diff --git a/Readme.md b/Readme.md
index 488d864ca64..a0611ff40b9 100644
--- a/Readme.md
+++ b/Readme.md
@@ -34,7 +34,7 @@ The AWS Amplify CLI is a toolchain which includes a robust feature set for simpl
 
 ## Install the CLI
 
-- Requires Node.js® version 10 or later
+- Requires Node.js® version 12 or later
 
 Install and configure the Amplify CLI as follows:
 
diff --git a/packages/amplify-category-auth/resources/cloudformation-templates/auth-template.yml.ejs b/packages/amplify-category-auth/resources/cloudformation-templates/auth-template.yml.ejs
index ea6242992e7..43bc61b7bd3 100644
--- a/packages/amplify-category-auth/resources/cloudformation-templates/auth-template.yml.ejs
+++ b/packages/amplify-category-auth/resources/cloudformation-templates/auth-template.yml.ejs
@@ -127,7 +127,7 @@ Resources:
           Mutable: true
         <% } %>
       <% } %>
-      <%if (!props.breakCircularDependency && props.triggers !== '{}' && props.dependsOn) { %>
+      <%if (!props.breakCircularDependency && props.triggers && props.dependsOn) { %>
       LambdaConfig:
         <%if (props.dependsOn.find(i => i.resourceName.includes('CreateAuthChallenge'))) { %>
           CreateAuthChallenge: !Ref function<%=props.resourceName%>CreateAuthChallengeArn
diff --git a/packages/amplify-cli/src/__tests__/init-steps/s1-initFrontend.test.ts b/packages/amplify-cli/src/__tests__/init-steps/s1-initFrontend.test.ts
new file mode 100644
index 00000000000..dd1da50ec12
--- /dev/null
+++ b/packages/amplify-cli/src/__tests__/init-steps/s1-initFrontend.test.ts
@@ -0,0 +1,18 @@
+import { getSuitableFrontend } from '../../init-steps/s1-initFrontend';
+
+describe('getSuitableFrontend', () => {
+  it('supports headless inputs', () => {
+    const context = {
+      exeInfo: {
+        inputParams: {
+          amplify: {
+            frontend: 'ios',
+          },
+        },
+      },
+    } as any;
+    const frontendPlugins = { ios: '' } as any;
+    const result = getSuitableFrontend(context, frontendPlugins, '');
+    expect(result).toStrictEqual('ios');
+  });
+});
diff --git a/packages/amplify-cli/src/init-steps/s0-analyzeProject.ts b/packages/amplify-cli/src/init-steps/s0-analyzeProject.ts
index d91fd8e5c0d..95e0ee5a2ef 100644
--- a/packages/amplify-cli/src/init-steps/s0-analyzeProject.ts
+++ b/packages/amplify-cli/src/init-steps/s0-analyzeProject.ts
@@ -72,7 +72,7 @@ async function displayAndSetDefaults(context: $TSContext, projectPath: string, p
   await displayConfigurationDefaults(context, defaultProjectName, defaultEnv, defaultEditorName);
 
   const frontendPlugins = getFrontendPlugins(context);
-  const defaultFrontend = getSuitableFrontend(frontendPlugins, projectPath);
+  const defaultFrontend = getSuitableFrontend(context, frontendPlugins, projectPath);
   const frontendModule = require(frontendPlugins[defaultFrontend]);
 
   await frontendModule.displayFrontendDefaults(context, projectPath);
diff --git a/packages/amplify-cli/src/init-steps/s1-initFrontend.ts b/packages/amplify-cli/src/init-steps/s1-initFrontend.ts
index a32130d93e5..df8710c179f 100644
--- a/packages/amplify-cli/src/init-steps/s1-initFrontend.ts
+++ b/packages/amplify-cli/src/init-steps/s1-initFrontend.ts
@@ -12,7 +12,7 @@ export async function initFrontend(context: $TSContext) {
   }
 
   const frontendPlugins = getFrontendPlugins(context);
-  const suitableFrontend = getSuitableFrontend(frontendPlugins, context.exeInfo.localEnvInfo.projectPath);
+  const suitableFrontend = getSuitableFrontend(context, frontendPlugins, context.exeInfo.localEnvInfo.projectPath);
   const frontend = await getFrontendHandler(context, frontendPlugins, suitableFrontend);
 
   context.exeInfo.projectConfig.frontend = frontend;
@@ -22,7 +22,13 @@ export async function initFrontend(context: $TSContext) {
   return context;
 }
 
-export function getSuitableFrontend(frontendPlugins: $TSAny, projectPath: string) {
+export function getSuitableFrontend(context: $TSContext, frontendPlugins: $TSAny, projectPath: string) {
+  let headlessFrontend = context?.exeInfo?.inputParams?.amplify?.frontend;
+
+  if (headlessFrontend && headlessFrontend in frontendPlugins) {
+    return headlessFrontend;
+  }
+
   let suitableFrontend;
   let fitToHandleScore = -1;
 
diff --git a/packages/amplify-cli/src/utils/post-install-initialization.ts b/packages/amplify-cli/src/utils/post-install-initialization.ts
index e1d7d364e4d..f3eb0ebdab8 100644
--- a/packages/amplify-cli/src/utils/post-install-initialization.ts
+++ b/packages/amplify-cli/src/utils/post-install-initialization.ts
@@ -49,6 +49,7 @@ const resolvePackageRoot = (packageName: string) => {
 // Registry of packages that have files that need to be copied to the .amplify folder on CLI installation
 const copyPkgAssetRegistry = [
   'amplify-dynamodb-simulator',
+  'amplify-frontend-ios',
   'amplify-go-function-runtime-provider',
   'amplify-java-function-runtime-provider',
   'amplify-python-function-runtime-provider',
diff --git a/packages/amplify-frontend-ios/index.js b/packages/amplify-frontend-ios/index.js
index bf1e2bc5dba..d440dd05ad8 100644
--- a/packages/amplify-frontend-ios/index.js
+++ b/packages/amplify-frontend-ios/index.js
@@ -1,6 +1,6 @@
 const path = require('path');
-const amplifyApp = require('amplify-app');
-const { FeatureFlags } = require('amplify-cli-core');
+const { FeatureFlags, pathManager } = require('amplify-cli-core');
+const { importConfig, importModels } = require('./lib/amplify-xcode');
 const initializer = require('./lib/initializer');
 const projectScanner = require('./lib/project-scanner');
 const configManager = require('./lib/configuration-manager');
@@ -59,22 +59,35 @@ async function executeAmplifyCommand(context) {
   await commandModule.run(context);
 }
 
-const postEvents = new Set(['PostInit', 'PostCodegenModels', 'PostPull']);
-
 async function handleAmplifyEvent(context, args) {
   const { frontend } = context.amplify.getProjectConfig();
   const isXcodeIntegrationEnabled = FeatureFlags.getBoolean('frontend-ios.enableXcodeIntegration');
   const isFrontendiOS = frontend === 'ios';
-  if (isFrontendiOS && isXcodeIntegrationEnabled && postEvents.has(args.event)) {
-    await amplifyApp.run({
-      skipEnvCheck: true,
-      platform: frontend,
-      skipInit: true,
-      internalOnlyIosCallback: true,
-    });
+  const isMacOs = process.platform === 'darwin';
+  if (!isFrontendiOS || !isXcodeIntegrationEnabled || !isMacOs) {
+    return;
+  }
+  context.print.info('Updating iOS project');
+  const projectPath = pathManager.findProjectRoot();
+  switch (args.event) {
+    case 'PostInit':
+      await importConfig({ path: projectPath });
+      break;
+    case 'PostCodegenModels':
+      await importModels({ path: projectPath });
+      break;
+    case 'PostPull':
+      await importConfig({ path: projectPath });
+      await importModels({ path: projectPath });
+      break;
+    default:
+      break;
   }
+  context.print.info('Amplify setup completed successfully.');
 }
 
+const getPackageAssetPaths = async () => ['resources'];
+
 module.exports = {
   constants,
   scanProject,
@@ -89,4 +102,5 @@ module.exports = {
   executeAmplifyCommand,
   handleAmplifyEvent,
   deleteConfig: deleteAmplifyConfig,
+  getPackageAssetPaths,
 };
diff --git a/packages/amplify-frontend-ios/lib/amplify-xcode.js b/packages/amplify-frontend-ios/lib/amplify-xcode.js
new file mode 100644
index 00000000000..a2b93b014d7
--- /dev/null
+++ b/packages/amplify-frontend-ios/lib/amplify-xcode.js
@@ -0,0 +1,71 @@
+//
+// Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
+//
+// Licensed under the Apache License, Version 2.0 (the "License").
+// You may not use this file except in compliance with the License.
+// A copy of the License is located at
+//
+// http://aws.amazon.com/apache2.0
+//
+// or in the "license" file accompanying this file. This file is distributed
+// on an "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either
+// express or implied. See the License for the specific language governing
+// permissions and limitations under the License.
+//
+
+// ############################################################################
+// Auto-generated file using `build` NPM script. Do not edit this file manually
+// ############################################################################
+
+const execa = require('execa');
+const path = require('path');
+const { pathManager } = require('amplify-cli-core');
+
+const BINARY_PATH = 'resources/amplify-xcode';
+const PACKAGE_NAME = 'amplify-frontend-ios';
+const amplifyXcodePath = () => path.join(pathManager.getAmplifyPackageLibDirPath(PACKAGE_NAME), BINARY_PATH);
+
+/**
+ * Import Amplify configuration files
+ * @param {Object} params
+ * @param {String} params.path - Project base path
+ */
+async function importConfig(params) {
+  let command = `${amplifyXcodePath()} import-config`;
+  if (params['path']) {
+    command += ` --path=${params['path']}`;
+  }
+  await execa.command(command, { stdout: 'inherit' });
+}
+
+/**
+ * Import Amplify models
+ * @param {Object} params
+ * @param {String} params.path - Project base path
+ */
+async function importModels(params) {
+  let command = `${amplifyXcodePath()} import-models`;
+  if (params['path']) {
+    command += ` --path=${params['path']}`;
+  }
+  await execa.command(command, { stdout: 'inherit' });
+}
+
+/**
+ * Generates a JSON description of the CLI and its commands
+ * @param {Object} params
+ * @param {String} params.output-path - Path to save the output of generated schema file
+ */
+async function generateSchema(params) {
+  let command = `${amplifyXcodePath()} generate-schema`;
+  if (params['output-path']) {
+    command += ` --output-path=${params['output-path']}`;
+  }
+  await execa.command(command, { stdout: 'inherit' });
+}
+
+module.exports = {
+  importConfig,
+  importModels,
+  generateSchema,
+};
diff --git a/packages/amplify-frontend-ios/native-bindings-codegen/index.js b/packages/amplify-frontend-ios/native-bindings-codegen/index.js
new file mode 100644
index 00000000000..fffc9d2f1e2
--- /dev/null
+++ b/packages/amplify-frontend-ios/native-bindings-codegen/index.js
@@ -0,0 +1,127 @@
+const path = require('path');
+const fs = require('fs');
+const _ = require('lodash');
+
+const CODEGEN_TEMPLATES_FOLDER = 'templates';
+
+const canonicalFunctionName = commandName => _.camelCase(commandName);
+
+const getTemplate = templatName => {
+  const templatePath = path.join(__dirname, CODEGEN_TEMPLATES_FOLDER, templatName);
+  const template = fs.readFileSync(templatePath).toString();
+  return _.template(template, { interpolate: /<%=([\s\S]+?)%>/g });
+};
+
+/**
+ * Generates function signature docs
+ * @param {String} abstract
+ * @param {Array<{name: String, type: String, help: String}>} parameters
+ */
+const generateFunctionDocs = (abstract, parameters) => {
+  return `
+/**
+ * ${abstract}
+ * @param {Object} params
+${parameters.map(p => ` * @param {${p.type}} params.${p.name} - ${p.help}`).join('\n')}
+ */`;
+};
+
+/**
+ * Given a list of parameters of type `Parameter` generates
+ * proper CLI call signature.
+ * Parameter {
+ *  kind: option | flag | argument
+ *  name: string
+ *  type: string
+ *  help: string
+ * }
+ * @param {Array<{
+ *    name: String,
+ *    kind:"option" | "flag" | "argument"
+ *    type: String,
+ *    help: String}>} parameters
+ * @returns {Array<Array<String>>}
+ */
+const generateCommandParameters = parameters => {
+  return parameters.map(param => {
+    const { kind, name } = param;
+    const funcParamValue = `params['${name}']`;
+    let output;
+    switch (kind) {
+      case 'option':
+        output = [`if (${funcParamValue}) {`, `    command += \` --${name}=\${${funcParamValue}}\`;`, `  }`];
+        break;
+      case 'flag':
+        output = [`if (${funcParamValue}) {`, `    command += \` --${name}\`;`, `  }`];
+        break;
+      case 'argument':
+        output = [`  command += \` \${${funcParamValue}}\`;`];
+    }
+    return output;
+  });
+};
+
+/**
+ * Given a command schema generates data used in
+ * template function declaration
+ * @param {Object} commandSchema
+ * @param {String} commandSchema.abstract
+ * @param {String} commandSchema.name
+ * @param {Array} commandSchema.parameters
+ */
+const generateFunctionBodyData = commandSchema => {
+  const { abstract, name, parameters } = commandSchema;
+  return {
+    __FUNCTION_DOCS__: generateFunctionDocs(abstract, parameters),
+    __FUNCTION_NAME__: canonicalFunctionName(name),
+    __COMMAND_NAME__: name,
+    __COMMAND_PARAMS__: generateCommandParameters(parameters)
+      .map(p => `  ${p.join('\n')}`)
+      .join('\n'),
+  };
+};
+
+/**
+ * Given an `amplify-xcode` schema, generates the commonjs
+ * exported module declaration
+ * @param {Object} schema amplify-xcode schema @see amplify-xcode.json
+ */
+const generateModuleExports = schema => {
+  let output = ['module.exports = {'];
+  schema.commands.forEach(command => {
+    output.push(`  ${canonicalFunctionName(command.name)},`);
+  });
+  output.push('};');
+
+  return output;
+};
+
+/**
+ * Given an `amplify-xcode` schema, generates JS
+ * bindings to safely call `amplify-xcode`.
+ * @param {Object} schema amplify-xcode schema
+ * @param {String} outputPath generated JS bindings file path
+ */
+const generateNativeBindings = (schema, outputPath) => {
+  const preamble = getTemplate('preamble.jst')();
+  const functionTemplate = getTemplate('function.jst');
+  // generate functions body
+  let output = preamble;
+  output += schema.commands
+    .map(command => {
+      return functionTemplate(generateFunctionBodyData(command));
+    })
+    .join('');
+
+  // generate exports
+  output += '\n' + generateModuleExports(schema).join('\n') + '\n';
+
+  fs.writeFileSync(outputPath, output);
+};
+
+module.exports = {
+  generateCommandParameters,
+  generateFunctionBodyData,
+  generateModuleExports,
+  generateNativeBindings,
+};
diff --git a/packages/amplify-frontend-ios/native-bindings-codegen/templates/function.jst b/packages/amplify-frontend-ios/native-bindings-codegen/templates/function.jst
new file mode 100644
index 00000000000..f547dc4548a
--- /dev/null
+++ b/packages/amplify-frontend-ios/native-bindings-codegen/templates/function.jst
@@ -0,0 +1,6 @@
+<%= __FUNCTION_DOCS__ %>
+async function <%= __FUNCTION_NAME__ %>(params) {
+  let command = `${amplifyXcodePath()} <%= __COMMAND_NAME__ %>`;
+<%=__COMMAND_PARAMS__ %>
+  await execa.command(command, { stdout: 'inherit' });
+}
diff --git a/packages/amplify-frontend-ios/native-bindings-codegen/templates/preamble.jst b/packages/amplify-frontend-ios/native-bindings-codegen/templates/preamble.jst
new file mode 100644
index 00000000000..e048867c6fa
--- /dev/null
+++ b/packages/amplify-frontend-ios/native-bindings-codegen/templates/preamble.jst
@@ -0,0 +1,26 @@
+//
+// Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
+//
+// Licensed under the Apache License, Version 2.0 (the "License").
+// You may not use this file except in compliance with the License.
+// A copy of the License is located at
+//
+// http://aws.amazon.com/apache2.0
+//
+// or in the "license" file accompanying this file. This file is distributed
+// on an "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either
+// express or implied. See the License for the specific language governing
+// permissions and limitations under the License.
+//
+
+// ############################################################################
+// Auto-generated file using `build` NPM script. Do not edit this file manually
+// ############################################################################
+
+const execa = require('execa');
+const path = require('path');
+const { pathManager } = require('amplify-cli-core');
+
+const BINARY_PATH = 'resources/amplify-xcode';
+const PACKAGE_NAME = 'amplify-frontend-ios';
+const amplifyXcodePath = () => path.join(pathManager.getAmplifyPackageLibDirPath(PACKAGE_NAME), BINARY_PATH);
diff --git a/packages/amplify-frontend-ios/package.json b/packages/amplify-frontend-ios/package.json
index c4cc541b417..daf5d4a2494 100644
--- a/packages/amplify-frontend-ios/package.json
+++ b/packages/amplify-frontend-ios/package.json
@@ -16,13 +16,16 @@
     "aws"
   ],
   "scripts": {
+    "generate-xcode-bindings": "node ./scripts/native-bindings-gen",
     "test": "jest",
     "test-watch": "jest --watch"
   },
   "dependencies": {
-    "amplify-app": "2.23.5",
+    "amplify-cli-core": "1.21.2",
+    "execa": "^4.1.0",
     "fs-extra": "^8.1.0",
-    "graphql-config": "^2.2.1"
+    "graphql-config": "^2.2.1",
+    "lodash": "^4.17.21"
   },
   "jest": {
     "collectCoverage": true,
diff --git a/packages/amplify-frontend-ios/resources/amplify-xcode b/packages/amplify-frontend-ios/resources/amplify-xcode
new file mode 100755
index 00000000000..3209bd7b34d
Binary files /dev/null and b/packages/amplify-frontend-ios/resources/amplify-xcode differ
diff --git a/packages/amplify-frontend-ios/resources/amplify-xcode.json b/packages/amplify-frontend-ios/resources/amplify-xcode.json
new file mode 100644
index 00000000000..2d22a55fd44
--- /dev/null
+++ b/packages/amplify-frontend-ios/resources/amplify-xcode.json
@@ -0,0 +1,41 @@
+{
+  "commands": [
+    {
+      "name": "import-config",
+      "abstract": "Import Amplify configuration files",
+      "parameters": [
+        {
+          "kind": "option",
+          "name": "path",
+          "type": "String",
+          "help": "Project base path"
+        }
+      ]
+    },
+    {
+      "name": "import-models",
+      "abstract": "Import Amplify models",
+      "parameters": [
+        {
+          "kind": "option",
+          "name": "path",
+          "type": "String",
+          "help": "Project base path"
+        }
+      ]
+    },
+    {
+      "name": "generate-schema",
+      "abstract": "Generates a JSON description of the CLI and its commands",
+      "parameters": [
+        {
+          "kind": "option",
+          "name": "output-path",
+          "type": "String",
+          "help": "Path to save the output of generated schema file"
+        }
+      ]
+    }
+  ],
+  "abstract": "Auto generated JSON representation of amplify-xcode CLI"
+}
diff --git a/packages/amplify-frontend-ios/scripts/native-bindings-gen.js b/packages/amplify-frontend-ios/scripts/native-bindings-gen.js
new file mode 100644
index 00000000000..ab321026714
--- /dev/null
+++ b/packages/amplify-frontend-ios/scripts/native-bindings-gen.js
@@ -0,0 +1,12 @@
+const path = require('path');
+const fs = require('fs');
+const { generateNativeBindings } = require('../native-bindings-codegen');
+
+const OUPUT_DIR = path.join('..', 'lib');
+const SCHEMA_RELATIVE_PATH = path.join('..', 'resources', 'amplify-xcode.json');
+
+const schemaPath = path.join(__dirname, SCHEMA_RELATIVE_PATH);
+const schema = JSON.parse(fs.readFileSync(schemaPath));
+const outputPath = path.join(__dirname, OUPUT_DIR, 'amplify-xcode.js');
+
+generateNativeBindings(schema, outputPath);
diff --git a/packages/amplify-frontend-ios/tests/native-bindings-codegen.test.js b/packages/amplify-frontend-ios/tests/native-bindings-codegen.test.js
new file mode 100644
index 00000000000..f5221543707
--- /dev/null
+++ b/packages/amplify-frontend-ios/tests/native-bindings-codegen.test.js
@@ -0,0 +1,74 @@
+const { generateCommandParameters, generateFunctionBodyData, generateModuleExports } = require('../native-bindings-codegen');
+
+describe('amplify-xcode native bindings codegen', () => {
+  describe('should generate command parameters list', () => {
+    it('option', () => {
+      const param = {
+        name: 'option-name',
+        kind: 'option',
+      };
+      const expected = [[`if (params['${param.name}']) {`, `    command += \` --${param.name}=\${params['${param.name}']}\`;`, `  }`]];
+      expect(generateCommandParameters([param])).toEqual(expected);
+    });
+
+    it('flag', () => {
+      const param = {
+        name: 'flagName',
+        kind: 'flag',
+      };
+      const expected = [[`if (params['${param.name}']) {`, `    command += \` --${param.name}\`;`, `  }`]];
+      expect(generateCommandParameters([param])).toEqual(expected);
+    });
+
+    it('argument', () => {
+      const param = {
+        name: 'argName',
+        kind: 'argument',
+      };
+      const expected = [["  command += ` ${params['argName']}`;"]];
+      expect(generateCommandParameters([param])).toEqual(expected);
+    });
+  });
+
+  describe('Functions bindings', () => {
+    it('should generate functions template data', () => {
+      const commandParam = {
+        name: 'option-name',
+        kind: 'option',
+        type: 'String',
+        help: 'Option description',
+      };
+      const commandSchema = {
+        name: 'command-name',
+        abstract: 'Command abstract',
+        parameters: [commandParam],
+      };
+      const expectedDocs = `
+/**
+ * ${commandSchema.abstract}
+ * @param {Object} params
+ * @param {String} params.${commandParam.name} - ${commandParam.help}
+ */`;
+      const result = generateFunctionBodyData(commandSchema);
+      expect(result.__FUNCTION_NAME__).toEqual('commandName');
+      expect(result.__FUNCTION_DOCS__).toEqual(expectedDocs);
+      expect(result.__COMMAND_NAME__).toEqual(commandSchema.name);
+    });
+
+    it('should generate commonjs module exports', () => {
+      const command1 = {
+        name: 'command-name',
+        abstract: 'Command abstract',
+      };
+      const command2 = {
+        name: 'another-command-name',
+        abstract: 'Another command abstract',
+      };
+      const schema = {
+        commands: [command1, command2],
+      };
+      const result = generateModuleExports(schema);
+      expect(result).toEqual(['module.exports = {', '  commandName,', '  anotherCommandName,', '};']);
+    });
+  });
+});
diff --git a/packages/amplify-python-function-runtime-provider/package.json b/packages/amplify-python-function-runtime-provider/package.json
index 647de320071..d9ff66f6150 100644
--- a/packages/amplify-python-function-runtime-provider/package.json
+++ b/packages/amplify-python-function-runtime-provider/package.json
@@ -26,6 +26,7 @@
     "archiver": "^3.1.1",
     "execa": "^4.1.0",
     "glob": "^7.1.6",
+    "ini": "^1.3.5",
     "semver": "^7.1.3",
     "which": "^2.0.2"
   },
diff --git a/packages/amplify-python-function-runtime-provider/src/util/pyUtils.ts b/packages/amplify-python-function-runtime-provider/src/util/pyUtils.ts
index 1b9ce1f79b5..961b40fb12a 100644
--- a/packages/amplify-python-function-runtime-provider/src/util/pyUtils.ts
+++ b/packages/amplify-python-function-runtime-provider/src/util/pyUtils.ts
@@ -3,6 +3,7 @@ import fs from 'fs-extra';
 import { ExecOptions } from 'child_process';
 import execa from 'execa';
 import * as which from 'which';
+import { parse } from 'ini';
 
 // Gets the pipenv dir where this function's dependencies are located
 export async function getPipenvDir(srcRoot: string): Promise<string> {
@@ -13,8 +14,7 @@ export async function getPipenvDir(srcRoot: string): Promise<string> {
     throw new Error(`Could not find 'python3' or 'python' executable in the PATH.`);
   }
 
-  const pyVersion = await execAsStringPromise(`${pyBinary} --version`);
-  let pipEnvPath = path.join(pipEnvDir, 'lib', 'python' + majMinPyVersion(pyVersion), 'site-packages');
+  let pipEnvPath = path.join(pipEnvDir, 'lib', `python${getPipfilePyVersion(path.join(srcRoot, 'Pipfile'))}`, 'site-packages');
   if (process.platform.startsWith('win')) {
     pipEnvPath = path.join(pipEnvDir, 'Lib', 'site-packages');
   }
@@ -29,10 +29,7 @@ export function majMinPyVersion(pyVersion: string): string {
     throw new Error(`Cannot interpret Python version "${pyVersion}"`);
   }
   const versionNum = pyVersion.split(' ')[1];
-  return versionNum
-    .split('.')
-    .slice(0, 2)
-    .join('.');
+  return versionNum.split('.').slice(0, 2).join('.');
 }
 
 // wrapper for executing a shell command and returning the result as a string promise
@@ -65,3 +62,12 @@ export const getPythonBinaryName = (): string | undefined => {
     }
   }
 };
+
+const getPipfilePyVersion = (pipfilePath: string) => {
+  const pipfile = parse(fs.readFileSync(pipfilePath, 'utf-8'));
+  const version = pipfile?.requires?.python_version;
+  if (!version) {
+    throw new Error(`Did not find Python version specified in ${pipfilePath}`);
+  }
+  return version as string;
+};