diff --git a/lib/ruby_lsp/base_server.rb b/lib/ruby_lsp/base_server.rb
index b97bea824..f125bf84c 100644
--- a/lib/ruby_lsp/base_server.rb
+++ b/lib/ruby_lsp/base_server.rb
@@ -8,9 +8,10 @@ class BaseServer
 
     abstract!
 
-    sig { params(options: T::Boolean).void }
+    sig { params(options: T.untyped).void }
     def initialize(**options)
       @test_mode = T.let(options[:test_mode], T.nilable(T::Boolean))
+      @setup_error = T.let(options[:setup_error], T.nilable(StandardError))
       @writer = T.let(Transport::Stdio::Writer.new, Transport::Stdio::Writer)
       @reader = T.let(Transport::Stdio::Reader.new, Transport::Stdio::Reader)
       @incoming_queue = T.let(Thread::Queue.new, Thread::Queue)
@@ -33,6 +34,11 @@ def initialize(**options)
 
       @global_state = T.let(GlobalState.new, GlobalState)
       Thread.main.priority = 1
+
+      # We read the initialize request in `exe/ruby-lsp` to be able to determine the workspace URI where Bundler should
+      # be setup
+      initialize_request = options[:initialize_request]
+      process_message(initialize_request) if initialize_request
     end
 
     sig { void }
diff --git a/lib/ruby_lsp/server.rb b/lib/ruby_lsp/server.rb
index d0960f1a1..da38ef472 100644
--- a/lib/ruby_lsp/server.rb
+++ b/lib/ruby_lsp/server.rb
@@ -290,6 +290,18 @@ def run_initialize(message)
       begin_progress("indexing-progress", "Ruby LSP: indexing files")
 
       global_state_notifications.each { |notification| send_message(notification) }
+
+      if @setup_error
+        message = <<~MESSAGE
+          An error occurred while setting up Bundler. This may be due to a failure when installing dependencies.
+          The Ruby LSP will continue to run, but features related to the missing dependencies will not be available.
+
+          Error:
+          #{@setup_error.full_message}
+        MESSAGE
+
+        send_message(Notification.window_log_message(message, type: Constant::MessageType::ERROR))
+      end
     end
 
     sig { void }