diff --git a/apps/blaze-dashboard/package.json b/apps/blaze-dashboard/package.json
index e3610c59465410..d4d78bbcd0149e 100644
--- a/apps/blaze-dashboard/package.json
+++ b/apps/blaze-dashboard/package.json
@@ -54,16 +54,16 @@
 		"@automattic/webpack-extensive-lodash-replacement-plugin": "workspace:^",
 		"@automattic/webpack-inline-constant-exports-plugin": "workspace:^",
 		"@automattic/wp-babel-makepot": "workspace:^",
-		"@wordpress/dependency-extraction-webpack-plugin": "^4.21.0",
+		"@wordpress/dependency-extraction-webpack-plugin": "^4.29.0",
 		"autoprefixer": "^10.2.5",
 		"gettext-parser": "^6.0.0",
-		"html-webpack-plugin": "^5.0.0-beta.4",
+		"html-webpack-plugin": "^5.5.3",
 		"lodash": "^4.17.21",
 		"mkdirp": "^1.0.4",
 		"node-fetch": "^2.6.6",
 		"path-browserify": "^1.0.1",
 		"postcss": "^8.3.11",
-		"webpack": "^5.68.0",
-		"webpack-bundle-analyzer": "^4.5.0"
+		"webpack": "^5.89.0",
+		"webpack-bundle-analyzer": "^4.10.1"
 	}
 }
diff --git a/apps/editing-toolkit/package.json b/apps/editing-toolkit/package.json
index d77ae99ec6ee03..9406467372a8f2 100644
--- a/apps/editing-toolkit/package.json
+++ b/apps/editing-toolkit/package.json
@@ -79,7 +79,7 @@
 		"@wordpress/data": "^9.14.0",
 		"@wordpress/data-controls": "^3.13.0",
 		"@wordpress/date": "^4.44.0",
-		"@wordpress/dependency-extraction-webpack-plugin": "^4.21.0",
+		"@wordpress/dependency-extraction-webpack-plugin": "^4.29.0",
 		"@wordpress/dom-ready": "^3.44.0",
 		"@wordpress/edit-post": "^7.21.0",
 		"@wordpress/element": "^5.21.0",
@@ -127,7 +127,7 @@
 		"@testing-library/react": "^14.1.0",
 		"@types/node": "^20.8.6",
 		"@wordpress/eslint-plugin": "^17.1.0",
-		"@wordpress/readable-js-assets-webpack-plugin": "^2.21.0",
+		"@wordpress/readable-js-assets-webpack-plugin": "^2.29.0",
 		"babel-jest": "^29.6.1",
 		"eslint-filtered-fix": "^0.3.0",
 		"eslint-nibble": "^8.1.0",
@@ -137,6 +137,6 @@
 		"eslint-plugin-you-dont-need-lodash-underscore": "^6.13.0",
 		"prettier": "npm:wp-prettier@3.0.3",
 		"wait-for-expect": "^3.0.2",
-		"webpack": "^5.68.0"
+		"webpack": "^5.89.0"
 	}
 }
diff --git a/apps/happy-blocks/package.json b/apps/happy-blocks/package.json
index d06e1a7e6bb6c6..0084f6cfb128f4 100644
--- a/apps/happy-blocks/package.json
+++ b/apps/happy-blocks/package.json
@@ -52,10 +52,10 @@
 		"@automattic/calypso-apps-builder": "workspace:^",
 		"@emotion/react": "^11.11.1",
 		"@testing-library/react": "^14.1.0",
-		"@wordpress/readable-js-assets-webpack-plugin": "^2.21.0",
-		"copy-webpack-plugin": "^10.1.0",
+		"@wordpress/readable-js-assets-webpack-plugin": "^2.29.0",
+		"copy-webpack-plugin": "^10.2.4",
 		"glob": "^7.1.6",
 		"postcss": "^8.4.5",
-		"webpack": "^5.68.0"
+		"webpack": "^5.89.0"
 	}
 }
diff --git a/apps/notifications/package.json b/apps/notifications/package.json
index e3fcaf64c4ca4b..290f0e6ed752fd 100644
--- a/apps/notifications/package.json
+++ b/apps/notifications/package.json
@@ -41,7 +41,7 @@
 		"react-redux": "^8.1.3",
 		"redux": "^4.2.1",
 		"redux-thunk": "^2.4.2",
-		"webpack-bundle-analyzer": "^4.5.0",
+		"webpack-bundle-analyzer": "^4.10.1",
 		"wpcom": "workspace:^",
 		"wpcom-proxy-request": "workspace:^",
 		"wpcom-xhr-request": "workspace:^"
@@ -50,10 +50,10 @@
 		"@automattic/calypso-apps-builder": "workspace:^",
 		"@automattic/calypso-build": "workspace:^",
 		"@automattic/calypso-eslint-overrides": "workspace:^",
-		"html-webpack-plugin": "^5.0.0-beta.4",
+		"html-webpack-plugin": "^5.5.3",
 		"postcss": "^8.4.5",
 		"postcss-custom-properties": "^11.0.0",
-		"webpack": "^5.68.0",
-		"webpack-dev-server": "^4.7.3"
+		"webpack": "^5.89.0",
+		"webpack-dev-server": "^4.15.1"
 	}
 }
diff --git a/apps/o2-blocks/package.json b/apps/o2-blocks/package.json
index 277044bc8105ee..b6d8b3727f598c 100644
--- a/apps/o2-blocks/package.json
+++ b/apps/o2-blocks/package.json
@@ -47,8 +47,8 @@
 	"devDependencies": {
 		"@automattic/calypso-apps-builder": "workspace:^",
 		"@automattic/calypso-eslint-overrides": "workspace:^",
-		"@wordpress/readable-js-assets-webpack-plugin": "^2.21.0",
+		"@wordpress/readable-js-assets-webpack-plugin": "^2.29.0",
 		"postcss": "^8.4.5",
-		"webpack": "^5.68.0"
+		"webpack": "^5.89.0"
 	}
 }
diff --git a/apps/odyssey-stats/package.json b/apps/odyssey-stats/package.json
index 6c7dce8be9b2e0..3dc91131b40627 100644
--- a/apps/odyssey-stats/package.json
+++ b/apps/odyssey-stats/package.json
@@ -62,11 +62,11 @@
 		"@automattic/wp-babel-makepot": "workspace:^",
 		"@babel/core": "^7.23.2",
 		"@size-limit/file": "^8.2.6",
-		"@wordpress/dependency-extraction-webpack-plugin": "^4.21.0",
+		"@wordpress/dependency-extraction-webpack-plugin": "^4.29.0",
 		"autoprefixer": "^10.2.5",
 		"babel-jest": "^29.6.1",
 		"gettext-parser": "^6.0.0",
-		"html-webpack-plugin": "^5.0.0-beta.4",
+		"html-webpack-plugin": "^5.5.3",
 		"jest": "^29.7.0",
 		"lodash": "^4.17.21",
 		"mkdirp": "^1.0.4",
@@ -74,7 +74,7 @@
 		"path-browserify": "^1.0.1",
 		"postcss": "^8.3.11",
 		"size-limit": "^8.2.6",
-		"webpack": "^5.68.0",
-		"webpack-bundle-analyzer": "^4.5.0"
+		"webpack": "^5.89.0",
+		"webpack-bundle-analyzer": "^4.10.1"
 	}
 }
diff --git a/apps/wpcom-block-editor/package.json b/apps/wpcom-block-editor/package.json
index 6157063de8b2f0..445ca23c4c1feb 100644
--- a/apps/wpcom-block-editor/package.json
+++ b/apps/wpcom-block-editor/package.json
@@ -56,9 +56,9 @@
 		"@automattic/calypso-apps-builder": "workspace:^",
 		"@automattic/calypso-build": "workspace:^",
 		"@automattic/calypso-eslint-overrides": "workspace:^",
-		"@wordpress/dependency-extraction-webpack-plugin": "^4.21.0",
+		"@wordpress/dependency-extraction-webpack-plugin": "^4.29.0",
 		"npm-run-all": "^4.1.5",
 		"postcss": "^8.4.5",
-		"webpack": "^5.68.0"
+		"webpack": "^5.89.0"
 	}
 }
diff --git a/bin/icfy-analyze.js b/bin/icfy-analyze.js
index c6a5060720cce4..c8b6edba96bc9e 100644
--- a/bin/icfy-analyze.js
+++ b/bin/icfy-analyze.js
@@ -3,9 +3,9 @@ const { getViewerData, readStatsFromFile } = require( 'webpack-bundle-analyzer/l
 
 analyzeBundle();
 
-function analyzeBundle() {
+async function analyzeBundle() {
 	console.log( 'Analyze: reading stats.json file' );
-	const stats = readStatsFromFile( 'client/stats.json' );
+	const stats = await readStatsFromFile( 'client/stats.json' );
 	console.log( 'Analyze: analyzing' );
 	const chart = getViewerData( stats, './public/evergreen' );
 	console.log( 'Analyze: writing chart.json file' );
diff --git a/client/package.json b/client/package.json
index 64335f5c59c367..afdc2a9e1a4943 100644
--- a/client/package.json
+++ b/client/package.json
@@ -206,10 +206,10 @@
 		"utility-types": "^3.10.0",
 		"uuid": "^8.3.2",
 		"valid-url": "^1.0.9",
-		"webpack": "^5.68.0",
-		"webpack-bundle-analyzer": "^4.5.0",
-		"webpack-dev-middleware": "^5.3.1",
-		"webpack-hot-middleware": "^2.25.1",
+		"webpack": "^5.89.0",
+		"webpack-bundle-analyzer": "^4.10.1",
+		"webpack-dev-middleware": "^5.3.3",
+		"webpack-hot-middleware": "^2.25.4",
 		"webpack-node-externals": "^3.0.0",
 		"wpcom": "workspace:^",
 		"wpcom-proxy-request": "workspace:^",
@@ -217,7 +217,7 @@
 	},
 	"devDependencies": {
 		"@automattic/calypso-eslint-overrides": "workspace:^",
-		"@sentry/webpack-plugin": "^1.18.8",
+		"@sentry/webpack-plugin": "^1.20.1",
 		"@storybook/addon-actions": "^7.5.3",
 		"@tanstack/query-sync-storage-persister": "^4.29.1",
 		"@testing-library/dom": "^9.3.3",
diff --git a/desktop/package.json b/desktop/package.json
index 98f80ca0f0f952..a07632bbdd8c1f 100644
--- a/desktop/package.json
+++ b/desktop/package.json
@@ -36,7 +36,7 @@
 	"devDependencies": {
 		"@automattic/calypso-build": "workspace:^",
 		"@automattic/calypso-eslint-overrides": "workspace:^",
-		"copy-webpack-plugin": "^10.1.0",
+		"copy-webpack-plugin": "^10.2.4",
 		"electron": "26.2.1",
 		"electron-builder": "23.0.3",
 		"electron-notarize": "^0.1.1",
@@ -47,8 +47,8 @@
 		"postcss": "^8.4.5",
 		"react": "^18.2.0",
 		"react-dom": "^18.2.0",
-		"webpack": "^5.68.0",
-		"webpack-cli": "^4.9.2"
+		"webpack": "^5.89.0",
+		"webpack-cli": "^4.10.0"
 	},
 	"dependencies": {
 		"archiver": "^3.1.1",
diff --git a/package.json b/package.json
index 2c0bd9a58639fa..c6d428a59c40cd 100644
--- a/package.json
+++ b/package.json
@@ -169,7 +169,7 @@
 		"@types/store": "^2.0.2",
 		"@types/uuid": "^8.3.4",
 		"@types/validator": "^13.7.1",
-		"@types/webpack-env": "^1.16.3",
+		"@types/webpack-env": "^1.18.4",
 		"@wordpress/base-styles": "^4.35.0",
 		"@wordpress/commands": "^0.15.0",
 		"@wordpress/components": "^25.10.0",
@@ -218,7 +218,7 @@
 		"@babel/register": "^7.22.15",
 		"@babel/runtime": "^7.23.2",
 		"@bartekbp/typescript-checkstyle": "^5.0.0",
-		"@pmmmwh/react-refresh-webpack-plugin": "^0.5.10",
+		"@pmmmwh/react-refresh-webpack-plugin": "^0.5.11",
 		"@signal-noise/stylelint-scales": "^2.0.3",
 		"@storybook/cli": "^7.5.3",
 		"@storybook/react": "^7.5.3",
@@ -237,7 +237,7 @@
 		"chalk": "^4.1.2",
 		"check-node-version": "^4.0.2",
 		"chroma-js": "^2.1.2",
-		"css-loader": "^6.5.1",
+		"css-loader": "^6.8.1",
 		"doctrine": "^3.0.0",
 		"eslint": "^8.53.0",
 		"eslint-config-prettier": "^9.0.0",
@@ -263,7 +263,7 @@
 		"jest-canvas-mock": "^2.5.2",
 		"jest-environment-jsdom": "^29.7.0",
 		"jest-teamcity": "^1.11.0",
-		"loader-utils": "^1.2.3",
+		"loader-utils": "^1.4.2",
 		"lunr": "^2.3.8",
 		"mixedindentlint": "^1.2.0",
 		"mkdirp": "^1.0.4",
@@ -287,10 +287,10 @@
 		"stylelint": "^14.16.1",
 		"tslib": "^2.3.0",
 		"typescript": "^5.2.2",
-		"webpack": "^5.68.0",
-		"webpack-bundle-analyzer": "^4.5.0",
-		"webpack-cli": "^4.9.2",
-		"webpack-dev-middleware": "^5.3.1",
+		"webpack": "^5.89.0",
+		"webpack-bundle-analyzer": "^4.10.1",
+		"webpack-cli": "^4.10.0",
+		"webpack-dev-middleware": "^5.3.3",
 		"whybundled": "^2.0.0",
 		"yargs": "^17.0.1"
 	},
@@ -327,7 +327,7 @@
 		"@wordpress/data-controls": "3.13.0",
 		"@wordpress/data": "^9.14.0",
 		"@wordpress/date": "4.44.0",
-		"@wordpress/dependency-extraction-webpack-plugin": "4.21.0",
+		"@wordpress/dependency-extraction-webpack-plugin": "4.29.0",
 		"@wordpress/deprecated": "3.44.0",
 		"@wordpress/docgen": "1.53.0",
 		"@wordpress/dom-ready": "3.44.0",
@@ -372,7 +372,7 @@
 		"@wordpress/private-apis": "^0.26.0",
 		"@wordpress/project-management-automation": "1.43.0",
 		"@wordpress/react-i18n": "3.42.0",
-		"@wordpress/readable-js-assets-webpack-plugin": "2.21.0",
+		"@wordpress/readable-js-assets-webpack-plugin": "2.29.0",
 		"@wordpress/redux-routine": "4.44.0",
 		"@wordpress/reusable-blocks": "4.21.0",
 		"@wordpress/rich-text": "6.21.0",
diff --git a/packages/calypso-apps-builder/package.json b/packages/calypso-apps-builder/package.json
index f988057ea13354..fc0acdd5e33010 100644
--- a/packages/calypso-apps-builder/package.json
+++ b/packages/calypso-apps-builder/package.json
@@ -16,10 +16,10 @@
 	},
 	"dependencies": {
 		"chokidar": "^3.5.2",
-		"html-webpack-plugin": "^5.0.0-beta.4",
+		"html-webpack-plugin": "^5.5.3",
 		"npm-run-all": "^4.1.5",
 		"tree-kill": "^1.2.2",
-		"webpack": "^5.68.0",
+		"webpack": "^5.89.0",
 		"yargs": "^17.0.1"
 	},
 	"devDependencies": {
diff --git a/packages/calypso-build/package.json b/packages/calypso-build/package.json
index bb406dfe8a5234..d69af933098260 100644
--- a/packages/calypso-build/package.json
+++ b/packages/calypso-build/package.json
@@ -37,27 +37,27 @@
 		"@automattic/webpack-rtl-plugin": "workspace:^",
 		"@babel/compat-data": "^7.23.2",
 		"@babel/core": "^7.23.2",
-		"@types/webpack-env": "^1.16.3",
+		"@types/webpack-env": "^1.18.4",
 		"@wordpress/browserslist-config": "^5.27.0",
-		"@wordpress/dependency-extraction-webpack-plugin": "^4.21.0",
+		"@wordpress/dependency-extraction-webpack-plugin": "^4.29.0",
 		"autoprefixer": "^10.2.5",
 		"babel-loader": "^8.2.3",
 		"browserslist": "^4.8.2",
-		"css-loader": "^6.5.1",
-		"css-minimizer-webpack-plugin": "^3.2.0",
+		"css-loader": "^6.8.1",
+		"css-minimizer-webpack-plugin": "^3.4.1",
 		"duplicate-package-checker-webpack-plugin": "^3.0.0",
 		"mini-css-extract-plugin": "^1.6.2",
 		"postcss-custom-properties": "^11.0.0",
-		"postcss-loader": "^6.2.0",
+		"postcss-loader": "^6.2.1",
 		"recursive-copy": "^2.0.14",
 		"sass": "^1.37.5",
 		"sass-loader": "^12.1.0",
 		"semver": "^7.3.2",
 		"stream-browserify": "^3.0.0",
-		"terser-webpack-plugin": "^5.2.4",
+		"terser-webpack-plugin": "^5.3.9",
 		"thread-loader": "^3.0.4",
 		"typescript": "^5.2.2",
-		"webpack-cli": "^4.9.2"
+		"webpack-cli": "^4.10.0"
 	},
 	"devDependencies": {
 		"@automattic/calypso-eslint-overrides": "workspace:^",
@@ -65,6 +65,6 @@
 	},
 	"peerDependencies": {
 		"postcss": "^8.4.5",
-		"webpack": "^5.68.0"
+		"webpack": "^5.89.0"
 	}
 }
diff --git a/packages/calypso-storybook/package.json b/packages/calypso-storybook/package.json
index 4239bc215cbd77..5e45fcde5aa02d 100644
--- a/packages/calypso-storybook/package.json
+++ b/packages/calypso-storybook/package.json
@@ -30,12 +30,12 @@
 		"@storybook/addon-controls": "^7.5.3",
 		"@storybook/preset-scss": "^1.0.3",
 		"@storybook/react-webpack5": "^7.5.3",
-		"css-loader": "^6.5.1",
+		"css-loader": "^6.8.1",
 		"react": "^18.2.0",
 		"react-dom": "^18.2.0",
 		"sass-loader": "^12.1.0",
-		"style-loader": "^1.2.1",
-		"webpack": "^5.68.0"
+		"style-loader": "^1.3.0",
+		"webpack": "^5.89.0"
 	},
 	"peerDependencies": {
 		"@storybook/react": "^7.5.3"
diff --git a/packages/design-carousel/package.json b/packages/design-carousel/package.json
index 9cf48ec2a67e79..bd2fc0d5cceb0e 100644
--- a/packages/design-carousel/package.json
+++ b/packages/design-carousel/package.json
@@ -47,7 +47,7 @@
 		"react-dom": "^18.2.0",
 		"redux": "^4.2.1",
 		"typescript": "^5.2.2",
-		"webpack": "^5.68.0"
+		"webpack": "^5.89.0"
 	},
 	"peerDependencies": {
 		"@wordpress/data": "^9.14.0",
diff --git a/packages/design-picker/package.json b/packages/design-picker/package.json
index 90e7916ecbb857..512c2e1c2c23c3 100644
--- a/packages/design-picker/package.json
+++ b/packages/design-picker/package.json
@@ -57,7 +57,7 @@
 		"react-dom": "^18.2.0",
 		"redux": "^4.2.1",
 		"typescript": "^5.2.2",
-		"webpack": "^5.68.0"
+		"webpack": "^5.89.0"
 	},
 	"peerDependencies": {
 		"@wordpress/data": "^9.14.0",
diff --git a/packages/domains-table/package.json b/packages/domains-table/package.json
index 6f4c437fdc008c..d4782427d63e79 100644
--- a/packages/domains-table/package.json
+++ b/packages/domains-table/package.json
@@ -52,7 +52,7 @@
 		"react-dom": "^18.2.0",
 		"resize-observer-polyfill": "^1.5.1",
 		"typescript": "^5.2.2",
-		"webpack": "^5.68.0"
+		"webpack": "^5.89.0"
 	},
 	"peerDependencies": {
 		"@wordpress/data": "^9.14.0",
diff --git a/packages/languages/package.json b/packages/languages/package.json
index 607f227c7b80eb..9154ce579f017b 100644
--- a/packages/languages/package.json
+++ b/packages/languages/package.json
@@ -40,6 +40,6 @@
 		"react-dom": "^18.2.0",
 		"redux": "^4.2.1",
 		"typescript": "^5.2.2",
-		"webpack": "^5.68.0"
+		"webpack": "^5.89.0"
 	}
 }
diff --git a/packages/launchpad-navigator/package.json b/packages/launchpad-navigator/package.json
index 23186a6d42e082..104628d33df590 100644
--- a/packages/launchpad-navigator/package.json
+++ b/packages/launchpad-navigator/package.json
@@ -47,7 +47,7 @@
 		"react-dom": "^18.2.0",
 		"redux": "^4.2.1",
 		"typescript": "^5.2.2",
-		"webpack": "^5.68.0"
+		"webpack": "^5.89.0"
 	},
 	"peerDependencies": {
 		"@wordpress/data": "^9.14.0",
diff --git a/packages/launchpad/package.json b/packages/launchpad/package.json
index 83f05b92fc14a5..011c508cf2ef19 100644
--- a/packages/launchpad/package.json
+++ b/packages/launchpad/package.json
@@ -46,7 +46,7 @@
 		"react-dom": "^18.2.0",
 		"redux": "^4.2.1",
 		"typescript": "^5.2.2",
-		"webpack": "^5.68.0"
+		"webpack": "^5.89.0"
 	},
 	"peerDependencies": {
 		"@wordpress/data": "^9.14.0",
diff --git a/packages/onboarding/package.json b/packages/onboarding/package.json
index e62f54e25688be..6918179d818b8c 100644
--- a/packages/onboarding/package.json
+++ b/packages/onboarding/package.json
@@ -51,9 +51,9 @@
 		"react-dom": "^18.2.0",
 		"redux": "^4.2.1",
 		"sass-loader": "^10.1.1",
-		"style-loader": "^1.2.1",
+		"style-loader": "^1.3.0",
 		"typescript": "^5.2.2",
-		"webpack": "^5.63.0"
+		"webpack": "^5.89.0"
 	},
 	"peerDependencies": {
 		"@wordpress/i18n": "^4.44.0",
diff --git a/packages/privacy-toolset/package.json b/packages/privacy-toolset/package.json
index 761564e9708cca..bcc523958b3722 100644
--- a/packages/privacy-toolset/package.json
+++ b/packages/privacy-toolset/package.json
@@ -53,6 +53,6 @@
 		"postcss": "^8.4.5",
 		"require-from-string": "^2.0.2",
 		"typescript": "^5.2.2",
-		"webpack": "^5.68.0"
+		"webpack": "^5.89.0"
 	}
 }
diff --git a/packages/search/package.json b/packages/search/package.json
index dfadccc33e2030..22126758ddb316 100644
--- a/packages/search/package.json
+++ b/packages/search/package.json
@@ -60,7 +60,7 @@
 		"react": "^18.2.0",
 		"react-dom": "^18.2.0",
 		"typescript": "^5.2.2",
-		"webpack": "^5.68.0"
+		"webpack": "^5.89.0"
 	},
 	"scripts": {
 		"clean": "tsc --build ./tsconfig.json ./tsconfig-cjs.json --clean && rm -rf dist",
diff --git a/packages/social-previews/package.json b/packages/social-previews/package.json
index 7d97db5adf592e..425fcf07891e56 100644
--- a/packages/social-previews/package.json
+++ b/packages/social-previews/package.json
@@ -57,7 +57,7 @@
 		"react": "^18.2.0",
 		"react-dom": "^18.2.0",
 		"typescript": "^5.2.2",
-		"webpack": "^5.68.0"
+		"webpack": "^5.89.0"
 	},
 	"peerDependencies": {
 		"@babel/runtime": "^7.23.2",
diff --git a/packages/webpack-config-flag-plugin/package.json b/packages/webpack-config-flag-plugin/package.json
index 47bcca1a12328c..1fe1e8fe338707 100644
--- a/packages/webpack-config-flag-plugin/package.json
+++ b/packages/webpack-config-flag-plugin/package.json
@@ -6,7 +6,7 @@
 	"bugs": "https://github.com/Automattic/wp-calypso/issues",
 	"main": "index.js",
 	"peerDependencies": {
-		"webpack": "^5.68.0"
+		"webpack": "^5.89.0"
 	},
 	"author": "Automattic Inc.",
 	"private": true,
diff --git a/packages/webpack-extensive-lodash-replacement-plugin/package.json b/packages/webpack-extensive-lodash-replacement-plugin/package.json
index 00fb3c370c5005..b73a0381afe232 100644
--- a/packages/webpack-extensive-lodash-replacement-plugin/package.json
+++ b/packages/webpack-extensive-lodash-replacement-plugin/package.json
@@ -20,7 +20,7 @@
 	},
 	"bugs": "https://github.com/Automattic/wp-calypso/issues",
 	"peerDependencies": {
-		"webpack": "^5.68.0"
+		"webpack": "^5.89.0"
 	},
 	"dependencies": {
 		"semver": "^7.0.0"
diff --git a/packages/webpack-inline-constant-exports-plugin/package.json b/packages/webpack-inline-constant-exports-plugin/package.json
index 72985644ffb94b..56933310c81bca 100644
--- a/packages/webpack-inline-constant-exports-plugin/package.json
+++ b/packages/webpack-inline-constant-exports-plugin/package.json
@@ -18,13 +18,13 @@
 	},
 	"bugs": "https://github.com/Automattic/wp-calypso/issues",
 	"peerDependencies": {
-		"webpack": "^5.68.0"
+		"webpack": "^5.89.0"
 	},
 	"devDependencies": {
 		"@automattic/calypso-eslint-overrides": "workspace:^",
 		"@automattic/calypso-typescript-config": "workspace:^",
 		"rimraf": "^3.0.2",
-		"webpack": "^5.68.0"
+		"webpack": "^5.89.0"
 	},
 	"files": [
 		"index.js"
diff --git a/packages/webpack-rtl-plugin/package.json b/packages/webpack-rtl-plugin/package.json
index b3b61e4531c161..7c2cc8c2aaf278 100644
--- a/packages/webpack-rtl-plugin/package.json
+++ b/packages/webpack-rtl-plugin/package.json
@@ -25,12 +25,12 @@
 	"license": "GPL-2.0-or-later",
 	"devDependencies": {
 		"@automattic/calypso-typescript-config": "workspace:^",
-		"css-loader": "^6.5.1",
+		"css-loader": "^6.8.1",
 		"mini-css-extract-plugin": "^1.6.2",
-		"webpack": "^5.68.0"
+		"webpack": "^5.89.0"
 	},
 	"peerDependencies": {
-		"webpack": "^5.68.0"
+		"webpack": "^5.89.0"
 	},
 	"dependencies": {
 		"rtlcss": "^3.1.2"
diff --git a/packages/wpcom-proxy-request/package.json b/packages/wpcom-proxy-request/package.json
index 9e2e9ba0209020..c31438a334c228 100644
--- a/packages/wpcom-proxy-request/package.json
+++ b/packages/wpcom-proxy-request/package.json
@@ -48,6 +48,6 @@
 		"@automattic/calypso-eslint-overrides": "workspace:^",
 		"@automattic/calypso-typescript-config": "workspace:^",
 		"postcss": "^8.4.5",
-		"webpack": "^5.68.0"
+		"webpack": "^5.89.0"
 	}
 }
diff --git a/packages/wpcom.js/package.json b/packages/wpcom.js/package.json
index 80e56b407b897d..f9a4ef8fd6b036 100644
--- a/packages/wpcom.js/package.json
+++ b/packages/wpcom.js/package.json
@@ -51,8 +51,8 @@
 		"@babel/core": "^7.23.2",
 		"babel-loader": "^8.2.3",
 		"npm-run-all": "^4.1.5",
-		"webpack": "^5.68.0",
-		"webpack-cli": "^4.9.2",
+		"webpack": "^5.89.0",
+		"webpack-cli": "^4.10.0",
 		"wpcom-oauth-cors": "^1.0.2-beta",
 		"wpcom-proxy-request": "workspace:^"
 	}
diff --git a/yarn.lock b/yarn.lock
index 42ee6a91c6f476..7ba3a82d9b289e 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -146,13 +146,13 @@ __metadata:
     "@automattic/webpack-inline-constant-exports-plugin": "workspace:^"
     "@automattic/wp-babel-makepot": "workspace:^"
     "@tanstack/react-query": "npm:^4.29.1"
-    "@wordpress/dependency-extraction-webpack-plugin": "npm:^4.21.0"
+    "@wordpress/dependency-extraction-webpack-plugin": "npm:^4.29.0"
     autoprefixer: "npm:^10.2.5"
     calypso: "workspace:^"
     classnames: "npm:^2.3.2"
     debug: "npm:^4.3.4"
     gettext-parser: "npm:^6.0.0"
-    html-webpack-plugin: "npm:^5.0.0-beta.4"
+    html-webpack-plugin: "npm:^5.5.3"
     lodash: "npm:^4.17.21"
     mkdirp: "npm:^1.0.4"
     moment: "npm:^2.26.0"
@@ -166,8 +166,8 @@ __metadata:
     react-redux: "npm:^8.1.3"
     redux: "npm:^4.2.1"
     redux-thunk: "npm:^2.4.2"
-    webpack: "npm:^5.68.0"
-    webpack-bundle-analyzer: "npm:^4.5.0"
+    webpack: "npm:^5.89.0"
+    webpack-bundle-analyzer: "npm:^4.10.1"
     wpcom: "workspace:^"
     wpcom-proxy-request: "workspace:^"
   languageName: unknown
@@ -233,10 +233,10 @@ __metadata:
     "@automattic/calypso-eslint-overrides": "workspace:^"
     "@automattic/calypso-typescript-config": "workspace:^"
     chokidar: "npm:^3.5.2"
-    html-webpack-plugin: "npm:^5.0.0-beta.4"
+    html-webpack-plugin: "npm:^5.5.3"
     npm-run-all: "npm:^4.1.5"
     tree-kill: "npm:^1.2.2"
-    webpack: "npm:^5.68.0"
+    webpack: "npm:^5.89.0"
     yargs: "npm:^17.0.1"
   bin:
     calypso-apps-builder: ./index.js
@@ -278,30 +278,30 @@ __metadata:
     "@automattic/webpack-rtl-plugin": "workspace:^"
     "@babel/compat-data": "npm:^7.23.2"
     "@babel/core": "npm:^7.23.2"
-    "@types/webpack-env": "npm:^1.16.3"
+    "@types/webpack-env": "npm:^1.18.4"
     "@wordpress/browserslist-config": "npm:^5.27.0"
-    "@wordpress/dependency-extraction-webpack-plugin": "npm:^4.21.0"
+    "@wordpress/dependency-extraction-webpack-plugin": "npm:^4.29.0"
     autoprefixer: "npm:^10.2.5"
     babel-loader: "npm:^8.2.3"
     browserslist: "npm:^4.8.2"
-    css-loader: "npm:^6.5.1"
-    css-minimizer-webpack-plugin: "npm:^3.2.0"
+    css-loader: "npm:^6.8.1"
+    css-minimizer-webpack-plugin: "npm:^3.4.1"
     duplicate-package-checker-webpack-plugin: "npm:^3.0.0"
     mini-css-extract-plugin: "npm:^1.6.2"
     postcss-custom-properties: "npm:^11.0.0"
-    postcss-loader: "npm:^6.2.0"
+    postcss-loader: "npm:^6.2.1"
     recursive-copy: "npm:^2.0.14"
     sass: "npm:^1.37.5"
     sass-loader: "npm:^12.1.0"
     semver: "npm:^7.3.2"
     stream-browserify: "npm:^3.0.0"
-    terser-webpack-plugin: "npm:^5.2.4"
+    terser-webpack-plugin: "npm:^5.3.9"
     thread-loader: "npm:^3.0.4"
     typescript: "npm:^5.2.2"
-    webpack-cli: "npm:^4.9.2"
+    webpack-cli: "npm:^4.10.0"
   peerDependencies:
     postcss: ^8.4.5
-    webpack: ^5.68.0
+    webpack: ^5.89.0
   bin:
     calypso-build: ./bin/calypso-build.js
     copy-assets: ./bin/copy-assets.js
@@ -473,12 +473,12 @@ __metadata:
     "@storybook/addon-viewport": "npm:^7.5.3"
     "@storybook/preset-scss": "npm:^1.0.3"
     "@storybook/react-webpack5": "npm:^7.5.3"
-    css-loader: "npm:^6.5.1"
+    css-loader: "npm:^6.8.1"
     react: "npm:^18.2.0"
     react-dom: "npm:^18.2.0"
     sass-loader: "npm:^12.1.0"
-    style-loader: "npm:^1.2.1"
-    webpack: "npm:^5.68.0"
+    style-loader: "npm:^1.3.0"
+    webpack: "npm:^5.89.0"
   peerDependencies:
     "@storybook/react": ^7.5.3
   languageName: unknown
@@ -664,7 +664,7 @@ __metadata:
     tslib: "npm:^2.3.0"
     typescript: "npm:^5.2.2"
     utility-types: "npm:^3.10.0"
-    webpack: "npm:^5.68.0"
+    webpack: "npm:^5.89.0"
     wpcom-proxy-request: "workspace:^"
   peerDependencies:
     "@wordpress/data": ^9.14.0
@@ -706,7 +706,7 @@ __metadata:
     tslib: "npm:^2.3.0"
     typescript: "npm:^5.2.2"
     utility-types: "npm:^3.10.0"
-    webpack: "npm:^5.68.0"
+    webpack: "npm:^5.89.0"
   peerDependencies:
     "@wordpress/data": ^9.14.0
     "@wordpress/element": ^5.21.0
@@ -810,7 +810,7 @@ __metadata:
     react-intersection-observer: "npm:^9.4.3"
     resize-observer-polyfill: "npm:^1.5.1"
     typescript: "npm:^5.2.2"
-    webpack: "npm:^5.68.0"
+    webpack: "npm:^5.89.0"
   peerDependencies:
     "@wordpress/data": ^9.14.0
     "@wordpress/i18n": ^4.44.0
@@ -1055,7 +1055,7 @@ __metadata:
     redux: "npm:^4.2.1"
     tslib: "npm:^2.3.0"
     typescript: "npm:^5.2.2"
-    webpack: "npm:^5.68.0"
+    webpack: "npm:^5.89.0"
   languageName: unknown
   linkType: soft
 
@@ -1088,7 +1088,7 @@ __metadata:
     redux: "npm:^4.2.1"
     tslib: "npm:^2.3.0"
     typescript: "npm:^5.2.2"
-    webpack: "npm:^5.68.0"
+    webpack: "npm:^5.89.0"
     wpcom-proxy-request: "workspace:^"
   peerDependencies:
     "@wordpress/data": ^9.14.0
@@ -1119,7 +1119,7 @@ __metadata:
     tslib: "npm:^2.3.0"
     typescript: "npm:^5.2.2"
     utility-types: "npm:^3.10.0"
-    webpack: "npm:^5.68.0"
+    webpack: "npm:^5.89.0"
     wpcom-proxy-request: "workspace:^"
   peerDependencies:
     "@wordpress/data": ^9.14.0
@@ -1207,7 +1207,7 @@ __metadata:
     calypso: "workspace:^"
     classnames: "npm:^2.3.2"
     debug: "npm:^4.3.3"
-    html-webpack-plugin: "npm:^5.0.0-beta.4"
+    html-webpack-plugin: "npm:^5.5.3"
     i18n-calypso: "workspace:^"
     page: "npm:^1.11.5"
     postcss: "npm:^8.4.5"
@@ -1218,9 +1218,9 @@ __metadata:
     react-redux: "npm:^8.1.3"
     redux: "npm:^4.2.1"
     redux-thunk: "npm:^2.4.2"
-    webpack: "npm:^5.68.0"
-    webpack-bundle-analyzer: "npm:^4.5.0"
-    webpack-dev-server: "npm:^4.7.3"
+    webpack: "npm:^5.89.0"
+    webpack-bundle-analyzer: "npm:^4.10.1"
+    webpack-dev-server: "npm:^4.15.1"
     wpcom: "workspace:^"
     wpcom-proxy-request: "workspace:^"
     wpcom-xhr-request: "workspace:^"
@@ -1247,7 +1247,7 @@ __metadata:
     "@wordpress/icons": "npm:^9.35.0"
     "@wordpress/is-shallow-equal": "npm:^4.44.0"
     "@wordpress/primitives": "npm:^3.42.0"
-    "@wordpress/readable-js-assets-webpack-plugin": "npm:^2.21.0"
+    "@wordpress/readable-js-assets-webpack-plugin": "npm:^2.29.0"
     classnames: "npm:^2.3.2"
     lodash: "npm:^4.17.21"
     moment: "npm:^2.26.0"
@@ -1256,7 +1256,7 @@ __metadata:
     react: "npm:^18.2.0"
     react-dom: "npm:^18.2.0"
     redux: "npm:^4.2.1"
-    webpack: "npm:^5.68.0"
+    webpack: "npm:^5.89.0"
   languageName: unknown
   linkType: soft
 
@@ -1282,7 +1282,7 @@ __metadata:
     "@tanstack/react-query": "npm:4.29.1"
     "@wordpress/base-styles": "npm:^4.35.0"
     "@wordpress/data": "npm:^9.14.0"
-    "@wordpress/dependency-extraction-webpack-plugin": "npm:^4.21.0"
+    "@wordpress/dependency-extraction-webpack-plugin": "npm:^4.29.0"
     "@wordpress/icons": "npm:^9.35.0"
     autoprefixer: "npm:^10.2.5"
     babel-jest: "npm:^29.6.1"
@@ -1290,7 +1290,7 @@ __metadata:
     classnames: "npm:^2.3.2"
     debug: "npm:^4.3.4"
     gettext-parser: "npm:^6.0.0"
-    html-webpack-plugin: "npm:^5.0.0-beta.4"
+    html-webpack-plugin: "npm:^5.5.3"
     jest: "npm:^29.7.0"
     lodash: "npm:^4.17.21"
     mkdirp: "npm:^1.0.4"
@@ -1306,8 +1306,8 @@ __metadata:
     redux: "npm:^4.2.1"
     redux-thunk: "npm:^2.4.2"
     size-limit: "npm:^8.2.6"
-    webpack: "npm:^5.68.0"
-    webpack-bundle-analyzer: "npm:^4.5.0"
+    webpack: "npm:^5.89.0"
+    webpack-bundle-analyzer: "npm:^4.10.1"
     wpcom: "workspace:^"
   languageName: unknown
   linkType: soft
@@ -1334,10 +1334,10 @@ __metadata:
     react-router-dom: "npm:^6.10.0"
     redux: "npm:^4.2.1"
     sass-loader: "npm:^10.1.1"
-    style-loader: "npm:^1.2.1"
+    style-loader: "npm:^1.3.0"
     tslib: "npm:^2.5.0"
     typescript: "npm:^5.2.2"
-    webpack: "npm:^5.63.0"
+    webpack: "npm:^5.89.0"
     wpcom-proxy-request: "workspace:^"
   peerDependencies:
     "@wordpress/i18n": ^4.44.0
@@ -1429,7 +1429,7 @@ __metadata:
     postcss: "npm:^8.4.5"
     require-from-string: "npm:^2.0.2"
     typescript: "npm:^5.2.2"
-    webpack: "npm:^5.68.0"
+    webpack: "npm:^5.89.0"
   peerDependencies:
     react: ^18.2.0
     react-dom: ^18.2.0
@@ -1490,7 +1490,7 @@ __metadata:
     redux: "npm:^4.2.1"
     tslib: "npm:^2.3.0"
     typescript: "npm:^5.2.2"
-    webpack: "npm:^5.68.0"
+    webpack: "npm:^5.89.0"
   peerDependencies:
     react: ^18.2.0
     react-dom: ^18.2.0
@@ -1568,7 +1568,7 @@ __metadata:
     react-dom: "npm:^18.2.0"
     tslib: "npm:^2.3.0"
     typescript: "npm:^5.2.2"
-    webpack: "npm:^5.68.0"
+    webpack: "npm:^5.89.0"
   peerDependencies:
     "@babel/runtime": ^7.23.2
     react: ^18.2.0
@@ -1705,7 +1705,7 @@ __metadata:
     "@automattic/calypso-typescript-config": "workspace:^"
     rimraf: "npm:^3.0.2"
   peerDependencies:
-    webpack: ^5.68.0
+    webpack: ^5.89.0
   languageName: unknown
   linkType: soft
 
@@ -1716,7 +1716,7 @@ __metadata:
     "@automattic/calypso-typescript-config": "workspace:^"
     semver: "npm:^7.0.0"
   peerDependencies:
-    webpack: ^5.68.0
+    webpack: ^5.89.0
   languageName: unknown
   linkType: soft
 
@@ -1727,9 +1727,9 @@ __metadata:
     "@automattic/calypso-eslint-overrides": "workspace:^"
     "@automattic/calypso-typescript-config": "workspace:^"
     rimraf: "npm:^3.0.2"
-    webpack: "npm:^5.68.0"
+    webpack: "npm:^5.89.0"
   peerDependencies:
-    webpack: ^5.68.0
+    webpack: ^5.89.0
   languageName: unknown
   linkType: soft
 
@@ -1738,12 +1738,12 @@ __metadata:
   resolution: "@automattic/webpack-rtl-plugin@workspace:packages/webpack-rtl-plugin"
   dependencies:
     "@automattic/calypso-typescript-config": "workspace:^"
-    css-loader: "npm:^6.5.1"
+    css-loader: "npm:^6.8.1"
     mini-css-extract-plugin: "npm:^1.6.2"
     rtlcss: "npm:^3.1.2"
-    webpack: "npm:^5.68.0"
+    webpack: "npm:^5.89.0"
   peerDependencies:
-    webpack: ^5.68.0
+    webpack: ^5.89.0
   languageName: unknown
   linkType: soft
 
@@ -1819,7 +1819,7 @@ __metadata:
     "@wordpress/components": "npm:^25.10.0"
     "@wordpress/compose": "npm:^6.21.0"
     "@wordpress/data": "npm:^9.14.0"
-    "@wordpress/dependency-extraction-webpack-plugin": "npm:^4.21.0"
+    "@wordpress/dependency-extraction-webpack-plugin": "npm:^4.29.0"
     "@wordpress/dom-ready": "npm:^3.44.0"
     "@wordpress/edit-post": "npm:^7.21.0"
     "@wordpress/edit-site": "npm:^5.21.0"
@@ -1841,7 +1841,7 @@ __metadata:
     react-dom: "npm:^18.2.0"
     redux: "npm:^4.2.1"
     tinymce: "npm:^5.0.0"
-    webpack: "npm:^5.68.0"
+    webpack: "npm:^5.89.0"
   languageName: unknown
   linkType: soft
 
@@ -1919,7 +1919,7 @@ __metadata:
     "@wordpress/data": "npm:^9.14.0"
     "@wordpress/data-controls": "npm:^3.13.0"
     "@wordpress/date": "npm:^4.44.0"
-    "@wordpress/dependency-extraction-webpack-plugin": "npm:^4.21.0"
+    "@wordpress/dependency-extraction-webpack-plugin": "npm:^4.29.0"
     "@wordpress/dom-ready": "npm:^3.44.0"
     "@wordpress/edit-post": "npm:^7.21.0"
     "@wordpress/element": "npm:^5.21.0"
@@ -1938,7 +1938,7 @@ __metadata:
     "@wordpress/plugins": "npm:^6.12.0"
     "@wordpress/primitives": "npm:^3.42.0"
     "@wordpress/private-apis": "npm:^0.26.0"
-    "@wordpress/readable-js-assets-webpack-plugin": "npm:^2.21.0"
+    "@wordpress/readable-js-assets-webpack-plugin": "npm:^2.29.0"
     "@wordpress/rich-text": "npm:^6.21.0"
     "@wordpress/server-side-render": "npm:^4.21.0"
     "@wordpress/url": "npm:^3.45.0"
@@ -1968,7 +1968,7 @@ __metadata:
     swiper: "npm:^8.4.5"
     utility-types: "npm:^3.10.0"
     wait-for-expect: "npm:^3.0.2"
-    webpack: "npm:^5.68.0"
+    webpack: "npm:^5.89.0"
   languageName: unknown
   linkType: soft
 
@@ -3682,7 +3682,7 @@ __metadata:
   languageName: node
   linkType: hard
 
-"@discoveryjs/json-ext@npm:^0.5.0, @discoveryjs/json-ext@npm:^0.5.2, @discoveryjs/json-ext@npm:^0.5.3":
+"@discoveryjs/json-ext@npm:0.5.7, @discoveryjs/json-ext@npm:^0.5.0, @discoveryjs/json-ext@npm:^0.5.2, @discoveryjs/json-ext@npm:^0.5.3":
   version: 0.5.7
   resolution: "@discoveryjs/json-ext@npm:0.5.7"
   checksum: e10f1b02b78e4812646ddf289b7d9f2cb567d336c363b266bd50cd223cf3de7c2c74018d91cd2613041568397ef3a4a2b500aba588c6e5bd78c38374ba68f38c
@@ -4774,9 +4774,9 @@ __metadata:
   languageName: node
   linkType: hard
 
-"@pmmmwh/react-refresh-webpack-plugin@npm:^0.5.10, @pmmmwh/react-refresh-webpack-plugin@npm:^0.5.5":
-  version: 0.5.10
-  resolution: "@pmmmwh/react-refresh-webpack-plugin@npm:0.5.10"
+"@pmmmwh/react-refresh-webpack-plugin@npm:^0.5.11, @pmmmwh/react-refresh-webpack-plugin@npm:^0.5.5":
+  version: 0.5.11
+  resolution: "@pmmmwh/react-refresh-webpack-plugin@npm:0.5.11"
   dependencies:
     ansi-html-community: "npm:^0.0.8"
     common-path-prefix: "npm:^3.0.0"
@@ -4791,7 +4791,7 @@ __metadata:
     "@types/webpack": 4.x || 5.x
     react-refresh: ">=0.10.0 <1.0.0"
     sockjs-client: ^1.4.0
-    type-fest: ">=0.17.0 <4.0.0"
+    type-fest: ">=0.17.0 <5.0.0"
     webpack: ">=4.43.0 <6.0.0"
     webpack-dev-server: 3.x || 4.x
     webpack-hot-middleware: 2.x
@@ -4809,14 +4809,14 @@ __metadata:
       optional: true
     webpack-plugin-serve:
       optional: true
-  checksum: e470b543c5e8d73eeaa73636e1976e6719db6ae29c93fa62818f5796c1883051f379a3cb1ff85d909ef2c6bb9ef13ca46c36f1878c48d143b1355fea6660e547
+  checksum: a9c8468417a14a23339e313cff6ddb8029e0637748973070e61d83a2534620b3492b9a42ecf9eb9d63cb709f53c17fe814bc7dd68d64c300db338e9fd7287bc4
   languageName: node
   linkType: hard
 
-"@polka/url@npm:^1.0.0-next.9":
-  version: 1.0.0-next.11
-  resolution: "@polka/url@npm:1.0.0-next.11"
-  checksum: bc361ca82d715377b38b547fef42b3adb616925f28a12ad3da1f6f77304ffd07a3ccd970d49e42bb01ff8a4d180740ce805bb1f6c8e265b2ebf298b274162a8d
+"@polka/url@npm:^1.0.0-next.20":
+  version: 1.0.0-next.23
+  resolution: "@polka/url@npm:1.0.0-next.23"
+  checksum: 78f6f5dbb56b56f5beaf5a99a88bed1bc9e6f6ec10d839f006b1680e6e7c0e0a8c3c91ce98c92a0bf01480ce8b04b37835089d212e8948fbb1f4a392863b275b
   languageName: node
   linkType: hard
 
@@ -6066,20 +6066,19 @@ __metadata:
   languageName: node
   linkType: hard
 
-"@sentry/cli@npm:^1.73.0":
-  version: 1.74.3
-  resolution: "@sentry/cli@npm:1.74.3"
+"@sentry/cli@npm:^1.77.1":
+  version: 1.77.1
+  resolution: "@sentry/cli@npm:1.77.1"
   dependencies:
     https-proxy-agent: "npm:^5.0.0"
     mkdirp: "npm:^0.5.5"
     node-fetch: "npm:^2.6.7"
-    npmlog: "npm:^4.1.2"
     progress: "npm:^2.0.3"
     proxy-from-env: "npm:^1.1.0"
     which: "npm:^2.0.2"
   bin:
     sentry-cli: bin/sentry-cli
-  checksum: 6e5ba95f9d7c756e8a7d6f6ec010cde8c39588dd19dc3994c628910a245db0feb32f411fb2410157a6af2c7352165625f58092f82d1191aa493d385eed7a2887
+  checksum: 92c9d9e26ca5667110a2546732c12d302753e76c47144103ca9d04d571f1933f4e0549b4b729a875dfafb1fbd071868b8b6c73855a581b8af07f39dee7636fcc
   languageName: node
   linkType: hard
 
@@ -6137,12 +6136,13 @@ __metadata:
   languageName: node
   linkType: hard
 
-"@sentry/webpack-plugin@npm:^1.18.8":
-  version: 1.18.8
-  resolution: "@sentry/webpack-plugin@npm:1.18.8"
+"@sentry/webpack-plugin@npm:^1.20.1":
+  version: 1.21.0
+  resolution: "@sentry/webpack-plugin@npm:1.21.0"
   dependencies:
-    "@sentry/cli": "npm:^1.73.0"
-  checksum: cad2e8a03804889db9521b05cfd1ce24221d1598acc54f5922fc91d16a4bc96806e55b86b4f21f1d62b42b2358239454ba00f6d98d6d14662551048f5e126618
+    "@sentry/cli": "npm:^1.77.1"
+    webpack-sources: "npm:^2.0.0 || ^3.0.0"
+  checksum: 743650dc65c06c4a682d4e80ca2dee3234c30a2d5f66d2f9702e6e5041e20f6151a604fcc76d5f08afb6c7a91feec71719637916a5674fefd00fc1dda0560c7f
   languageName: node
   linkType: hard
 
@@ -7541,15 +7541,6 @@ __metadata:
   languageName: node
   linkType: hard
 
-"@types/cssnano@npm:^4.0.1":
-  version: 4.0.1
-  resolution: "@types/cssnano@npm:4.0.1"
-  dependencies:
-    postcss: "npm:5 - 7"
-  checksum: 4a5f72721caa4c2cb4961ee4ec29af697550b4d28067fd9b753891049767cd54f56554709ea0ccbf460a8934a93b153dde62c64546e6db22e107dcf7be9fc2b2
-  languageName: node
-  linkType: hard
-
 "@types/debug@npm:^4.0.0, @types/debug@npm:^4.1.6, @types/debug@npm:^4.1.7":
   version: 4.1.8
   resolution: "@types/debug@npm:4.1.8"
@@ -7786,6 +7777,13 @@ __metadata:
   languageName: node
   linkType: hard
 
+"@types/http-errors@npm:*":
+  version: 2.0.4
+  resolution: "@types/http-errors@npm:2.0.4"
+  checksum: 494670a57ad4062fee6c575047ad5782506dd35a6b9ed3894cea65830a94367bd84ba302eb3dde331871f6d70ca287bfedb1b2cf658e6132cd2cbd427ab56836
+  languageName: node
+  linkType: hard
+
 "@types/http-proxy@npm:^1.17.8":
   version: 1.17.8
   resolution: "@types/http-proxy@npm:1.17.8"
@@ -7915,6 +7913,13 @@ __metadata:
   languageName: node
   linkType: hard
 
+"@types/mime@npm:*":
+  version: 3.0.4
+  resolution: "@types/mime@npm:3.0.4"
+  checksum: db478bc0f99e40f7b3e01d356a9bdf7817060808a294978111340317bcd80ca35382855578c5b60fbc84ae449674bd9bb38427b18417e1f8f19e4f72f8b242cd
+  languageName: node
+  linkType: hard
+
 "@types/mime@npm:^1":
   version: 1.3.2
   resolution: "@types/mime@npm:1.3.2"
@@ -7960,6 +7965,15 @@ __metadata:
   languageName: node
   linkType: hard
 
+"@types/node-forge@npm:^1.3.0":
+  version: 1.3.9
+  resolution: "@types/node-forge@npm:1.3.9"
+  dependencies:
+    "@types/node": "npm:*"
+  checksum: 735dc138b9140c6bda605efa093a177bbb6b433c6967db74fe7f887754a2fdefc0d89db73993b9a4e22108f6721ba0a583167e46527a8b79a4306fd85b3a7204
+  languageName: node
+  linkType: hard
+
 "@types/node@npm:*, @types/node@npm:^20.8.6":
   version: 20.8.7
   resolution: "@types/node@npm:20.8.7"
@@ -8202,13 +8216,14 @@ __metadata:
   languageName: node
   linkType: hard
 
-"@types/serve-static@npm:*":
-  version: 1.13.10
-  resolution: "@types/serve-static@npm:1.13.10"
+"@types/serve-static@npm:*, @types/serve-static@npm:^1.13.10":
+  version: 1.15.5
+  resolution: "@types/serve-static@npm:1.15.5"
   dependencies:
-    "@types/mime": "npm:^1"
+    "@types/http-errors": "npm:*"
+    "@types/mime": "npm:*"
     "@types/node": "npm:*"
-  checksum: 7f3de245cbb11f3a9d7977b6e763585c6022ebfc079fa746f8d824411bb6b343521c1cff5407edc0d5196f4b7d6fea431fb36455843f4a6717d295c235065cf2
+  checksum: 811d1a2f7e74a872195e7a013bcd87a2fb1edf07eaedcb9dcfd20c1eb4bc56ad4ea0d52141c13192c91ccda7c8aeb8a530d8a7e60b9c27f5990d7e62e0fecb03
   languageName: node
   linkType: hard
 
@@ -8326,10 +8341,10 @@ __metadata:
   languageName: node
   linkType: hard
 
-"@types/webpack-env@npm:^1.16.3":
-  version: 1.16.3
-  resolution: "@types/webpack-env@npm:1.16.3"
-  checksum: 136ece45e58fbcb4d8e02fe7892213105d6874223a66209bccaf4a18ca78ab81a10d121ee9d0944904cfad1274ca730efc9643b9cd8444239f505676adee22a0
+"@types/webpack-env@npm:^1.18.4":
+  version: 1.18.4
+  resolution: "@types/webpack-env@npm:1.18.4"
+  checksum: 3fa77dbff0ed71685404576b0a1cf74587567fe2ee1cfd11d56d6eefcab7a61e4c9ead0eced264e289d2cf0fc74296dbd55ed6c95774fe0fd6264d156c5a59f0
   languageName: node
   linkType: hard
 
@@ -8340,12 +8355,12 @@ __metadata:
   languageName: node
   linkType: hard
 
-"@types/ws@npm:^8.5.1":
-  version: 8.5.3
-  resolution: "@types/ws@npm:8.5.3"
+"@types/ws@npm:^8.5.5":
+  version: 8.5.9
+  resolution: "@types/ws@npm:8.5.9"
   dependencies:
     "@types/node": "npm:*"
-  checksum: af36857b804e6df615b401bacf34e9312f073ed9dbeda35be16ee3352d18a4449f27066169893166a6ec17ae51557c3adf8d232ac4a4a0226aafb3267e1f1b39
+  checksum: 678bdd6461c4653f2975c537fb673cb1918c331558e2d2422b69761c9ced67200bb07c664e2593f3864077a891cb7c13ef2a40d303b4aacb06173d095d8aa3ce
   languageName: node
   linkType: hard
 
@@ -9279,15 +9294,15 @@ __metadata:
   languageName: node
   linkType: hard
 
-"@wordpress/dependency-extraction-webpack-plugin@npm:4.21.0":
-  version: 4.21.0
-  resolution: "@wordpress/dependency-extraction-webpack-plugin@npm:4.21.0"
+"@wordpress/dependency-extraction-webpack-plugin@npm:4.29.0":
+  version: 4.29.0
+  resolution: "@wordpress/dependency-extraction-webpack-plugin@npm:4.29.0"
   dependencies:
     json2php: "npm:^0.0.7"
     webpack-sources: "npm:^3.2.2"
   peerDependencies:
     webpack: ^4.8.3 || ^5.0.0
-  checksum: 32ec63e21fa38246e5f216a090e9eabfe364d95b7f9eab011e7688fb40d0455d9dc2c94ff2558a7f299346973c8b9c9bcb8041188a4da203f604bed56093c035
+  checksum: f3b0d8232c7b2dcae3b1f476fa110192ac92cbca54ff15c0c82fc5e35423b034154323f45a2966b20e471644287ad2ff8ef9f32bf10b336ae5a9601769cbfff6
   languageName: node
   linkType: hard
 
@@ -9840,12 +9855,12 @@ __metadata:
   languageName: node
   linkType: hard
 
-"@wordpress/readable-js-assets-webpack-plugin@npm:2.21.0":
-  version: 2.21.0
-  resolution: "@wordpress/readable-js-assets-webpack-plugin@npm:2.21.0"
+"@wordpress/readable-js-assets-webpack-plugin@npm:2.29.0":
+  version: 2.29.0
+  resolution: "@wordpress/readable-js-assets-webpack-plugin@npm:2.29.0"
   peerDependencies:
     webpack: ^4.8.3 || ^5.0.0
-  checksum: df3a97222212deb53afd45fe1f37799801f43288b4ce4e0e5cc63dc63b5d3060a5365a634f01950de107cda3c3ee6964000e4e60193ae799adfb98ad2452cf15
+  checksum: af957e429e21ba40f22927286d362677d4603e35eb9665fa5ee34c17261182a0fe4bea583c2dd7e624144a12e176e7677ee98543b1e869ab4257e384aa1e91a3
   languageName: node
   linkType: hard
 
@@ -10123,7 +10138,7 @@ __metadata:
     "@automattic/calypso-build": "workspace:^"
     "@automattic/calypso-eslint-overrides": "workspace:^"
     archiver: "npm:^3.1.1"
-    copy-webpack-plugin: "npm:^10.1.0"
+    copy-webpack-plugin: "npm:^10.2.4"
     cross-env: "npm:^7.0.3"
     electron: "npm:26.2.1"
     electron-builder: "npm:23.0.3"
@@ -10142,8 +10157,8 @@ __metadata:
     react-dom: "npm:^18.2.0"
     semver: "npm:^7.3.2"
     superagent: "npm:^3.8.3"
-    webpack: "npm:^5.68.0"
-    webpack-cli: "npm:^4.9.2"
+    webpack: "npm:^5.89.0"
+    webpack-cli: "npm:^4.10.0"
     winston: "npm:^3.3.3"
     wpcom-xhr-request: "workspace:^"
     ws: "npm:^7.3.1"
@@ -10193,12 +10208,12 @@ __metadata:
   languageName: node
   linkType: hard
 
-"acorn-import-assertions@npm:^1.7.6":
-  version: 1.7.6
-  resolution: "acorn-import-assertions@npm:1.7.6"
+"acorn-import-assertions@npm:^1.9.0":
+  version: 1.9.0
+  resolution: "acorn-import-assertions@npm:1.9.0"
   peerDependencies:
     acorn: ^8
-  checksum: ccd6960363aaaf78386e4ee895fb79e4bf12c33d5f1876918f91aae4e30c9bc7583dc8a6767badfc5e351c42161747fa355a7795ea659296fae62a6b7530a43b
+  checksum: 3b4a194e128efdc9b86c2b1544f623aba4c1aa70d638f8ab7dc3971a5b4aa4c57bd62f99af6e5325bb5973c55863b4112e708a6f408bad7a138647ca72283afe
   languageName: node
   linkType: hard
 
@@ -11011,7 +11026,7 @@ __metadata:
   languageName: node
   linkType: hard
 
-"async@npm:^2.6.2, async@npm:^2.6.3":
+"async@npm:^2.6.3":
   version: 2.6.3
   resolution: "async@npm:2.6.3"
   dependencies:
@@ -12056,7 +12071,7 @@ __metadata:
     "@emotion/react": "npm:^11.11.1"
     "@emotion/styled": "npm:^11.11.0"
     "@github/webauthn-json": "npm:^0.4.1"
-    "@sentry/webpack-plugin": "npm:^1.18.8"
+    "@sentry/webpack-plugin": "npm:^1.20.1"
     "@storybook/addon-actions": "npm:^7.5.3"
     "@stripe/react-stripe-js": "npm:^2.1.0"
     "@stripe/stripe-js": "npm:^1.53.0"
@@ -12207,10 +12222,10 @@ __metadata:
     utility-types: "npm:^3.10.0"
     uuid: "npm:^8.3.2"
     valid-url: "npm:^1.0.9"
-    webpack: "npm:^5.68.0"
-    webpack-bundle-analyzer: "npm:^4.5.0"
-    webpack-dev-middleware: "npm:^5.3.1"
-    webpack-hot-middleware: "npm:^2.25.1"
+    webpack: "npm:^5.89.0"
+    webpack-bundle-analyzer: "npm:^4.10.1"
+    webpack-dev-middleware: "npm:^5.3.3"
+    webpack-hot-middleware: "npm:^2.25.4"
     webpack-node-externals: "npm:^3.0.0"
     wpcom: "workspace:^"
     wpcom-proxy-request: "workspace:^"
@@ -13291,10 +13306,10 @@ __metadata:
   languageName: node
   linkType: hard
 
-"connect-history-api-fallback@npm:^1.6.0":
-  version: 1.6.0
-  resolution: "connect-history-api-fallback@npm:1.6.0"
-  checksum: 6d59c68070fcb2f6d981992f88d050d7544e8e1af6600c23ad680d955e316216794a742a1669d1f14ed5171fc628b916f8a4e15c5a1e55bffc8ccc60bfeb0b2c
+"connect-history-api-fallback@npm:^2.0.0":
+  version: 2.0.0
+  resolution: "connect-history-api-fallback@npm:2.0.0"
+  checksum: 90fa8b16ab76e9531646cc70b010b1dbd078153730c510d3142f6cf07479ae8a812c5a3c0e40a28528dd1681a62395d0cfdef67da9e914c4772ac85d69a3ed87
   languageName: node
   linkType: hard
 
@@ -13416,7 +13431,7 @@ __metadata:
   languageName: node
   linkType: hard
 
-"copy-webpack-plugin@npm:^10.1.0":
+"copy-webpack-plugin@npm:^10.2.4":
   version: 10.2.4
   resolution: "copy-webpack-plugin@npm:10.2.4"
   dependencies:
@@ -13782,29 +13797,28 @@ __metadata:
   languageName: node
   linkType: hard
 
-"css-loader@npm:^6.5.1, css-loader@npm:^6.7.1":
-  version: 6.7.4
-  resolution: "css-loader@npm:6.7.4"
+"css-loader@npm:^6.7.1, css-loader@npm:^6.8.1":
+  version: 6.8.1
+  resolution: "css-loader@npm:6.8.1"
   dependencies:
     icss-utils: "npm:^5.1.0"
     postcss: "npm:^8.4.21"
     postcss-modules-extract-imports: "npm:^3.0.0"
-    postcss-modules-local-by-default: "npm:^4.0.1"
+    postcss-modules-local-by-default: "npm:^4.0.3"
     postcss-modules-scope: "npm:^3.0.0"
     postcss-modules-values: "npm:^4.0.0"
     postcss-value-parser: "npm:^4.2.0"
     semver: "npm:^7.3.8"
   peerDependencies:
     webpack: ^5.0.0
-  checksum: 8dde268a3ae2014a6abd9ad2167b8c153ac06394171b335a00f53ed9eebe5b1f11c3942bba830e5e28d0f940a67ce0ebb2cf0c394cbad84dd271529ff09e4fcf
+  checksum: a6e23de4ec1d2832f10b8ca3cfec6b6097a97ca3c73f64338ae5cd110ac270f1b218ff0273d39f677a7a561f1a9d9b0d332274664d0991bcfafaae162c2669c4
   languageName: node
   linkType: hard
 
-"css-minimizer-webpack-plugin@npm:^3.2.0":
-  version: 3.2.0
-  resolution: "css-minimizer-webpack-plugin@npm:3.2.0"
+"css-minimizer-webpack-plugin@npm:^3.4.1":
+  version: 3.4.1
+  resolution: "css-minimizer-webpack-plugin@npm:3.4.1"
   dependencies:
-    "@types/cssnano": "npm:^4.0.1"
     cssnano: "npm:^5.0.6"
     jest-worker: "npm:^27.0.2"
     postcss: "npm:^8.3.5"
@@ -13814,13 +13828,15 @@ __metadata:
   peerDependencies:
     webpack: ^5.0.0
   peerDependenciesMeta:
+    "@parcel/css":
+      optional: true
     clean-css:
       optional: true
     csso:
       optional: true
     esbuild:
       optional: true
-  checksum: b978f471e3c9cb74d8cdabb826374fb6c03c3550b8f52118c9b7e7a4fcd1799f84a2fdf0a0e1f1ea082c814dd072f55b7932b6c42bc65c1018a18c1ef8d28196
+  checksum: a6b749a136f7a62a173e576a10c8f2ada18013800a2698ede08dfdf6df6761b9ad24cabfce153ef4958ffcf8509e7b6a40c6ddffa6eb06f3624a97c17b825e06
   languageName: node
   linkType: hard
 
@@ -14192,6 +14208,13 @@ __metadata:
   languageName: node
   linkType: hard
 
+"debounce@npm:^1.2.1":
+  version: 1.2.1
+  resolution: "debounce@npm:1.2.1"
+  checksum: 6c9320aa0973fc42050814621a7a8a78146c1975799b5b3cc1becf1f77ba9a5aa583987884230da0842a03f385def452fad5d60db97c3d1c8b824e38a8edf500
+  languageName: node
+  linkType: hard
+
 "debug@npm:2.6.9, debug@npm:^2.2.0, debug@npm:^2.3.3, debug@npm:^2.6.8, debug@npm:^2.6.9":
   version: 2.6.9
   resolution: "debug@npm:2.6.9"
@@ -14222,7 +14245,7 @@ __metadata:
   languageName: node
   linkType: hard
 
-"debug@npm:^3.1.0, debug@npm:^3.1.1, debug@npm:^3.2.7":
+"debug@npm:^3.1.0, debug@npm:^3.2.7":
   version: 3.2.7
   resolution: "debug@npm:3.2.7"
   dependencies:
@@ -15387,13 +15410,13 @@ __metadata:
   languageName: node
   linkType: hard
 
-"enhanced-resolve@npm:^5.14.0, enhanced-resolve@npm:^5.8.3":
-  version: 5.14.0
-  resolution: "enhanced-resolve@npm:5.14.0"
+"enhanced-resolve@npm:^5.15.0, enhanced-resolve@npm:^5.8.3":
+  version: 5.15.0
+  resolution: "enhanced-resolve@npm:5.15.0"
   dependencies:
     graceful-fs: "npm:^4.2.4"
     tapable: "npm:^2.2.0"
-  checksum: 33e68715860246929e30db0128e60bfd2d351987fa2b39a1052f7e555656992c87e856b67083019a6212841c36b1efdde9394961e7cf9dffff400b80848d341c
+  checksum: 69984a7990913948b4150855aed26a84afb4cb1c5a94fb8e3a65bd00729a73fc2eaff6871fb8e345377f294831afe349615c93560f2f54d61b43cdfdf668f19a
   languageName: node
   linkType: hard
 
@@ -18258,15 +18281,15 @@ __metadata:
     "@wordpress/data": "npm:^9.14.0"
     "@wordpress/element": "npm:^5.21.0"
     "@wordpress/i18n": "npm:^4.44.0"
-    "@wordpress/readable-js-assets-webpack-plugin": "npm:^2.21.0"
+    "@wordpress/readable-js-assets-webpack-plugin": "npm:^2.29.0"
     classnames: "npm:^2.3.2"
-    copy-webpack-plugin: "npm:^10.1.0"
+    copy-webpack-plugin: "npm:^10.2.4"
     glob: "npm:^7.1.6"
     i18n-calypso: "workspace:^"
     postcss: "npm:^8.4.5"
     react: "npm:^18.2.0"
     react-dom: "npm:^18.2.0"
-    webpack: "npm:^5.68.0"
+    webpack: "npm:^5.89.0"
   languageName: unknown
   linkType: soft
 
@@ -18583,10 +18606,10 @@ __metadata:
   languageName: node
   linkType: hard
 
-"html-escaper@npm:^2.0.0":
-  version: 2.0.0
-  resolution: "html-escaper@npm:2.0.0"
-  checksum: d9d00b5ef377bc0c9e71f68a4b133d0ddfc6e5efc223c64d2e10905484f242cb95dd406bda3d64786812d3fd2dda402c9181a1216ba6a898083c54c7a26f70cb
+"html-escaper@npm:^2.0.0, html-escaper@npm:^2.0.2":
+  version: 2.0.2
+  resolution: "html-escaper@npm:2.0.2"
+  checksum: 208e8a12de1a6569edbb14544f4567e6ce8ecc30b9394fcaa4e7bb1e60c12a7c9a1ed27e31290817157e8626f3a4f29e76c8747030822eb84a6abb15c255f0a0
   languageName: node
   linkType: hard
 
@@ -18656,9 +18679,9 @@ __metadata:
   languageName: node
   linkType: hard
 
-"html-webpack-plugin@npm:^5.0.0-beta.4, html-webpack-plugin@npm:^5.5.0":
-  version: 5.5.1
-  resolution: "html-webpack-plugin@npm:5.5.1"
+"html-webpack-plugin@npm:^5.5.0, html-webpack-plugin@npm:^5.5.3":
+  version: 5.5.3
+  resolution: "html-webpack-plugin@npm:5.5.3"
   dependencies:
     "@types/html-minifier-terser": "npm:^6.0.0"
     html-minifier-terser: "npm:^6.0.2"
@@ -18667,7 +18690,7 @@ __metadata:
     tapable: "npm:^2.0.0"
   peerDependencies:
     webpack: ^5.20.0
-  checksum: d36511f213d4fed6dc1f4eaba42c1541ce3c1ca9c424ab002d1daf3fbd6b3722009dab34fbe2ae2d3ab986d64c786522c673cb35ab3586a5f6e311e3383c461f
+  checksum: 7ba0d0f87d08f5c4c51f821842d736ec1762940bc39798932528adaec1e9cca8f52944987b88789007f5706d15110edbdfa30df445d61c6628b02ebe163c4f42
   languageName: node
   linkType: hard
 
@@ -21310,6 +21333,16 @@ __metadata:
   languageName: node
   linkType: hard
 
+"launch-editor@npm:^2.6.0":
+  version: 2.6.1
+  resolution: "launch-editor@npm:2.6.1"
+  dependencies:
+    picocolors: "npm:^1.0.0"
+    shell-quote: "npm:^1.8.1"
+  checksum: 82d0bd9a44e7a972157719e63dac1b8196db6ec7066c1ec57a495f6c3d6e734f3c4da89549e7b33eb3b0356668ad02a9e7782b6733f5ebd7a61b7c5f635a3ee9
+  languageName: node
+  linkType: hard
+
 "lazy-universal-dotenv@npm:^4.0.0":
   version: 4.0.0
   resolution: "lazy-universal-dotenv@npm:4.0.0"
@@ -21443,7 +21476,7 @@ __metadata:
   languageName: node
   linkType: hard
 
-"loader-utils@npm:^1.1.0, loader-utils@npm:^1.2.3, loader-utils@npm:^1.4.0":
+"loader-utils@npm:^1.1.0, loader-utils@npm:^1.2.3, loader-utils@npm:^1.4.0, loader-utils@npm:^1.4.2":
   version: 1.4.2
   resolution: "loader-utils@npm:1.4.2"
   dependencies:
@@ -22255,7 +22288,7 @@ __metadata:
   languageName: node
   linkType: hard
 
-"memfs@npm:^3.4.1, memfs@npm:^3.4.12":
+"memfs@npm:^3.4.1, memfs@npm:^3.4.12, memfs@npm:^3.4.3":
   version: 3.5.3
   resolution: "memfs@npm:3.5.3"
   dependencies:
@@ -22644,7 +22677,7 @@ __metadata:
   languageName: node
   linkType: hard
 
-"mime@npm:2.6.0, mime@npm:^2.0.3, mime@npm:^2.3.1, mime@npm:^2.5.2":
+"mime@npm:2.6.0, mime@npm:^2.0.3, mime@npm:^2.5.2":
   version: 2.6.0
   resolution: "mime@npm:2.6.0"
   bin:
@@ -22989,6 +23022,13 @@ __metadata:
   languageName: node
   linkType: hard
 
+"mrmime@npm:^1.0.0":
+  version: 1.0.1
+  resolution: "mrmime@npm:1.0.1"
+  checksum: ab071441da76fd23b3b0d1823d77aacf8679d379a4a94cacd83e487d3d906763b277f3203a594c613602e31ab5209c26a8119b0477c4541ef8555b293a9db6d3
+  languageName: node
+  linkType: hard
+
 "ms@npm:2.0.0":
   version: 2.0.0
   resolution: "ms@npm:2.0.0"
@@ -24718,17 +24758,6 @@ __metadata:
   languageName: node
   linkType: hard
 
-"portfinder@npm:^1.0.28":
-  version: 1.0.28
-  resolution: "portfinder@npm:1.0.28"
-  dependencies:
-    async: "npm:^2.6.2"
-    debug: "npm:^3.1.1"
-    mkdirp: "npm:^0.5.5"
-  checksum: fefd3d65a6464b498e0e9b4a4b82f29489441bb1892a3350403cfdf6e591e583d9e75bac1c6ae8ca2cdf1a942ae18890831a0a855bb1bb977678acdf9e5a560f
-  languageName: node
-  linkType: hard
-
 "posix-character-classes@npm:^0.1.0":
   version: 0.1.1
   resolution: "posix-character-classes@npm:0.1.1"
@@ -24854,7 +24883,7 @@ __metadata:
   languageName: node
   linkType: hard
 
-"postcss-loader@npm:^6.2.0":
+"postcss-loader@npm:^6.2.1":
   version: 6.2.1
   resolution: "postcss-loader@npm:6.2.1"
   dependencies:
@@ -24981,16 +25010,16 @@ __metadata:
   languageName: node
   linkType: hard
 
-"postcss-modules-local-by-default@npm:^4.0.1":
-  version: 4.0.1
-  resolution: "postcss-modules-local-by-default@npm:4.0.1"
+"postcss-modules-local-by-default@npm:^4.0.3":
+  version: 4.0.3
+  resolution: "postcss-modules-local-by-default@npm:4.0.3"
   dependencies:
     icss-utils: "npm:^5.0.0"
     postcss-selector-parser: "npm:^6.0.2"
     postcss-value-parser: "npm:^4.1.0"
   peerDependencies:
     postcss: ^8.1.0
-  checksum: b8ed23dc36cca4701deb924b700e5d023efb7d79e39c64160e60ea1e3e147397eeb290b90f451a4a6e09aad7ca82c16f2656b6fe6ec32eb33837cd9a7a700a5d
+  checksum: be49b86efbfb921f42287e227584aac91af9826fc1083db04958ae283dfe215ca539421bfba71f9da0f0b10651f28e95a64b5faca7166f578a1933b8646051f7
   languageName: node
   linkType: hard
 
@@ -25281,7 +25310,7 @@ __metadata:
   languageName: node
   linkType: hard
 
-"postcss@npm:5 - 7, postcss@npm:^7.0.14, postcss@npm:^7.0.16, postcss@npm:^7.0.32, postcss@npm:^7.0.5, postcss@npm:^7.0.6":
+"postcss@npm:^7.0.14, postcss@npm:^7.0.16, postcss@npm:^7.0.32, postcss@npm:^7.0.5, postcss@npm:^7.0.6":
   version: 7.0.39
   resolution: "postcss@npm:7.0.39"
   dependencies:
@@ -25695,13 +25724,6 @@ __metadata:
   languageName: node
   linkType: hard
 
-"querystring@npm:^0.2.0":
-  version: 0.2.0
-  resolution: "querystring@npm:0.2.0"
-  checksum: 2036c9424beaacd3978bac9e4ba514331cc73163bea7bf3ad7e2c7355e55501938ec195312c607753f9c6e70b1bf9dfcda38db6241bd299c034e27ac639d64ed
-  languageName: node
-  linkType: hard
-
 "querystringify@npm:^2.1.1":
   version: 2.2.0
   resolution: "querystringify@npm:2.2.0"
@@ -28191,14 +28213,14 @@ __metadata:
   languageName: node
   linkType: hard
 
-"schema-utils@npm:^3.0.0, schema-utils@npm:^3.1.1, schema-utils@npm:^3.1.2":
-  version: 3.1.2
-  resolution: "schema-utils@npm:3.1.2"
+"schema-utils@npm:^3.0.0, schema-utils@npm:^3.1.1, schema-utils@npm:^3.2.0":
+  version: 3.3.0
+  resolution: "schema-utils@npm:3.3.0"
   dependencies:
     "@types/json-schema": "npm:^7.0.8"
     ajv: "npm:^6.12.5"
     ajv-keywords: "npm:^3.5.2"
-  checksum: 33fa502462d0f957b6fb7097f15ba72aa19a14b0313fc7815c591ba47d8607b193055fa1d2ed928a53fd6c1ae8bdc429af2fd4a9e7fae7403014a6bb90763977
+  checksum: fafdbde91ad8aa1316bc543d4b61e65ea86970aebbfb750bfb6d8a6c287a23e415e0e926c2498696b242f63af1aab8e585252637fabe811fd37b604351da6500
   languageName: node
   linkType: hard
 
@@ -28235,12 +28257,13 @@ __metadata:
   languageName: node
   linkType: hard
 
-"selfsigned@npm:^2.0.1":
-  version: 2.0.1
-  resolution: "selfsigned@npm:2.0.1"
+"selfsigned@npm:^2.1.1":
+  version: 2.4.1
+  resolution: "selfsigned@npm:2.4.1"
   dependencies:
+    "@types/node-forge": "npm:^1.3.0"
     node-forge: "npm:^1"
-  checksum: 3f5d5b88f072db51d1c8184db571a466c5a60d46f888dee62b7396c9c27a10cc98c151fde5441140da29abc493a82530666911468d3a57bd8c6d81b8e6a8f830
+  checksum: 521829ec36ea042f7e9963bf1da2ed040a815cf774422544b112ec53b7edc0bc50a0f8cc2ae7aa6cc19afa967c641fd96a15de0fc650c68651e41277d2e1df09
   languageName: node
   linkType: hard
 
@@ -28478,10 +28501,10 @@ __metadata:
   languageName: node
   linkType: hard
 
-"shell-quote@npm:^1.6.1":
-  version: 1.7.2
-  resolution: "shell-quote@npm:1.7.2"
-  checksum: 656aefdcdc394560ca091140a58b95e97f43d5e14bb60ff4a92556ca48841e49af6e837441e887c7890c7a86ae8542960c90e460a86799b68c53271784909edb
+"shell-quote@npm:^1.6.1, shell-quote@npm:^1.8.1":
+  version: 1.8.1
+  resolution: "shell-quote@npm:1.8.1"
+  checksum: 8cec6fd827bad74d0a49347057d40dfea1e01f12a6123bf82c4649f3ef152fc2bc6d6176e6376bffcd205d9d0ccb4f1f9acae889384d20baff92186f01ea455a
   languageName: node
   linkType: hard
 
@@ -28572,14 +28595,14 @@ __metadata:
   languageName: node
   linkType: hard
 
-"sirv@npm:^1.0.7":
-  version: 1.0.10
-  resolution: "sirv@npm:1.0.10"
+"sirv@npm:^2.0.3":
+  version: 2.0.3
+  resolution: "sirv@npm:2.0.3"
   dependencies:
-    "@polka/url": "npm:^1.0.0-next.9"
-    mime: "npm:^2.3.1"
-    totalist: "npm:^1.0.0"
-  checksum: 455ed904135576da7cca3edf54102a429f8caeb32e0cf4d1700593c559a8f699c9699f1717904b658c5ed472a8b1a3f5e790e3d1b40915ed09bb89f7d74825ca
+    "@polka/url": "npm:^1.0.0-next.20"
+    mrmime: "npm:^1.0.0"
+    totalist: "npm:^3.0.0"
+  checksum: 333bd665ee5ac3805047ea47757e04e2b18ca562749b9a07f5bbbee6dabd99ff00011604689b1ada3d22e46a4198c61e05e2d1abd5454d94da483ce3a3813205
   languageName: node
   linkType: hard
 
@@ -28738,14 +28761,14 @@ __metadata:
   languageName: node
   linkType: hard
 
-"sockjs@npm:^0.3.21":
-  version: 0.3.21
-  resolution: "sockjs@npm:0.3.21"
+"sockjs@npm:^0.3.24":
+  version: 0.3.24
+  resolution: "sockjs@npm:0.3.24"
   dependencies:
     faye-websocket: "npm:^0.11.3"
-    uuid: "npm:^3.4.0"
+    uuid: "npm:^8.3.2"
     websocket-driver: "npm:^0.7.4"
-  checksum: a0ea76a465bd9544c12874c044dd4229caaff9a37cf549d547dc3594f083887961d3a2bb476ce6e2eba847aceffb1edddb703c29072ac63eae2a80bb4a4bfeaf
+  checksum: aa102c7d921bf430215754511c81ea7248f2dcdf268fbdb18e4d8183493a86b8793b164c636c52f474a886f747447c962741df2373888823271efdb9d2594f33
   languageName: node
   linkType: hard
 
@@ -29406,7 +29429,7 @@ __metadata:
   languageName: node
   linkType: hard
 
-"style-loader@npm:^1.2.1":
+"style-loader@npm:^1.3.0":
   version: 1.3.0
   resolution: "style-loader@npm:1.3.0"
   dependencies:
@@ -29926,7 +29949,7 @@ __metadata:
   languageName: node
   linkType: hard
 
-"terser-webpack-plugin@npm:^5.2.4, terser-webpack-plugin@npm:^5.3.1, terser-webpack-plugin@npm:^5.3.7":
+"terser-webpack-plugin@npm:^5.3.1, terser-webpack-plugin@npm:^5.3.7, terser-webpack-plugin@npm:^5.3.9":
   version: 5.3.9
   resolution: "terser-webpack-plugin@npm:5.3.9"
   dependencies:
@@ -30257,10 +30280,10 @@ __metadata:
   languageName: node
   linkType: hard
 
-"totalist@npm:^1.0.0":
-  version: 1.1.0
-  resolution: "totalist@npm:1.1.0"
-  checksum: 2adbd4501c8290c2a96617a83dc67dfdd02bcbd360032017e27ccf27bbb09649bbe8dad1c45d97be6874281178aca5b3f62ed059d1eeda77c479cfb8eb3a9266
+"totalist@npm:^3.0.0":
+  version: 3.0.1
+  resolution: "totalist@npm:3.0.1"
+  checksum: 4bb1fadb69c3edbef91c73ebef9d25b33bbf69afe1e37ce544d5f7d13854cda15e47132f3e0dc4cafe300ddb8578c77c50a65004d8b6e97e77934a69aa924863
   languageName: node
   linkType: hard
 
@@ -31435,7 +31458,7 @@ __metadata:
   languageName: node
   linkType: hard
 
-"uuid@npm:^3.3.2, uuid@npm:^3.4.0":
+"uuid@npm:^3.3.2":
   version: 3.4.0
   resolution: "uuid@npm:3.4.0"
   bin:
@@ -31735,26 +31758,30 @@ __metadata:
   languageName: node
   linkType: hard
 
-"webpack-bundle-analyzer@npm:^4.5.0":
-  version: 4.5.0
-  resolution: "webpack-bundle-analyzer@npm:4.5.0"
+"webpack-bundle-analyzer@npm:^4.10.1":
+  version: 4.10.1
+  resolution: "webpack-bundle-analyzer@npm:4.10.1"
   dependencies:
+    "@discoveryjs/json-ext": "npm:0.5.7"
     acorn: "npm:^8.0.4"
     acorn-walk: "npm:^8.0.0"
-    chalk: "npm:^4.1.0"
     commander: "npm:^7.2.0"
+    debounce: "npm:^1.2.1"
+    escape-string-regexp: "npm:^4.0.0"
     gzip-size: "npm:^6.0.0"
-    lodash: "npm:^4.17.20"
+    html-escaper: "npm:^2.0.2"
+    is-plain-object: "npm:^5.0.0"
     opener: "npm:^1.5.2"
-    sirv: "npm:^1.0.7"
+    picocolors: "npm:^1.0.0"
+    sirv: "npm:^2.0.3"
     ws: "npm:^7.3.1"
   bin:
     webpack-bundle-analyzer: lib/bin/analyzer.js
-  checksum: 5130be9fa58645e412e9824f98bd961afe540b9918951ddc87b688f3e176f4a101fcb16a304c74f0d1ddd9f2528ec2fa44bcfcea3fe07635fa9af0e3104644aa
+  checksum: 6a94c8f6aa03296fb2eb00d6ad3b27bd5c551590fd253772bc61debf3177414d42701014079d4f85c74ba1ca685ae9f0cb4063812b58c21f294d108e9908e5cd
   languageName: node
   linkType: hard
 
-"webpack-cli@npm:^4.9.2":
+"webpack-cli@npm:^4.10.0":
   version: 4.10.0
   resolution: "webpack-cli@npm:4.10.0"
   dependencies:
@@ -31787,18 +31814,18 @@ __metadata:
   languageName: node
   linkType: hard
 
-"webpack-dev-middleware@npm:^5.3.1":
-  version: 5.3.1
-  resolution: "webpack-dev-middleware@npm:5.3.1"
+"webpack-dev-middleware@npm:^5.3.1, webpack-dev-middleware@npm:^5.3.3":
+  version: 5.3.3
+  resolution: "webpack-dev-middleware@npm:5.3.3"
   dependencies:
     colorette: "npm:^2.0.10"
-    memfs: "npm:^3.4.1"
+    memfs: "npm:^3.4.3"
     mime-types: "npm:^2.1.31"
     range-parser: "npm:^1.2.1"
     schema-utils: "npm:^4.0.0"
   peerDependencies:
     webpack: ^4.0.0 || ^5.0.0
-  checksum: 705553c7af45eae6d8f93c5d8e6a6254085d7e1a7a789c58b1aec1c6c6c8f4bb65d5663a7c34c793920351d3c580cf566690d4fd5776a198d39a3b2c708e6ca5
+  checksum: 378ceed430b61c0b0eccdbb55a97173aa36231bb88e20ad12bafb3d553e542708fa31f08474b9c68d4ac95174a047def9e426e193b7134be3736afa66a0d1708
   languageName: node
   linkType: hard
 
@@ -31820,59 +31847,61 @@ __metadata:
   languageName: node
   linkType: hard
 
-"webpack-dev-server@npm:^4.7.3":
-  version: 4.8.1
-  resolution: "webpack-dev-server@npm:4.8.1"
+"webpack-dev-server@npm:^4.15.1":
+  version: 4.15.1
+  resolution: "webpack-dev-server@npm:4.15.1"
   dependencies:
     "@types/bonjour": "npm:^3.5.9"
     "@types/connect-history-api-fallback": "npm:^1.3.5"
     "@types/express": "npm:^4.17.13"
     "@types/serve-index": "npm:^1.9.1"
+    "@types/serve-static": "npm:^1.13.10"
     "@types/sockjs": "npm:^0.3.33"
-    "@types/ws": "npm:^8.5.1"
+    "@types/ws": "npm:^8.5.5"
     ansi-html-community: "npm:^0.0.8"
     bonjour-service: "npm:^1.0.11"
     chokidar: "npm:^3.5.3"
     colorette: "npm:^2.0.10"
     compression: "npm:^1.7.4"
-    connect-history-api-fallback: "npm:^1.6.0"
+    connect-history-api-fallback: "npm:^2.0.0"
     default-gateway: "npm:^6.0.3"
     express: "npm:^4.17.3"
     graceful-fs: "npm:^4.2.6"
     html-entities: "npm:^2.3.2"
     http-proxy-middleware: "npm:^2.0.3"
     ipaddr.js: "npm:^2.0.1"
+    launch-editor: "npm:^2.6.0"
     open: "npm:^8.0.9"
     p-retry: "npm:^4.5.0"
-    portfinder: "npm:^1.0.28"
     rimraf: "npm:^3.0.2"
     schema-utils: "npm:^4.0.0"
-    selfsigned: "npm:^2.0.1"
+    selfsigned: "npm:^2.1.1"
     serve-index: "npm:^1.9.1"
-    sockjs: "npm:^0.3.21"
+    sockjs: "npm:^0.3.24"
     spdy: "npm:^4.0.2"
     webpack-dev-middleware: "npm:^5.3.1"
-    ws: "npm:^8.4.2"
+    ws: "npm:^8.13.0"
   peerDependencies:
     webpack: ^4.37.0 || ^5.0.0
   peerDependenciesMeta:
+    webpack:
+      optional: true
     webpack-cli:
       optional: true
   bin:
     webpack-dev-server: bin/webpack-dev-server.js
-  checksum: 9ba5b127e3ef51f9a24df35563042b61f60473d319b895fa5877a1c1b4d5e03214605423db7c6a9ddb5c70616933e4a62eb5038acfe0beee2341c3bf792eeccf
+  checksum: 2cf3edf556dcafdfc938e0adeac3dadf97fb959ed66b88bdd70acdb0b77b0f25be5e2d4b30cca2da8732548451418cadf00eb09e751e7674ff914fd9ab646b26
   languageName: node
   linkType: hard
 
-"webpack-hot-middleware@npm:^2.25.1":
-  version: 2.25.1
-  resolution: "webpack-hot-middleware@npm:2.25.1"
+"webpack-hot-middleware@npm:^2.25.1, webpack-hot-middleware@npm:^2.25.4":
+  version: 2.25.4
+  resolution: "webpack-hot-middleware@npm:2.25.4"
   dependencies:
     ansi-html-community: "npm:0.0.8"
     html-entities: "npm:^2.1.0"
-    querystring: "npm:^0.2.0"
     strip-ansi: "npm:^6.0.0"
-  checksum: 2b8cc2841d6168c5e9f0edd116289fb441039e8de784baf375b1156883a860ee0917a3498b8198f47ad056dd90cdd8eb053253127a0f923c76b18fa7987d0c05
+  checksum: c0702d308a39bdbc9277d66df50272e8c358c2238cecb0881df57136f54cb7a3d8291320b13075325b58f7a3cbf7a1ef10829554a5bc2ddfa3effbf416dc8e8c
   languageName: node
   linkType: hard
 
@@ -31903,7 +31932,7 @@ __metadata:
   languageName: node
   linkType: hard
 
-"webpack-sources@npm:^3.2.2, webpack-sources@npm:^3.2.3":
+"webpack-sources@npm:^2.0.0 || ^3.0.0, webpack-sources@npm:^3.2.2, webpack-sources@npm:^3.2.3":
   version: 3.2.3
   resolution: "webpack-sources@npm:3.2.3"
   checksum: 2ef63d77c4fad39de4a6db17323d75eb92897b32674e97d76f0a1e87c003882fc038571266ad0ef581ac734cbe20952912aaa26155f1905e96ce251adbb1eb4e
@@ -31917,9 +31946,9 @@ __metadata:
   languageName: node
   linkType: hard
 
-"webpack@npm:5, webpack@npm:^5.63.0, webpack@npm:^5.68.0":
-  version: 5.83.1
-  resolution: "webpack@npm:5.83.1"
+"webpack@npm:5, webpack@npm:^5.63.0, webpack@npm:^5.89.0":
+  version: 5.89.0
+  resolution: "webpack@npm:5.89.0"
   dependencies:
     "@types/eslint-scope": "npm:^3.7.3"
     "@types/estree": "npm:^1.0.0"
@@ -31927,10 +31956,10 @@ __metadata:
     "@webassemblyjs/wasm-edit": "npm:^1.11.5"
     "@webassemblyjs/wasm-parser": "npm:^1.11.5"
     acorn: "npm:^8.7.1"
-    acorn-import-assertions: "npm:^1.7.6"
+    acorn-import-assertions: "npm:^1.9.0"
     browserslist: "npm:^4.14.5"
     chrome-trace-event: "npm:^1.0.2"
-    enhanced-resolve: "npm:^5.14.0"
+    enhanced-resolve: "npm:^5.15.0"
     es-module-lexer: "npm:^1.2.1"
     eslint-scope: "npm:5.1.1"
     events: "npm:^3.2.0"
@@ -31940,7 +31969,7 @@ __metadata:
     loader-runner: "npm:^4.2.0"
     mime-types: "npm:^2.1.27"
     neo-async: "npm:^2.6.2"
-    schema-utils: "npm:^3.1.2"
+    schema-utils: "npm:^3.2.0"
     tapable: "npm:^2.1.1"
     terser-webpack-plugin: "npm:^5.3.7"
     watchpack: "npm:^2.4.0"
@@ -31950,7 +31979,7 @@ __metadata:
       optional: true
   bin:
     webpack: bin/webpack.js
-  checksum: 5a3b12776dd4fbc73c757762d100781c97e2edf70b574a29653613a3b89b447d55ec534419c52bc6aeb78a77c432f5106f01af5742fbc2fe9cd8533bcffcedcd
+  checksum: 2562bf48788d651634fb7db6a5378c2fe3fce7f66831af38468da3944bd98756d68efea94a6909593993fb57b2d14cf802cbef2c83c6ef0047f7f606d59bec50
   languageName: node
   linkType: hard
 
@@ -32243,7 +32272,7 @@ __metadata:
     "@babel/register": "npm:^7.22.15"
     "@babel/runtime": "npm:^7.23.2"
     "@bartekbp/typescript-checkstyle": "npm:^5.0.0"
-    "@pmmmwh/react-refresh-webpack-plugin": "npm:^0.5.10"
+    "@pmmmwh/react-refresh-webpack-plugin": "npm:^0.5.11"
     "@signal-noise/stylelint-scales": "npm:^2.0.3"
     "@storybook/cli": "npm:^7.5.3"
     "@storybook/react": "npm:^7.5.3"
@@ -32268,7 +32297,7 @@ __metadata:
     "@types/superagent": "npm:^4.1.15"
     "@types/uuid": "npm:^8.3.4"
     "@types/validator": "npm:^13.7.1"
-    "@types/webpack-env": "npm:^1.16.3"
+    "@types/webpack-env": "npm:^1.18.4"
     "@typescript-eslint/eslint-plugin": "npm:^6.10.0"
     "@typescript-eslint/parser": "npm:^6.10.0"
     "@wordpress/base-styles": "npm:^4.35.0"
@@ -32293,7 +32322,7 @@ __metadata:
     chroma-js: "npm:^2.1.2"
     cmdk: "npm:^0.2.0"
     config: "npm:^3.3.6"
-    css-loader: "npm:^6.5.1"
+    css-loader: "npm:^6.8.1"
     debug: "npm:^4.3.3"
     doctrine: "npm:^3.0.0"
     enhanced-resolve: "npm:5.9.3"
@@ -32325,7 +32354,7 @@ __metadata:
     jest-environment-jsdom: "npm:^29.7.0"
     jest-teamcity: "npm:^1.11.0"
     jsdom: "npm:^20.0.1"
-    loader-utils: "npm:^1.2.3"
+    loader-utils: "npm:^1.4.2"
     lodash: "npm:^4.17.21"
     lottie-web: "npm:^5.9.6"
     lunr: "npm:^2.3.8"
@@ -32360,10 +32389,10 @@ __metadata:
     swiper: "npm:^10.1.0"
     tslib: "npm:^2.3.0"
     typescript: "npm:^5.2.2"
-    webpack: "npm:^5.68.0"
-    webpack-bundle-analyzer: "npm:^4.5.0"
-    webpack-cli: "npm:^4.9.2"
-    webpack-dev-middleware: "npm:^5.3.1"
+    webpack: "npm:^5.89.0"
+    webpack-bundle-analyzer: "npm:^4.10.1"
+    webpack-cli: "npm:^4.10.0"
+    webpack-dev-middleware: "npm:^5.3.3"
     whybundled: "npm:^2.0.0"
     workspace: "npm:^0.0.1-preview.1"
     wpcom: "workspace:^"
@@ -32441,7 +32470,7 @@ __metadata:
     debug: "npm:^4.3.3"
     postcss: "npm:^8.4.5"
     uuid: "npm:^8.3.2"
-    webpack: "npm:^5.68.0"
+    webpack: "npm:^5.89.0"
     wp-error: "npm:^1.3.0"
   languageName: unknown
   linkType: soft
@@ -32470,8 +32499,8 @@ __metadata:
     npm-run-all: "npm:^4.1.5"
     qs: "npm:^6.5.2"
     tus-js-client: "npm:2.3.0"
-    webpack: "npm:^5.68.0"
-    webpack-cli: "npm:^4.9.2"
+    webpack: "npm:^5.89.0"
+    webpack-cli: "npm:^4.10.0"
     wpcom-oauth-cors: "npm:^1.0.2-beta"
     wpcom-proxy-request: "workspace:^"
   languageName: unknown
@@ -32614,9 +32643,9 @@ __metadata:
   languageName: node
   linkType: hard
 
-"ws@npm:^8.11.0, ws@npm:^8.2.3, ws@npm:^8.4.2":
-  version: 8.13.0
-  resolution: "ws@npm:8.13.0"
+"ws@npm:^8.11.0, ws@npm:^8.13.0, ws@npm:^8.2.3":
+  version: 8.14.2
+  resolution: "ws@npm:8.14.2"
   peerDependencies:
     bufferutil: ^4.0.1
     utf-8-validate: ">=5.0.2"
@@ -32625,7 +32654,7 @@ __metadata:
       optional: true
     utf-8-validate:
       optional: true
-  checksum: 579817dbbab3ee46669129c220cfd81ba6cdb9ab5c3e9a105702dd045743c4ab72e33bb384573827c0c481213417cc880e41bc097e0fc541a0b79fa3eb38207d
+  checksum: 35b4c2da048b8015c797fd14bcb5a5766216ce65c8a5965616a5440ca7b6c3681ee3cbd0ea0c184a59975556e9d58f2002abf8485a14d11d3371770811050a16
   languageName: node
   linkType: hard