diff --git a/.vscode/settings.json b/.vscode/settings.json
index a714a9a7d0..dfd935ea64 100644
--- a/.vscode/settings.json
+++ b/.vscode/settings.json
@@ -18,6 +18,21 @@
     "editor.formatOnType": true,
     "editor.semanticHighlighting.enabled": true,
   },
+  "sorbet.enabled": true,
+  "sorbet.lspConfigs": [
+    {
+      "id": "default",
+      "name": "Brew Typecheck",
+      "description": "Default configuration",
+      "cwd": "${workspaceFolder}",
+      "command": [
+        "./bin/brew",
+        "typecheck",
+        "--lsp",
+      ]
+    }
+  ],
+  "sorbet.selectedLspConfigId": "default",
   "shellcheck.customArgs": [
     "--shell=bash",
     "--enable=all",
diff --git a/Library/Homebrew/dev-cmd/typecheck.rb b/Library/Homebrew/dev-cmd/typecheck.rb
index 4e6af62914..3d570a9c63 100644
--- a/Library/Homebrew/dev-cmd/typecheck.rb
+++ b/Library/Homebrew/dev-cmd/typecheck.rb
@@ -24,6 +24,8 @@ module Homebrew
         switch "--suggest-typed",
                depends_on:  "--update",
                description: "Try upgrading `typed` sigils."
+        switch "--lsp",
+               description: "Start the Sorbet LSP server."
         flag   "--dir=",
                description: "Typecheck all files in a specific directory."
         flag   "--file=",
@@ -33,6 +35,9 @@ module Homebrew
                             "in their paths (relative to the input path passed to Sorbet)."
 
         conflicts "--dir", "--file"
+        conflicts "--lsp", "--update"
+        conflicts "--lsp", "--update-all"
+        conflicts "--lsp", "--fix"
 
         named_args :none
       end
@@ -80,6 +85,15 @@ module Homebrew
             srb_exec << "--autocorrect"
           end
 
+          if args.lsp?
+            srb_exec << "--lsp"
+            if (watchman = which("watchman", ORIGINAL_PATHS))
+              srb_exec << "--watchman-path" << watchman
+            else
+              srb_exec << "--disable-watchman" unless which("watchman", ORIGINAL_PATHS)
+            end
+          end
+
           srb_exec += ["--ignore", args.ignore] if args.ignore.present?
           if args.file.present? || args.dir.present?
             cd("sorbet") do