diff --git a/lib/ruby_indexer/lib/ruby_indexer/configuration.rb b/lib/ruby_indexer/lib/ruby_indexer/configuration.rb
index 46afacca99..70a8407d4e 100644
--- a/lib/ruby_indexer/lib/ruby_indexer/configuration.rb
+++ b/lib/ruby_indexer/lib/ruby_indexer/configuration.rb
@@ -39,7 +39,7 @@ def initialize
 
       # We start the included patterns with only the non excluded directories so that we can avoid paying the price of
       # traversing large directories that don't include Ruby files like `node_modules`
-      @included_patterns = ["{#{top_level_directories.join(",")}}/**/*.rb", "*.rb"] #: Array[String]
+      @included_patterns = ["*.rb", *top_level_directories.map {|name| "#{name}/**/*.rb"}] #: Array[String]
       @excluded_magic_comments = [
         "frozen_string_literal:",
         "typed:",
@@ -56,7 +56,7 @@ def initialize
     end
 
     #: -> Array[URI::Generic]
-    def indexable_uris
+    def indexable_uris(&logging)
       excluded_gems = @excluded_gems - @included_gems
       locked_gems = Bundler.locked_gems&.specs
 
@@ -68,7 +68,16 @@ def indexable_uris
       uris = @included_patterns.flat_map do |pattern|
         load_path_entry = nil #: String?
 
-        Dir.glob(File.join(@workspace_path, pattern), flags).map! do |path|
+        begin
+          glob_pattern = File.join(@workspace_path, pattern)
+          glob_results = Dir.glob(glob_pattern, flags)
+        rescue StandardError => error
+          message = "Indexation error on included_pattern: '#{pattern}': (#{error.class.name} - #{error.message})"
+          logging.call(error: message)
+          next
+        end
+
+        glob_results.map! do |path|
           # All entries for the same pattern match the same $LOAD_PATH entry. Since searching the $LOAD_PATH for every
           # entry is expensive, we memoize it until we find a path that doesn't belong to that $LOAD_PATH. This happens
           # on repositories that define multiple gems, like Rails. All frameworks are defined inside the current
@@ -79,7 +88,7 @@ def indexable_uris
 
           URI::Generic.from_path(path: path, load_path_entry: load_path_entry)
         end
-      end
+      end.compact
 
       # If the patterns are relative, we make it relative to the workspace path. If they are absolute, then we shouldn't
       # concatenate anything
@@ -177,8 +186,11 @@ def apply_config(config)
 
       @excluded_gems.concat(config["excluded_gems"]) if config["excluded_gems"]
       @included_gems.concat(config["included_gems"]) if config["included_gems"]
-      @excluded_patterns.concat(config["excluded_patterns"]) if config["excluded_patterns"]
       @included_patterns.concat(config["included_patterns"]) if config["included_patterns"]
+      if config["excluded_patterns"]
+        @excluded_patterns.concat(config["excluded_patterns"])
+        @included_patterns -= config["excluded_patterns"]
+      end
       @excluded_magic_comments.concat(config["excluded_magic_comments"]) if config["excluded_magic_comments"]
     end
 
diff --git a/lib/ruby_indexer/lib/ruby_indexer/index.rb b/lib/ruby_indexer/lib/ruby_indexer/index.rb
index 4cf8895d69..21a0ce1556 100644
--- a/lib/ruby_indexer/lib/ruby_indexer/index.rb
+++ b/lib/ruby_indexer/lib/ruby_indexer/index.rb
@@ -354,7 +354,9 @@ def resolve(name, nesting, seen_names = [])
     # indexing progress. That block is invoked with the current progress percentage and should return `true` to continue
     # indexing or `false` to stop indexing.
     #: (?uris: Array[URI::Generic]) ?{ (Integer progress) -> bool } -> void
-    def index_all(uris: @configuration.indexable_uris, &block)
+    def index_all(uris: [], &block)
+      uris = @configuration.indexable_uris(&block) if uris.empty?
+
       # When troubleshooting an indexing issue, e.g. through irb, it's not obvious that `index_all` will augment the
       # existing index values, meaning it may contain 'stale' entries. This check ensures that the user is aware of this
       # behavior and can take appropriate action.
diff --git a/lib/ruby_lsp/addon.rb b/lib/ruby_lsp/addon.rb
index c346d6ea61..a1dd23cbfb 100644
--- a/lib/ruby_lsp/addon.rb
+++ b/lib/ruby_lsp/addon.rb
@@ -49,14 +49,27 @@ def inherited(child_class)
 
       # Discovers and loads all add-ons. Returns a list of errors when trying to require add-ons
       #: (GlobalState global_state, Thread::Queue outgoing_queue, ?include_project_addons: bool) -> Array[StandardError]
-      def load_addons(global_state, outgoing_queue, include_project_addons: true)
+      def load_addons(global_state, outgoing_queue, include_project_addons: true, &logging)
         # Require all add-ons entry points, which should be placed under
         # `some_gem/lib/ruby_lsp/your_gem_name/addon.rb` or in the workspace under
         # `your_project/ruby_lsp/project_name/addon.rb`
         addon_files = Gem.find_files("ruby_lsp/**/addon.rb")
 
         if include_project_addons
-          project_addons = Dir.glob("#{global_state.workspace_path}/**/ruby_lsp/**/addon.rb")
+          workspace_path = global_state.workspace_path
+          spaces         = top_level_directories.map do |space|
+            "#{workspace_path}/#{space}/**/ruby_lsp/**/addon.rb"
+          end
+          spaces << "#{workspace_path}/ruby_lsp/**/addon.rb"
+
+          project_addons = spaces.flat_map do |pattern|
+            Dir.glob(pattern)
+          rescue StandardError => error
+            message  = "Addon discovery failed with pattern: '#{pattern}': (#{error.class.name} - #{error.message})"
+            logging.call(error: message)
+            next
+          end.compact
+
           bundle_path = Bundler.bundle_path.to_s
           gems_dir = Bundler.bundle_path.join("gems")
 
@@ -162,6 +175,18 @@ def depend_on_ruby_lsp!(*version_constraints)
             "Add-on is not compatible with this version of the Ruby LSP. Skipping its activation"
         end
       end
+
+      private
+
+      #: -> Array[String]
+      def top_level_directories
+        Dir.glob("#{Dir.pwd}/*").filter_map do |path|
+          dir_name = File.basename(path)
+          next unless File.directory?(path)
+
+          dir_name
+        end
+      end
     end
 
     #: -> void
diff --git a/lib/ruby_lsp/server.rb b/lib/ruby_lsp/server.rb
index 170c755daa..88317dd9c1 100644
--- a/lib/ruby_lsp/server.rb
+++ b/lib/ruby_lsp/server.rb
@@ -172,7 +172,18 @@ def load_addons(include_project_addons: true)
       # different versions of the same files. We cannot load add-ons if Bundler.setup failed
       return if @setup_error
 
-      errors = Addon.load_addons(@global_state, @outgoing_queue, include_project_addons: include_project_addons)
+      errors = Addon.load_addons(
+        @global_state,
+        @outgoing_queue,
+        include_project_addons: include_project_addons
+      ) do |log: nil, error: nil|
+        send_log_message(log) if log
+        if error
+          send_log_message(error, type: Constant::MessageType::ERROR)
+          send_message(Notification.window_show_message(error, type: Constant::MessageType::ERROR))
+        end
+      end
+
       return if test_mode?
 
       if errors.any?
@@ -1232,8 +1243,15 @@ def perform_initial_indexing
       # stuck indexing files
       Thread.new do
         begin
-          @global_state.index.index_all do |percentage|
-            progress("indexing-progress", percentage)
+          @global_state.index.index_all do |percentage = nil, log: nil, error: nil|
+            send_log_message(log) if log
+            if error
+              send_log_message(error, type: Constant::MessageType::ERROR)
+              send_message(Notification.window_show_message(error, type: Constant::MessageType::ERROR))
+            end
+
+            progress("indexing-progress", percentage) unless percentage.nil?
+
             true
           rescue ClosedQueueError
             # Since we run indexing on a separate thread, it's possible to kill the server before indexing is complete.
@@ -1244,6 +1262,8 @@ def perform_initial_indexing
         rescue StandardError => error
           message = "Error while indexing (see [troubleshooting steps]" \
             "(https://shopify.github.io/ruby-lsp/troubleshooting#indexing)): #{error.message}"
+
+          send_log_message("#{message}\n\n#{error.backtrace.join("\n")}", type: Constant::MessageType::ERROR)
           send_message(Notification.window_show_message(message, type: Constant::MessageType::ERROR))
         end