diff --git a/docs/configuration.md b/docs/configuration.md
index 025267c230..3998e199bd 100644
--- a/docs/configuration.md
+++ b/docs/configuration.md
@@ -154,6 +154,22 @@ The `python` target requires two configuration entries:
 * `module` - the name of the generated **Python** module, which will be used by
   users in `import` directives.
 * `distName` - the [PyPI] distribution name for the package.
+* `classifiers` - a list of [trove classifiers] to declare on the package. It is
+  the user's responsibility to specify *valid* values (the authoritative list of
+  valid [trove classifiers] is masted in the [pypa/trove-classifiers] package).
+  * Some classifiers are automatically included (and should not be added to the
+  `classifiers` property) based on relevant configuration from the
+  `package.json` file:
+    * `Development Status :: ` is determined based on the package's `stability`
+    * `License ::` is determined based on the package's `license`
+    * `Operating System :: OS Independent` is always set
+    * `Typing :: Typed` is always set
+  * Additionally, the following `Programming Language ::` classifiers are
+    already set (more could be added by the user if relevant):
+    * `Programming Language :: Python :: 3 :: Only`
+    * `Programming Language :: Python :: 3.6`
+    * `Programming Language :: Python :: 3.7`
+    * `Programming Language :: Python :: 3.8`
 
 Example:
 ```js
@@ -162,7 +178,11 @@ Example:
     "targets": {
       "python": {
         "module": "hello_jsii",   // Required
-        "distName": "hello-jsii"  // Required
+        "distName": "hello-jsii", // Required
+        "classifiers": [          // Optional
+          "Framework :: AWS CDK",
+          "Framework :: AWS CDK :: 1"
+        ]
       },
       // ...
     }
@@ -175,6 +195,8 @@ Example:
 The resulting package can be published to [PyPI].
 
 [PyPI]: https://pypi.org/
+[trove classifiers]: https://www.python.org/dev/peps/pep-0301/#distutils-trove-classification
+[pypa/trove-classifiers]: https://github.com/pypa/trove-classifiers
 
 #### Configuring `Java`
 
diff --git a/packages/@jsii/kernel/test/kernel.test.ts b/packages/@jsii/kernel/test/kernel.test.ts
index e8ab48b1ee..504bcb724a 100644
--- a/packages/@jsii/kernel/test/kernel.test.ts
+++ b/packages/@jsii/kernel/test/kernel.test.ts
@@ -406,7 +406,11 @@ defineTest(
         },
       },
       js: { npm: 'jsii-calc' },
-      python: { distName: 'jsii-calc', module: 'jsii_calc' },
+      python: {
+        distName: 'jsii-calc',
+        module: 'jsii_calc',
+        classifiers: ['Test :: Classifier :: Is Dummy'],
+      },
     });
     expect(sandbox.naming({ assembly: '@scope/jsii-calc-lib' }).naming).toEqual(
       {
diff --git a/packages/jsii-calc/package.json b/packages/jsii-calc/package.json
index 99de1914a7..96561044ad 100644
--- a/packages/jsii-calc/package.json
+++ b/packages/jsii-calc/package.json
@@ -73,7 +73,10 @@
       },
       "python": {
         "distName": "jsii-calc",
-        "module": "jsii_calc"
+        "module": "jsii_calc",
+        "classifiers": [
+          "Test :: Classifier :: Is Dummy"
+        ]
       }
     },
     "metadata": {
diff --git a/packages/jsii-calc/test/assembly.jsii b/packages/jsii-calc/test/assembly.jsii
index fc62bbbf1a..321c8da7f6 100644
--- a/packages/jsii-calc/test/assembly.jsii
+++ b/packages/jsii-calc/test/assembly.jsii
@@ -247,6 +247,9 @@
       "npm": "jsii-calc"
     },
     "python": {
+      "classifiers": [
+        "Test :: Classifier :: Is Dummy"
+      ],
       "distName": "jsii-calc",
       "module": "jsii_calc"
     }
@@ -13819,5 +13822,5 @@
     }
   },
   "version": "0.0.0",
-  "fingerprint": "NsqdwWgXi+kjrpLQtQ27eA/znULJ7TtXy03ht68N9Ms="
+  "fingerprint": "TXGVwLZ10oZ08NxDzu6i+fqPtaw5aEqME8+d+KEhL08="
 }
diff --git a/packages/jsii-pacmak/lib/targets/python.ts b/packages/jsii-pacmak/lib/targets/python.ts
index fc56f31e62..8450c28ca0 100644
--- a/packages/jsii-pacmak/lib/targets/python.ts
+++ b/packages/jsii-pacmak/lib/targets/python.ts
@@ -1709,10 +1709,54 @@ class Package {
       setupKwargs.classifiers.push('License :: OSI Approved');
     }
 
+    const additionalClassifiers = this.metadata.targets?.python?.classifiers;
+    if (additionalClassifiers != null) {
+      if (!Array.isArray(additionalClassifiers)) {
+        throw new Error(
+          `The "jsii.targets.python.classifiers" value must be an array of strings if provided, but found ${JSON.stringify(
+            additionalClassifiers,
+            null,
+            2,
+          )}`,
+        );
+      }
+      // We discourage using those since we automatically set a value for them
+      for (let classifier of additionalClassifiers.sort()) {
+        if (typeof classifier !== 'string') {
+          throw new Error(
+            `The "jsii.targets.python.classifiers" value can only contain strings, but found ${JSON.stringify(
+              classifier,
+              null,
+              2,
+            )}`,
+          );
+        }
+        // We'll split on `::` and re-join later so classifiers are "normalized" to a standard spacing
+        const parts = classifier.split('::').map((part) => part.trim());
+        const reservedClassifiers = [
+          'Development Status',
+          'License',
+          'Operating System',
+          'Typing',
+        ];
+        if (reservedClassifiers.includes(parts[0])) {
+          warn(
+            `Classifiers starting with ${reservedClassifiers
+              .map((x) => `"${x} ::"`)
+              .join(
+                ', ',
+              )} are automatically set and should not be manually configured`,
+          );
+        }
+        classifier = parts.join(' :: ');
+        if (setupKwargs.classifiers.includes(classifier)) {
+          continue;
+        }
+        setupKwargs.classifiers.push(classifier);
+      }
+    }
+
     // We Need a setup.py to make this Package, actually a Package.
-    // TODO:
-    //      - License
-    //      - Classifiers
     code.openFile('setup.py');
     code.line('import json');
     code.line('import setuptools');
diff --git a/packages/jsii-pacmak/test/__snapshots__/jsii-pacmak.test.ts.snap b/packages/jsii-pacmak/test/__snapshots__/jsii-pacmak.test.ts.snap
index f428ff92a9..2618d8b6bf 100644
--- a/packages/jsii-pacmak/test/__snapshots__/jsii-pacmak.test.ts.snap
+++ b/packages/jsii-pacmak/test/__snapshots__/jsii-pacmak.test.ts.snap
@@ -7100,6 +7100,9 @@ exports[`Generated code for "jsii-calc": <outDir>/dotnet/Amazon.JSII.Tests.Calcu
       "npm": "jsii-calc"
     },
     "python": {
+      "classifiers": [
+        "Test :: Classifier :: Is Dummy"
+      ],
       "distName": "jsii-calc",
       "module": "jsii_calc"
     }
@@ -20672,7 +20675,7 @@ exports[`Generated code for "jsii-calc": <outDir>/dotnet/Amazon.JSII.Tests.Calcu
     }
   },
   "version": "0.0.0",
-  "fingerprint": "NsqdwWgXi+kjrpLQtQ27eA/znULJ7TtXy03ht68N9Ms="
+  "fingerprint": "TXGVwLZ10oZ08NxDzu6i+fqPtaw5aEqME8+d+KEhL08="
 }
 
 `;
@@ -55774,7 +55777,8 @@ kwargs = json.loads(
         "Programming Language :: Python :: 3.8",
         "Typing :: Typed",
         "Development Status :: 4 - Beta",
-        "License :: OSI Approved"
+        "License :: OSI Approved",
+        "Test :: Classifier :: Is Dummy"
     ]
 }
 """