diff --git a/.github/workflows/yarn-upgrade.yml b/.github/workflows/yarn-upgrade.yml
index dc037202423fd..c2fe94062d081 100644
--- a/.github/workflows/yarn-upgrade.yml
+++ b/.github/workflows/yarn-upgrade.yml
@@ -13,7 +13,6 @@ jobs:
       contents: read
     runs-on: ubuntu-latest
     steps:
-
       - name: Check Out
         uses: actions/checkout@v4
 
@@ -53,16 +52,17 @@ jobs:
         # Upgrade special cases:
         # - Various `@types/*` packages need to be pinned to specific versions due to breaking changes in minor upgrades https://github.com/DefinitelyTyped/DefinitelyTyped/issues/64266
         # - `typescript` is not semantically versioned, so we only upgrade the patch version
+        # - `jsii`, `jsii-rosetta` is not semantically versioned and needs to be upgrades alongside typescript
         # - `constructs` because we need to stay in control of the minimum compatible version
         # - `aws-sdk-mock` because of breaking changes in type exports https://github.com/dwyl/aws-sdk-mock/pull/260. We are not respecting `@ts-ignore`.
         # - `@aws-cdk/aws-service-spec` and `@aws-cdk/service-spec-types` have their own update workflow
         run: |-
           # Upgrade dependencies at repository root
-          ncu --upgrade --filter=typescript --target=patch
-          ncu --upgrade --reject=@types/node,@types/prettier,constructs,typescript --target=minor
+          ncu --upgrade --filter=jsii,jsii-rosetta,typescript --target=patch
+          ncu --upgrade --reject=@types/node,@types/prettier,constructs,jsii,jsii-rosetta,typescript --target=minor
           # Upgrade all the packages
-          lerna exec --parallel ncu -- --upgrade --filter=typescript --target=patch
-          lerna exec --parallel ncu -- --upgrade --reject='@types/conventional-commits-parser,@types/node,@types/prettier,constructs,typescript,aws-sdk-mock,@aws-sdk/*,@aws-cdk/aws-service-spec,@aws-cdk/service-spec-types,${{ steps.list-packages.outputs.list }}' --target=minor
+          lerna exec --parallel ncu -- --upgrade --filter=jsii,jsii-rosetta,typescript --target=patch
+          lerna exec --parallel ncu -- --upgrade --reject='@types/conventional-commits-parser,@types/node,@types/prettier,constructs,jsii,jsii-rosetta,typescript,aws-sdk-mock,@aws-sdk/*,@aws-cdk/aws-service-spec,@aws-cdk/service-spec-types,${{ steps.list-packages.outputs.list }}' --target=minor
           # Upgrade package.json files in init templates
           for pj in $(find packages/aws-cdk/lib/init-templates -name package.json); do
             (cd $(dirname $pj) && ncu --upgrade --reject='constructs,${{ steps.list-packages.outputs.list }}')
diff --git a/package.json b/package.json
index c511d639131c6..f2b270e93dad5 100644
--- a/package.json
+++ b/package.json
@@ -20,7 +20,7 @@
     "@types/prettier": "2.6.0",
     "@yarnpkg/lockfile": "^1.1.0",
     "aws-sdk-js-codemod": "^0.28.2",
-    "cdk-generate-synthetic-examples": "^0.1.309",
+    "cdk-generate-synthetic-examples": "^0.2.0",
     "conventional-changelog-cli": "^2.2.2",
     "fs-extra": "^9.1.0",
     "graceful-fs": "^4.2.11",
@@ -28,7 +28,6 @@
     "jsii-diff": "1.97.0",
     "jsii-pacmak": "1.97.0",
     "jsii-reflect": "1.97.0",
-    "jsii-rosetta": "~5.4.2",
     "lerna": "^8.1.2",
     "nx": "^18.3.1",
     "patch-package": "^6.5.1",
@@ -36,7 +35,7 @@
     "standard-version": "^9.5.0",
     "ts-jest": "^29.1.2",
     "ts-node": "^10.9.2",
-    "typescript": "~5.1.6"
+    "typescript": "~5.4.5"
   },
   "resolutions": {
     "colors": "1.4.0",
diff --git a/packages/aws-cdk-lib/package.json b/packages/aws-cdk-lib/package.json
index 40bbff2be61ef..2bab74bb40802 100644
--- a/packages/aws-cdk-lib/package.json
+++ b/packages/aws-cdk-lib/package.json
@@ -183,7 +183,7 @@
     "sinon": "^9.2.4",
     "ts-mock-imports": "^1.3.8",
     "ts-node": "^10.9.2",
-    "typescript": "~5.1.6",
+    "typescript": "~5.4.5",
     "typescript-json-schema": "^0.63.0"
   },
   "peerDependencies": {
diff --git a/packages/awslint/package.json b/packages/awslint/package.json
index 469b11a7ea3a1..b09950719f81b 100644
--- a/packages/awslint/package.json
+++ b/packages/awslint/package.json
@@ -39,7 +39,7 @@
     "eslint-plugin-import": "^2.29.1",
     "eslint-plugin-jest": "^24.7.0",
     "jest": "^29.7.0",
-    "typescript": "~5.1.6"
+    "typescript": "~5.4.5"
   },
   "repository": {
     "type": "git",
diff --git a/tools/@aws-cdk/cdk-build-tools/package.json b/tools/@aws-cdk/cdk-build-tools/package.json
index be482129710cb..5aeea5635c107 100644
--- a/tools/@aws-cdk/cdk-build-tools/package.json
+++ b/tools/@aws-cdk/cdk-build-tools/package.json
@@ -60,14 +60,15 @@
     "glob": "^7.2.3",
     "jest": "^29.7.0",
     "jest-junit": "^13.2.0",
-    "jsii": "~5.4.3",
+    "jsii": "~5.4.6",
+    "jsii-rosetta": "~5.4.6",
     "jsii-pacmak": "1.97.0",
     "jsii-reflect": "1.97.0",
     "markdownlint-cli": "^0.39.0",
     "nyc": "^15.1.0",
     "semver": "^7.6.0",
     "ts-jest": "^29.1.2",
-    "typescript": "~5.1.6",
+    "typescript": "~5.4.5",
     "yargs": "^16.2.0"
   },
   "keywords": [
diff --git a/tools/@aws-cdk/eslint-plugin/package.json b/tools/@aws-cdk/eslint-plugin/package.json
index 4b310380f1efd..fd53d24b13694 100644
--- a/tools/@aws-cdk/eslint-plugin/package.json
+++ b/tools/@aws-cdk/eslint-plugin/package.json
@@ -19,7 +19,7 @@
     "@types/jest": "^29.5.12",
     "@types/estree": "*",
     "jest": "^29.7.0",
-    "typescript": "~5.1.6"
+    "typescript": "~5.4.5"
   },
   "dependencies": {
     "@typescript-eslint/parser": "^6.21.0",
diff --git a/tools/@aws-cdk/lazify/package.json b/tools/@aws-cdk/lazify/package.json
index dc88425423955..e2113599a542a 100644
--- a/tools/@aws-cdk/lazify/package.json
+++ b/tools/@aws-cdk/lazify/package.json
@@ -20,7 +20,7 @@
     "@aws-cdk/cdk-build-tools": "0.0.0",
     "jest": "^29",
     "ts-jest": "^29",
-    "typescript": "^4.5.5",
+    "typescript": "~5.4.5",
     "cjs-module-lexer": "^1.2.3"
   },
   "dependencies": {
@@ -30,4 +30,4 @@
   },
   "main": "lib/index.js",
   "license": "Apache-2.0"
-}
\ No newline at end of file
+}
diff --git a/tools/@aws-cdk/node-bundle/package.json b/tools/@aws-cdk/node-bundle/package.json
index 83c71114c626b..c48d0be3fec42 100644
--- a/tools/@aws-cdk/node-bundle/package.json
+++ b/tools/@aws-cdk/node-bundle/package.json
@@ -28,7 +28,7 @@
     "npm-check-updates": "^16",
     "standard-version": "^9",
     "ts-jest": "^29",
-    "typescript": "^4.5.5"
+    "typescript": "~5.4.5"
   },
   "dependencies": {
     "esbuild": "^0.20.2",
@@ -87,4 +87,4 @@
   },
   "types": "lib/index.d.ts",
   "private": true
-}
\ No newline at end of file
+}
diff --git a/tools/@aws-cdk/pkglint/package.json b/tools/@aws-cdk/pkglint/package.json
index f67b1e2636f91..1c6e5c3c30efc 100644
--- a/tools/@aws-cdk/pkglint/package.json
+++ b/tools/@aws-cdk/pkglint/package.json
@@ -51,7 +51,7 @@
     "eslint-plugin-import": "^2.29.1",
     "eslint-plugin-jest": "^24.7.0",
     "jest": "^29.7.0",
-    "typescript": "~5.1.6"
+    "typescript": "~5.4.5"
   },
   "nozem": {
     "ostools": [
diff --git a/tools/@aws-cdk/prlint/package.json b/tools/@aws-cdk/prlint/package.json
index cc73800813d20..a3e16a36692ab 100644
--- a/tools/@aws-cdk/prlint/package.json
+++ b/tools/@aws-cdk/prlint/package.json
@@ -25,7 +25,7 @@
     "@types/jest": "^29.5.12",
     "jest": "^29.7.0",
     "make-runnable": "^1.4.1",
-    "typescript": "~5.1.6",
+    "typescript": "~5.4.5",
     "eslint": "^7.32.0",
     "eslint-import-resolver-node": "^0.3.9",
     "eslint-import-resolver-typescript": "^2.7.1",
diff --git a/tools/@aws-cdk/yarn-cling/package.json b/tools/@aws-cdk/yarn-cling/package.json
index 58171289d6934..513bd5a36d0d7 100644
--- a/tools/@aws-cdk/yarn-cling/package.json
+++ b/tools/@aws-cdk/yarn-cling/package.json
@@ -43,7 +43,7 @@
     "@types/semver": "^7.5.8",
     "@types/yarnpkg__lockfile": "^1.1.9",
     "jest": "^29.7.0",
-    "typescript": "~5.1.6"
+    "typescript": "~5.4.5"
   },
   "dependencies": {
     "@yarnpkg/lockfile": "^1.1.0",
diff --git a/yarn.lock b/yarn.lock
index a69e825f134bd..e172a12c8fc64 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -6882,16 +6882,13 @@ cdk-from-cfn@^0.156.0:
   resolved "https://registry.npmjs.org/cdk-from-cfn/-/cdk-from-cfn-0.156.0.tgz#921134095983db664bd68556463dcde115d73cdb"
   integrity sha512-nYK6SCC4yOPPxkPbrg23d6wTiu6Mtms5dWPI9kymwblpcXfIr+YaoiVlvlT9CFyyddGugG7AaTA6UN7U9LUOAg==
 
-cdk-generate-synthetic-examples@^0.1.309:
-  version "0.1.309"
-  resolved "https://registry.npmjs.org/cdk-generate-synthetic-examples/-/cdk-generate-synthetic-examples-0.1.309.tgz#16b3520f43b7853ccb96eddad5efda7e87a405dd"
-  integrity sha512-QoBhKAvIBCbH9+Z8zRLleR4+m/8+mwTYju1nZ5jZ8AOaNxO1XHNXDtU7GnNGce8oGwqo+hyoFVpEKSDdd5AqJg==
+cdk-generate-synthetic-examples@^0.2.0:
+  version "0.2.0"
+  resolved "https://registry.npmjs.org/cdk-generate-synthetic-examples/-/cdk-generate-synthetic-examples-0.2.0.tgz#019d4a2a9fa0fdab0b8d48b0426c0fa0ea8b5183"
+  integrity sha512-FaVV/TkTwIz9PUkG1+aT1DB13877jreoGbaud1W9bYY4F6u52DT7LqjLkvgETP8OKYTKqqUP+OikxmLt/OQ3aw==
   dependencies:
     "@jsii/spec" "^1.97.0"
-    fs-extra "^10.1.0"
-    jsii "^1.97.0"
     jsii-reflect "^1.97.0"
-    jsii-rosetta "^1.97.0"
     yargs "^17.7.2"
 
 cdk8s-plus-27@2.7.88:
@@ -10895,10 +10892,10 @@ jsii-rosetta@^1.97.0:
     workerpool "^6.5.1"
     yargs "^16.2.0"
 
-jsii-rosetta@~5.4.2:
-  version "5.4.2"
-  resolved "https://registry.npmjs.org/jsii-rosetta/-/jsii-rosetta-5.4.2.tgz#ba51a331f4a5c42892d3b6d5766f7e4b83afd282"
-  integrity sha512-Bo+8lLuRQ0YiXiNImJ6XLrmAY/GzildnYd1B5MLlc+IpjbgFbynhFIyGjYAVf4+/VLFJRoOCJtZ40sM+ua8Ecw==
+jsii-rosetta@~5.4.6:
+  version "5.4.6"
+  resolved "https://registry.npmjs.org/jsii-rosetta/-/jsii-rosetta-5.4.6.tgz#ada3dd6218acb0e5960dbfc15e8b1f67e045ede8"
+  integrity sha512-RyTtc3hJmmrpbiWCLVvgHfy0Is4PWIYDy+Al6/d1xwZDq64DHJU6yU+H99SgL7LRLLwDyCod2QqRmZ1VIywwcQ==
   dependencies:
     "@jsii/check-node" "1.97.0"
     "@jsii/spec" "^1.97.0"
@@ -10914,7 +10911,7 @@ jsii-rosetta@~5.4.2:
     workerpool "^6.5.1"
     yargs "^17.7.2"
 
-jsii@1.97.0, jsii@^1.97.0:
+jsii@1.97.0:
   version "1.97.0"
   resolved "https://registry.npmjs.org/jsii/-/jsii-1.97.0.tgz#5ceee9f1b4715b82e37ec5a24b509336d8ebef83"
   integrity sha512-C3GA2Q50DkHnFozg7HKel7ZaBMCUKb/dzgH2ykfrbuJ/C/KebkPkqY/XRf95zGB42mzagPfawSLDFQiGGueQ9w==
@@ -10933,10 +10930,10 @@ jsii@1.97.0, jsii@^1.97.0:
     typescript "~3.9.10"
     yargs "^16.2.0"
 
-jsii@~5.4.0, jsii@~5.4.3:
-  version "5.4.3"
-  resolved "https://registry.npmjs.org/jsii/-/jsii-5.4.3.tgz#dedac3cc9f1d209193f1388dcf9e55c142ff4a8d"
-  integrity sha512-+alxW2wfBQBCjesy2kvMl6yML8m7hD/buIkVVQNSGt0R0ObhsLvlanS2lRWpNkdfVtDnNk/ke5UFmMSfJ/vy0Q==
+jsii@~5.4.0, jsii@~5.4.6:
+  version "5.4.6"
+  resolved "https://registry.npmjs.org/jsii/-/jsii-5.4.6.tgz#5389695696d7d8fc8e34942c6efef97ef0236fe0"
+  integrity sha512-Ohqz39ecBfmL/Pd5nnkERnikyOoZmNdqoSqedl+yXATM+js7XLlUGgQ+BdBXaO0rzQU2AEQ40C0COtF0jFXw4A==
   dependencies:
     "@jsii/check-node" "1.97.0"
     "@jsii/spec" "^1.97.0"
@@ -14805,16 +14802,7 @@ string-length@^4.0.1:
     char-regex "^1.0.2"
     strip-ansi "^6.0.0"
 
-"string-width-cjs@npm:string-width@^4.2.0":
-  version "4.2.3"
-  resolved "https://registry.npmjs.org/string-width/-/string-width-4.2.3.tgz#269c7117d27b05ad2e536830a8ec895ef9c6d010"
-  integrity sha512-wKyQRQpjJ0sIp62ErSZdGsjMJWsap5oRNihHhu6G7JVO/9jIB6UyevL+tXuOqrng8j/cxKTWyWUwvSTriiZz/g==
-  dependencies:
-    emoji-regex "^8.0.0"
-    is-fullwidth-code-point "^3.0.0"
-    strip-ansi "^6.0.1"
-
-string-width@*, string-width@^1.0.1, "string-width@^1.0.2 || 2 || 3 || 4", string-width@^4.1.0, string-width@^4.2.0, string-width@^4.2.3, string-width@^5.0.1, string-width@^5.1.2:
+"string-width-cjs@npm:string-width@^4.2.0", string-width@*, string-width@^1.0.1, "string-width@^1.0.2 || 2 || 3 || 4", string-width@^4.1.0, string-width@^4.2.0, string-width@^4.2.3, string-width@^5.0.1, string-width@^5.1.2:
   version "4.2.3"
   resolved "https://registry.npmjs.org/string-width/-/string-width-4.2.3.tgz#269c7117d27b05ad2e536830a8ec895ef9c6d010"
   integrity sha512-wKyQRQpjJ0sIp62ErSZdGsjMJWsap5oRNihHhu6G7JVO/9jIB6UyevL+tXuOqrng8j/cxKTWyWUwvSTriiZz/g==
@@ -14892,7 +14880,7 @@ stringify-package@^1.0.1:
   resolved "https://registry.npmjs.org/stringify-package/-/stringify-package-1.0.1.tgz#e5aa3643e7f74d0f28628b72f3dad5cecfc3ba85"
   integrity sha512-sa4DUQsYciMP1xhKWGuFM04fB0LG/9DlluZoSVywUMRNvzid6XucHK0/90xGxRoHrAaROrcHK1aPKaijCtSrhg==
 
-"strip-ansi-cjs@npm:strip-ansi@^6.0.1":
+"strip-ansi-cjs@npm:strip-ansi@^6.0.1", strip-ansi@^6.0.0, strip-ansi@^6.0.1:
   version "6.0.1"
   resolved "https://registry.npmjs.org/strip-ansi/-/strip-ansi-6.0.1.tgz#9e26c63d30f53443e9489495b2105d37b67a85d9"
   integrity sha512-Y38VPSHcqkFrCpFnQ9vuSXmquuv5oXOKpGeT6aGrr3o3Gc9AlVa6JBfUSOCnbxGGZF+/0ooI7KrPuUSztUdU5A==
@@ -14906,13 +14894,6 @@ strip-ansi@^3.0.1:
   dependencies:
     ansi-regex "^2.0.0"
 
-strip-ansi@^6.0.0, strip-ansi@^6.0.1:
-  version "6.0.1"
-  resolved "https://registry.npmjs.org/strip-ansi/-/strip-ansi-6.0.1.tgz#9e26c63d30f53443e9489495b2105d37b67a85d9"
-  integrity sha512-Y38VPSHcqkFrCpFnQ9vuSXmquuv5oXOKpGeT6aGrr3o3Gc9AlVa6JBfUSOCnbxGGZF+/0ooI7KrPuUSztUdU5A==
-  dependencies:
-    ansi-regex "^5.0.1"
-
 strip-ansi@^7.0.1, strip-ansi@^7.1.0:
   version "7.1.0"
   resolved "https://registry.npmjs.org/strip-ansi/-/strip-ansi-7.1.0.tgz#d5b6568ca689d8561370b0707685d22434faff45"
@@ -15468,7 +15449,7 @@ typescript-json-schema@^0.63.0:
     typescript "~5.1.0"
     yargs "^17.1.1"
 
-"typescript@>=3 < 6", typescript@~5.4:
+"typescript@>=3 < 6", typescript@~5.4, typescript@~5.4.5:
   version "5.4.5"
   resolved "https://registry.npmjs.org/typescript/-/typescript-5.4.5.tgz#42ccef2c571fdbd0f6718b1d1f5e6e5ef006f611"
   integrity sha512-vcI4UpRgg81oIRUFwR0WSIHKt11nJ7SAVlYNIu+QpqeyXP+gpQJy/Z4+F0aGxSE4MqwjyXvW/TzgkLAx2AGHwQ==
@@ -15478,17 +15459,12 @@ typescript@^3.9.10, typescript@^3.9.5, typescript@^3.9.7, typescript@~3.9.10:
   resolved "https://registry.npmjs.org/typescript/-/typescript-3.9.10.tgz#70f3910ac7a51ed6bef79da7800690b19bf778b8"
   integrity sha512-w6fIxVE/H1PkLKcCPsFqKE7Kv7QUwhU8qQY2MueZXWx5cPZdwFupLgKK3vntcK98BtNHZtAF4LA/yl2a7k8R6Q==
 
-typescript@^4.5.5:
-  version "4.9.5"
-  resolved "https://registry.npmjs.org/typescript/-/typescript-4.9.5.tgz#095979f9bcc0d09da324d58d03ce8f8374cbe65a"
-  integrity sha512-1FXk9E2Hm+QzZQ7z+McJiHL4NW1F2EzMu9Nq9i3zAaGqibafqYwCVU6WyWAuyQRRzOlxou8xZSyXLEN8oKj24g==
-
 typescript@next:
   version "5.5.0-dev.20240417"
   resolved "https://registry.npmjs.org/typescript/-/typescript-5.5.0-dev.20240417.tgz#2558a2442be5b8541ce8168c53fb5ef4ee3c4995"
   integrity sha512-BjMYWxzDLRaNlnnMC/NHf0uUIZEnw5VLe7q0h7hEi5Q4H1XoIDdjBjk6stBS2nj6R/HrsdEqhWdPz6+DLx+sRw==
 
-typescript@~5.1.0, typescript@~5.1.6:
+typescript@~5.1.0:
   version "5.1.6"
   resolved "https://registry.npmjs.org/typescript/-/typescript-5.1.6.tgz#02f8ac202b6dad2c0dd5e0913745b47a37998274"
   integrity sha512-zaWCozRZ6DLEWAWFrVDz1H6FVXzUSfTy5FUMWsQlU8Ym5JP9eO4xkTIROFCQvhQf61z6O/G6ugw3SgAnvvm+HA==
@@ -15898,7 +15874,7 @@ workerpool@^6.5.1:
   resolved "https://registry.npmjs.org/workerpool/-/workerpool-6.5.1.tgz#060f73b39d0caf97c6db64da004cd01b4c099544"
   integrity sha512-Fs4dNYcsdpYSAfVxhnl1L5zTksjvOJxtC5hzMNl+1t9B8hTJTdKDyZ5ju7ztgPy+ft9tBFXoOlDNiOT9WUXZlA==
 
-"wrap-ansi-cjs@npm:wrap-ansi@^7.0.0":
+"wrap-ansi-cjs@npm:wrap-ansi@^7.0.0", wrap-ansi@^7.0.0:
   version "7.0.0"
   resolved "https://registry.npmjs.org/wrap-ansi/-/wrap-ansi-7.0.0.tgz#67e145cff510a6a6984bdf1152911d69d2eb9e43"
   integrity sha512-YVGIj2kamLSTxw6NsZjoBxfSwsn0ycdesmc4p+Q21c5zPuZ1pl+NfxVdxPtdHvmNVOQ6XSYG4AUtyt/Fi7D16Q==
@@ -15916,15 +15892,6 @@ wrap-ansi@^6.0.1, wrap-ansi@^6.2.0:
     string-width "^4.1.0"
     strip-ansi "^6.0.0"
 
-wrap-ansi@^7.0.0:
-  version "7.0.0"
-  resolved "https://registry.npmjs.org/wrap-ansi/-/wrap-ansi-7.0.0.tgz#67e145cff510a6a6984bdf1152911d69d2eb9e43"
-  integrity sha512-YVGIj2kamLSTxw6NsZjoBxfSwsn0ycdesmc4p+Q21c5zPuZ1pl+NfxVdxPtdHvmNVOQ6XSYG4AUtyt/Fi7D16Q==
-  dependencies:
-    ansi-styles "^4.0.0"
-    string-width "^4.1.0"
-    strip-ansi "^6.0.0"
-
 wrap-ansi@^8.1.0:
   version "8.1.0"
   resolved "https://registry.npmjs.org/wrap-ansi/-/wrap-ansi-8.1.0.tgz#56dc22368ee570face1b49819975d9b9a5ead214"