diff --git a/packages/jsii-pacmak/lib/targets/python.ts b/packages/jsii-pacmak/lib/targets/python.ts
index f07e1db1d7..cdc79f73e5 100644
--- a/packages/jsii-pacmak/lib/targets/python.ts
+++ b/packages/jsii-pacmak/lib/targets/python.ts
@@ -1,5 +1,5 @@
-import path = require('path');
-
+import * as path from 'path';
+import * as semver from 'semver';
 import { CodeMaker, toSnakeCase } from 'codemaker';
 import * as escapeStringRegexp from 'escape-string-regexp';
 import * as reflect from 'jsii-reflect';
@@ -1161,17 +1161,21 @@ class Package {
     const expectedDeps = this.metadata.dependencies ?? {};
     for (const depName of Object.keys(expectedDeps)) {
       const depInfo = expectedDeps[depName];
-      // We need to figure out what our version range is.
-      // Basically, if it starts with Zero we want to restrict things to
-      // ~=X.Y.Z. If it does not start with zero, then we want to do ~=X.Y,>=X.Y.Z.
-      const versionParts = depInfo.version.split('.');
-      let versionSpecifier: string;
-      if (versionParts[0] === '0') {
-        versionSpecifier = `~=${versionParts.slice(0, 3).join('.')}`;
+      const { version } = depInfo;
+
+      // Parse either a single version or version range.
+      const parsedVersion = semver.valid(version);
+      const parsedVersionRange = semver.validRange(version);
+      let versionSpecifier;
+
+      // Convert parsed version info to expected format
+      if (parsedVersion) {
+        versionSpecifier = `==${version}`;
+      } else if (parsedVersionRange) {
+        versionSpecifier = parsedVersionRange.replace(' ', ', ');
       } else {
-        versionSpecifier = `~=${versionParts.slice(0, 2).join('.')},>=${versionParts.slice(0, 3).join('.')}`;
+        throw new Error(`Unexpected version format '${version}' for dependency: 'depName'`);
       }
-
       dependencies.push(`${depInfo.targets!.python!.distName}${versionSpecifier}`);
     }
 
diff --git a/packages/jsii-pacmak/package.json b/packages/jsii-pacmak/package.json
index 65743d777c..5f0610cbf8 100644
--- a/packages/jsii-pacmak/package.json
+++ b/packages/jsii-pacmak/package.json
@@ -42,6 +42,7 @@
     "jsii-reflect": "^0.20.8",
     "jsii-rosetta": "^0.20.8",
     "jsii-spec": "^0.20.8",
+    "semver": "^6.3.0",
     "spdx-license-list": "^6.1.0",
     "xmlbuilder": "^13.0.2",
     "yargs": "^15.0.2"
@@ -54,6 +55,7 @@
     "@types/jest": "^24.0.23",
     "@types/mock-fs": "^4.10.0",
     "@types/node": "^10.17.6",
+    "@types/semver": "^6.2.0",
     "@types/yargs": "^13.0.3",
     "@typescript-eslint/eslint-plugin": "^2.9.0",
     "@typescript-eslint/parser": "^2.9.0",
diff --git a/packages/jsii-pacmak/test/expected.jsii-calc-base/python/setup.py b/packages/jsii-pacmak/test/expected.jsii-calc-base/python/setup.py
index 6447be1672..815faa8474 100644
--- a/packages/jsii-pacmak/test/expected.jsii-calc-base/python/setup.py
+++ b/packages/jsii-pacmak/test/expected.jsii-calc-base/python/setup.py
@@ -32,7 +32,7 @@
     "install_requires": [
         "jsii~=0.20.8",
         "publication>=0.0.3",
-        "scope.jsii-calc-base-of-base~=0.20.8"
+        "scope.jsii-calc-base-of-base==0.20.8"
     ],
     "classifiers": [
         "Intended Audience :: Developers",
diff --git a/packages/jsii-pacmak/test/expected.jsii-calc-lib/python/setup.py b/packages/jsii-pacmak/test/expected.jsii-calc-lib/python/setup.py
index b09f751913..cea84cea21 100644
--- a/packages/jsii-pacmak/test/expected.jsii-calc-lib/python/setup.py
+++ b/packages/jsii-pacmak/test/expected.jsii-calc-lib/python/setup.py
@@ -32,7 +32,7 @@
     "install_requires": [
         "jsii~=0.20.8",
         "publication>=0.0.3",
-        "scope.jsii-calc-base~=0.20.8"
+        "scope.jsii-calc-base==0.20.8"
     ],
     "classifiers": [
         "Intended Audience :: Developers",
diff --git a/packages/jsii-pacmak/test/expected.jsii-calc/python/setup.py b/packages/jsii-pacmak/test/expected.jsii-calc/python/setup.py
index 4a002726f2..74e31a0518 100644
--- a/packages/jsii-pacmak/test/expected.jsii-calc/python/setup.py
+++ b/packages/jsii-pacmak/test/expected.jsii-calc/python/setup.py
@@ -32,9 +32,9 @@
     "install_requires": [
         "jsii~=0.20.8",
         "publication>=0.0.3",
-        "scope.jsii-calc-base~=0.20.8",
-        "scope.jsii-calc-base-of-base~=0.20.8",
-        "scope.jsii-calc-lib~=0.20.8"
+        "scope.jsii-calc-base==0.20.8",
+        "scope.jsii-calc-base-of-base==0.20.8",
+        "scope.jsii-calc-lib==0.20.8"
     ],
     "classifiers": [
         "Intended Audience :: Developers",