diff --git a/package.json b/package.json
index 2523235fd21f2..a43d18d48d795 100644
--- a/package.json
+++ b/package.json
@@ -75,7 +75,7 @@
     "express-useragent": "1.0.7",
     "filesize": "3.2.1",
     "flag-icon-css": "2.3.0",
-    "flux": "2.1.1",
+    "flux": "4.0.1",
     "fuse.js": "2.6.1",
     "get-video-id": "2.1.4",
     "globby": "6.1.0",
@@ -84,8 +84,8 @@
     "hard-source-webpack-plugin": "0.3.12",
     "hash.js": "1.1.3",
     "he": "0.5.0",
-    "html-loader": "0.4.0",
-    "i18n-calypso": "1.7.3",
+    "html-loader": "1.0.0",
+    "i18n-calypso": "6.0.0",
     "immutable": "3.7.6",
     "imports-loader": "0.6.5",
     "inherits": "2.0.1",
@@ -106,15 +106,15 @@
     "morgan": "1.2.0",
     "ms": "0.7.1",
     "name-all-modules-plugin": "1.0.1",
-    "node-sass": "3.7.0",
+    "node-sass": "7.0.2",
     "notifications-panel": "1.2.4",
-    "npm-run-all": "4.0.2",
+    "npm-run-all": "4.1.0",
     "numeral": "2.0.4",
     "page": "1.6.4",
     "percentage-regex": "3.0.0",
     "phone": "git+https://github.com/Automattic/node-phone.git#1.0.8",
     "photon": "2.0.0",
-    "postcss-cli": "2.5.1",
+    "postcss-cli": "7.0.0",
     "prismjs": "1.6.0",
     "prop-types": "15.5.10",
     "q": "1.0.1",
@@ -137,11 +137,11 @@
     "redux": "3.0.4",
     "redux-form": "7.0.2",
     "redux-thunk": "1.0.0",
-    "rtlcss": "2.0.5",
+    "rtlcss": "2.2.0",
     "sanitize-html": "1.11.1",
     "semver": "5.1.0",
     "social-logos": "1.0.1",
-    "socket.io-client": "1.4.5",
+    "socket.io-client": "2.0.0",
     "source-map": "0.1.39",
     "source-map-loader": "0.1.5",
     "source-map-support": "0.3.2",
@@ -157,8 +157,8 @@
     "uuid": "2.0.1",
     "valid-url": "1.0.9",
     "walk": "2.3.4",
-    "webpack": "3.4.1",
-    "webpack-dashboard": "0.2.1",
+    "webpack": "5.0.0",
+    "webpack-dashboard": "2.0.0",
     "webpack-dev-middleware": "1.11.0",
     "webpack-hot-middleware": "2.15.0",
     "wpcom": "5.4.0",