diff --git a/.devcontainer/devcontainer.json b/.devcontainer/devcontainer.json
index 1e51053a73..93d33c77c4 100644
--- a/.devcontainer/devcontainer.json
+++ b/.devcontainer/devcontainer.json
@@ -13,7 +13,6 @@
       // Installing all necessary extensions for vscode
       // Taken from: .vscode/extensions.json
       "extensions": [
-        "kaiwood.endwise",
         "Shopify.ruby-lsp",
         "sorbet.sorbet-vscode-extension",
         "github.vscode-github-actions",
diff --git a/.devcontainer/ubuntu18.04/devcontainer.json b/.devcontainer/ubuntu18.04/devcontainer.json
index d9363db75c..f5bdaa1eef 100644
--- a/.devcontainer/ubuntu18.04/devcontainer.json
+++ b/.devcontainer/ubuntu18.04/devcontainer.json
@@ -13,7 +13,6 @@
       // Installing all necessary extensions for vscode
       // Taken from: .vscode/extensions.json
       "extensions": [
-        "kaiwood.endwise",
         "Shopify.ruby-lsp",
         "sorbet.sorbet-vscode-extension",
         "github.vscode-github-actions",
diff --git a/.vscode/extensions.json b/.vscode/extensions.json
index 93789d0339..88fd850ae1 100644
--- a/.vscode/extensions.json
+++ b/.vscode/extensions.json
@@ -1,6 +1,5 @@
 {
   "recommendations": [
-    "kaiwood.endwise",
     "Shopify.ruby-lsp",
     "sorbet.sorbet-vscode-extension",
     "github.vscode-github-actions",
diff --git a/.vscode/ruby-lsp-activate.sh b/.vscode/ruby-lsp-activate.sh
new file mode 100644
index 0000000000..a0d3297309
--- /dev/null
+++ b/.vscode/ruby-lsp-activate.sh
@@ -0,0 +1,7 @@
+#!/bin/bash
+HOMEBREW_PREFIX="$(cd "$(dirname "$0")"/../ && pwd)/"
+
+"${HOMEBREW_PREFIX}bin/brew" install-bundler-gems --add-groups=style,typecheck,vscode >/dev/null 2>&1
+
+export PATH="${HOMEBREW_PREFIX}/Library/Homebrew/vendor/portable-ruby/current/bin:${PATH}"
+export BUNDLE_WITH="style:typecheck:vscode"
diff --git a/.vscode/settings.json b/.vscode/settings.json
index 12a50f740d..a714a9a7d0 100644
--- a/.vscode/settings.json
+++ b/.vscode/settings.json
@@ -9,12 +9,13 @@
   "rubyLsp.rubyVersionManager": {
     "identifier": "custom"
   },
-  "rubyLsp.customRubyCommand": "PATH=${workspaceFolder}/Library/Homebrew/vendor/portable-ruby/current/bin:$PATH",
+  "rubyLsp.customRubyCommand": "source ../../.vscode/ruby-lsp-activate.sh",
   "rubyLsp.bundleGemfile": "Library/Homebrew/Gemfile",
   "rubyLsp.formatter": "rubocop",
   "[ruby]": {
     "editor.defaultFormatter": "Shopify.ruby-lsp",
     "editor.formatOnSave": true,
+    "editor.formatOnType": true,
     "editor.semanticHighlighting.enabled": true,
   },
   "shellcheck.customArgs": [