diff --git a/packages/calypso-build/package.json b/packages/calypso-build/package.json
index ae1b6bfc0a64f..d5249211d0f91 100644
--- a/packages/calypso-build/package.json
+++ b/packages/calypso-build/package.json
@@ -45,9 +45,9 @@
 		"@babel/preset-typescript": "7.3.3",
 		"@wordpress/babel-plugin-import-jsx-pragma": "2.3.0",
 		"@wordpress/browserslist-config": "2.3.0",
-		"@wordpress/dependency-extraction-webpack-plugin": "1.1.0",
+		"@wordpress/dependency-extraction-webpack-plugin": "2.9.0",
 		"autoprefixer": "9.4.4",
-		"babel-jest": "^24.9.0",
+		"babel-jest": "^27.0.0",
 		"babel-loader": "8.0.5",
 		"browserslist": "4.6.6",
 		"caniuse-api": "3.0.0",
@@ -57,9 +57,9 @@
 		"enzyme-adapter-react-16": "1.14.0",
 		"enzyme-to-json": "3.4.0",
 		"file-loader": "3.0.1",
-		"jest-config": "24.9.0",
+		"jest-config": "27.0.0",
 		"mini-css-extract-plugin-with-rtl": "github:Automattic/mini-css-extract-plugin-with-rtl#v0.7.0-with-rtl",
-		"node-sass": "4.11.0",
+		"node-sass": "7.0.2",
 		"postcss-custom-properties": "8.0.9",
 		"postcss-loader": "3.0.0",
 		"recursive-copy": "2.0.10",
@@ -67,8 +67,8 @@
 		"terser-webpack-plugin": "1.2.3",
 		"thread-loader": "2.1.2",
 		"typescript": "3.4.3",
-		"webpack": "4.29.6",
-		"webpack-cli": "3.3.0",
+		"webpack": "5.0.0",
+		"webpack-cli": "4.0.0",
 		"webpack-filter-warnings-plugin": "1.2.1",
 		"webpack-rtl-plugin": "1.8.0"
 	}