diff --git a/packages/aws-cdk/test/integ/init/test-typescript-versions.sh b/packages/aws-cdk/test/integ/init/test-typescript-versions.sh
new file mode 100755
index 0000000000000..8df00129a7bff
--- /dev/null
+++ b/packages/aws-cdk/test/integ/init/test-typescript-versions.sh
@@ -0,0 +1,29 @@
+#!/bin/bash
+#------------------------------------------------------------------
+# setup
+#------------------------------------------------------------------
+set -eu
+scriptdir=$(cd $(dirname $0) && pwd)
+integdir=$(dirname $scriptdir)
+source ${scriptdir}/common.bash
+
+header TypeScript Versions
+
+#------------------------------------------------------------------
+
+MIN_SUPPORTED_TS_VERSION=${1:-"3.9"}
+SUPPORTED_TS_VERSIONS=$(node ${integdir}/typescript-versions.js ${MIN_SUPPORTED_TS_VERSION})
+
+for version in $SUPPORTED_TS_VERSIONS; do
+    echo "Testing against TypeScript v$version"
+
+    setup
+
+    cdk init -l typescript sample-app --generate-only
+    npm pkg delete devDependencies
+    npm install --save-dev typescript@$version
+    npm prune && npm ls
+    rm test/*
+    npm run build
+    cdk synth
+done
diff --git a/packages/aws-cdk/test/integ/typescript-versions.ts b/packages/aws-cdk/test/integ/typescript-versions.ts
new file mode 100644
index 0000000000000..cf86653b99793
--- /dev/null
+++ b/packages/aws-cdk/test/integ/typescript-versions.ts
@@ -0,0 +1,10 @@
+import { spawnSync } from 'child_process';
+
+const minSupportedVersion = process.argv.slice(2, 3);
+
+const { stdout } = spawnSync('npm', ['--silent', 'view', `typescript@>=${minSupportedVersion}`, 'version', '--json']);
+
+const versions: string[] = JSON.parse(stdout);
+const minorVersions = Array.from(new Set(versions.map(v => v.split('.').slice(0, 2).join('.'))));
+
+process.stdout.write(minorVersions.join(' '));