diff --git a/packages/@jsii/python-runtime/setup.py b/packages/@jsii/python-runtime/setup.py
index d735772c62..b22dbea4b5 100644
--- a/packages/@jsii/python-runtime/setup.py
+++ b/packages/@jsii/python-runtime/setup.py
@@ -34,7 +34,8 @@
         "cattrs>=1.8,<24.2",
         "importlib_resources>=5.2.0",
         "publication>=0.0.3",  # This is used by all generated code.
-        "typeguard>=2.13.3,<5.0.0",  # This is used by all generated code.
+        # 4.3.0 is incompatible with generated bindings, see https://github.com/aws/jsii/issues/4658
+        "typeguard>=2.13.3,<4.3.0",  # This is used by all generated code.
         "python-dateutil",
         "typing_extensions>=3.8,<5.0",
     ],
diff --git a/packages/jsii-pacmak/lib/targets/python.ts b/packages/jsii-pacmak/lib/targets/python.ts
index 938f0aea2b..75226ca26c 100644
--- a/packages/jsii-pacmak/lib/targets/python.ts
+++ b/packages/jsii-pacmak/lib/targets/python.ts
@@ -1730,7 +1730,9 @@ class PythonModule implements PythonType {
     code.line();
 
     code.line('import typeguard');
-    code.line('from importlib.metadata import version as _metadata_package_version');
+    code.line(
+      'from importlib.metadata import version as _metadata_package_version',
+    );
     code.line(
       "TYPEGUARD_MAJOR_VERSION = int(_metadata_package_version('typeguard').split('.')[0])",
     );
@@ -2166,7 +2168,8 @@ class Package {
       install_requires: [
         `jsii${toPythonVersionRange(`^${VERSION}`)}`,
         'publication>=0.0.3',
-        'typeguard>=2.13.3,<5.0.0',
+        // 4.3.0 is incompatible with generated bindings, see https://github.com/aws/jsii/issues/4658
+        'typeguard>=2.13.3,<4.3.0',
       ]
         .concat(dependencies)
         .sort(),
diff --git a/packages/jsii-pacmak/test/generated-code/__snapshots__/examples.test.js.snap b/packages/jsii-pacmak/test/generated-code/__snapshots__/examples.test.js.snap
index e336eb85d5..3e81e47dd8 100644
--- a/packages/jsii-pacmak/test/generated-code/__snapshots__/examples.test.js.snap
+++ b/packages/jsii-pacmak/test/generated-code/__snapshots__/examples.test.js.snap
@@ -1270,7 +1270,7 @@ kwargs = json.loads(
     "install_requires": [
         "jsii<0.0.1",
         "publication>=0.0.3",
-        "typeguard>=2.13.3,<5.0.0"
+        "typeguard>=2.13.3,<4.3.0"
     ],
     "classifiers": [
         "Intended Audience :: Developers",
@@ -2727,7 +2727,7 @@ kwargs = json.loads(
     "install_requires": [
         "jsii<0.0.1",
         "publication>=0.0.3",
-        "typeguard>=2.13.3,<5.0.0"
+        "typeguard>=2.13.3,<4.3.0"
     ],
     "classifiers": [
         "Intended Audience :: Developers",
diff --git a/packages/jsii-pacmak/test/generated-code/__snapshots__/prerelease-identifiers.test.js.snap b/packages/jsii-pacmak/test/generated-code/__snapshots__/prerelease-identifiers.test.js.snap
index 28b1cecf14..82ade498b9 100644
--- a/packages/jsii-pacmak/test/generated-code/__snapshots__/prerelease-identifiers.test.js.snap
+++ b/packages/jsii-pacmak/test/generated-code/__snapshots__/prerelease-identifiers.test.js.snap
@@ -459,7 +459,7 @@ kwargs = json.loads(
         "bar>=2.0.0.rc42, <3.0.0",
         "jsii<0.0.1",
         "publication>=0.0.3",
-        "typeguard>=2.13.3,<5.0.0"
+        "typeguard>=2.13.3,<4.3.0"
     ],
     "classifiers": [
         "Intended Audience :: Developers",
@@ -991,7 +991,7 @@ kwargs = json.loads(
         "bar>=4.5.6.dev1337, <5.0.0",
         "jsii<0.0.1",
         "publication>=0.0.3",
-        "typeguard>=2.13.3,<5.0.0"
+        "typeguard>=2.13.3,<4.3.0"
     ],
     "classifiers": [
         "Intended Audience :: Developers",
@@ -1502,7 +1502,7 @@ kwargs = json.loads(
     "install_requires": [
         "jsii<0.0.1",
         "publication>=0.0.3",
-        "typeguard>=2.13.3,<5.0.0"
+        "typeguard>=2.13.3,<4.3.0"
     ],
     "classifiers": [
         "Intended Audience :: Developers",
@@ -2011,7 +2011,7 @@ kwargs = json.loads(
     "install_requires": [
         "jsii<0.0.1",
         "publication>=0.0.3",
-        "typeguard>=2.13.3,<5.0.0"
+        "typeguard>=2.13.3,<4.3.0"
     ],
     "classifiers": [
         "Intended Audience :: Developers",
diff --git a/packages/jsii-pacmak/test/generated-code/__snapshots__/target-python.test.js.snap b/packages/jsii-pacmak/test/generated-code/__snapshots__/target-python.test.js.snap
index f678c870ee..e67b662154 100644
--- a/packages/jsii-pacmak/test/generated-code/__snapshots__/target-python.test.js.snap
+++ b/packages/jsii-pacmak/test/generated-code/__snapshots__/target-python.test.js.snap
@@ -294,7 +294,7 @@ kwargs = json.loads(
         "jsii<0.0.1",
         "publication>=0.0.3",
         "scope.jsii-calc-base-of-base>=2.1.1, <3.0.0",
-        "typeguard>=2.13.3,<5.0.0"
+        "typeguard>=2.13.3,<4.3.0"
     ],
     "classifiers": [
         "Intended Audience :: Developers",
@@ -883,7 +883,7 @@ kwargs = json.loads(
     "install_requires": [
         "jsii<0.0.1",
         "publication>=0.0.3",
-        "typeguard>=2.13.3,<5.0.0"
+        "typeguard>=2.13.3,<4.3.0"
     ],
     "classifiers": [
         "Intended Audience :: Developers",
@@ -1450,7 +1450,7 @@ kwargs = json.loads(
         "publication>=0.0.3",
         "scope.jsii-calc-base-of-base>=2.1.1, <3.0.0",
         "scope.jsii-calc-base<0.0.1",
-        "typeguard>=2.13.3,<5.0.0"
+        "typeguard>=2.13.3,<4.3.0"
     ],
     "classifiers": [
         "Intended Audience :: Developers",
@@ -3219,7 +3219,7 @@ kwargs = json.loads(
         "publication>=0.0.3",
         "scope.jsii-calc-base<0.0.1",
         "scope.jsii-calc-lib<0.0.1",
-        "typeguard>=2.13.3,<5.0.0"
+        "typeguard>=2.13.3,<4.3.0"
     ],
     "classifiers": [
         "Intended Audience :: Developers",