diff --git a/lua/orgmode/init.lua b/lua/orgmode/init.lua
index 2321ddd20..af7110806 100644
--- a/lua/orgmode/init.lua
+++ b/lua/orgmode/init.lua
@@ -1,5 +1,5 @@
 _G.orgmode = _G.orgmode or {}
-local ts_revision = '1c3eb533a9cf6800067357b59e03ac3f91fc3a54'
+local ts_revision = '9a595e51c1f69b9ac986f0e0b788804eda0e755d'
 local setup_ts_grammar_used = false
 local instance = nil
 
@@ -75,10 +75,10 @@ local function setup_ts_grammar(revision)
 end
 
 local function check_ts_grammar()
-  if setup_ts_grammar_used then
-    return
-  end
   vim.defer_fn(function()
+    if setup_ts_grammar_used then
+      return
+    end
     local parser_config = require('nvim-treesitter.parsers').get_parser_configs()
     if parser_config and parser_config.org and parser_config.org.install_info.revision ~= ts_revision then
       require('orgmode.utils').echo_error({
diff --git a/lua/orgmode/org/mappings.lua b/lua/orgmode/org/mappings.lua
index 74fbada73..79d5159c3 100644
--- a/lua/orgmode/org/mappings.lua
+++ b/lua/orgmode/org/mappings.lua
@@ -454,16 +454,26 @@ function OrgMappings:handle_return(suffix)
     item = Files.get_current_file():get_current_node()
   end
 
-  if item.type == 'itemtext' or item.type == 'bullet' or item.type == 'checkbox' or item.type == 'description' then
+  if item.type == 'paragraph' or item.type == 'bullet' then
     local list_item = item.node:parent()
     if list_item:type() ~= 'listitem' then
       return
     end
     local line = vim.fn.getline(list_item:start() + 1)
     local end_row, _ = list_item:end_()
+    local next_line_node = current_file:get_node_at_cursor({ end_row + 1, 0 })
+    local second_line_node = current_file:get_node_at_cursor({ end_row + 2, 0 })
+    local is_end_of_file = next_line_node
+      and vim.tbl_contains({ 'paragraph', 'list' }, next_line_node:type())
+      and second_line_node
+      and second_line_node:type() == 'document'
+    -- Range for list items at the very end of the file are not calculated properly
+    if (end_row + 1) == vim.fn.line('$') and is_end_of_file then
+      end_row = end_row + 1
+    end
     local range = {
-      start = { line = end_row + 1, character = 0 },
-      ['end'] = { line = end_row + 1, character = 0 },
+      start = { line = end_row, character = 0 },
+      ['end'] = { line = end_row, character = 0 },
     }
 
     local checkbox = line:match('^(%s*[%+%-])%s*%[[%sXx%-]?%]')
@@ -512,7 +522,7 @@ function OrgMappings:handle_return(suffix)
     if #text_edits > 0 then
       vim.lsp.util.apply_text_edits(text_edits, 0, constants.default_offset_encoding)
 
-      vim.fn.cursor(end_row + 2 + (add_empty_line and 1 or 0), 0) -- +1 for 0 index and +1 for next line
+      vim.fn.cursor(end_row + 1 + (add_empty_line and 1 or 0), 0) -- +1 for next line
       vim.cmd([[startinsert!]])
     end
   end
diff --git a/queries/org/highlights.scm b/queries/org/highlights.scm
index 773480fa4..b83605308 100644
--- a/queries/org/highlights.scm
+++ b/queries/org/highlights.scm
@@ -9,10 +9,9 @@
 (headline (stars) @stars (#eq? @stars "*******")) @OrgTSHeadlineLevel7
 (headline (stars) @stars (#eq? @stars "********")) @OrgTSHeadlineLevel8
  (bullet) @OrgTSBullet
- (checkbox) @OrgTSCheckbox
- ((checkbox) @check (#eq? @check "\[-\]")) @OrgTSCheckboxHalfChecked
- ((checkbox) @check (#eq? @check "\[ \]")) @OrgTSCheckboxUnchecked
- ((checkbox) @check (#match? @check "\[[xX]\]")) @OrgTSCheckboxChecked
+(listitem . (bullet) . (paragraph . (expr "[" "str" @OrgCheckDone "]") @OrgTSCheckboxChecked (#match? @OrgTSCheckboxChecked "\[[xX]\]")))
+(listitem . (bullet) . (paragraph . (expr "[" "-" @OrgCheckInProgress "]") @OrgTSCheckboxHalfChecked (#eq? @OrgTSCheckboxHalfChecked "[-]")))
+(listitem . (bullet) . (paragraph . ((expr "[") @OrgTSCheckbox.left (#eq? @OrgTSCheckbox.left "[") . (expr "]") @OrgTSCheckbox.right (#eq? @OrgTSCheckbox.right "]"))))
  (property_drawer) @OrgTSPropertyDrawer
  (drawer) @OrgTSDrawer
  (tag) @OrgTSTag