diff --git a/packages/@aws-cdk/aws-lambda-python/lib/bundling.ts b/packages/@aws-cdk/aws-lambda-python/lib/bundling.ts
index d5747e169abb2..a4446611d9a9d 100644
--- a/packages/@aws-cdk/aws-lambda-python/lib/bundling.ts
+++ b/packages/@aws-cdk/aws-lambda-python/lib/bundling.ts
@@ -31,15 +31,56 @@ export interface BundlingOptions {
    * Output path suffix ('python' for a layer, '.' otherwise)
    */
   readonly outputPathSuffix: string;
+
+  /**
+   * Determines how asset hash is calculated. Assets will get rebuild and
+   * uploaded only if their hash has changed.
+   *
+   * If asset hash is set to `SOURCE` (default), then only changes to the source
+   * directory will cause the asset to rebuild. This means, for example, that in
+   * order to pick up a new dependency version, a change must be made to the
+   * source tree. Ideally, this can be implemented by including a dependency
+   * lockfile in your source tree or using fixed dependencies.
+   *
+   * If the asset hash is set to `OUTPUT`, the hash is calculated after
+   * bundling. This means that any change in the output will cause the asset to
+   * be invalidated and uploaded. Bear in mind that `pip` adds timestamps to
+   * dependencies it installs, which implies that in this mode Python bundles
+   * will _always_ get rebuild and uploaded. Normally this is an anti-pattern
+   * since build
+   *
+   * @default AssetHashType.SOURCE By default, hash is calculated based on the
+   * contents of the source directory. If `assetHash` is also specified, the
+   * default is `CUSTOM`. This means that only updates to the source will cause
+   * the asset to rebuild.
+   */
+  readonly assetHashType?: cdk.AssetHashType;
+
+  /**
+   * Specify a custom hash for this asset. If `assetHashType` is set it must
+   * be set to `AssetHashType.CUSTOM`. For consistency, this custom hash will
+   * be SHA256 hashed and encoded as hex. The resulting hash will be the asset
+   * hash.
+   *
+   * NOTE: the hash is used in order to identify a specific revision of the asset, and
+   * used for optimizing and caching deployment activities related to this asset such as
+   * packaging, uploading to Amazon S3, etc. If you chose to customize the hash, you will
+   * need to make sure it is updated every time the asset changes, or otherwise it is
+   * possible that some deployments will not be invalidated.
+   *
+   * @default - based on `assetHashType`
+   */
+  readonly assetHash?: string;
 }
 
 /**
  * Produce bundled Lambda asset code
  */
-export function bundle(options: BundlingOptions): lambda.AssetCode {
+export function bundle(options: BundlingOptions): lambda.Code {
   const { entry, runtime, outputPathSuffix } = options;
 
-  const hasDeps = hasDependencies(entry);
+  const stagedir = cdk.FileSystem.mkdtemp('python-bundling-');
+  const hasDeps = stageDependencies(entry, stagedir);
 
   const depsCommand = chain([
     hasDeps ? `rsync -r ${BUNDLER_DEPENDENCIES_CACHE}/. ${cdk.AssetStaging.BUNDLING_OUTPUT_DIR}/${outputPathSuffix}` : '',
@@ -54,15 +95,19 @@ export function bundle(options: BundlingOptions): lambda.AssetCode {
     ? 'Dockerfile.dependencies'
     : 'Dockerfile';
 
-  const image = cdk.BundlingDockerImage.fromAsset(entry, {
+  // copy Dockerfile to workdir
+  fs.copyFileSync(path.join(__dirname, dockerfile), path.join(stagedir, dockerfile));
+
+  const image = cdk.BundlingDockerImage.fromAsset(stagedir, {
     buildArgs: {
       IMAGE: runtime.bundlingDockerImage.image,
     },
-    file: path.join(__dirname, dockerfile),
+    file: dockerfile,
   });
 
   return lambda.Code.fromAsset(entry, {
-    assetHashType: cdk.AssetHashType.BUNDLE,
+    assetHashType: options.assetHashType,
+    assetHash: options.assetHash,
     exclude: DEPENDENCY_EXCLUDES,
     bundling: {
       image,
@@ -75,20 +120,25 @@ export function bundle(options: BundlingOptions): lambda.AssetCode {
  * Checks to see if the `entry` directory contains a type of dependency that
  * we know how to install.
  */
-export function hasDependencies(entry: string): boolean {
-  if (fs.existsSync(path.join(entry, 'Pipfile'))) {
-    return true;
-  }
-
-  if (fs.existsSync(path.join(entry, 'poetry.lock'))) {
-    return true;
-  }
-
-  if (fs.existsSync(path.join(entry, 'requirements.txt'))) {
-    return true;
+export function stageDependencies(entry: string, stagedir: string): boolean {
+  const prefixes = [
+    'Pipfile',
+    'pyproject',
+    'poetry',
+    'requirements.txt',
+  ];
+
+  let found = false;
+  for (const file of fs.readdirSync(entry)) {
+    for (const prefix of prefixes) {
+      if (file.startsWith(prefix)) {
+        fs.copyFileSync(path.join(entry, file), path.join(stagedir, file));
+        found = true;
+      }
+    }
   }
 
-  return false;
+  return found;
 }
 
 function chain(commands: string[]): string {
diff --git a/packages/@aws-cdk/aws-lambda-python/lib/function.ts b/packages/@aws-cdk/aws-lambda-python/lib/function.ts
index 267245738cbe6..733c115c0383d 100644
--- a/packages/@aws-cdk/aws-lambda-python/lib/function.ts
+++ b/packages/@aws-cdk/aws-lambda-python/lib/function.ts
@@ -1,6 +1,7 @@
 import * as fs from 'fs';
 import * as path from 'path';
 import * as lambda from '@aws-cdk/aws-lambda';
+import { AssetHashType } from '@aws-cdk/core';
 import { bundle } from './bundling';
 
 // keep this import separate from other imports to reduce chance for merge conflicts with v2-main
@@ -37,6 +38,45 @@ export interface PythonFunctionProps extends lambda.FunctionOptions {
    * @default lambda.Runtime.PYTHON_3_7
    */
   readonly runtime?: lambda.Runtime;
+
+  /**
+   * Determines how asset hash is calculated. Assets will get rebuild and
+   * uploaded only if their hash has changed.
+   *
+   * If asset hash is set to `SOURCE` (default), then only changes to the source
+   * directory will cause the asset to rebuild. This means, for example, that in
+   * order to pick up a new dependency version, a change must be made to the
+   * source tree. Ideally, this can be implemented by including a dependency
+   * lockfile in your source tree or using fixed dependencies.
+   *
+   * If the asset hash is set to `OUTPUT`, the hash is calculated after
+   * bundling. This means that any change in the output will cause the asset to
+   * be invalidated and uploaded. Bear in mind that `pip` adds timestamps to
+   * dependencies it installs, which implies that in this mode Python bundles
+   * will _always_ get rebuild and uploaded. Normally this is an anti-pattern
+   * since build
+   *
+   * @default AssetHashType.SOURCE By default, hash is calculated based on the
+   * contents of the source directory. This means that only updates to the
+   * source will cause the asset to rebuild.
+   */
+  readonly assetHashType?: AssetHashType;
+
+  /**
+   * Specify a custom hash for this asset. If `assetHashType` is set it must
+   * be set to `AssetHashType.CUSTOM`. For consistency, this custom hash will
+   * be SHA256 hashed and encoded as hex. The resulting hash will be the asset
+   * hash.
+   *
+   * NOTE: the hash is used in order to identify a specific revision of the asset, and
+   * used for optimizing and caching deployment activities related to this asset such as
+   * packaging, uploading to Amazon S3, etc. If you chose to customize the hash, you will
+   * need to make sure it is updated every time the asset changes, or otherwise it is
+   * possible that some deployments will not be invalidated.
+   *
+   * @default - based on `assetHashType`
+   */
+  readonly assetHash?: string;
 }
 
 /**
@@ -70,6 +110,8 @@ export class PythonFunction extends lambda.Function {
         runtime,
         entry,
         outputPathSuffix: '.',
+        assetHashType: props.assetHashType,
+        assetHash: props.assetHash,
       }),
       handler: `${index.slice(0, -3)}.${handler}`,
     });
diff --git a/packages/@aws-cdk/aws-lambda-python/test/bundling.test.ts b/packages/@aws-cdk/aws-lambda-python/test/bundling.test.ts
index 4286d092adf8f..d6de4ee23aedd 100644
--- a/packages/@aws-cdk/aws-lambda-python/test/bundling.test.ts
+++ b/packages/@aws-cdk/aws-lambda-python/test/bundling.test.ts
@@ -1,11 +1,10 @@
 import * as fs from 'fs';
 import * as path from 'path';
 import { Code, Runtime } from '@aws-cdk/aws-lambda';
-import { hasDependencies, bundle } from '../lib/bundling';
+import { FileSystem } from '@aws-cdk/core';
+import { stageDependencies, bundle } from '../lib/bundling';
 
 jest.mock('@aws-cdk/aws-lambda');
-const existsSyncOriginal = fs.existsSync;
-const existsSyncMock = jest.spyOn(fs, 'existsSync');
 
 jest.mock('child_process', () => ({
   spawnSync: jest.fn(() => {
@@ -41,9 +40,6 @@ test('Bundling a function without dependencies', () => {
       ],
     }),
   }));
-
-  // Searches for requirements.txt in entry
-  expect(existsSyncMock).toHaveBeenCalledWith(path.join(entry, 'requirements.txt'));
 });
 
 test('Bundling a function with requirements.txt installed', () => {
@@ -63,9 +59,6 @@ test('Bundling a function with requirements.txt installed', () => {
       ],
     }),
   }));
-
-  // Searches for requirements.txt in entry
-  expect(existsSyncMock).toHaveBeenCalledWith(path.join(entry, 'requirements.txt'));
 });
 
 test('Bundling Python 2.7 with requirements.txt installed', () => {
@@ -85,9 +78,6 @@ test('Bundling Python 2.7 with requirements.txt installed', () => {
       ],
     }),
   }));
-
-  // Searches for requirements.txt in entry
-  expect(existsSyncMock).toHaveBeenCalledWith(path.join(entry, 'requirements.txt'));
 });
 
 test('Bundling a layer with dependencies', () => {
@@ -128,42 +118,24 @@ test('Bundling a python code layer', () => {
   }));
 });
 
-describe('Dependency detection', () => {
-  test('Detects pipenv', () => {
-    existsSyncMock.mockImplementation((p: fs.PathLike) => {
-      if (/Pipfile/.test(p.toString())) {
-        return true;
-      }
-      return existsSyncOriginal(p);
-    });
-
-    expect(hasDependencies('/asset-input')).toEqual(true);
-  });
-
-  test('Detects poetry', () => {
-    existsSyncMock.mockImplementation((p: fs.PathLike) => {
-      if (/poetry.lock/.test(p.toString())) {
-        return true;
-      }
-      return existsSyncOriginal(p);
-    });
-
-    expect(hasDependencies('/asset-input')).toEqual(true);
-  });
 
-  test('Detects requirements.txt', () => {
-    existsSyncMock.mockImplementation((p: fs.PathLike) => {
-      if (/requirements.txt/.test(p.toString())) {
-        return true;
-      }
-      return existsSyncOriginal(p);
-    });
-
-    expect(hasDependencies('/asset-input')).toEqual(true);
+describe('Dependency detection', () => {
+  test.each(['Pipfile', 'poetry.lock', 'requirements.txt'])('detect dependency %p', filename => {
+    // GIVEN
+    const sourcedir = FileSystem.mkdtemp('source-');
+    const stagedir = FileSystem.mkdtemp('stage-');
+    fs.writeFileSync(path.join(sourcedir, filename), 'dummy!');
+
+    // WHEN
+    const found = stageDependencies(sourcedir, stagedir);
+
+    // THEN
+    expect(found).toBeTruthy();
+    expect(fs.existsSync(path.join(stagedir, filename))).toBeTruthy();
   });
 
   test('No known dependencies', () => {
-    existsSyncMock.mockImplementation(() => false);
-    expect(hasDependencies('/asset-input')).toEqual(false);
+    const sourcedir = FileSystem.mkdtemp('source-');
+    expect(stageDependencies(sourcedir, '/dummy')).toEqual(false);
   });
 });
diff --git a/packages/@aws-cdk/aws-lambda-python/test/function.test.ts b/packages/@aws-cdk/aws-lambda-python/test/function.test.ts
index 98bab1cf35be4..d1f9d64241b61 100644
--- a/packages/@aws-cdk/aws-lambda-python/test/function.test.ts
+++ b/packages/@aws-cdk/aws-lambda-python/test/function.test.ts
@@ -1,16 +1,36 @@
 import '@aws-cdk/assert/jest';
-import { Runtime } from '@aws-cdk/aws-lambda';
-import { Stack } from '@aws-cdk/core';
+import { Code, Runtime } from '@aws-cdk/aws-lambda';
+import { AssetHashType, AssetOptions, Stack } from '@aws-cdk/core';
 import { PythonFunction } from '../lib';
 import { bundle } from '../lib/bundling';
 
 jest.mock('../lib/bundling', () => {
   return {
-    bundle: jest.fn().mockReturnValue({
-      bind: () => {
-        return { inlineCode: 'code' };
-      },
-      bindToResource: () => { return; },
+    bundle: jest.fn().mockImplementation((options: AssetOptions): Code => {
+      const mockObjectKey = (() => {
+        const hashType = options.assetHashType ?? (options.assetHash ? 'custom' : 'source');
+        switch (hashType) {
+          case 'source': return 'SOURCE_MOCK';
+          case 'output': return 'OUTPUT_MOCK';
+          case 'custom': {
+            if (!options.assetHash) { throw new Error('no custom hash'); }
+            return options.assetHash;
+          }
+        }
+
+        throw new Error('unexpected asset hash type');
+      })();
+
+      return {
+        isInline: false,
+        bind: () => ({
+          s3Location: {
+            bucketName: 'mock-bucket-name',
+            objectKey: mockObjectKey,
+          },
+        }),
+        bindToResource: () => { return; },
+      };
     }),
     hasDependencies: jest.fn().mockReturnValue(false),
   };
@@ -73,3 +93,53 @@ test('throws with the wrong runtime family', () => {
     runtime: Runtime.NODEJS_12_X,
   })).toThrow(/Only `PYTHON` runtimes are supported/);
 });
+
+test('allows specifying hash type', () => {
+  new PythonFunction(stack, 'source1', {
+    entry: 'test/lambda-handler-nodeps',
+    index: 'index.py',
+    handler: 'handler',
+  });
+
+  new PythonFunction(stack, 'source2', {
+    entry: 'test/lambda-handler-nodeps',
+    index: 'index.py',
+    handler: 'handler',
+    assetHashType: AssetHashType.SOURCE,
+  });
+
+  new PythonFunction(stack, 'output', {
+    entry: 'test/lambda-handler-nodeps',
+    index: 'index.py',
+    handler: 'handler',
+    assetHashType: AssetHashType.OUTPUT,
+  });
+
+  new PythonFunction(stack, 'custom', {
+    entry: 'test/lambda-handler-nodeps',
+    index: 'index.py',
+    handler: 'handler',
+    assetHash: 'MY_CUSTOM_HASH',
+  });
+
+  expect(stack).toHaveResource('AWS::Lambda::Function', {
+    Code: {
+      S3Bucket: 'mock-bucket-name',
+      S3Key: 'SOURCE_MOCK',
+    },
+  });
+
+  expect(stack).toHaveResource('AWS::Lambda::Function', {
+    Code: {
+      S3Bucket: 'mock-bucket-name',
+      S3Key: 'OUTPUT_MOCK',
+    },
+  });
+
+  expect(stack).toHaveResource('AWS::Lambda::Function', {
+    Code: {
+      S3Bucket: 'mock-bucket-name',
+      S3Key: 'MY_CUSTOM_HASH',
+    },
+  });
+});
\ No newline at end of file
diff --git a/packages/@aws-cdk/aws-lambda-python/test/integ.function.expected.json b/packages/@aws-cdk/aws-lambda-python/test/integ.function.expected.json
index 3690005685439..45fb46b70aeb9 100644
--- a/packages/@aws-cdk/aws-lambda-python/test/integ.function.expected.json
+++ b/packages/@aws-cdk/aws-lambda-python/test/integ.function.expected.json
@@ -36,7 +36,7 @@
       "Properties": {
         "Code": {
           "S3Bucket": {
-            "Ref": "AssetParameters4ee6ce8b6ee4bd51743dc0c39d6e52baebaeafff9c9dfea0ff84de98d1dbf353S3Bucket414E0E30"
+            "Ref": "AssetParameters79d8f328899b90e2c16929e9393ebf344f098abde8981abdff0168fc9b0589acS3Bucket424FEB44"
           },
           "S3Key": {
             "Fn::Join": [
@@ -49,7 +49,7 @@
                       "Fn::Split": [
                         "||",
                         {
-                          "Ref": "AssetParameters4ee6ce8b6ee4bd51743dc0c39d6e52baebaeafff9c9dfea0ff84de98d1dbf353S3VersionKey5ABC9098"
+                          "Ref": "AssetParameters79d8f328899b90e2c16929e9393ebf344f098abde8981abdff0168fc9b0589acS3VersionKeyCEB2635C"
                         }
                       ]
                     }
@@ -62,7 +62,7 @@
                       "Fn::Split": [
                         "||",
                         {
-                          "Ref": "AssetParameters4ee6ce8b6ee4bd51743dc0c39d6e52baebaeafff9c9dfea0ff84de98d1dbf353S3VersionKey5ABC9098"
+                          "Ref": "AssetParameters79d8f328899b90e2c16929e9393ebf344f098abde8981abdff0168fc9b0589acS3VersionKeyCEB2635C"
                         }
                       ]
                     }
@@ -87,17 +87,17 @@
     }
   },
   "Parameters": {
-    "AssetParameters4ee6ce8b6ee4bd51743dc0c39d6e52baebaeafff9c9dfea0ff84de98d1dbf353S3Bucket414E0E30": {
+    "AssetParameters79d8f328899b90e2c16929e9393ebf344f098abde8981abdff0168fc9b0589acS3Bucket424FEB44": {
       "Type": "String",
-      "Description": "S3 bucket for asset \"4ee6ce8b6ee4bd51743dc0c39d6e52baebaeafff9c9dfea0ff84de98d1dbf353\""
+      "Description": "S3 bucket for asset \"79d8f328899b90e2c16929e9393ebf344f098abde8981abdff0168fc9b0589ac\""
     },
-    "AssetParameters4ee6ce8b6ee4bd51743dc0c39d6e52baebaeafff9c9dfea0ff84de98d1dbf353S3VersionKey5ABC9098": {
+    "AssetParameters79d8f328899b90e2c16929e9393ebf344f098abde8981abdff0168fc9b0589acS3VersionKeyCEB2635C": {
       "Type": "String",
-      "Description": "S3 key for asset version \"4ee6ce8b6ee4bd51743dc0c39d6e52baebaeafff9c9dfea0ff84de98d1dbf353\""
+      "Description": "S3 key for asset version \"79d8f328899b90e2c16929e9393ebf344f098abde8981abdff0168fc9b0589ac\""
     },
-    "AssetParameters4ee6ce8b6ee4bd51743dc0c39d6e52baebaeafff9c9dfea0ff84de98d1dbf353ArtifactHashECA6C88C": {
+    "AssetParameters79d8f328899b90e2c16929e9393ebf344f098abde8981abdff0168fc9b0589acArtifactHashE38133D4": {
       "Type": "String",
-      "Description": "Artifact hash for asset \"4ee6ce8b6ee4bd51743dc0c39d6e52baebaeafff9c9dfea0ff84de98d1dbf353\""
+      "Description": "Artifact hash for asset \"79d8f328899b90e2c16929e9393ebf344f098abde8981abdff0168fc9b0589ac\""
     }
   },
   "Outputs": {
diff --git a/packages/@aws-cdk/aws-lambda-python/test/integ.function.pipenv.expected.json b/packages/@aws-cdk/aws-lambda-python/test/integ.function.pipenv.expected.json
index ef1f355e528c3..aa7bc5fbbcd68 100644
--- a/packages/@aws-cdk/aws-lambda-python/test/integ.function.pipenv.expected.json
+++ b/packages/@aws-cdk/aws-lambda-python/test/integ.function.pipenv.expected.json
@@ -36,7 +36,7 @@
       "Properties": {
         "Code": {
           "S3Bucket": {
-            "Ref": "AssetParameters94972df8a01484c56b50bec3793ac6c4302bc044db29d3502007bdc0f83db45cS3BucketA501FC08"
+            "Ref": "AssetParameters50fe6f46cf18fb257f00fed007da5c80fbf5dee08bec37fe765c50188eecae0bS3Bucket4125B4E4"
           },
           "S3Key": {
             "Fn::Join": [
@@ -49,7 +49,7 @@
                       "Fn::Split": [
                         "||",
                         {
-                          "Ref": "AssetParameters94972df8a01484c56b50bec3793ac6c4302bc044db29d3502007bdc0f83db45cS3VersionKey1C3AFB39"
+                          "Ref": "AssetParameters50fe6f46cf18fb257f00fed007da5c80fbf5dee08bec37fe765c50188eecae0bS3VersionKey1CF28CF5"
                         }
                       ]
                     }
@@ -62,7 +62,7 @@
                       "Fn::Split": [
                         "||",
                         {
-                          "Ref": "AssetParameters94972df8a01484c56b50bec3793ac6c4302bc044db29d3502007bdc0f83db45cS3VersionKey1C3AFB39"
+                          "Ref": "AssetParameters50fe6f46cf18fb257f00fed007da5c80fbf5dee08bec37fe765c50188eecae0bS3VersionKey1CF28CF5"
                         }
                       ]
                     }
@@ -121,7 +121,7 @@
       "Properties": {
         "Code": {
           "S3Bucket": {
-            "Ref": "AssetParameters3b0b0f3cd46ea1490006d6cefca359385ec059bb00a0fbee4de2eecf48038e28S3Bucket7DE4D4D5"
+            "Ref": "AssetParameters314bcf2cee9a5b01d3be2c2815602d1d784611fac220dde672aca6cb54299076S3BucketD6F6E4F2"
           },
           "S3Key": {
             "Fn::Join": [
@@ -134,7 +134,7 @@
                       "Fn::Split": [
                         "||",
                         {
-                          "Ref": "AssetParameters3b0b0f3cd46ea1490006d6cefca359385ec059bb00a0fbee4de2eecf48038e28S3VersionKeyAEB67E87"
+                          "Ref": "AssetParameters314bcf2cee9a5b01d3be2c2815602d1d784611fac220dde672aca6cb54299076S3VersionKeyE0B47D8E"
                         }
                       ]
                     }
@@ -147,7 +147,7 @@
                       "Fn::Split": [
                         "||",
                         {
-                          "Ref": "AssetParameters3b0b0f3cd46ea1490006d6cefca359385ec059bb00a0fbee4de2eecf48038e28S3VersionKeyAEB67E87"
+                          "Ref": "AssetParameters314bcf2cee9a5b01d3be2c2815602d1d784611fac220dde672aca6cb54299076S3VersionKeyE0B47D8E"
                         }
                       ]
                     }
@@ -206,7 +206,7 @@
       "Properties": {
         "Code": {
           "S3Bucket": {
-            "Ref": "AssetParameters876959f777c5a23bf4408991959c55c91810329d159608feb7ede69418b35009S3BucketA66E9035"
+            "Ref": "AssetParameters11846740cde0308720709e44dce627bf1ceb557ee9d0dbb556a05632da565ef2S3BucketE17A9F3E"
           },
           "S3Key": {
             "Fn::Join": [
@@ -219,7 +219,7 @@
                       "Fn::Split": [
                         "||",
                         {
-                          "Ref": "AssetParameters876959f777c5a23bf4408991959c55c91810329d159608feb7ede69418b35009S3VersionKeyAFEB5FDA"
+                          "Ref": "AssetParameters11846740cde0308720709e44dce627bf1ceb557ee9d0dbb556a05632da565ef2S3VersionKey0A0F7F93"
                         }
                       ]
                     }
@@ -232,7 +232,7 @@
                       "Fn::Split": [
                         "||",
                         {
-                          "Ref": "AssetParameters876959f777c5a23bf4408991959c55c91810329d159608feb7ede69418b35009S3VersionKeyAFEB5FDA"
+                          "Ref": "AssetParameters11846740cde0308720709e44dce627bf1ceb557ee9d0dbb556a05632da565ef2S3VersionKey0A0F7F93"
                         }
                       ]
                     }
@@ -257,41 +257,41 @@
     }
   },
   "Parameters": {
-    "AssetParameters94972df8a01484c56b50bec3793ac6c4302bc044db29d3502007bdc0f83db45cS3BucketA501FC08": {
+    "AssetParameters50fe6f46cf18fb257f00fed007da5c80fbf5dee08bec37fe765c50188eecae0bS3Bucket4125B4E4": {
       "Type": "String",
-      "Description": "S3 bucket for asset \"94972df8a01484c56b50bec3793ac6c4302bc044db29d3502007bdc0f83db45c\""
+      "Description": "S3 bucket for asset \"50fe6f46cf18fb257f00fed007da5c80fbf5dee08bec37fe765c50188eecae0b\""
     },
-    "AssetParameters94972df8a01484c56b50bec3793ac6c4302bc044db29d3502007bdc0f83db45cS3VersionKey1C3AFB39": {
+    "AssetParameters50fe6f46cf18fb257f00fed007da5c80fbf5dee08bec37fe765c50188eecae0bS3VersionKey1CF28CF5": {
       "Type": "String",
-      "Description": "S3 key for asset version \"94972df8a01484c56b50bec3793ac6c4302bc044db29d3502007bdc0f83db45c\""
+      "Description": "S3 key for asset version \"50fe6f46cf18fb257f00fed007da5c80fbf5dee08bec37fe765c50188eecae0b\""
     },
-    "AssetParameters94972df8a01484c56b50bec3793ac6c4302bc044db29d3502007bdc0f83db45cArtifactHash99DC751A": {
+    "AssetParameters50fe6f46cf18fb257f00fed007da5c80fbf5dee08bec37fe765c50188eecae0bArtifactHashC28E4EDF": {
       "Type": "String",
-      "Description": "Artifact hash for asset \"94972df8a01484c56b50bec3793ac6c4302bc044db29d3502007bdc0f83db45c\""
+      "Description": "Artifact hash for asset \"50fe6f46cf18fb257f00fed007da5c80fbf5dee08bec37fe765c50188eecae0b\""
     },
-    "AssetParameters3b0b0f3cd46ea1490006d6cefca359385ec059bb00a0fbee4de2eecf48038e28S3Bucket7DE4D4D5": {
+    "AssetParameters314bcf2cee9a5b01d3be2c2815602d1d784611fac220dde672aca6cb54299076S3BucketD6F6E4F2": {
       "Type": "String",
-      "Description": "S3 bucket for asset \"3b0b0f3cd46ea1490006d6cefca359385ec059bb00a0fbee4de2eecf48038e28\""
+      "Description": "S3 bucket for asset \"314bcf2cee9a5b01d3be2c2815602d1d784611fac220dde672aca6cb54299076\""
     },
-    "AssetParameters3b0b0f3cd46ea1490006d6cefca359385ec059bb00a0fbee4de2eecf48038e28S3VersionKeyAEB67E87": {
+    "AssetParameters314bcf2cee9a5b01d3be2c2815602d1d784611fac220dde672aca6cb54299076S3VersionKeyE0B47D8E": {
       "Type": "String",
-      "Description": "S3 key for asset version \"3b0b0f3cd46ea1490006d6cefca359385ec059bb00a0fbee4de2eecf48038e28\""
+      "Description": "S3 key for asset version \"314bcf2cee9a5b01d3be2c2815602d1d784611fac220dde672aca6cb54299076\""
     },
-    "AssetParameters3b0b0f3cd46ea1490006d6cefca359385ec059bb00a0fbee4de2eecf48038e28ArtifactHashE51CE860": {
+    "AssetParameters314bcf2cee9a5b01d3be2c2815602d1d784611fac220dde672aca6cb54299076ArtifactHash45C2DF56": {
       "Type": "String",
-      "Description": "Artifact hash for asset \"3b0b0f3cd46ea1490006d6cefca359385ec059bb00a0fbee4de2eecf48038e28\""
+      "Description": "Artifact hash for asset \"314bcf2cee9a5b01d3be2c2815602d1d784611fac220dde672aca6cb54299076\""
     },
-    "AssetParameters876959f777c5a23bf4408991959c55c91810329d159608feb7ede69418b35009S3BucketA66E9035": {
+    "AssetParameters11846740cde0308720709e44dce627bf1ceb557ee9d0dbb556a05632da565ef2S3BucketE17A9F3E": {
       "Type": "String",
-      "Description": "S3 bucket for asset \"876959f777c5a23bf4408991959c55c91810329d159608feb7ede69418b35009\""
+      "Description": "S3 bucket for asset \"11846740cde0308720709e44dce627bf1ceb557ee9d0dbb556a05632da565ef2\""
     },
-    "AssetParameters876959f777c5a23bf4408991959c55c91810329d159608feb7ede69418b35009S3VersionKeyAFEB5FDA": {
+    "AssetParameters11846740cde0308720709e44dce627bf1ceb557ee9d0dbb556a05632da565ef2S3VersionKey0A0F7F93": {
       "Type": "String",
-      "Description": "S3 key for asset version \"876959f777c5a23bf4408991959c55c91810329d159608feb7ede69418b35009\""
+      "Description": "S3 key for asset version \"11846740cde0308720709e44dce627bf1ceb557ee9d0dbb556a05632da565ef2\""
     },
-    "AssetParameters876959f777c5a23bf4408991959c55c91810329d159608feb7ede69418b35009ArtifactHashB9A1080D": {
+    "AssetParameters11846740cde0308720709e44dce627bf1ceb557ee9d0dbb556a05632da565ef2ArtifactHash743A82BD": {
       "Type": "String",
-      "Description": "Artifact hash for asset \"876959f777c5a23bf4408991959c55c91810329d159608feb7ede69418b35009\""
+      "Description": "Artifact hash for asset \"11846740cde0308720709e44dce627bf1ceb557ee9d0dbb556a05632da565ef2\""
     }
   },
   "Outputs": {
diff --git a/packages/@aws-cdk/aws-lambda-python/test/integ.function.poetry.expected.json b/packages/@aws-cdk/aws-lambda-python/test/integ.function.poetry.expected.json
index 5ea17bca31920..c2ad372f25649 100644
--- a/packages/@aws-cdk/aws-lambda-python/test/integ.function.poetry.expected.json
+++ b/packages/@aws-cdk/aws-lambda-python/test/integ.function.poetry.expected.json
@@ -36,7 +36,7 @@
       "Properties": {
         "Code": {
           "S3Bucket": {
-            "Ref": "AssetParameters61d8d26f10d1d73dee2732bec7ed381d2c987fc2912a339f2f119f3b0ea175efS3BucketD53ED9C5"
+            "Ref": "AssetParameters3bc4d0e28b60c2b2468004185dabbe33a91c04563872cafb35b5b71e8a8f33d4S3Bucket68AF28A9"
           },
           "S3Key": {
             "Fn::Join": [
@@ -49,7 +49,7 @@
                       "Fn::Split": [
                         "||",
                         {
-                          "Ref": "AssetParameters61d8d26f10d1d73dee2732bec7ed381d2c987fc2912a339f2f119f3b0ea175efS3VersionKey3C218A3E"
+                          "Ref": "AssetParameters3bc4d0e28b60c2b2468004185dabbe33a91c04563872cafb35b5b71e8a8f33d4S3VersionKeyACC0084B"
                         }
                       ]
                     }
@@ -62,7 +62,7 @@
                       "Fn::Split": [
                         "||",
                         {
-                          "Ref": "AssetParameters61d8d26f10d1d73dee2732bec7ed381d2c987fc2912a339f2f119f3b0ea175efS3VersionKey3C218A3E"
+                          "Ref": "AssetParameters3bc4d0e28b60c2b2468004185dabbe33a91c04563872cafb35b5b71e8a8f33d4S3VersionKeyACC0084B"
                         }
                       ]
                     }
@@ -121,7 +121,7 @@
       "Properties": {
         "Code": {
           "S3Bucket": {
-            "Ref": "AssetParameters1d66b06c3b3ee86b3126fb58d7a06ff055d366d8aeeb4dfbaf28d40f0930956dS3BucketFDE171D0"
+            "Ref": "AssetParametersc1614067648b8b7e151e321ce82879d259a2b8f2bd10dddd61f0f2ce26287c17S3Bucket980A99E7"
           },
           "S3Key": {
             "Fn::Join": [
@@ -134,7 +134,7 @@
                       "Fn::Split": [
                         "||",
                         {
-                          "Ref": "AssetParameters1d66b06c3b3ee86b3126fb58d7a06ff055d366d8aeeb4dfbaf28d40f0930956dS3VersionKey6209E240"
+                          "Ref": "AssetParametersc1614067648b8b7e151e321ce82879d259a2b8f2bd10dddd61f0f2ce26287c17S3VersionKeyC4E1E9B5"
                         }
                       ]
                     }
@@ -147,7 +147,7 @@
                       "Fn::Split": [
                         "||",
                         {
-                          "Ref": "AssetParameters1d66b06c3b3ee86b3126fb58d7a06ff055d366d8aeeb4dfbaf28d40f0930956dS3VersionKey6209E240"
+                          "Ref": "AssetParametersc1614067648b8b7e151e321ce82879d259a2b8f2bd10dddd61f0f2ce26287c17S3VersionKeyC4E1E9B5"
                         }
                       ]
                     }
@@ -206,7 +206,7 @@
       "Properties": {
         "Code": {
           "S3Bucket": {
-            "Ref": "AssetParameters96a447e468bf9d3b52d13213757160cd43f28737a29b8682c281fde388762e68S3BucketA23E6312"
+            "Ref": "AssetParameters3610bde00ecd0013f7806e2ab0e80d7ac26232cd3ffc2934b5ca28fef120bdf6S3Bucket91AABE39"
           },
           "S3Key": {
             "Fn::Join": [
@@ -219,7 +219,7 @@
                       "Fn::Split": [
                         "||",
                         {
-                          "Ref": "AssetParameters96a447e468bf9d3b52d13213757160cd43f28737a29b8682c281fde388762e68S3VersionKey1E21AF83"
+                          "Ref": "AssetParameters3610bde00ecd0013f7806e2ab0e80d7ac26232cd3ffc2934b5ca28fef120bdf6S3VersionKeyEE0FAD90"
                         }
                       ]
                     }
@@ -232,7 +232,7 @@
                       "Fn::Split": [
                         "||",
                         {
-                          "Ref": "AssetParameters96a447e468bf9d3b52d13213757160cd43f28737a29b8682c281fde388762e68S3VersionKey1E21AF83"
+                          "Ref": "AssetParameters3610bde00ecd0013f7806e2ab0e80d7ac26232cd3ffc2934b5ca28fef120bdf6S3VersionKeyEE0FAD90"
                         }
                       ]
                     }
@@ -257,41 +257,41 @@
     }
   },
   "Parameters": {
-    "AssetParameters61d8d26f10d1d73dee2732bec7ed381d2c987fc2912a339f2f119f3b0ea175efS3BucketD53ED9C5": {
+    "AssetParameters3bc4d0e28b60c2b2468004185dabbe33a91c04563872cafb35b5b71e8a8f33d4S3Bucket68AF28A9": {
       "Type": "String",
-      "Description": "S3 bucket for asset \"61d8d26f10d1d73dee2732bec7ed381d2c987fc2912a339f2f119f3b0ea175ef\""
+      "Description": "S3 bucket for asset \"3bc4d0e28b60c2b2468004185dabbe33a91c04563872cafb35b5b71e8a8f33d4\""
     },
-    "AssetParameters61d8d26f10d1d73dee2732bec7ed381d2c987fc2912a339f2f119f3b0ea175efS3VersionKey3C218A3E": {
+    "AssetParameters3bc4d0e28b60c2b2468004185dabbe33a91c04563872cafb35b5b71e8a8f33d4S3VersionKeyACC0084B": {
       "Type": "String",
-      "Description": "S3 key for asset version \"61d8d26f10d1d73dee2732bec7ed381d2c987fc2912a339f2f119f3b0ea175ef\""
+      "Description": "S3 key for asset version \"3bc4d0e28b60c2b2468004185dabbe33a91c04563872cafb35b5b71e8a8f33d4\""
     },
-    "AssetParameters61d8d26f10d1d73dee2732bec7ed381d2c987fc2912a339f2f119f3b0ea175efArtifactHash6A1881A8": {
+    "AssetParameters3bc4d0e28b60c2b2468004185dabbe33a91c04563872cafb35b5b71e8a8f33d4ArtifactHashC2D4B1C3": {
       "Type": "String",
-      "Description": "Artifact hash for asset \"61d8d26f10d1d73dee2732bec7ed381d2c987fc2912a339f2f119f3b0ea175ef\""
+      "Description": "Artifact hash for asset \"3bc4d0e28b60c2b2468004185dabbe33a91c04563872cafb35b5b71e8a8f33d4\""
     },
-    "AssetParameters1d66b06c3b3ee86b3126fb58d7a06ff055d366d8aeeb4dfbaf28d40f0930956dS3BucketFDE171D0": {
+    "AssetParametersc1614067648b8b7e151e321ce82879d259a2b8f2bd10dddd61f0f2ce26287c17S3Bucket980A99E7": {
       "Type": "String",
-      "Description": "S3 bucket for asset \"1d66b06c3b3ee86b3126fb58d7a06ff055d366d8aeeb4dfbaf28d40f0930956d\""
+      "Description": "S3 bucket for asset \"c1614067648b8b7e151e321ce82879d259a2b8f2bd10dddd61f0f2ce26287c17\""
     },
-    "AssetParameters1d66b06c3b3ee86b3126fb58d7a06ff055d366d8aeeb4dfbaf28d40f0930956dS3VersionKey6209E240": {
+    "AssetParametersc1614067648b8b7e151e321ce82879d259a2b8f2bd10dddd61f0f2ce26287c17S3VersionKeyC4E1E9B5": {
       "Type": "String",
-      "Description": "S3 key for asset version \"1d66b06c3b3ee86b3126fb58d7a06ff055d366d8aeeb4dfbaf28d40f0930956d\""
+      "Description": "S3 key for asset version \"c1614067648b8b7e151e321ce82879d259a2b8f2bd10dddd61f0f2ce26287c17\""
     },
-    "AssetParameters1d66b06c3b3ee86b3126fb58d7a06ff055d366d8aeeb4dfbaf28d40f0930956dArtifactHash02B929EC": {
+    "AssetParametersc1614067648b8b7e151e321ce82879d259a2b8f2bd10dddd61f0f2ce26287c17ArtifactHash5B02FA4D": {
       "Type": "String",
-      "Description": "Artifact hash for asset \"1d66b06c3b3ee86b3126fb58d7a06ff055d366d8aeeb4dfbaf28d40f0930956d\""
+      "Description": "Artifact hash for asset \"c1614067648b8b7e151e321ce82879d259a2b8f2bd10dddd61f0f2ce26287c17\""
     },
-    "AssetParameters96a447e468bf9d3b52d13213757160cd43f28737a29b8682c281fde388762e68S3BucketA23E6312": {
+    "AssetParameters3610bde00ecd0013f7806e2ab0e80d7ac26232cd3ffc2934b5ca28fef120bdf6S3Bucket91AABE39": {
       "Type": "String",
-      "Description": "S3 bucket for asset \"96a447e468bf9d3b52d13213757160cd43f28737a29b8682c281fde388762e68\""
+      "Description": "S3 bucket for asset \"3610bde00ecd0013f7806e2ab0e80d7ac26232cd3ffc2934b5ca28fef120bdf6\""
     },
-    "AssetParameters96a447e468bf9d3b52d13213757160cd43f28737a29b8682c281fde388762e68S3VersionKey1E21AF83": {
+    "AssetParameters3610bde00ecd0013f7806e2ab0e80d7ac26232cd3ffc2934b5ca28fef120bdf6S3VersionKeyEE0FAD90": {
       "Type": "String",
-      "Description": "S3 key for asset version \"96a447e468bf9d3b52d13213757160cd43f28737a29b8682c281fde388762e68\""
+      "Description": "S3 key for asset version \"3610bde00ecd0013f7806e2ab0e80d7ac26232cd3ffc2934b5ca28fef120bdf6\""
     },
-    "AssetParameters96a447e468bf9d3b52d13213757160cd43f28737a29b8682c281fde388762e68ArtifactHash0043D2A0": {
+    "AssetParameters3610bde00ecd0013f7806e2ab0e80d7ac26232cd3ffc2934b5ca28fef120bdf6ArtifactHash09CEB444": {
       "Type": "String",
-      "Description": "Artifact hash for asset \"96a447e468bf9d3b52d13213757160cd43f28737a29b8682c281fde388762e68\""
+      "Description": "Artifact hash for asset \"3610bde00ecd0013f7806e2ab0e80d7ac26232cd3ffc2934b5ca28fef120bdf6\""
     }
   },
   "Outputs": {
diff --git a/packages/@aws-cdk/aws-lambda-python/test/integ.function.project.expected.json b/packages/@aws-cdk/aws-lambda-python/test/integ.function.project.expected.json
index 9a81c901d7451..aa13e73295e64 100644
--- a/packages/@aws-cdk/aws-lambda-python/test/integ.function.project.expected.json
+++ b/packages/@aws-cdk/aws-lambda-python/test/integ.function.project.expected.json
@@ -5,7 +5,7 @@
       "Properties": {
         "Content": {
           "S3Bucket": {
-            "Ref": "AssetParameters6a4b9ce26d3228c4effd7b46ed51ab439e79a530934ad9bde7d77d7f6b6ebd4aS3BucketCCD07444"
+            "Ref": "AssetParameterse174a6a88cb48eb510c29b2bf0203c181cfa059320745e6ae6429e522b36c66eS3Bucket7A00FCB4"
           },
           "S3Key": {
             "Fn::Join": [
@@ -18,7 +18,7 @@
                       "Fn::Split": [
                         "||",
                         {
-                          "Ref": "AssetParameters6a4b9ce26d3228c4effd7b46ed51ab439e79a530934ad9bde7d77d7f6b6ebd4aS3VersionKeyA8B74284"
+                          "Ref": "AssetParameterse174a6a88cb48eb510c29b2bf0203c181cfa059320745e6ae6429e522b36c66eS3VersionKey8BF2F9D6"
                         }
                       ]
                     }
@@ -31,7 +31,7 @@
                       "Fn::Split": [
                         "||",
                         {
-                          "Ref": "AssetParameters6a4b9ce26d3228c4effd7b46ed51ab439e79a530934ad9bde7d77d7f6b6ebd4aS3VersionKeyA8B74284"
+                          "Ref": "AssetParameterse174a6a88cb48eb510c29b2bf0203c181cfa059320745e6ae6429e522b36c66eS3VersionKey8BF2F9D6"
                         }
                       ]
                     }
@@ -82,7 +82,7 @@
       "Properties": {
         "Code": {
           "S3Bucket": {
-            "Ref": "AssetParameters71de8786d26e9f9205375b6cea9342e92d8a622a97d01d7e7d2f7661f056f218S3Bucket89C9DB12"
+            "Ref": "AssetParameters907ec4b12820d4b2dc64e7f0f1f1f6267c1db622bc42aa57f5361efa12b1aafbS3Bucket16F02289"
           },
           "S3Key": {
             "Fn::Join": [
@@ -95,7 +95,7 @@
                       "Fn::Split": [
                         "||",
                         {
-                          "Ref": "AssetParameters71de8786d26e9f9205375b6cea9342e92d8a622a97d01d7e7d2f7661f056f218S3VersionKey435DAD55"
+                          "Ref": "AssetParameters907ec4b12820d4b2dc64e7f0f1f1f6267c1db622bc42aa57f5361efa12b1aafbS3VersionKeyDAF0A5BD"
                         }
                       ]
                     }
@@ -108,7 +108,7 @@
                       "Fn::Split": [
                         "||",
                         {
-                          "Ref": "AssetParameters71de8786d26e9f9205375b6cea9342e92d8a622a97d01d7e7d2f7661f056f218S3VersionKey435DAD55"
+                          "Ref": "AssetParameters907ec4b12820d4b2dc64e7f0f1f1f6267c1db622bc42aa57f5361efa12b1aafbS3VersionKeyDAF0A5BD"
                         }
                       ]
                     }
@@ -138,29 +138,29 @@
     }
   },
   "Parameters": {
-    "AssetParameters6a4b9ce26d3228c4effd7b46ed51ab439e79a530934ad9bde7d77d7f6b6ebd4aS3BucketCCD07444": {
+    "AssetParameterse174a6a88cb48eb510c29b2bf0203c181cfa059320745e6ae6429e522b36c66eS3Bucket7A00FCB4": {
       "Type": "String",
-      "Description": "S3 bucket for asset \"6a4b9ce26d3228c4effd7b46ed51ab439e79a530934ad9bde7d77d7f6b6ebd4a\""
+      "Description": "S3 bucket for asset \"e174a6a88cb48eb510c29b2bf0203c181cfa059320745e6ae6429e522b36c66e\""
     },
-    "AssetParameters6a4b9ce26d3228c4effd7b46ed51ab439e79a530934ad9bde7d77d7f6b6ebd4aS3VersionKeyA8B74284": {
+    "AssetParameterse174a6a88cb48eb510c29b2bf0203c181cfa059320745e6ae6429e522b36c66eS3VersionKey8BF2F9D6": {
       "Type": "String",
-      "Description": "S3 key for asset version \"6a4b9ce26d3228c4effd7b46ed51ab439e79a530934ad9bde7d77d7f6b6ebd4a\""
+      "Description": "S3 key for asset version \"e174a6a88cb48eb510c29b2bf0203c181cfa059320745e6ae6429e522b36c66e\""
     },
-    "AssetParameters6a4b9ce26d3228c4effd7b46ed51ab439e79a530934ad9bde7d77d7f6b6ebd4aArtifactHashB3093591": {
+    "AssetParameterse174a6a88cb48eb510c29b2bf0203c181cfa059320745e6ae6429e522b36c66eArtifactHash2DECF34E": {
       "Type": "String",
-      "Description": "Artifact hash for asset \"6a4b9ce26d3228c4effd7b46ed51ab439e79a530934ad9bde7d77d7f6b6ebd4a\""
+      "Description": "Artifact hash for asset \"e174a6a88cb48eb510c29b2bf0203c181cfa059320745e6ae6429e522b36c66e\""
     },
-    "AssetParameters71de8786d26e9f9205375b6cea9342e92d8a622a97d01d7e7d2f7661f056f218S3Bucket89C9DB12": {
+    "AssetParameters907ec4b12820d4b2dc64e7f0f1f1f6267c1db622bc42aa57f5361efa12b1aafbS3Bucket16F02289": {
       "Type": "String",
-      "Description": "S3 bucket for asset \"71de8786d26e9f9205375b6cea9342e92d8a622a97d01d7e7d2f7661f056f218\""
+      "Description": "S3 bucket for asset \"907ec4b12820d4b2dc64e7f0f1f1f6267c1db622bc42aa57f5361efa12b1aafb\""
     },
-    "AssetParameters71de8786d26e9f9205375b6cea9342e92d8a622a97d01d7e7d2f7661f056f218S3VersionKey435DAD55": {
+    "AssetParameters907ec4b12820d4b2dc64e7f0f1f1f6267c1db622bc42aa57f5361efa12b1aafbS3VersionKeyDAF0A5BD": {
       "Type": "String",
-      "Description": "S3 key for asset version \"71de8786d26e9f9205375b6cea9342e92d8a622a97d01d7e7d2f7661f056f218\""
+      "Description": "S3 key for asset version \"907ec4b12820d4b2dc64e7f0f1f1f6267c1db622bc42aa57f5361efa12b1aafb\""
     },
-    "AssetParameters71de8786d26e9f9205375b6cea9342e92d8a622a97d01d7e7d2f7661f056f218ArtifactHash0EDF3CD0": {
+    "AssetParameters907ec4b12820d4b2dc64e7f0f1f1f6267c1db622bc42aa57f5361efa12b1aafbArtifactHashD7592B0F": {
       "Type": "String",
-      "Description": "Artifact hash for asset \"71de8786d26e9f9205375b6cea9342e92d8a622a97d01d7e7d2f7661f056f218\""
+      "Description": "Artifact hash for asset \"907ec4b12820d4b2dc64e7f0f1f1f6267c1db622bc42aa57f5361efa12b1aafb\""
     }
   },
   "Outputs": {
diff --git a/packages/@aws-cdk/aws-lambda-python/test/integ.function.py38.expected.json b/packages/@aws-cdk/aws-lambda-python/test/integ.function.py38.expected.json
index b5b137205752f..c49f5e312d873 100644
--- a/packages/@aws-cdk/aws-lambda-python/test/integ.function.py38.expected.json
+++ b/packages/@aws-cdk/aws-lambda-python/test/integ.function.py38.expected.json
@@ -36,7 +36,7 @@
       "Properties": {
         "Code": {
           "S3Bucket": {
-            "Ref": "AssetParameters1482f01217b8bed41000ca172724dc762f68208d3faa315bd6e8e07bbea148adS3BucketA9379638"
+            "Ref": "AssetParameters6cc4994756d4085a860e734568c92826773e52c22c58894ce368b1e698da413dS3Bucket74CBB570"
           },
           "S3Key": {
             "Fn::Join": [
@@ -49,7 +49,7 @@
                       "Fn::Split": [
                         "||",
                         {
-                          "Ref": "AssetParameters1482f01217b8bed41000ca172724dc762f68208d3faa315bd6e8e07bbea148adS3VersionKey4376B462"
+                          "Ref": "AssetParameters6cc4994756d4085a860e734568c92826773e52c22c58894ce368b1e698da413dS3VersionKey3CBAF21A"
                         }
                       ]
                     }
@@ -62,7 +62,7 @@
                       "Fn::Split": [
                         "||",
                         {
-                          "Ref": "AssetParameters1482f01217b8bed41000ca172724dc762f68208d3faa315bd6e8e07bbea148adS3VersionKey4376B462"
+                          "Ref": "AssetParameters6cc4994756d4085a860e734568c92826773e52c22c58894ce368b1e698da413dS3VersionKey3CBAF21A"
                         }
                       ]
                     }
@@ -87,17 +87,17 @@
     }
   },
   "Parameters": {
-    "AssetParameters1482f01217b8bed41000ca172724dc762f68208d3faa315bd6e8e07bbea148adS3BucketA9379638": {
+    "AssetParameters6cc4994756d4085a860e734568c92826773e52c22c58894ce368b1e698da413dS3Bucket74CBB570": {
       "Type": "String",
-      "Description": "S3 bucket for asset \"1482f01217b8bed41000ca172724dc762f68208d3faa315bd6e8e07bbea148ad\""
+      "Description": "S3 bucket for asset \"6cc4994756d4085a860e734568c92826773e52c22c58894ce368b1e698da413d\""
     },
-    "AssetParameters1482f01217b8bed41000ca172724dc762f68208d3faa315bd6e8e07bbea148adS3VersionKey4376B462": {
+    "AssetParameters6cc4994756d4085a860e734568c92826773e52c22c58894ce368b1e698da413dS3VersionKey3CBAF21A": {
       "Type": "String",
-      "Description": "S3 key for asset version \"1482f01217b8bed41000ca172724dc762f68208d3faa315bd6e8e07bbea148ad\""
+      "Description": "S3 key for asset version \"6cc4994756d4085a860e734568c92826773e52c22c58894ce368b1e698da413d\""
     },
-    "AssetParameters1482f01217b8bed41000ca172724dc762f68208d3faa315bd6e8e07bbea148adArtifactHashB9B928DC": {
+    "AssetParameters6cc4994756d4085a860e734568c92826773e52c22c58894ce368b1e698da413dArtifactHash750F3AF8": {
       "Type": "String",
-      "Description": "Artifact hash for asset \"1482f01217b8bed41000ca172724dc762f68208d3faa315bd6e8e07bbea148ad\""
+      "Description": "Artifact hash for asset \"6cc4994756d4085a860e734568c92826773e52c22c58894ce368b1e698da413d\""
     }
   },
   "Outputs": {
diff --git a/packages/@aws-cdk/aws-lambda-python/test/integ.function.requirements.removed.expected.json b/packages/@aws-cdk/aws-lambda-python/test/integ.function.requirements.removed.expected.json
index 6b3b8230c2874..c70f4a0ca8933 100644
--- a/packages/@aws-cdk/aws-lambda-python/test/integ.function.requirements.removed.expected.json
+++ b/packages/@aws-cdk/aws-lambda-python/test/integ.function.requirements.removed.expected.json
@@ -36,7 +36,7 @@
       "Properties": {
         "Code": {
           "S3Bucket": {
-            "Ref": "AssetParametersaf41a5381eff9302e9acdfeb9c3bcf160b56a97091242b2d599ed5a861af966aS3BucketEE202B67"
+            "Ref": "AssetParameters6fa8e0c54d06a6402126a86fab5da1fa1397bcce628a0fb56f8356a2edf6280dS3Bucket2F189DB9"
           },
           "S3Key": {
             "Fn::Join": [
@@ -49,7 +49,7 @@
                       "Fn::Split": [
                         "||",
                         {
-                          "Ref": "AssetParametersaf41a5381eff9302e9acdfeb9c3bcf160b56a97091242b2d599ed5a861af966aS3VersionKey8097C675"
+                          "Ref": "AssetParameters6fa8e0c54d06a6402126a86fab5da1fa1397bcce628a0fb56f8356a2edf6280dS3VersionKeyDF03C812"
                         }
                       ]
                     }
@@ -62,7 +62,7 @@
                       "Fn::Split": [
                         "||",
                         {
-                          "Ref": "AssetParametersaf41a5381eff9302e9acdfeb9c3bcf160b56a97091242b2d599ed5a861af966aS3VersionKey8097C675"
+                          "Ref": "AssetParameters6fa8e0c54d06a6402126a86fab5da1fa1397bcce628a0fb56f8356a2edf6280dS3VersionKeyDF03C812"
                         }
                       ]
                     }
@@ -87,17 +87,17 @@
     }
   },
   "Parameters": {
-    "AssetParametersaf41a5381eff9302e9acdfeb9c3bcf160b56a97091242b2d599ed5a861af966aS3BucketEE202B67": {
+    "AssetParameters6fa8e0c54d06a6402126a86fab5da1fa1397bcce628a0fb56f8356a2edf6280dS3Bucket2F189DB9": {
       "Type": "String",
-      "Description": "S3 bucket for asset \"af41a5381eff9302e9acdfeb9c3bcf160b56a97091242b2d599ed5a861af966a\""
+      "Description": "S3 bucket for asset \"6fa8e0c54d06a6402126a86fab5da1fa1397bcce628a0fb56f8356a2edf6280d\""
     },
-    "AssetParametersaf41a5381eff9302e9acdfeb9c3bcf160b56a97091242b2d599ed5a861af966aS3VersionKey8097C675": {
+    "AssetParameters6fa8e0c54d06a6402126a86fab5da1fa1397bcce628a0fb56f8356a2edf6280dS3VersionKeyDF03C812": {
       "Type": "String",
-      "Description": "S3 key for asset version \"af41a5381eff9302e9acdfeb9c3bcf160b56a97091242b2d599ed5a861af966a\""
+      "Description": "S3 key for asset version \"6fa8e0c54d06a6402126a86fab5da1fa1397bcce628a0fb56f8356a2edf6280d\""
     },
-    "AssetParametersaf41a5381eff9302e9acdfeb9c3bcf160b56a97091242b2d599ed5a861af966aArtifactHash3E92B1F8": {
+    "AssetParameters6fa8e0c54d06a6402126a86fab5da1fa1397bcce628a0fb56f8356a2edf6280dArtifactHash1F692755": {
       "Type": "String",
-      "Description": "Artifact hash for asset \"af41a5381eff9302e9acdfeb9c3bcf160b56a97091242b2d599ed5a861af966a\""
+      "Description": "Artifact hash for asset \"6fa8e0c54d06a6402126a86fab5da1fa1397bcce628a0fb56f8356a2edf6280d\""
     }
   },
   "Outputs": {
diff --git a/packages/@aws-cdk/aws-lambda-python/test/integ.function.vpc.expected.json b/packages/@aws-cdk/aws-lambda-python/test/integ.function.vpc.expected.json
index 63fad4c61de14..6787327a15e40 100644
--- a/packages/@aws-cdk/aws-lambda-python/test/integ.function.vpc.expected.json
+++ b/packages/@aws-cdk/aws-lambda-python/test/integ.function.vpc.expected.json
@@ -296,7 +296,7 @@
       "Properties": {
         "Code": {
           "S3Bucket": {
-            "Ref": "AssetParameters4ee6ce8b6ee4bd51743dc0c39d6e52baebaeafff9c9dfea0ff84de98d1dbf353S3Bucket414E0E30"
+            "Ref": "AssetParameters83be407310ab5911f40fa4934091a233f92ce3be1d81c48846f30fa0a9330530S3Bucket82392CBF"
           },
           "S3Key": {
             "Fn::Join": [
@@ -309,7 +309,7 @@
                       "Fn::Split": [
                         "||",
                         {
-                          "Ref": "AssetParameters4ee6ce8b6ee4bd51743dc0c39d6e52baebaeafff9c9dfea0ff84de98d1dbf353S3VersionKey5ABC9098"
+                          "Ref": "AssetParameters83be407310ab5911f40fa4934091a233f92ce3be1d81c48846f30fa0a9330530S3VersionKey292822E7"
                         }
                       ]
                     }
@@ -322,7 +322,7 @@
                       "Fn::Split": [
                         "||",
                         {
-                          "Ref": "AssetParameters4ee6ce8b6ee4bd51743dc0c39d6e52baebaeafff9c9dfea0ff84de98d1dbf353S3VersionKey5ABC9098"
+                          "Ref": "AssetParameters83be407310ab5911f40fa4934091a233f92ce3be1d81c48846f30fa0a9330530S3VersionKey292822E7"
                         }
                       ]
                     }
@@ -368,17 +368,17 @@
     }
   },
   "Parameters": {
-    "AssetParameters4ee6ce8b6ee4bd51743dc0c39d6e52baebaeafff9c9dfea0ff84de98d1dbf353S3Bucket414E0E30": {
+    "AssetParameters83be407310ab5911f40fa4934091a233f92ce3be1d81c48846f30fa0a9330530S3Bucket82392CBF": {
       "Type": "String",
-      "Description": "S3 bucket for asset \"4ee6ce8b6ee4bd51743dc0c39d6e52baebaeafff9c9dfea0ff84de98d1dbf353\""
+      "Description": "S3 bucket for asset \"83be407310ab5911f40fa4934091a233f92ce3be1d81c48846f30fa0a9330530\""
     },
-    "AssetParameters4ee6ce8b6ee4bd51743dc0c39d6e52baebaeafff9c9dfea0ff84de98d1dbf353S3VersionKey5ABC9098": {
+    "AssetParameters83be407310ab5911f40fa4934091a233f92ce3be1d81c48846f30fa0a9330530S3VersionKey292822E7": {
       "Type": "String",
-      "Description": "S3 key for asset version \"4ee6ce8b6ee4bd51743dc0c39d6e52baebaeafff9c9dfea0ff84de98d1dbf353\""
+      "Description": "S3 key for asset version \"83be407310ab5911f40fa4934091a233f92ce3be1d81c48846f30fa0a9330530\""
     },
-    "AssetParameters4ee6ce8b6ee4bd51743dc0c39d6e52baebaeafff9c9dfea0ff84de98d1dbf353ArtifactHashECA6C88C": {
+    "AssetParameters83be407310ab5911f40fa4934091a233f92ce3be1d81c48846f30fa0a9330530ArtifactHash8818CE02": {
       "Type": "String",
-      "Description": "Artifact hash for asset \"4ee6ce8b6ee4bd51743dc0c39d6e52baebaeafff9c9dfea0ff84de98d1dbf353\""
+      "Description": "Artifact hash for asset \"83be407310ab5911f40fa4934091a233f92ce3be1d81c48846f30fa0a9330530\""
     }
   },
   "Outputs": {
diff --git a/packages/@aws-cdk/aws-lambda-python/test/layer.test.ts b/packages/@aws-cdk/aws-lambda-python/test/layer.test.ts
index 8ace2ec3f7a18..255adb0dae646 100644
--- a/packages/@aws-cdk/aws-lambda-python/test/layer.test.ts
+++ b/packages/@aws-cdk/aws-lambda-python/test/layer.test.ts
@@ -2,7 +2,7 @@ import '@aws-cdk/assert/jest';
 import * as path from 'path';
 import { Runtime } from '@aws-cdk/aws-lambda';
 import { Stack } from '@aws-cdk/core';
-import { hasDependencies, bundle } from '../lib/bundling';
+import { stageDependencies, bundle } from '../lib/bundling';
 import { PythonLayerVersion } from '../lib/layer';
 
 jest.mock('../lib/bundling', () => {
@@ -18,11 +18,11 @@ jest.mock('../lib/bundling', () => {
       },
       bindToResource: () => { return; },
     }),
-    hasDependencies: jest.fn().mockReturnValue(true),
+    stageDependencies: jest.fn().mockReturnValue(true),
   };
 });
 
-const hasDependenciesMock = (hasDependencies as jest.Mock);
+const hasDependenciesMock = (stageDependencies as jest.Mock);
 
 let stack: Stack;
 beforeEach(() => {
diff --git a/packages/@aws-cdk/core/lib/bundling.ts b/packages/@aws-cdk/core/lib/bundling.ts
index b1247fd913ea0..0179b07d2f8f3 100644
--- a/packages/@aws-cdk/core/lib/bundling.ts
+++ b/packages/@aws-cdk/core/lib/bundling.ts
@@ -1,5 +1,6 @@
 import { spawnSync, SpawnSyncOptions } from 'child_process';
 import * as crypto from 'crypto';
+import { isAbsolute, join } from 'path';
 import { FileSystem } from './fs';
 
 /**
@@ -120,16 +121,18 @@ export class BundlingDockerImage {
   public static fromAsset(path: string, options: DockerBuildOptions = {}) {
     const buildArgs = options.buildArgs || {};
 
+    if (options.file && isAbsolute(options.file)) {
+      throw new Error(`"file" must be relative to the docker build directory. Got ${options.file}`);
+    }
+
     // Image tag derived from path and build options
-    const tagHash = crypto.createHash('sha256').update(JSON.stringify({
-      path,
-      ...options,
-    })).digest('hex');
+    const input = JSON.stringify({ path, ...options });
+    const tagHash = crypto.createHash('sha256').update(input).digest('hex');
     const tag = `cdk-${tagHash}`;
 
     const dockerArgs: string[] = [
       'build', '-t', tag,
-      ...(options.file ? ['-f', options.file] : []),
+      ...(options.file ? ['-f', join(path, options.file)] : []),
       ...flatten(Object.entries(buildArgs).map(([k, v]) => ['--build-arg', `${k}=${v}`])),
       path,
     ];
@@ -315,9 +318,9 @@ export interface DockerBuildOptions {
   readonly buildArgs?: { [key: string]: string };
 
   /**
-   * Name of the Dockerfile
+   * Name of the Dockerfile, must relative to the docker build path.
    *
-   * @default - The Dockerfile immediately within the build context path
+   * @default `Dockerfile`
    */
   readonly file?: string;
 }
diff --git a/packages/@aws-cdk/core/test/bundling.test.ts b/packages/@aws-cdk/core/test/bundling.test.ts
index 258860d65585c..cac2b494eb003 100644
--- a/packages/@aws-cdk/core/test/bundling.test.ts
+++ b/packages/@aws-cdk/core/test/bundling.test.ts
@@ -161,12 +161,14 @@ nodeunitShim({
       signal: null,
     });
 
-    BundlingDockerImage.fromAsset(path.join(__dirname, 'fs/fixtures/test1'), {
+    const imagePath = path.join(__dirname, 'fs/fixtures/test1');
+    BundlingDockerImage.fromAsset(imagePath, {
       file: 'my-dockerfile',
     });
 
     test.ok(spawnSyncStub.calledOnce);
-    test.ok(/-f my-dockerfile/.test(spawnSyncStub.firstCall.args[1]?.join(' ') ?? ''));
+    const expected = path.join(imagePath, 'my-dockerfile');
+    test.ok(new RegExp(`-f ${expected}`).test(spawnSyncStub.firstCall.args[1]?.join(' ') ?? ''));
 
     test.done();
   },