diff --git a/packages/jsii-pacmak/test/generated-code/harness.ts b/packages/jsii-pacmak/test/generated-code/harness.ts
index 4ca7fb43da..92098e81e1 100644
--- a/packages/jsii-pacmak/test/generated-code/harness.ts
+++ b/packages/jsii-pacmak/test/generated-code/harness.ts
@@ -280,10 +280,15 @@ async function runPacmak(
 
 export async function preparePythonVirtualEnv({
   install = [],
+  installOptions = [],
   venvDir = __dirname,
   systemSitePackages = true,
 }: {
   install?: readonly string[];
+  // some options like `--config-settings` should only be
+  // passed once. If they are passed multiple times
+  // then it registers as an array with multiple values
+  installOptions?: readonly string[];
   venvDir?: string;
   systemSitePackages?: boolean;
 } = {}) {
@@ -345,6 +350,7 @@ export async function preparePythonVirtualEnv({
         'pip',
         'install',
         '--no-input',
+        ...installOptions,
         // Additional install parameters
         ...install,
         // Note: this resolution is a little ugly, but it's there to avoid creating a dependency cycle
diff --git a/packages/jsii-pacmak/test/generated-code/python-pyright.test.ts b/packages/jsii-pacmak/test/generated-code/python-pyright.test.ts
index 40d29f1e60..a06a7eeb77 100644
--- a/packages/jsii-pacmak/test/generated-code/python-pyright.test.ts
+++ b/packages/jsii-pacmak/test/generated-code/python-pyright.test.ts
@@ -48,11 +48,13 @@ beforeAll(async () => {
     install: TEST_PACKAGES.flatMap(({ moduleName }) => [
       '-e',
       JSON.stringify(path.join(pythonSource, moduleName, TargetName.PYTHON)),
+    ]),
+    installOptions: [
       // setuptools >=64 requires this
       // https://github.com/pypa/setuptools/issues/3518
       '--config-settings',
       'editable_mode=strict',
-    ]),
+    ],
     venvDir: pythonSource,
     systemSitePackages: false, // Interferes with pyright resolutions...
   });
diff --git a/packages/jsii-pacmak/test/generated-code/requirements-dev.txt b/packages/jsii-pacmak/test/generated-code/requirements-dev.txt
index f2cd70f3d0..a1c43aa24a 100644
--- a/packages/jsii-pacmak/test/generated-code/requirements-dev.txt
+++ b/packages/jsii-pacmak/test/generated-code/requirements-dev.txt
@@ -1,2 +1,2 @@
 mypy==1.3.0
-pip==23.0.1 # required to use --config-settings
+pip==23.1.2 # required to use --config-settings