diff --git a/lua/orgmode/org/indent.lua b/lua/orgmode/org/indent.lua
index 756bf3b15..f8b0b3422 100644
--- a/lua/orgmode/org/indent.lua
+++ b/lua/orgmode/org/indent.lua
@@ -62,8 +62,10 @@ local function get_indent_for_match(matches, linenr, mode, bufnr)
     end
     return indent
   end
-  if mode:match('^[iR]') and prev_line_match.type == 'listitem' and linenr - prev_linenr < 3 then
-    -- In insert mode, we also count the non-listitem line *after* a listitem as
+  -- node type is nil while inserting!
+  local is_inserting = (not match.type) or mode:match('^[iR]')
+  if is_inserting and prev_line_match.type == 'listitem' and linenr - prev_linenr < 3 then
+    -- While inserting, we also count the non-listitem line *after* a listitem as
     -- part of the listitem. Keep in mind that double empty lines end a list as
     -- per Orgmode syntax.
     --
@@ -217,6 +219,9 @@ local get_matches = ts_utils.memoize_by_buf_tick(function(bufnr)
       end
     elseif type == 'paragraph' or type == 'drawer' or type == 'property_drawer' then
       opts.indent_type = 'other'
+      for i = range.start.line, range['end'].line - 1 do
+        matches[i + 1] = opts
+      end
     end
   end
 
@@ -254,9 +259,7 @@ local function indentexpr(linenr, bufnr)
   end
 
   local indentexpr_cache = buf_indentexpr_cache[bufnr] or { prev_linenr = -1 }
-  if indentexpr_cache.prev_linenr ~= linenr - 1 or not mode:lower():find('n') then
-    indentexpr_cache.matches = get_matches(bufnr)
-  end
+  indentexpr_cache.matches = get_matches(bufnr)
 
   -- Treesitter failed to parse the document (due to errors or missing tree)
   -- So we just fallback to autoindent
diff --git a/tests/plenary/org/indent_spec.lua b/tests/plenary/org/indent_spec.lua
index fabd96a0d..66f8327f0 100644
--- a/tests/plenary/org/indent_spec.lua
+++ b/tests/plenary/org/indent_spec.lua
@@ -237,6 +237,19 @@ local function test_add_line_breaks_to_existing_file()
   expect_whole_buffer(expected)
 end
 
+local function test_insertion_from_normal_mode()
+  helpers.create_file({ '- first item' })
+  vim.cmd([[normal! o]])
+  local user_input = vim.api.nvim_replace_termcodes('i- second item<Esc>ocontent', true, true, true)
+  vim.api.nvim_feedkeys(user_input, 'ntix', false)
+  local expected = {
+    '- first item',
+    '- second item',
+    '  content',
+  }
+  expect_whole_buffer(expected)
+end
+
 -- The actual tests are here.
 
 describe('with "indent",', function()
@@ -259,6 +272,10 @@ describe('with "indent",', function()
   it('adding line breaks to list items maintains indent', function()
     test_add_line_breaks_to_existing_file()
   end)
+
+  it('inserting content from nomral mode is well indented', function()
+    test_insertion_from_normal_mode()
+  end)
 end)
 
 describe('with "noindent",', function()