws-lambda-go-alpha/test/function.test.ts
index d557ea2d2fcda..c1989bbc4acbb 100644
--- a/packages/@aws-cdk/aws-lambda-go-alpha/test/function.test.ts
+++ b/packages/@aws-cdk/aws-lambda-go-alpha/test/function.test.ts
@@ -27,7 +27,7 @@ beforeEach(() => {
 test('GoFunction with defaults', () => {
   // WHEN
   new GoFunction(stack, 'handler', {
-    entry: path.join(__dirname, 'lambda-handler-vendor/cmd/api'),
+    entry: path.join(__dirname, 'lambda-handler-vendor', 'cmd', 'api'),
   });
 
   expect(Bundling.bundle).toHaveBeenCalledWith(expect.objectContaining({
@@ -43,7 +43,7 @@ test('GoFunction with defaults', () => {
 test('GoFunction with using provided runtime', () => {
   // WHEN
   new GoFunction(stack, 'handler', {
-    entry: path.join(__dirname, 'lambda-handler-vendor/cmd/api'),
+    entry: path.join(__dirname, 'lambda-handler-vendor', 'cmd', 'api'),
     runtime: Runtime.PROVIDED,
   });
 
@@ -60,7 +60,7 @@ test('GoFunction with using provided runtime', () => {
 test('GoFunction with using golang runtime', () => {
   // WHEN
   new GoFunction(stack, 'handler', {
-    entry: path.join(__dirname, 'lambda-handler-vendor/cmd/api'),
+    entry: path.join(__dirname, 'lambda-handler-vendor', 'cmd', 'api'),
     runtime: Runtime.GO_1_X,
   });
 
@@ -77,7 +77,7 @@ test('GoFunction with using golang runtime', () => {
 test('GoFunction with container env vars', () => {
   // WHEN
   new GoFunction(stack, 'handler', {
-    entry: path.join(__dirname, 'lambda-handler-vendor/cmd/api'),
+    entry: path.join(__dirname, 'lambda-handler-vendor', 'cmd', 'api'),
     bundling: {
       environment: {
         KEY: 'VALUE',
@@ -94,7 +94,7 @@ test('GoFunction with container env vars', () => {
 
 test('throws with the wrong runtime family', () => {
   expect(() => new GoFunction(stack, 'handler', {
-    entry: path.join(__dirname, 'lambda-handler-vendor/cmd/api'),
+    entry: path.join(__dirname, 'lambda-handler-vendor', 'cmd', 'api'),
     runtime: Runtime.PYTHON_3_8,
   })).toThrow(/Only `go` and `provided` runtimes are supported/);
 });
@@ -102,7 +102,7 @@ test('throws with the wrong runtime family', () => {
 test('resolves entry to an absolute path', () => {
   // WHEN
   new GoFunction(stack, 'fn', {
-    entry: path.join(__dirname, 'lambda-handler-vendor/cmd/api/main.go'),
+    entry: path.join(__dirname, 'lambda-handler-vendor', 'cmd', 'api', 'main.go'),
   });
 
   expect(Bundling.bundle).toHaveBeenCalledWith(expect.objectContaining({
@@ -112,21 +112,21 @@ test('resolves entry to an absolute path', () => {
 
 test('throws with no existing go.mod file', () => {
   expect(() => new GoFunction(stack, 'handler', {
-    entry: path.join(__dirname, 'lambda-handler-vendor/cmd/api'),
+    entry: path.join(__dirname, 'lambda-handler-vendor', 'cmd', 'api'),
     moduleDir: '/does/not/exist/go.mod',
   })).toThrow(/go.mod file at \/does\/not\/exist\/go.mod doesn't exist/);
 });
 
 test('throws with incorrect moduleDir file', () => {
   expect(() => new GoFunction(stack, 'handler', {
-    entry: path.join(__dirname, 'lambda-handler-vendor/cmd/api'),
+    entry: path.join(__dirname, 'lambda-handler-vendor', 'cmd', 'api'),
     moduleDir: '/does/not/exist.mod',
   })).toThrow(/moduleDir is specifying a file that is not go.mod/);
 });
 
 test('custom moduleDir can be used', () => {
   new GoFunction(stack, 'handler', {
-    entry: path.join(__dirname, 'lambda-handler-vendor/cmd/api'),
+    entry: path.join(__dirname, 'lambda-handler-vendor', 'cmd', 'api'),
     moduleDir: path.join(__dirname, 'lambda-handler-vendor'),
   });
 
@@ -137,8 +137,8 @@ test('custom moduleDir can be used', () => {
 
 test('custom moduleDir with file path can be used', () => {
   new GoFunction(stack, 'handler', {
-    entry: path.join(__dirname, 'lambda-handler-vendor/cmd/api'),
-    moduleDir: path.join(__dirname, 'lambda-handler-vendor/go.mod'),
+    entry: path.join(__dirname, 'lambda-handler-vendor', 'cmd', 'api'),
+    moduleDir: path.join(__dirname, 'lambda-handler-vendor', 'go.mod'),
   });
 
   Template.fromStack(stack).hasResourceProperties('AWS::Lambda::Function', {
diff --git a/packages/@aws-cdk/aws-lambda-go-alpha/test/integ.function.provided.al2023.ts b/packages/@aws-cdk/aws-lambda-go-alpha/test/integ.function.provided.al2023.ts
index bf2d4945812a6..128a5727b290c 100644
--- a/packages/@aws-cdk/aws-lambda-go-alpha/test/integ.function.provided.al2023.ts
+++ b/packages/@aws-cdk/aws-lambda-go-alpha/test/integ.function.provided.al2023.ts
@@ -15,7 +15,7 @@ class TestStack extends Stack {
     super(scope, id, props);
 
     new lambda.GoFunction(this, 'go-handler-docker', {
-      entry: path.join(__dirname, 'lambda-handler-vendor/cmd/api'),
+      entry: path.join(__dirname, 'lambda-handler-vendor', 'cmd', 'api'),
       runtime: Runtime.PROVIDED_AL2023,
       bundling: {
         forcedDockerBundling: true,
diff --git a/packages/@aws-cdk/aws-lambda-go-alpha/test/integ.function.ts b/packages/@aws-cdk/aws-lambda-go-alpha/test/integ.function.ts
index 7d6e4afebcf84..ee5a0898c03f8 100644
--- a/packages/@aws-cdk/aws-lambda-go-alpha/test/integ.function.ts
+++ b/packages/@aws-cdk/aws-lambda-go-alpha/test/integ.function.ts
@@ -13,7 +13,7 @@ class TestStack extends Stack {
     super(scope, id, props);
 
     new lambda.GoFunction(this, 'go-handler-docker', {
-      entry: path.join(__dirname, 'lambda-handler-vendor/cmd/api'),
+      entry: path.join(__dirname, 'lambda-handler-vendor', 'cmd', 'api'),
       bundling: {
         forcedDockerBundling: true,
         goBuildFlags: ['-mod=readonly', '-ldflags "-s -w"'],
diff --git a/packages/@aws-cdk/aws-lambda-python-alpha/lib/bundling.ts b/packages/@aws-cdk/aws-lambda-python-alpha/lib/bundling.ts
index de64c44908706..dc489300d63d4 100644
--- a/packages/@aws-cdk/aws-lambda-python-alpha/lib/bundling.ts
+++ b/packages/@aws-cdk/aws-lambda-python-alpha/lib/bundling.ts
@@ -99,7 +99,7 @@ export class Bundling implements CdkBundlingOptions {
       assetExcludes,
     });
 
-    this.image = image ?? DockerImage.fromBuild(path.join(__dirname, '../lib'), {
+    this.image = image ?? DockerImage.fromBuild(path.join(__dirname, '..', 'lib'), {
       buildArgs: {
         ...props.buildArgs,
         IMAGE: runtime.bundlingImage.image,
diff --git a/packages/@aws-cdk/aws-lambda-python-alpha/test/bundling.test.ts b/packages/@aws-cdk/aws-lambda-python-alpha/test/bundling.test.ts
index a05fc4dab6834..54b61b3c03a34 100644
--- a/packages/@aws-cdk/aws-lambda-python-alpha/test/bundling.test.ts
+++ b/packages/@aws-cdk/aws-lambda-python-alpha/test/bundling.test.ts
@@ -42,7 +42,7 @@ test('Bundling a function without dependencies', () => {
     }),
   }));
 
-  expect(DockerImage.fromBuild).toHaveBeenCalledWith(expect.stringMatching(path.join(__dirname, '../lib')), expect.objectContaining({
+  expect(DockerImage.fromBuild).toHaveBeenCalledWith(expect.stringMatching(path.join(__dirname, '..', 'lib')), expect.objectContaining({
     buildArgs: expect.objectContaining({
       IMAGE: expect.stringMatching(/build-python/),
     }),
@@ -394,7 +394,7 @@ test('Bundling with custom build args', () => {
     buildArgs: { PIP_INDEX_URL: testPypi },
   });
 
-  expect(DockerImage.fromBuild).toHaveBeenCalledWith(expect.stringMatching(path.join(__dirname, '../lib')), expect.objectContaining({
+  expect(DockerImage.fromBuild).toHaveBeenCalledWith(expect.stringMatching(path.join(__dirname, '..', 'lib')), expect.objectContaining({
     buildArgs: expect.objectContaining({
       PIP_INDEX_URL: testPypi,
     }),
diff --git a/packages/@aws-cdk/aws-lambda-python-alpha/test/layer.test.ts b/packages/@aws-cdk/aws-lambda-python-alpha/test/layer.test.ts
index 3d17d896ab527..548b9579a8b10 100644
--- a/packages/@aws-cdk/aws-lambda-python-alpha/test/layer.test.ts
+++ b/packages/@aws-cdk/aws-lambda-python-alpha/test/layer.test.ts
@@ -30,7 +30,7 @@ beforeEach(() => {
 });
 
 test('Bundling a layer from files', () => {
-  const entry = path.join(__dirname, 'test/lambda-handler-project');
+  const entry = path.join(__dirname, 'test', 'lambda-handler-project');
   new PythonLayerVersion(stack, 'layer', {
     entry,
   });
diff --git a/packages/@aws-cdk/integ-runner/lib/cli.ts b/packages/@aws-cdk/integ-runner/lib/cli.ts
index 5847cec812e99..7ed6a5455f478 100644
--- a/packages/@aws-cdk/integ-runner/lib/cli.ts
+++ b/packages/@aws-cdk/integ-runner/lib/cli.ts
@@ -107,7 +107,7 @@ export async function main(args: string[]) {
     return;
   }
 
-  const pool = workerpool.pool(path.join(__dirname, '../lib/workers/extract/index.js'), {
+  const pool = workerpool.pool(path.join(__dirname, '..', 'lib', 'workers', 'extract', 'index.js'), {
     maxWorkers: options.watch ? 1 : options.maxWorkers,
   });
 
diff --git a/packages/@aws-cdk/integ-runner/test/runner/snapshot-test-runner.test.ts b/packages/@aws-cdk/integ-runner/test/runner/snapshot-test-runner.test.ts
index 6a67c30eb00d5..87743e59b564e 100644
--- a/packages/@aws-cdk/integ-runner/test/runner/snapshot-test-runner.test.ts
+++ b/packages/@aws-cdk/integ-runner/test/runner/snapshot-test-runner.test.ts
@@ -10,7 +10,7 @@ let cdkMock: MockCdkProvider;
 
 const currentCwd = process.cwd();
 beforeAll(() => {
-  process.chdir(path.join(__dirname, '../..'));
+  process.chdir(path.join(__dirname, '..', '..'));
 });
 afterAll(() => {
   process.chdir(currentCwd);
diff --git a/packages/@aws-cdk/integ-runner/test/workers/integ-worker.test.ts b/packages/@aws-cdk/integ-runner/test/workers/integ-worker.test.ts
index e97e45bf48689..dfe028f9599df 100644
--- a/packages/@aws-cdk/integ-runner/test/workers/integ-worker.test.ts
+++ b/packages/@aws-cdk/integ-runner/test/workers/integ-worker.test.ts
@@ -9,7 +9,7 @@ let stderrMock: jest.SpyInstance;
 let pool: workerpool.WorkerPool;
 let spawnSyncMock: jest.SpyInstance;
 beforeAll(() => {
-  pool = workerpool.pool(path.join(__dirname, './mock-extract_worker.js'));
+  pool = workerpool.pool(path.join(__dirname, 'mock-extract_worker.js'));
 });
 beforeEach(() => {
   jest.spyOn(fs, 'moveSync').mockImplementation(() => { return true; });
diff --git a/packages/@aws-cdk/integ-runner/test/workers/snapshot-worker.test.ts b/packages/@aws-cdk/integ-runner/test/workers/snapshot-worker.test.ts
index 015b53861b622..8c53833710837 100644
--- a/packages/@aws-cdk/integ-runner/test/workers/snapshot-worker.test.ts
+++ b/packages/@aws-cdk/integ-runner/test/workers/snapshot-worker.test.ts
@@ -16,7 +16,7 @@ afterEach(() => {
   jest.restoreAllMocks();
 });
 
-const directory = path.join(__dirname, '../test-data');
+const directory = path.join(__dirname, '..', 'test-data');
 describe('Snapshot tests', () => {
   test('no snapshot', () => {
     // WHEN
diff --git a/packages/aws-cdk-lib/aws-appsync/test/appsync-caching-config.test.ts b/packages/aws-cdk-lib/aws-appsync/test/appsync-caching-config.test.ts
index b1475e412f3ff..655ba2a914e9c 100644
--- a/packages/aws-cdk-lib/aws-appsync/test/appsync-caching-config.test.ts
+++ b/packages/aws-cdk-lib/aws-appsync/test/appsync-caching-config.test.ts
@@ -23,7 +23,7 @@ describe('Lambda caching config', () => {
 
   beforeEach(() => {
     func = new lambda.Function(stack, 'func', {
-      code: lambda.Code.fromAsset(path.join(__dirname, 'verify/lambda-tutorial')),
+      code: lambda.Code.fromAsset(path.join(__dirname, 'verify', 'lambda-tutorial')),
       handler: 'lambda-tutorial.handler',
       runtime: lambda.Runtime.NODEJS_LATEST,
     });
diff --git a/packages/aws-cdk-lib/aws-appsync/test/appsync-lambda.test.ts b/packages/aws-cdk-lib/aws-appsync/test/appsync-lambda.test.ts
index 29ba4d27f6446..e709e445b2d98 100644
--- a/packages/aws-cdk-lib/aws-appsync/test/appsync-lambda.test.ts
+++ b/packages/aws-cdk-lib/aws-appsync/test/appsync-lambda.test.ts
@@ -20,7 +20,7 @@ describe('Lambda Data Source configuration', () => {
   let func: lambda.Function;
   beforeEach(() => {
     func = new lambda.Function(stack, 'func', {
-      code: lambda.Code.fromAsset(path.join(__dirname, 'verify/iam-query')),
+      code: lambda.Code.fromAsset(path.join(__dirname, 'verify', 'iam-query')),
       handler: 'iam-query.handler',
       runtime: lambda.Runtime.NODEJS_LATEST,
     });
@@ -76,7 +76,7 @@ describe('Lambda Data Source configuration', () => {
         schema: appsync.SchemaFile.fromAsset(path.join(__dirname, 'appsync.test.graphql')),
       });
       const dummyFunction = new lambda.Function(newStack, 'func', {
-        code: lambda.Code.fromAsset(path.join(__dirname, 'verify/iam-query')),
+        code: lambda.Code.fromAsset(path.join(__dirname, 'verify', 'iam-query')),
         handler: 'iam-query.handler',
         runtime: lambda.Runtime.NODEJS_LATEST,
       });
@@ -130,7 +130,7 @@ describe('adding lambda data source from imported api', () => {
   let func: lambda.Function;
   beforeEach(() => {
     func = new lambda.Function(stack, 'func', {
-      code: lambda.Code.fromAsset(path.join(__dirname, 'verify/iam-query')),
+      code: lambda.Code.fromAsset(path.join(__dirname, 'verify', 'iam-query')),
       handler: 'iam-query.handler',
       runtime: lambda.Runtime.NODEJS_LATEST,
     });
diff --git a/packages/aws-cdk-lib/aws-appsync/test/appsync-mapping-template.test.ts b/packages/aws-cdk-lib/aws-appsync/test/appsync-mapping-template.test.ts
index fd9ab94b91341..972138159dd36 100644
--- a/packages/aws-cdk-lib/aws-appsync/test/appsync-mapping-template.test.ts
+++ b/packages/aws-cdk-lib/aws-appsync/test/appsync-mapping-template.test.ts
@@ -24,7 +24,7 @@ describe('Lambda Mapping Templates', () => {
 
   beforeEach(() => {
     func = new lambda.Function(stack, 'func', {
-      code: lambda.Code.fromAsset(path.join(__dirname, 'verify/lambda-tutorial')),
+      code: lambda.Code.fromAsset(path.join(__dirname, 'verify', 'lambda-tutorial')),
       handler: 'lambda-tutorial.handler',
       runtime: lambda.Runtime.NODEJS_LATEST,
     });
diff --git a/packages/aws-cdk-lib/aws-ec2/test/cfn-init-element.test.ts b/packages/aws-cdk-lib/aws-ec2/test/cfn-init-element.test.ts
index 7ce066f2c1c69..2d3656e423322 100644
--- a/packages/aws-cdk-lib/aws-ec2/test/cfn-init-element.test.ts
+++ b/packages/aws-cdk-lib/aws-ec2/test/cfn-init-element.test.ts
@@ -352,7 +352,7 @@ describe('InitFile', () => {
           default: new ec2.InitConfig([
             ec2.InitFile.fromAsset(
               '/target/path/config.json',
-              path.join(__dirname, 'init-configs/configFileForFirstInstance.json'),
+              path.join(__dirname, 'init-configs', 'configFileForFirstInstance.json'),
             ),
           ]),
         },
@@ -377,7 +377,7 @@ describe('InitFile', () => {
             default: new ec2.InitConfig([
               ec2.InitFile.fromAsset(
                 '/target/path/config.json',
-                path.join(__dirname, 'init-configs/configFileForSecondInstance.json'),
+                path.join(__dirname, 'init-configs', 'configFileForSecondInstance.json'),
               ),
             ]),
           },
diff --git a/packages/aws-cdk-lib/aws-ecs/test/container-definition.test.ts b/packages/aws-cdk-lib/aws-ecs/test/container-definition.test.ts
index 76c1d5c254109..8a5c5ea165249 100644
--- a/packages/aws-cdk-lib/aws-ecs/test/container-definition.test.ts
+++ b/packages/aws-cdk-lib/aws-ecs/test/container-definition.test.ts
@@ -479,7 +479,7 @@ describe('container definition', () => {
           key: 'foo',
           value: 'bar',
         },
-        environmentFiles: [ecs.EnvironmentFile.fromAsset(path.join(__dirname, 'demo-envfiles/test-envfile.env'))],
+        environmentFiles: [ecs.EnvironmentFile.fromAsset(path.join(__dirname, 'demo-envfiles', 'test-envfile.env'))],
         essential: true,
         extraHosts: {
           name: 'dev-db.hostname.pvt',
@@ -1305,7 +1305,7 @@ describe('container definition', () => {
         taskDefinition.addContainer('cont', {
           image: ecs.ContainerImage.fromRegistry('test'),
           memoryLimitMiB: 1024,
-          environmentFiles: [ecs.EnvironmentFile.fromAsset(path.join(__dirname, 'demo-envfiles/test-envfile.env'))],
+          environmentFiles: [ecs.EnvironmentFile.fromAsset(path.join(__dirname, 'demo-envfiles', 'test-envfile.env'))],
         });
 
         // THEN
@@ -1417,7 +1417,7 @@ describe('container definition', () => {
         taskDefinition.addContainer('cont', {
           image: ecs.ContainerImage.fromRegistry('test'),
           memoryLimitMiB: 1024,
-          environmentFiles: [ecs.EnvironmentFile.fromAsset(path.join(__dirname, 'demo-envfiles/test-envfile.env'))],
+          environmentFiles: [ecs.EnvironmentFile.fromAsset(path.join(__dirname, 'demo-envfiles', 'test-envfile.env'))],
         });
 
         // THEN
diff --git a/packages/aws-cdk-lib/aws-ecs/test/ec2/ec2-task-definition.test.ts b/packages/aws-cdk-lib/aws-ecs/test/ec2/ec2-task-definition.test.ts
index a7109bfc5c7d8..a66bad6fe1eed 100644
--- a/packages/aws-cdk-lib/aws-ecs/test/ec2/ec2-task-definition.test.ts
+++ b/packages/aws-cdk-lib/aws-ecs/test/ec2/ec2-task-definition.test.ts
@@ -247,7 +247,7 @@ describe('ec2 task definition', () => {
         dockerSecurityOptions: ['ECS_SELINUX_CAPABLE=true'],
         entryPoint: ['/app/node_modules/.bin/cdk'],
         environment: { TEST_ENVIRONMENT_VARIABLE: 'test environment variable value' },
-        environmentFiles: [ecs.EnvironmentFile.fromAsset(path.join(__dirname, '../demo-envfiles/test-envfile.env'))],
+        environmentFiles: [ecs.EnvironmentFile.fromAsset(path.join(__dirname, '..', 'demo-envfiles', 'test-envfile.env'))],
         essential: true,
         extraHosts: { EXTRAHOST: 'extra host' },
         healthCheck: {
diff --git a/packages/aws-cdk-lib/aws-ecs/test/environment-file.test.ts b/packages/aws-cdk-lib/aws-ecs/test/environment-file.test.ts
index d0ad2f53b7b7c..736523a2dcd46 100644
--- a/packages/aws-cdk-lib/aws-ecs/test/environment-file.test.ts
+++ b/packages/aws-cdk-lib/aws-ecs/test/environment-file.test.ts
@@ -21,7 +21,7 @@ describe('environment file', () => {
       // GIVEN
       const app = new cdk.App({ context: { [cxapi.NEW_STYLE_STACK_SYNTHESIS_CONTEXT]: false } });
       const stack = new cdk.Stack(app);
-      const fileAsset = ecs.EnvironmentFile.fromAsset(path.join(__dirname, 'demo-envfiles/test-envfile.env'));
+      const fileAsset = ecs.EnvironmentFile.fromAsset(path.join(__dirname, 'demo-envfiles', 'test-envfile.env'));
 
       // WHEN
       const image = ecs.ContainerImage.fromRegistry('/aws/aws-example-app');
diff --git a/packages/aws-cdk-lib/aws-ecs/test/external/external-task-definition.test.ts b/packages/aws-cdk-lib/aws-ecs/test/external/external-task-definition.test.ts
index a78872cfbba2b..3ac58eaa8c680 100644
--- a/packages/aws-cdk-lib/aws-ecs/test/external/external-task-definition.test.ts
+++ b/packages/aws-cdk-lib/aws-ecs/test/external/external-task-definition.test.ts
@@ -162,7 +162,7 @@ describe('external task definition', () => {
         dockerSecurityOptions: ['ECS_SELINUX_CAPABLE=true'],
         entryPoint: ['/app/node_modules/.bin/cdk'],
         environment: { TEST_ENVIRONMENT_VARIABLE: 'test environment variable value' },
-        environmentFiles: [ecs.EnvironmentFile.fromAsset(path.join(__dirname, '../demo-envfiles/test-envfile.env'))],
+        environmentFiles: [ecs.EnvironmentFile.fromAsset(path.join(__dirname, '..', 'demo-envfiles', 'test-envfile.env'))],
         essential: true,
         extraHosts: { EXTRAHOST: 'extra host' },
         healthCheck: {
diff --git a/packages/aws-cdk-lib/aws-eks/lib/cluster.ts b/packages/aws-cdk-lib/aws-eks/lib/cluster.ts
index f24beeab72346..639344f9c25f0 100644
--- a/packages/aws-cdk-lib/aws-eks/lib/cluster.ts
+++ b/packages/aws-cdk-lib/aws-eks/lib/cluster.ts
@@ -1967,7 +1967,7 @@ export class Cluster extends ClusterBase {
    */
   private addNeuronDevicePlugin() {
     if (!this._neuronDevicePlugin) {
-      const fileContents = fs.readFileSync(path.join(__dirname, 'addons/neuron-device-plugin.yaml'), 'utf8');
+      const fileContents = fs.readFileSync(path.join(__dirname, 'addons', 'neuron-device-plugin.yaml'), 'utf8');
       const sanitized = YAML.parse(fileContents);
       this._neuronDevicePlugin = this.addManifest('NeuronDevicePlugin', sanitized);
     }
diff --git a/packages/aws-cdk-lib/aws-eks/test/cluster.test.ts b/packages/aws-cdk-lib/aws-eks/test/cluster.test.ts
index d46980277d152..fe48cc76355ae 100644
--- a/packages/aws-cdk-lib/aws-eks/test/cluster.test.ts
+++ b/packages/aws-cdk-lib/aws-eks/test/cluster.test.ts
@@ -2183,7 +2183,7 @@ describe('cluster', () => {
         instanceType: new ec2.InstanceType('inf1.2xlarge'),
         minCapacity: 1,
       });
-      const fileContents = fs.readFileSync(path.join(__dirname, '../lib', 'addons/neuron-device-plugin.yaml'), 'utf8');
+      const fileContents = fs.readFileSync(path.join(__dirname, '..', 'lib', 'addons', 'neuron-device-plugin.yaml'), 'utf8');
       const sanitized = YAML.parse(fileContents);
 
       // THEN
@@ -2201,7 +2201,7 @@ describe('cluster', () => {
         instanceType: new ec2.InstanceType('inf2.xlarge'),
         minCapacity: 1,
       });
-      const fileContents = fs.readFileSync(path.join(__dirname, '../lib', 'addons/neuron-device-plugin.yaml'), 'utf8');
+      const fileContents = fs.readFileSync(path.join(__dirname, '..', 'lib', 'addons', 'neuron-device-plugin.yaml'), 'utf8');
       const sanitized = YAML.parse(fileContents);
 
       // THEN
@@ -2219,7 +2219,7 @@ describe('cluster', () => {
       cluster.addNodegroupCapacity('InferenceInstances', {
         instanceTypes: [new ec2.InstanceType('inf1.2xlarge')],
       });
-      const fileContents = fs.readFileSync(path.join(__dirname, '../lib', 'addons/neuron-device-plugin.yaml'), 'utf8');
+      const fileContents = fs.readFileSync(path.join(__dirname, '..', 'lib', 'addons', 'neuron-device-plugin.yaml'), 'utf8');
       const sanitized = YAML.parse(fileContents);
 
       // THEN
@@ -2236,7 +2236,7 @@ describe('cluster', () => {
       cluster.addNodegroupCapacity('InferenceInstances', {
         instanceTypes: [new ec2.InstanceType('inf2.xlarge')],
       });
-      const fileContents = fs.readFileSync(path.join(__dirname, '../lib', 'addons/neuron-device-plugin.yaml'), 'utf8');
+      const fileContents = fs.readFileSync(path.join(__dirname, '..', 'lib', 'addons', 'neuron-device-plugin.yaml'), 'utf8');
       const sanitized = YAML.parse(fileContents);
 
       // THEN
diff --git a/packages/aws-cdk-lib/aws-lambda-nodejs/lib/bundling.ts b/packages/aws-cdk-lib/aws-lambda-nodejs/lib/bundling.ts
index c5bd7c4243e47..1f3fdd0cb3ed4 100644
--- a/packages/aws-cdk-lib/aws-lambda-nodejs/lib/bundling.ts
+++ b/packages/aws-cdk-lib/aws-lambda-nodejs/lib/bundling.ts
@@ -154,7 +154,7 @@ export class Bundling implements cdk.BundlingOptions {
 
     // Docker bundling
     const shouldBuildImage = props.forceDockerBundling || !Bundling.esbuildInstallation;
-    this.image = shouldBuildImage ? props.dockerImage ?? cdk.DockerImage.fromBuild(path.join(__dirname, '../lib'),
+    this.image = shouldBuildImage ? props.dockerImage ?? cdk.DockerImage.fromBuild(path.join(__dirname, '..', 'lib'),
       {
         buildArgs: {
           ...props.buildArgs ?? {},
diff --git a/packages/aws-cdk-lib/aws-lambda-nodejs/test/bundling.test.ts b/packages/aws-cdk-lib/aws-lambda-nodejs/test/bundling.test.ts
index 10cfe72adf154..c0010a3328fe6 100644
--- a/packages/aws-cdk-lib/aws-lambda-nodejs/test/bundling.test.ts
+++ b/packages/aws-cdk-lib/aws-lambda-nodejs/test/bundling.test.ts
@@ -626,7 +626,7 @@ test('esbuild bundling with projectRoot', () => {
 });
 
 test('esbuild bundling with projectRoot and externals and dependencies', () => {
-  const repoRoot = path.join(__dirname, '../../../..');
+  const repoRoot = path.join(__dirname, '..', '..', '..', '..');
   const packageLock = path.join(repoRoot, 'common', 'package-lock.json');
   Bundling.bundle(stack, {
     entry: __filename,
diff --git a/packages/aws-cdk-lib/aws-lambda-nodejs/test/docker.test.ts b/packages/aws-cdk-lib/aws-lambda-nodejs/test/docker.test.ts
index e25938452357a..a29c4cbfe7954 100644
--- a/packages/aws-cdk-lib/aws-lambda-nodejs/test/docker.test.ts
+++ b/packages/aws-cdk-lib/aws-lambda-nodejs/test/docker.test.ts
@@ -3,7 +3,7 @@ import * as path from 'path';
 
 const docker = process.env.CDK_DOCKER ?? 'docker';
 beforeAll(() => {
-  const process = spawnSync(docker, ['build', '-t', 'esbuild', path.join(__dirname, '../lib')], { stdio: 'inherit' });
+  const process = spawnSync(docker, ['build', '-t', 'esbuild', path.join(__dirname, '..', 'lib')], { stdio: 'inherit' });
   expect(process.error).toBeUndefined();
   expect(process.status).toBe(0);
 });
diff --git a/packages/aws-cdk-lib/aws-stepfunctions-tasks/test/batch/run-batch-job.test.ts b/packages/aws-cdk-lib/aws-stepfunctions-tasks/test/batch/run-batch-job.test.ts
index 15d9bb1617b5d..9870096ac6cbf 100644
--- a/packages/aws-cdk-lib/aws-stepfunctions-tasks/test/batch/run-batch-job.test.ts
+++ b/packages/aws-cdk-lib/aws-stepfunctions-tasks/test/batch/run-batch-job.test.ts
@@ -18,7 +18,7 @@ beforeEach(() => {
   batchJobDefinition = new batch.EcsJobDefinition(stack, 'JobDefinition', {
     container: new batch.EcsEc2ContainerDefinition(stack, 'Container', {
       image: ecs.ContainerImage.fromAsset(
-        path.join(__dirname, './batchjob-image'),
+        path.join(__dirname, 'batchjob-image'),
       ),
       cpu: 256,
       memory: cdk.Size.mebibytes(2048),
diff --git a/packages/aws-cdk-lib/aws-stepfunctions-tasks/test/batch/submit-job.test.ts b/packages/aws-cdk-lib/aws-stepfunctions-tasks/test/batch/submit-job.test.ts
index 500dea14c5128..46c996ecfba1f 100644
--- a/packages/aws-cdk-lib/aws-stepfunctions-tasks/test/batch/submit-job.test.ts
+++ b/packages/aws-cdk-lib/aws-stepfunctions-tasks/test/batch/submit-job.test.ts
@@ -17,7 +17,7 @@ beforeEach(() => {
   batchJobDefinition = new batch.EcsJobDefinition(stack, 'JobDefinition', {
     container: new batch.EcsEc2ContainerDefinition(stack, 'Container', {
       image: ecs.ContainerImage.fromAsset(
-        path.join(__dirname, './batchjob-image'),
+        path.join(__dirname, 'batchjob-image'),
       ),
       cpu: 256,
       memory: cdk.Size.mebibytes(2048),
diff --git a/packages/aws-cdk-lib/core/test/bundling.test.ts b/packages/aws-cdk-lib/core/test/bundling.test.ts
index 9e074c992efed..ea74e92998637 100644
--- a/packages/aws-cdk-lib/core/test/bundling.test.ts
+++ b/packages/aws-cdk-lib/core/test/bundling.test.ts
@@ -312,7 +312,7 @@ describe('bundling', () => {
       signal: null,
     });
 
-    const imagePath = path.join(__dirname, 'fs/fixtures/test1');
+    const imagePath = path.join(__dirname, 'fs', 'fixtures', 'test1');
     DockerImage.fromAsset(imagePath, {
       file: 'my-dockerfile',
     });
@@ -332,7 +332,7 @@ describe('bundling', () => {
       signal: null,
     });
 
-    const imagePath = path.join(__dirname, 'fs/fixtures/test1');
+    const imagePath = path.join(__dirname, 'fs', 'fixtures', 'test1');
     const image = DockerImage.fromAsset(imagePath, {
       file: 'my-dockerfile',
     });
diff --git a/packages/aws-cdk-lib/cx-api/build-tools/update-vnext.ts b/packages/aws-cdk-lib/cx-api/build-tools/update-vnext.ts
index 554eeb4b2e699..007beab6f5ee2 100644
--- a/packages/aws-cdk-lib/cx-api/build-tools/update-vnext.ts
+++ b/packages/aws-cdk-lib/cx-api/build-tools/update-vnext.ts
@@ -8,7 +8,8 @@ import { MAGIC_V2NEXT } from '../lib/private/flag-modeling';
 async function main() {
   const featuresSourceFile = path.join(__dirname, '..', 'lib', 'features.ts');
 
-  let currentv2: string | undefined = JSON.parse(await fs.readFile(path.join(__dirname, '../../../../version.v2.json'), { encoding: 'utf-8' })).version;
+  // eslint-disable-next-line @aws-cdk/no-invalid-path
+  let currentv2: string | undefined = JSON.parse(await fs.readFile(path.join(__dirname, '..', '..', '..', '..', 'version.v2.json'), { encoding: 'utf-8' })).version;
   currentv2 = currentv2?.match(/^[0-9\.]+/)?.[0]; // Make sure to only retain the actual version number, not any '-rc.X' suffix
 
   if (!currentv2) {
diff --git a/packages/aws-cdk-lib/cx-api/test/features.test.ts b/packages/aws-cdk-lib/cx-api/test/features.test.ts
index 1aa592b15114c..e9119613c33b6 100644
--- a/packages/aws-cdk-lib/cx-api/test/features.test.ts
+++ b/packages/aws-cdk-lib/cx-api/test/features.test.ts
@@ -70,7 +70,8 @@ test.each([
   expect(compareVersions(b, a)).toBeCloseTo(-expected, 10); // Gets around expect(-0).toEqual(0) failing... :x
 });
 
-const currentv2: string = JSON.parse(fs.readFileSync(path.join(__dirname, '../../../../version.v2.json'), { encoding: 'utf-8' })).version;
+// eslint-disable-next-line @aws-cdk/no-invalid-path
+const currentv2: string = JSON.parse(fs.readFileSync(path.join(__dirname, '..', '..', '..', '..', 'version.v2.json'), { encoding: 'utf-8' })).version;
 
 describe(`introducedIn.v2 is either <= ${currentv2} or magic value "${MAGIC_V2NEXT}"`, () => {
   test.each(Object.keys(feats.FLAGS))('for flag %p', flag => {
diff --git a/packages/aws-cdk/test/notices.test.ts b/packages/aws-cdk/test/notices.test.ts
index f95605a710cdb..db1023f842a9d 100644
--- a/packages/aws-cdk/test/notices.test.ts
+++ b/packages/aws-cdk/test/notices.test.ts
@@ -147,11 +147,11 @@ describe('cli notices', () => {
       const notices = [FRAMEWORK_2_1_0_AFFECTED_NOTICE];
 
       expect(filterNotices(notices, {
-        outdir: path.join(__dirname, 'cloud-assembly-trees/built-with-2_12_0'),
+        outdir: path.join(__dirname, 'cloud-assembly-trees', 'built-with-2_12_0'),
       })).toEqual([]);
 
       expect(filterNotices(notices, {
-        outdir: path.join(__dirname, 'cloud-assembly-trees/built-with-1_144_0'),
+        outdir: path.join(__dirname, 'cloud-assembly-trees', 'built-with-1_144_0'),
       })).toEqual([FRAMEWORK_2_1_0_AFFECTED_NOTICE]);
     });
 
@@ -160,22 +160,22 @@ describe('cli notices', () => {
 
       // module-level match
       expect(filterNotices(notices, {
-        outdir: path.join(__dirname, 'cloud-assembly-trees/experimental-module'),
+        outdir: path.join(__dirname, 'cloud-assembly-trees', 'experimental-module'),
       })).toEqual([NOTICE_FOR_APIGATEWAYV2]);
 
       // no apigatewayv2 in the tree
       expect(filterNotices(notices, {
-        outdir: path.join(__dirname, 'cloud-assembly-trees/built-with-2_12_0'),
+        outdir: path.join(__dirname, 'cloud-assembly-trees', 'built-with-2_12_0'),
       })).toEqual([]);
 
       // module name mismatch: apigateway != apigatewayv2
       expect(filterNotices([NOTICE_FOR_APIGATEWAY], {
-        outdir: path.join(__dirname, 'cloud-assembly-trees/experimental-module'),
+        outdir: path.join(__dirname, 'cloud-assembly-trees', 'experimental-module'),
       })).toEqual([]);
 
       // construct-level match
       expect(filterNotices([NOTICE_FOR_APIGATEWAYV2_CFN_STAGE], {
-        outdir: path.join(__dirname, 'cloud-assembly-trees/experimental-module'),
+        outdir: path.join(__dirname, 'cloud-assembly-trees', 'experimental-module'),
       })).toEqual([NOTICE_FOR_APIGATEWAYV2_CFN_STAGE]);
     });
 
diff --git a/packages/aws-cdk/test/tree.test.ts b/packages/aws-cdk/test/tree.test.ts
index e6e92579f2282..52966973820cd 100644
--- a/packages/aws-cdk/test/tree.test.ts
+++ b/packages/aws-cdk/test/tree.test.ts
@@ -104,12 +104,12 @@ describe('some', () => {
 
 describe('loadTreeFromDir', () => {
   test('can find tree', () => {
-    const tree = loadTreeFromDir(path.join(__dirname, 'cloud-assembly-trees/built-with-1_144_0'));
+    const tree = loadTreeFromDir(path.join(__dirname, 'cloud-assembly-trees', 'built-with-1_144_0'));
     expect(tree.id).toEqual('App');
   });
 
   test('cannot find tree', () => {
-    const tree = loadTreeFromDir(path.join(__dirname, 'cloud-assembly-trees/foo'));
+    const tree = loadTreeFromDir(path.join(__dirname, 'cloud-assembly-trees', 'foo'));
     expect(tree).toEqual({});
   });
 });
\ No newline at end of file
diff --git a/tools/@aws-cdk/cdk-build-tools/config/eslintrc.js b/tools/@aws-cdk/cdk-build-tools/config/eslintrc.js
index 3eb417a86a437..065265d141003 100644
--- a/tools/@aws-cdk/cdk-build-tools/config/eslintrc.js
+++ b/tools/@aws-cdk/cdk-build-tools/config/eslintrc.js
@@ -44,6 +44,7 @@ module.exports = {
     '@aws-cdk/no-core-construct': ['error'],
     '@aws-cdk/invalid-cfn-imports': ['error'],
     '@aws-cdk/no-literal-partition': ['error'],
+    '@aws-cdk/no-invalid-path': [ 'error' ],
     // Require use of the `import { foo } from 'bar';` form instead of `import foo = require('bar');`
     '@typescript-eslint/no-require-imports': ['error'],
     '@typescript-eslint/indent': ['error', 2],
diff --git a/tools/@aws-cdk/cdk-build-tools/lib/package-info.ts b/tools/@aws-cdk/cdk-build-tools/lib/package-info.ts
index 025c0101aa1f9..c8a4ac4d6b574 100644
--- a/tools/@aws-cdk/cdk-build-tools/lib/package-info.ts
+++ b/tools/@aws-cdk/cdk-build-tools/lib/package-info.ts
@@ -104,6 +104,8 @@ export function packageCompiler(compilers: CompilerOverrides, options?: CDKBuild
       args.push('--compress-assembly');
     }
     if (options?.stripDeprecated) {
+      // This package is not published to npm so the linter rule is invalid
+      // eslint-disable-next-line @aws-cdk/no-invalid-path
       args.push(`--strip-deprecated ${path.join(__dirname, '..', '..', '..', '..', 'deprecated_apis.txt')}`);
     }
     return [compilers.jsii || require.resolve('jsii/bin/jsii'), ...args];
diff --git a/tools/@aws-cdk/eslint-plugin/README.md b/tools/@aws-cdk/eslint-plugin/README.md
index 386c1c0f2040c..65c28cc8d0f1f 100644
--- a/tools/@aws-cdk/eslint-plugin/README.md
+++ b/tools/@aws-cdk/eslint-plugin/README.md
@@ -11,6 +11,9 @@ Eslint plugin for the CDK repository. Contains rules that need to be applied spe
   Instead use `Construct` and `IConstruct` from the "constructs" module.
   Rule only applies to typescript files under the `test/` folder.
 
+* `no-invalid-path`: Checks paths specified using `path.join()` for validity, including not going backwards (`'..'`)
+  multiple times in the path and not going backwards beyond a package's `package.json`.
+
 * `no-literal-partition`: Forbids the use of literal partitions (usually `aws`). Instead, use
   `Aws.PARTITION` to ensure that the code works for other partitions too.
 
@@ -26,4 +29,4 @@ Eslint plugin for the CDK repository. Contains rules that need to be applied spe
   as well!
 * You can now run the test in debugging mode (make sure to have `npx tsc -w` running, then from a debugging terminal, `npx jest --no-coverage -it 'your rule name'`), set a breakpoint, and inspect the typeless objects.
 
-To activate it for real on the repo, also add it to `cdk-build-tools/config/eslintrc.js`.
\ No newline at end of file
+To activate it for real on the repo, also add it to `cdk-build-tools/config/eslintrc.js`.
diff --git a/tools/@aws-cdk/eslint-plugin/lib/index.ts b/tools/@aws-cdk/eslint-plugin/lib/index.ts
index e25149d1b615a..834c6bf781d7d 100644
--- a/tools/@aws-cdk/eslint-plugin/lib/index.ts
+++ b/tools/@aws-cdk/eslint-plugin/lib/index.ts
@@ -2,4 +2,5 @@ export const rules = {
   'no-core-construct': require('./rules/no-core-construct'),
   'invalid-cfn-imports': require('./rules/invalid-cfn-imports'),
   'no-literal-partition': require('./rules/no-literal-partition'),
+  'no-invalid-path': require('./rules/no-invalid-path'),
 };
diff --git a/tools/@aws-cdk/eslint-plugin/lib/rules/no-invalid-path.ts b/tools/@aws-cdk/eslint-plugin/lib/rules/no-invalid-path.ts
new file mode 100644
index 0000000000000..f8dbd374a7e03
--- /dev/null
+++ b/tools/@aws-cdk/eslint-plugin/lib/rules/no-invalid-path.ts
@@ -0,0 +1,91 @@
+import { Rule } from 'eslint';
+import * as path from 'path';
+import * as fs from 'fs';
+
+function isPathJoinFuncCall(node: any): boolean {
+  return (
+    node.callee?.property?.name === 'join' &&
+    (node.parent?.expression?.callee?.object?.name === 'path' ||
+    node.parent?.arguments?.some((a: any) => a.callee?.object?.name === 'path'))
+  );
+}
+
+function noArgumentVariables(node: any): boolean {
+  // Outside of the first argument, all arguments should be strings
+  const components = node.arguments.slice(1);
+  return components.every((a: any) => a.value !== undefined);
+}
+
+function hasSlashes(args: string[]): boolean {
+  return args.some((a) => a.includes('/'));
+}
+
+function firstArgIsDirname(node: any): boolean {
+  return node.arguments[0].name && node.arguments[0].name === '__dirname';
+}
+
+function argumentList(node: any): string[] {
+  // Already confirmed that first argument is '__dirname', so can safely remove it
+  const args: string[] = node.arguments.slice(1).map((a: any) => { return a.value; });
+  return args;
+}
+
+function recreatePath(args: string[]): string {
+  return `path.join(__dirname, '${args.join('\', \'')}')`;
+}
+
+export function create(context: Rule.RuleContext): Rule.NodeListener {
+  return {
+    CallExpression(node: any) {
+      if (isPathJoinFuncCall(node)) {
+        if (node.arguments.length === 0) {
+          // ERROR: this is 'path.join()'
+          context.report({ node, message: '\'path.join()\' is not a valid path. You must specify arguments into the function.'})
+          return;
+        }
+
+        if (!noArgumentVariables(node)) {
+          // WARNING: unexpected non-string in the argument list. This happens if part of the argument list is a variable, i.e. `path.join(__dirname, myPath)`.
+          // We may be able to do something about this, but we currently are just going to let it pass.
+          return;
+        }
+
+        // We currently do not lint any path.join without '__dirname' as the first argument
+        if (!firstArgIsDirname(node)) {
+          return;
+        }
+
+        const args = argumentList(node);
+
+        if (hasSlashes(args)) {
+          // ERROR: This path looks like 'path.join(__dirname, 'a/b')' and should be changed to 'path.join(__dirname, 'a', 'b')'
+          context.report({ node, message: `${recreatePath(args)} is not a valid path. It has '/' in the arguments which is not allowed. Each directory should be its own separate argument.`});
+          return;
+        }
+
+        const firstDownDir = args.findIndex((p) => p !== '..');
+
+        // Confirm path does not have any unnecessary '..' paths
+        // This allows us to validate subsequent checks
+        if (firstDownDir > 0 && args.some((p, i) => p === '..' && i > firstDownDir)) {
+          // ERROR: This path oscillates between up and down commands
+          context.report({ node, message: `${recreatePath(args)} is not a valid path. It goes backwards and forwards and backwards again, and can be simplified.`});
+          return;
+        }
+
+        // Exclude the case where there are no '..' at all in the path -- those are never invalid
+        const currentFile = context.getFilename();
+        if (firstDownDir > 0) {
+          for (let i = 0; i < firstDownDir; i++) {
+            const pjFile = path.join(...[path.dirname(currentFile), ...args.slice(0, i), 'package.json']);
+            if (fs.existsSync(pjFile)) {
+              // ERROR: this path will end up going out of the package.json directory
+              context.report({ node, message: `${recreatePath(args)} is not a valid path. It goes beyond the parent library's package.json file so the file it points to will not be available after the library is packaged.`});
+              return;
+            }
+          }
+        }
+      }
+    }
+  }
+}
diff --git a/tools/@aws-cdk/eslint-plugin/test/rules/fixtures.test.ts b/tools/@aws-cdk/eslint-plugin/test/rules/fixtures.test.ts
index 714df1b9db6ae..7f382e0d92b97 100644
--- a/tools/@aws-cdk/eslint-plugin/test/rules/fixtures.test.ts
+++ b/tools/@aws-cdk/eslint-plugin/test/rules/fixtures.test.ts
@@ -20,7 +20,7 @@ fs.readdirSync(fixturesRoot).filter(f => fs.lstatSync(path.join(fixturesRoot, f)
         },
         overrideConfigFile: path.join(fixturesDir, 'eslintrc.js'),
         rulePaths: [
-          path.join(__dirname, '../../lib/rules'),
+          path.join(__dirname, '..', '..', 'lib', 'rules'),
         ],
         fix: true,
       });
diff --git a/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/eslintrc.js b/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/eslintrc.js
new file mode 100644
index 0000000000000..9ae156ccc1ced
--- /dev/null
+++ b/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/eslintrc.js
@@ -0,0 +1,6 @@
+module.exports = {
+  plugins: ['@aws-cdk'],
+  rules: {
+    '@aws-cdk/no-invalid-path': [ 'error' ],
+  }
+}
\ No newline at end of file
diff --git a/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/no-path.error.txt b/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/no-path.error.txt
new file mode 100644
index 0000000000000..671706f27a204
--- /dev/null
+++ b/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/no-path.error.txt
@@ -0,0 +1 @@
+'path.join()' is not a valid path. You must specify arguments into the function.
\ No newline at end of file
diff --git a/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/no-path.ts b/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/no-path.ts
new file mode 100644
index 0000000000000..4cc707705fde1
--- /dev/null
+++ b/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/no-path.ts
@@ -0,0 +1,3 @@
+import * as path from 'path';
+
+path.join();
\ No newline at end of file
diff --git a/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/path-beyond-packagejson.error.txt b/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/path-beyond-packagejson.error.txt
new file mode 100644
index 0000000000000..304d6e7fb16d2
--- /dev/null
+++ b/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/path-beyond-packagejson.error.txt
@@ -0,0 +1 @@
+path.join(__dirname, '..', '..', '..', '..', '..', 'cfn2ts', 'README.md') is not a valid path. It goes beyond the parent library's package.json file so the file it points to will not be available after the library is packaged.
\ No newline at end of file
diff --git a/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/path-beyond-packagejson.ts b/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/path-beyond-packagejson.ts
new file mode 100644
index 0000000000000..32592280df2c0
--- /dev/null
+++ b/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/path-beyond-packagejson.ts
@@ -0,0 +1,4 @@
+import path from 'path';
+
+// depends on eslint-plugin to have a package.json
+path.join(__dirname, '..', '..', '..', '..', '..', 'cfn2ts', 'README.md');
\ No newline at end of file
diff --git a/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/path-oscillates.error.txt b/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/path-oscillates.error.txt
new file mode 100644
index 0000000000000..fffe5d427cdf1
--- /dev/null
+++ b/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/path-oscillates.error.txt
@@ -0,0 +1 @@
+path.join(__dirname, '..', '..', 'no-path-outside-module', '..', '..', 'fixtures.test.ts') is not a valid path. It goes backwards and forwards and backwards again, and can be simplified.
\ No newline at end of file
diff --git a/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/path-oscillates.ts b/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/path-oscillates.ts
new file mode 100644
index 0000000000000..bce94ee028c4e
--- /dev/null
+++ b/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/path-oscillates.ts
@@ -0,0 +1,3 @@
+import path from 'path';
+
+path.join(__dirname, '..', '..', 'no-path-outside-module', '..', '..', 'fixtures.test.ts');
diff --git a/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/path-with-slashes.error.txt b/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/path-with-slashes.error.txt
new file mode 100644
index 0000000000000..4c9e26a535c1e
--- /dev/null
+++ b/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/path-with-slashes.error.txt
@@ -0,0 +1 @@
+ath.join(__dirname, '../..', 'fixtures.test.ts') is not a valid path. It has '/' in the arguments which is not allowed. Each directory should be its own separate argument.
\ No newline at end of file
diff --git a/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/path-with-slashes.ts b/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/path-with-slashes.ts
new file mode 100644
index 0000000000000..1750443533fc9
--- /dev/null
+++ b/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/path-with-slashes.ts
@@ -0,0 +1,3 @@
+import * as path from 'path';
+
+path.join(__dirname, '../..', 'fixtures.test.ts');
\ No newline at end of file
diff --git a/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/within-function.error.txt b/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/within-function.error.txt
new file mode 100644
index 0000000000000..64e8b877be8a0
--- /dev/null
+++ b/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/within-function.error.txt
@@ -0,0 +1 @@
+path.join(__dirname, './asdf') is not a valid path. It has '/' in the arguments which is not allowed. Each directory should be its own separate argument.
\ No newline at end of file
diff --git a/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/within-function.ts b/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/within-function.ts
new file mode 100644
index 0000000000000..72f86b4bc2d36
--- /dev/null
+++ b/tools/@aws-cdk/eslint-plugin/test/rules/fixtures/no-invalid-path/within-function.ts
@@ -0,0 +1,5 @@
+import * as path from 'path';
+
+function Myfunction(_a: string, _p: string) {}
+
+Myfunction('arg1', path.join(__dirname, './asdf'));
\ No newline at end of file