diff --git a/package.json b/package.json
index 7b02980076157..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",
@@ -35,7 +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 9bd8e184415af..5aeea5635c107 100644
--- a/tools/@aws-cdk/cdk-build-tools/package.json
+++ b/tools/@aws-cdk/cdk-build-tools/package.json
@@ -60,15 +60,15 @@
     "glob": "^7.2.3",
     "jest": "^29.7.0",
     "jest-junit": "^13.2.0",
-    "jsii": "~5.1.12",
-    "jsii-rosetta": "~5.1.24",
+    "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 774a9d56a07d1..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": "^5.1.6",
+    "typescript": "~5.4.5",
     "cjs-module-lexer": "^1.2.3"
   },
   "dependencies": {
diff --git a/tools/@aws-cdk/node-bundle/package.json b/tools/@aws-cdk/node-bundle/package.json
index c15c77b2bb44d..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": "^5.1.6"
+    "typescript": "~5.4.5"
   },
   "dependencies": {
     "esbuild": "^0.20.2",
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 336d62202e680..e172a12c8fc64 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -3825,22 +3825,6 @@
     "@jridgewell/resolve-uri" "^3.1.0"
     "@jridgewell/sourcemap-codec" "^1.4.14"
 
-"@jsii/check-node@1.88.0":
-  version "1.88.0"
-  resolved "https://registry.npmjs.org/@jsii/check-node/-/check-node-1.88.0.tgz#fa20e012230c692ad36976cde29301be1ed28c67"
-  integrity sha512-AveFyqkJIb8qZvGk5nZal/8mEJB6lWhwqvAQLodHmqE3WzpmZD5+h+aspBVt0El5cEFRJ1k1mrQqhAnJCVpvxg==
-  dependencies:
-    chalk "^4.1.2"
-    semver "^7.5.4"
-
-"@jsii/check-node@1.93.0":
-  version "1.93.0"
-  resolved "https://registry.npmjs.org/@jsii/check-node/-/check-node-1.93.0.tgz#3adcc6012654bb69fb8dc508e757b83ea9cd1708"
-  integrity sha512-NLn1Js6wEG2hYjH7gE5Q8s/hPlp3I+KhK/T8ykGdYVod7iODnk/0QVSZsk2iEyuw8NzvvgXUDBWreadUIWSz+g==
-  dependencies:
-    chalk "^4.1.2"
-    semver "^7.5.4"
-
 "@jsii/check-node@1.97.0":
   version "1.97.0"
   resolved "https://registry.npmjs.org/@jsii/check-node/-/check-node-1.97.0.tgz#aeeb3fd1a9f4d5c7a2f24faeb106f31e6015cc4f"
@@ -3849,7 +3833,7 @@
     chalk "^4.1.2"
     semver "^7.5.4"
 
-"@jsii/spec@1.97.0", "@jsii/spec@^1.88.0", "@jsii/spec@^1.93.0", "@jsii/spec@^1.97.0":
+"@jsii/spec@1.97.0", "@jsii/spec@^1.97.0":
   version "1.97.0"
   resolved "https://registry.npmjs.org/@jsii/spec/-/spec-1.97.0.tgz#951109ad43bdd7c1ea2de96a74e4fa645bd9a413"
   integrity sha512-5YIq1fgOtToH6eUyTNlqAXuZzUzTD6wBukE7m5DpsxHjQlbR7TVP750FcPqH9qCitCwaePPl5IdCZJ/AS0IwEA==
@@ -6898,16 +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:
@@ -7288,6 +7269,16 @@ commonmark@^0.30.0:
     minimist ">=1.2.2"
     string.prototype.repeat "^0.2.0"
 
+commonmark@^0.31.0:
+  version "0.31.0"
+  resolved "https://registry.npmjs.org/commonmark/-/commonmark-0.31.0.tgz#4ac57c61f0d7f5ef82d79447a972c61226ef5abc"
+  integrity sha512-nuDsQ34gjmgAqjyIz6mbRWBW/XPE9wsBempAMBk2V/AA88ekztjTM46oi07J6c6Y/2Y8TdYCZi9L0pIBt/oMZw==
+  dependencies:
+    entities "~3.0.1"
+    mdurl "~1.0.1"
+    minimist "~1.2.5"
+    string.prototype.repeat "^1.0.0"
+
 compare-func@^2.0.0:
   version "2.0.0"
   resolved "https://registry.npmjs.org/compare-func/-/compare-func-2.0.0.tgz#fb65e75edbddfd2e568554e8b5b05fff7a51fcb3"
@@ -8246,6 +8237,11 @@ entities@~2.1.0:
   resolved "https://registry.npmjs.org/entities/-/entities-2.1.0.tgz#992d3129cf7df6870b96c57858c249a120f8b8b5"
   integrity sha512-hCx1oky9PFrJ611mf0ifBLBRW8lUUVRlFolb5gWRfIELabBlbp9xZvrqZLZAs+NxFnbfQoeGd8wDkygjg7U85w==
 
+entities@~3.0.1:
+  version "3.0.1"
+  resolved "https://registry.npmjs.org/entities/-/entities-3.0.1.tgz#2b887ca62585e96db3903482d336c1006c3001d4"
+  integrity sha512-WiyBqoomrwMdFG1e0kqvASYfnlb0lp8M5o5Fw2OFq1hNZxxcNk8Ik0Xm7LxzBhuidnZB/UtBqVCgUz3kBOP51Q==
+
 env-paths@^2.2.0:
   version "2.2.1"
   resolved "https://registry.npmjs.org/env-paths/-/env-paths-2.2.1.tgz#420399d416ce1fbe9bc0a07c62fa68d67fd0f8f2"
@@ -8268,7 +8264,7 @@ error-ex@^1.3.1:
   dependencies:
     is-arrayish "^0.2.1"
 
-es-abstract@^1.22.1, es-abstract@^1.22.3, es-abstract@^1.23.0, es-abstract@^1.23.2:
+es-abstract@^1.17.5, es-abstract@^1.22.1, es-abstract@^1.22.3, es-abstract@^1.23.0, es-abstract@^1.23.2:
   version "1.23.3"
   resolved "https://registry.npmjs.org/es-abstract/-/es-abstract-1.23.3.tgz#8f0c5a35cd215312573c5a27c87dfd6c881a0aa0"
   integrity sha512-e+HfNH61Bj1X9/jLc5v1owaLYuHdeHHSQlkhCBiTK8rBvKaULl/beGMxwrMXjpYrv4pz22BlY570vVePA2ho4A==
@@ -10896,26 +10892,26 @@ jsii-rosetta@^1.97.0:
     workerpool "^6.5.1"
     yargs "^16.2.0"
 
-jsii-rosetta@~5.1.24:
-  version "5.1.24"
-  resolved "https://registry.npmjs.org/jsii-rosetta/-/jsii-rosetta-5.1.24.tgz#ead75edc6f33f3218c6a4bf23dde28a52d4c88b0"
-  integrity sha512-2JUv5LCX5pvtTK/xAC8mKNCSVVc/uGUaPv3lIgQSnZosWcXOlP8jqwjSvAdGX0gIWqCpHzIMle4TQlfuUpHzlg==
+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" "1.93.0"
-    "@jsii/spec" "^1.93.0"
+    "@jsii/check-node" "1.97.0"
+    "@jsii/spec" "^1.97.0"
     "@xmldom/xmldom" "^0.8.10"
     chalk "^4"
-    commonmark "^0.30.0"
+    commonmark "^0.31.0"
     fast-glob "^3.3.2"
-    jsii "~5.1.5"
-    semver "^7.5.4"
+    jsii "~5.4.0"
+    semver "^7.6.0"
     semver-intersect "^1.5.0"
     stream-json "^1.8.0"
-    typescript "~5.1.6"
+    typescript "~5.4"
     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==
@@ -10934,23 +10930,23 @@ jsii@1.97.0, jsii@^1.97.0:
     typescript "~3.9.10"
     yargs "^16.2.0"
 
-jsii@~5.1.12, jsii@~5.1.5:
-  version "5.1.12"
-  resolved "https://registry.npmjs.org/jsii/-/jsii-5.1.12.tgz#0ac6d92d52c6732a6e0e3e27f9f07453318715f2"
-  integrity sha512-iY3zLosUEKbeua6IAGJXjFxibiiI0xHFjyYPyewOc56MBRHC7nczWSVGRP+Jgwyo7HWXs4TvJKLG6w8zSuAZrg==
+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" "1.88.0"
-    "@jsii/spec" "^1.88.0"
+    "@jsii/check-node" "1.97.0"
+    "@jsii/spec" "^1.97.0"
     case "^1.6.3"
     chalk "^4"
     downlevel-dts "^0.11.0"
     fast-deep-equal "^3.1.3"
     log4js "^6.9.1"
-    semver "^7.5.4"
-    semver-intersect "^1.4.0"
+    semver "^7.6.0"
+    semver-intersect "^1.5.0"
     sort-json "^2.0.1"
-    spdx-license-list "^6.6.0"
-    typescript "~5.1.6"
+    spdx-license-list "^6.9.0"
+    typescript "~5.4"
     yargs "^17.7.2"
 
 json-buffer@3.0.1:
@@ -11952,7 +11948,7 @@ minimist-options@4.1.0:
     is-plain-obj "^1.1.0"
     kind-of "^6.0.3"
 
-minimist@>=1.2.2, minimist@^1.2.0, minimist@^1.2.5, minimist@^1.2.6, minimist@^1.2.8:
+minimist@>=1.2.2, minimist@^1.2.0, minimist@^1.2.5, minimist@^1.2.6, minimist@^1.2.8, minimist@~1.2.5:
   version "1.2.8"
   resolved "https://registry.npmjs.org/minimist/-/minimist-1.2.8.tgz#c1a464e7693302e082a075cee0c057741ac4772c"
   integrity sha512-2yyAR8qBkN3YuheJanUpWC5U3bb5osDywNB8RzDVlDwDHbocAJveqqj1u8+SVD7jkWT4yvsHCpWqqWqAxb0zCA==
@@ -14688,7 +14684,7 @@ spdx-license-ids@^3.0.0:
   resolved "https://registry.npmjs.org/spdx-license-ids/-/spdx-license-ids-3.0.17.tgz#887da8aa73218e51a1d917502d79863161a93f9c"
   integrity sha512-sh8PWc/ftMqAAdFiBu6Fy6JUOYjqDJBJvIhpfDMyHrr0Rbp5liZqd4TjtQ/RgfLjKFZb+LMx5hpml5qOWy0qvg==
 
-spdx-license-list@^6.6.0, spdx-license-list@^6.8.0:
+spdx-license-list@^6.8.0, spdx-license-list@^6.9.0:
   version "6.9.0"
   resolved "https://registry.npmjs.org/spdx-license-list/-/spdx-license-list-6.9.0.tgz#5543abb3a15f985a12808f642a622d2721c372ad"
   integrity sha512-L2jl5vc2j6jxWcNCvcVj/BW9A8yGIG02Dw+IUw0ZxDM70f7Ylf5Hq39appV1BI9yxyWQRpq2TQ1qaXvf+yjkqA==
@@ -14820,6 +14816,14 @@ string.prototype.repeat@^0.2.0:
   resolved "https://registry.npmjs.org/string.prototype.repeat/-/string.prototype.repeat-0.2.0.tgz#aba36de08dcee6a5a337d49b2ea1da1b28fc0ecf"
   integrity sha512-1BH+X+1hSthZFW+X+JaUkjkkUPwIlLEMJBLANN3hOob3RhEk5snLWNECDnYbgn/m5c5JV7Ersu1Yubaf+05cIA==
 
+string.prototype.repeat@^1.0.0:
+  version "1.0.0"
+  resolved "https://registry.npmjs.org/string.prototype.repeat/-/string.prototype.repeat-1.0.0.tgz#e90872ee0308b29435aa26275f6e1b762daee01a"
+  integrity sha512-0u/TldDbKD8bFCQ/4f5+mNRrXwZ8hg2w7ZR8wa16e8z9XpePWl3eGEcUD0OXpEH/VJH/2G3gjUtR3ZOiBe2S/w==
+  dependencies:
+    define-properties "^1.1.3"
+    es-abstract "^1.17.5"
+
 string.prototype.trim@^1.2.9:
   version "1.2.9"
   resolved "https://registry.npmjs.org/string.prototype.trim/-/string.prototype.trim-1.2.9.tgz#b6fa326d72d2c78b6df02f7759c73f8f6274faa4"
@@ -15445,7 +15449,7 @@ typescript-json-schema@^0.63.0:
     typescript "~5.1.0"
     yargs "^17.1.1"
 
-"typescript@>=3 < 6", typescript@^5.1.6:
+"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==
@@ -15460,7 +15464,7 @@ typescript@next:
   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==