diff --git a/doc/rocks.txt b/doc/rocks.txt
index 12c9fc92..80ffaf85 100644
--- a/doc/rocks.txt
+++ b/doc/rocks.txt
@@ -156,6 +156,9 @@ RocksOpts                                                            *RocksOpts*
                                                                           Whether to re-generate plugins help pages after installation/upgrade. (Default: `true`).
         {update_remote_plugins?}          (boolean)
                                                                           Whether to update remote plugins after installation/upgrade. (Default: `true`).
+        {auto_sync?}                      (boolean)
+                                                                          Whether to auto-sync if plugins cannot be found on startup. (Default: `false`).
+                                                                          If unset, rocks.nvim will prompt to sync.
         {reinstall_dev_rocks_on_update?}  (boolean)
                                                                           Whether to reinstall 'dev' rocks on update
                                                                           (Default: `true`, as rocks.nvim cannot determine if 'dev' rocks are up to date).
diff --git a/lua/rocks/config/init.lua b/lua/rocks/config/init.lua
index 851782ab..5b334b21 100644
--- a/lua/rocks/config/init.lua
+++ b/lua/rocks/config/init.lua
@@ -42,6 +42,10 @@ local config = {}
 --- Whether to update remote plugins after installation/upgrade. (Default: `true`).
 ---@field update_remote_plugins? boolean
 ---
+--- Whether to auto-sync if plugins cannot be found on startup. (Default: `false`).
+--- If unset, rocks.nvim will prompt to sync.
+---@field auto_sync? boolean
+---
 --- Whether to reinstall 'dev' rocks on update
 --- (Default: `true`, as rocks.nvim cannot determine if 'dev' rocks are up to date).
 ---@field reinstall_dev_rocks_on_update? boolean
diff --git a/lua/rocks/config/internal.lua b/lua/rocks/config/internal.lua
index ac70f410..7ab45f69 100644
--- a/lua/rocks/config/internal.lua
+++ b/lua/rocks/config/internal.lua
@@ -60,6 +60,8 @@ local default_config = {
     update_remote_plugins = true,
     ---@type boolean Whether to reinstall 'dev' rocks on update
     reinstall_dev_rocks_on_update = true,
+    ---@type boolean Whether to auto-sync if plugins cannot be found on startup
+    auto_sync = false,
     ---@type boolean Whether to use the luarocks loader to support multiple dependencies
     enable_luarocks_loader = true,
 
diff --git a/lua/rocks/runtime.lua b/lua/rocks/runtime.lua
index bd5e8d69..dff34c49 100644
--- a/lua/rocks/runtime.lua
+++ b/lua/rocks/runtime.lua
@@ -78,20 +78,26 @@ function runtime.source_start_plugins(user_rocks)
         end
     end
     if #not_found > 0 then
+        local config = require("rocks.config.internal")
+        if config.auto_sync then
+            require("rocks.operations").sync()
+            return
+        end
         local rock_names = vim
             .iter(not_found)
             ---@param rock_spec RockSpec
             :map(function(rock_spec)
                 return rock_spec.name
             end)
-            :totable()
+            :join(", ")
+        local prompt = ("rocks.nvim: The following plugins were not found:\n%s.\n\nRun 'Rocks sync'?"):format(
+            rock_names
+        )
         vim.schedule(function()
-            vim.notify(
-                ("rocks.nvim: You may need to run 'Rocks sync'.\nThe following plugins were not found:\n%s."):format(
-                    vim.inspect(rock_names)
-                ),
-                vim.log.levels.WARN
-            )
+            local choice = vim.fn.confirm(prompt, "&Yes\n&No", 1, "Question")
+            if choice == 1 then
+                require("rocks.operations").sync()
+            end
         end)
     end
 end