diff --git a/README.md b/README.md
index b008d58..b6fcf3d 100644
--- a/README.md
+++ b/README.md
@@ -92,7 +92,12 @@ Capybara integration testing. ❤️
 - [x] detect lists that have multiline bullets (should have no empty lines between
   lines).
 - [x] add alphabetic list
-- [ ] support for intelligent alphanumeric indented bullets e.g. 1. \t a. \t 1.
+- [x] support for intelligent alphanumeric indented bullets e.g. 1. \t a. \t 1.
+- [ ] update documentation for nested bullets
+- [ ] support for nested numerical bullets, e.g., 1. -> 1.1 -> 1.1.1, 1.1.2
+- [ ] change nested outline levels in visual mode
+- [ ] support renumbering of alphabetical, roman numerals, and nested lists
+- [ ] add option to turn non-bullet lines into new bullets with `C-t`/`>>`
 
 ---
 
diff --git a/plugin/bullets.vim b/plugin/bullets.vim
index 5dce508..ac17001 100644
--- a/plugin/bullets.vim
+++ b/plugin/bullets.vim
@@ -1,5 +1,5 @@
 " Vim plugin for automated bulleted lists
-" Last Change: February 23, 2020
+" Last Change: March 2, 2020
 " Maintainer: Dorian Karter
 " License: MIT
 " FileTypes: markdown, text, gitcommit
@@ -55,6 +55,13 @@ while s:power >= 0
   let s:abc_max += pow(26,s:power)
   let s:power -= 1
 endwhile
+
+if !exists('g:bullets_outline_levels')
+  " Capitalization matters: all caps will make the symbol caps, lower = lower
+  " Standard bullets should include the marker symbol after 'std'
+  let g:bullets_outline_levels = ['ROM', 'ABC', 'num', 'abc', 'rom', 'std-', 'std*', 'std+']
+endif
+
 " ------------------------------------------------------   }}}
 
 " Parse Bullet Type -------------------------------------------  {{{
@@ -197,7 +204,7 @@ fun! s:match_checkbox_bullet_item(input_text)
 endfun
 
 fun! s:match_bullet_list_item(input_text)
-  let l:std_bullet_regex  = '\v(^\s*(-|\*+|\.+|#\.|\\item)(\s+))(.*)'
+  let l:std_bullet_regex  = '\v(^(\s*)(-|\*+|\.+|#\.|\+|\\item)(\s+))(.*)'
   let l:matches           = matchlist(a:input_text, l:std_bullet_regex)
 
   if empty(l:matches)
@@ -205,14 +212,17 @@ fun! s:match_bullet_list_item(input_text)
   endif
 
   let l:bullet_length     = strlen(l:matches[1])
-  let l:whole_bullet      = l:matches[1]
-  let l:trailing_space    = l:matches[3]
-  let l:text_after_bullet = l:matches[4]
+  let l:leading_space     = l:matches[2]
+  let l:bullet            = l:matches[3]
+  let l:trailing_space    = l:matches[4]
+  let l:text_after_bullet = l:matches[5]
 
   return {
         \ 'bullet_type':       'std',
         \ 'bullet_length':     l:bullet_length,
-        \ 'whole_bullet':      l:whole_bullet,
+        \ 'leading_space':     l:leading_space,
+        \ 'bullet':            l:bullet,
+        \ 'closure':           '',
         \ 'trailing_space':    l:trailing_space,
         \ 'text_after_bullet': l:text_after_bullet
         \ }
@@ -220,17 +230,24 @@ endfun
 " -------------------------------------------------------  }}}
 
 " Resolve Bullet Type ----------------------------------- {{{
-fun! s:closest_bullet_types(from_line_num)
+fun! s:closest_bullet_types(from_line_num, max_indent)
   let l:lnum = a:from_line_num
   let l:ltxt = getline(l:lnum)
+  let l:curr_indent = indent(l:lnum)
   let l:bullet_kinds = s:parse_bullet(l:lnum, l:ltxt)
 
   " Support for wrapped text bullets
   " DEMO: https://raw.githubusercontent.com/dkarter/bullets.vim/master/img/wrapped-bullets.gif
-  while l:lnum > 1 && s:is_indented(l:ltxt) && l:bullet_kinds == []
-    let l:lnum = l:lnum - 1
+  while l:lnum > 1 && (l:curr_indent != 0 || l:bullet_kinds != [])
+        \ && (a:max_indent < l:curr_indent || l:bullet_kinds == [])
+    if l:bullet_kinds != []
+      let l:lnum = l:lnum - g:bullets_line_spacing
+    else
+      let l:lnum = l:lnum - 1
+    endif
     let l:ltxt = getline(l:lnum)
     let l:bullet_kinds = s:parse_bullet(l:lnum, l:ltxt)
+    let l:curr_indent = indent(l:lnum)
   endwhile
 
   return l:bullet_kinds
@@ -259,8 +276,14 @@ endfun
 " Roman Numeral vs Alphabetic Bullets ---------------------------------- {{{
 fun! s:resolve_rom_or_abc(bullet_types)
     let l:first_type = a:bullet_types[0]
-    let l:prev_search_starting_line = get(l:first_type, 'starting_at_line_num') - 1
-    let l:prev_bullet_types = s:closest_bullet_types(l:prev_search_starting_line)
+    let l:prev_search_starting_line = l:first_type.starting_at_line_num - g:bullets_line_spacing
+    let l:bullet_indent = indent(l:first_type.starting_at_line_num)
+    let l:prev_bullet_types = s:closest_bullet_types(l:prev_search_starting_line, l:bullet_indent)
+
+    while l:prev_bullet_types != [] && l:bullet_indent > indent(l:prev_search_starting_line)
+      let l:prev_search_starting_line -= g:bullets_line_spacing
+      let l:prev_bullet_types = s:closest_bullet_types(l:prev_search_starting_line, l:bullet_indent)
+    endwhile
 
     if len(l:prev_bullet_types) == 0
 
@@ -319,37 +342,36 @@ fun! s:next_bullet_str(bullet)
   let l:bullet_type = get(a:bullet, 'bullet_type')
 
   if l:bullet_type ==# 'rom'
-    return s:next_rom_bullet(a:bullet)
+    let l:next_bullet_marker = s:next_rom_bullet(a:bullet)
   elseif l:bullet_type ==# 'abc'
-    return s:next_abc_bullet(a:bullet)
+    let l:next_bullet_marker = s:next_abc_bullet(a:bullet)
   elseif l:bullet_type ==# 'num'
-    return s:next_num_bullet(a:bullet)
+    let l:next_bullet_marker = s:next_num_bullet(a:bullet)
   elseif l:bullet_type ==# 'chk'
-    return s:next_chk_bullet(a:bullet)
+    let l:next_bullet_marker = s:next_chk_bullet(a:bullet)
   else
-    return a:bullet.whole_bullet
+    let l:next_bullet_marker = a:bullet.bullet
   endif
+  let l:closure = has_key(a:bullet, 'closure') ? a:bullet.closure : ''
+  return a:bullet.leading_space . l:next_bullet_marker . l:closure  . ' '
 endfun
 
 fun! s:next_rom_bullet(bullet)
   let l:islower = a:bullet.bullet ==# tolower(a:bullet.bullet)
-  let l:next_num = s:arabic2roman(s:roman2arabic(a:bullet.bullet) + 1, l:islower)
-  return a:bullet.leading_space . l:next_num . a:bullet.closure  . ' '
+  return s:arabic2roman(s:roman2arabic(a:bullet.bullet) + 1, l:islower)
 endfun
 
 fun! s:next_abc_bullet(bullet)
   let l:islower = a:bullet.bullet ==# tolower(a:bullet.bullet)
-  let l:next_num = s:dec2abc(s:abc2dec(a:bullet.bullet) + 1, l:islower)
-  return a:bullet.leading_space . l:next_num . a:bullet.closure  . ' '
+  return s:dec2abc(s:abc2dec(a:bullet.bullet) + 1, l:islower)
 endfun
 
 fun! s:next_num_bullet(bullet)
-  let l:next_num = a:bullet.bullet + 1
-  return a:bullet.leading_space . l:next_num . a:bullet.closure  . ' '
+  return a:bullet.bullet + 1
 endfun
 
 fun! s:next_chk_bullet(bullet)
-  return a:bullet.leading_space . '- [ ] '
+  return '- [ ]'
 endfun
 " }}}
 
@@ -363,7 +385,8 @@ endfun
 fun! s:insert_new_bullet()
   let l:curr_line_num = line('.')
   let l:next_line_num = l:curr_line_num + g:bullets_line_spacing
-  let l:closest_bullet_types = s:closest_bullet_types(l:curr_line_num)
+  let l:curr_indent = indent(l:curr_line_num)
+  let l:closest_bullet_types = s:closest_bullet_types(l:curr_line_num, l:curr_indent)
   let l:bullet = s:resolve_bullet_type(l:closest_bullet_types)
   " need to find which line starts the previous bullet started at and start
   " searching up from there
@@ -573,6 +596,137 @@ endfun
 command! -range=% RenumberSelection call <SID>renumber_selection()
 " --------------------------------------------------------- }}}
 
+" Changing outline level ---------------------------------- {{{
+fun! s:change_bullet_level(direction)
+  let l:lnum = line('.')
+  let l:curr_line = s:parse_bullet(l:lnum, getline(l:lnum))
+
+  if a:direction == 1
+    if l:curr_line != [] && indent(l:lnum) == 0
+      " Promoting a bullet at the highest level will delete the bullet
+      call setline(l:lnum, l:curr_line[0].text_after_bullet)
+    else
+      execute "normal! a\<C-d>"
+    endif
+  else
+    execute "normal! a\<C-t>"
+  endif
+
+  let l:curr_indent = indent(l:lnum)
+  let l:curr_bullet= s:closest_bullet_types(l:lnum, l:curr_indent)
+  let l:curr_bullet = s:resolve_bullet_type(l:curr_bullet)
+
+  if l:curr_bullet == {}
+    " Only change the bullet level if it's currently a bullet.
+    return
+  endif
+
+  let l:curr_line = l:curr_bullet.starting_at_line_num
+  let l:closest_bullet = s:closest_bullet_types(l:curr_line - g:bullets_line_spacing, l:curr_indent)
+  let l:closest_bullet = s:resolve_bullet_type(l:closest_bullet)
+
+  if l:closest_bullet == {}
+    " If there is no parent/sibling bullet then this bullet shouldn't change.
+    return
+  endif
+
+  let l:islower = l:closest_bullet.bullet ==# tolower(l:closest_bullet.bullet)
+  let l:closest_type = l:islower ? l:closest_bullet.bullet_type :
+        \ toupper(l:closest_bullet.bullet_type)
+
+  if l:closest_bullet.bullet_type ==# 'std'
+    " Append the bullet marker to the type, e.g., 'std*'
+
+    let l:closest_type = l:closest_type . l:closest_bullet.bullet
+  endif
+
+  let l:closest_index = index(g:bullets_outline_levels, l:closest_type)
+
+  if l:closest_index == -1
+    " We are in a list using markers that aren't specified in
+    " g:bullets_outline_levels so we shouldn't try to change the current
+    " bullet.
+    return
+  endif
+
+  let l:closest_indent = indent(l:closest_bullet.starting_at_line_num)
+
+  if (l:curr_indent == l:closest_indent)
+    " The closest bullet is a sibling so the current bullet should
+    " increment to the next bullet marker.
+
+    let l:next_bullet = s:next_bullet_str(l:closest_bullet)
+    let l:next_bullet_str = s:pad_to_length(l:next_bullet, l:closest_bullet.bullet_length)
+          \ . l:curr_bullet.text_after_bullet
+
+  elseif l:closest_index + 1 < len(g:bullets_outline_levels) || l:curr_indent < l:closest_indent
+    " The current bullet is a child of the closest bullet so figure out
+    " what bullet type it should have and set its marker to the first
+    " character of that type.
+
+    let l:next_index = l:closest_index + 1
+    let l:next_type = g:bullets_outline_levels[l:next_index]
+    let l:next_islower = l:next_type ==# tolower(l:next_type)
+    let l:trailing_space = ' '
+
+    let l:curr_bullet.closure = l:closest_bullet.closure
+
+    " set the bullet marker to the first character of that type
+    if l:next_type ==? 'rom'
+      let l:next_num = s:arabic2roman(1, l:next_islower)
+    elseif l:next_type ==? 'abc'
+      let l:next_num = s:dec2abc(1, l:next_islower)
+    elseif l:next_type ==# 'num'
+      let l:next_num = '1'
+    else
+      " standard bullet; l:next_type contains the bullet symbol to use
+      let l:next_num = strpart(l:next_type, len(l:next_type) - 1)
+      let l:curr_bullet.closure = ''
+    endif
+
+    let l:next_bullet_str =
+          \ l:curr_bullet.leading_space
+          \ . l:next_num
+          \ . l:curr_bullet.closure
+          \ . l:trailing_space
+          \ . l:curr_bullet.text_after_bullet
+
+  else
+    " We're outside of the defined outline levels
+    let l:next_bullet_str =
+          \ l:curr_bullet.leading_space
+          \ . l:curr_bullet.text_after_bullet
+  endif
+
+  " Apply the new bullet
+  if l:next_bullet_str !=# ''
+    call setline(l:lnum, l:next_bullet_str)
+    execute 'normal! $'
+
+  elseif g:bullets_delete_last_bullet_if_empty
+    let l:orig_line = s:parse_bullet(l:lnum, getline(l:lnum))
+    if l:orig_line != []
+      call setline(l:lnum, l:orig_line[0].leading_space . l:orig_line[0].text_after_bullet)
+    endif
+  endif
+
+  return
+endfun
+
+fun! s:bullet_demote()
+  call s:change_bullet_level(-1)
+endfun
+
+fun! s:bullet_promote()
+  call s:change_bullet_level(1)
+endfun
+
+command! BulletDemote call <SID>bullet_demote()
+command! BulletPromote call <SID>bullet_promote()
+
+
+" --------------------------------------------------------- }}}
+
 " Keyboard mappings --------------------------------------- {{{
 fun! s:add_local_mapping(mapping_type, mapping, action)
   let l:file_types = join(g:bullets_enabled_file_types, ',')
@@ -613,6 +767,13 @@ augroup TextBulletsMappings
 
     " Toggle checkbox
     call s:add_local_mapping('nnoremap', '<leader>x', ':ToggleCheckbox<cr>')
+
+    " Promote and Demote outline level
+    call s:add_local_mapping('inoremap', '<C-t>', '<C-o>:call <SID>bullet_demote()<cr>')
+    call s:add_local_mapping('nnoremap', '>>', ':call <SID>bullet_demote()<cr>')
+    call s:add_local_mapping('inoremap', '<C-d>', '<C-o>:call <SID>bullet_promote()<cr>')
+    call s:add_local_mapping('nnoremap', '<<', ':call <SID>bullet_promote()<cr>')
+
   end
 augroup END
 " --------------------------------------------------------- }}}
diff --git a/spec/alphabetic_bullets_spec.rb b/spec/alphabetic_bullets_spec.rb
index 303dfd0..c175d0d 100644
--- a/spec/alphabetic_bullets_spec.rb
+++ b/spec/alphabetic_bullets_spec.rb
@@ -132,6 +132,49 @@
       TEXT
     end
 
+    it 'does not add a new bullet when mixed case' do
+      test_bullet_inserted('not a bullet', <<-INIT, <<-EXPECTED)
+        # Hello there
+        Ab. this is the first bullet
+      INIT
+        # Hello there
+        Ab. this is the first bullet
+        not a bullet
+      EXPECTED
+    end
+
+    # it 'correctly numbers after wrapped lines starting with short words' do
+    # # TODO: maybe take guidance from Pandoc and require two spaces after the
+    # closure to allow us to differentiate between bullets and abbreviations
+    # and words. Might also consider only allowing single letters.
+    #   test_bullet_inserted('second bullet', <<-INIT, <<-EXPECTED)
+    #     # Hello there
+    #     a. first bullet might not catch
+    #        me. second line.
+    #   INIT
+    #     # Hello there
+    #     a. first bullet might not catch
+    #     \tme. second line.
+    #     b. second bullet
+    #   EXPECTED
+    # end
+
+    # it 'correctly numbers after lines beginning with initialized names' do
+    # # TODO: maybe take guidance from Pandoc and require two spaces after the
+    # closure to allow us to differentiate between bullets and abbreviations
+    # and words. Might also consider only allowing single letters.
+    #   test_bullet_inserted('Second bullet', <<-INIT, <<-EXPECTED)
+    #     # Hello there
+    #     I. The first president of the USA was
+    #        G. Washington.
+    #   INIT
+    #     # Hello there
+    #     I. The first president of the USA was
+    #        G. Washington.
+    #     II. Second bullet
+    #   EXPECTED
+    # end
+
     describe 'g:bullets_max_alpha_characters' do
       it 'stops adding items after configured max (default 2)' do
         filename = "#{SecureRandom.hex(6)}.txt"
diff --git a/spec/nested_bullets_spec.rb b/spec/nested_bullets_spec.rb
new file mode 100644
index 0000000..5f5f2a7
--- /dev/null
+++ b/spec/nested_bullets_spec.rb
@@ -0,0 +1,641 @@
+# frozen_string_literal: true
+
+require 'spec_helper'
+
+RSpec.describe 'Bullets.vim' do
+  describe 'nested bullets' do
+    it 'demotes an existing bullet' do
+      filename = "#{SecureRandom.hex(6)}.txt"
+      write_file(filename, <<-TEXT)
+          # Hello there
+          I. this is the first bullet
+          II. second bullet
+          III. third bullet
+          IV. fourth bullet
+          V. fifth bullet
+          VI. sixth bullet
+          VII. seventh bullet
+          VIII. eighth bullet
+          IX. ninth bullet
+      TEXT
+
+      vim.edit filename
+      vim.normal '2ji'
+      vim.feedkeys '\<C-t>'
+      vim.normal 'j'
+      vim.feedkeys '>>>>>>'
+      vim.normal 'j'
+      vim.feedkeys '>>>>>>>>'
+      vim.normal 'j'
+      vim.feedkeys '>>>>>>>>>>'
+      vim.normal 'j'
+      vim.feedkeys '>>>>>>>>>>>>'
+      vim.normal 'j'
+      vim.feedkeys '>>>>>>>>>>>>>>'
+      vim.normal 'j'
+      vim.feedkeys '>>>>>>>>>>>>>>>>'
+      vim.normal 'j'
+      vim.feedkeys '>>>>>>>>>>>>>>>>>>'
+      vim.write
+
+      file_contents = IO.read(filename)
+
+      expect(file_contents).to eq normalize_string_indent(<<-TEXT)
+          # Hello there
+          I. this is the first bullet
+          \tA. second bullet
+          \t\t\t1. third bullet
+          \t\t\t\ta. fourth bullet
+          \t\t\t\t\ti. fifth bullet
+          \t\t\t\t\t\t- sixth bullet
+          \t\t\t\t\t\t\t* seventh bullet
+          \t\t\t\t\t\t\t\t+ eighth bullet
+          \t\t\t\t\t\t\t\t\tninth bullet
+
+      TEXT
+    end
+
+    it 'promotes an existing bullet' do
+      filename = "#{SecureRandom.hex(6)}.txt"
+      write_file(filename, <<-TEXT)
+          # Hello there
+          I. this is the first bullet
+          \tA. second bullet
+          \t\t\t1. third bullet
+          \t\t\t\ta. fourth bullet
+          \t\t\t\t\ti. fifth bullet
+          \t\t\t\t\t\t- sixth bullet
+          \t\t\t\t\t\t\t* seventh bullet
+          \t\t\t\t\t\t\t\t+ eighth bullet
+      TEXT
+
+      vim.edit filename
+      vim.normal '2j'
+      vim.feedkeys '<<'
+      vim.normal 'ji'
+      vim.feedkeys '\<C-d>'
+      vim.feedkeys '\<C-d>'
+      vim.normal 'j'
+      vim.feedkeys '<<<<<<'
+      vim.normal 'j'
+      vim.feedkeys '<<<<<<<<<<'
+      vim.normal 'j'
+      vim.feedkeys '<<<<<<<<<<<<'
+      vim.normal 'j'
+      vim.feedkeys '<<<<<<<<<<<<<<'
+      vim.normal 'j'
+      vim.feedkeys '<<<<<<<<<<<<<<<<'
+      vim.write
+
+      file_contents = IO.read(filename)
+
+      expect(file_contents).to eq normalize_string_indent(<<-TEXT)
+          # Hello there
+          I. this is the first bullet
+          II. second bullet
+          \tA. third bullet
+          \tB. fourth bullet
+          III. fifth bullet
+          IV.  sixth bullet
+          V.   seventh bullet
+          VI.  eighth bullet
+
+      TEXT
+    end
+
+    it 'demotes an empty bullet' do
+      filename = "#{SecureRandom.hex(6)}.txt"
+      write_file(filename, <<-TEXT)
+          # Hello there
+          I. this is the first bullet
+      TEXT
+
+      vim.edit filename
+      vim.normal 'GA'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<C-t>'
+      vim.type 'second bullet'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<C-t>\<C-t>'
+      vim.type 'third bullet'
+      vim.feedkeys '\<esc>'
+      vim.feedkeys 'o'
+      vim.feedkeys '\<C-t>'
+      vim.type 'fourth bullet'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<C-t>'
+      vim.type 'fifth bullet'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<C-t>'
+      vim.type 'sixth bullet'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<C-t>'
+      vim.type 'seventh bullet'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<C-t>'
+      vim.type 'eighth bullet'
+      vim.write
+
+      file_contents = IO.read(filename)
+
+      expect(file_contents).to eq normalize_string_indent(<<-TEXT)
+          # Hello there
+          I. this is the first bullet
+          \tA. second bullet
+          \t\t\t1. third bullet
+          \t\t\t\ta. fourth bullet
+          \t\t\t\t\ti. fifth bullet
+          \t\t\t\t\t\t- sixth bullet
+          \t\t\t\t\t\t\t* seventh bullet
+          \t\t\t\t\t\t\t\t+ eighth bullet
+
+      TEXT
+    end
+
+    it 'promotes an empty bullet' do
+      filename = "#{SecureRandom.hex(6)}.txt"
+      write_file(filename, <<-TEXT)
+          # Hello there
+          I. this is the first bullet
+          \tA. second bullet
+          \t\t1. third bullet
+          \t\t\ta. fourth bullet
+          \t\t\t\ti. fifth bullet
+          \t\t\t\t\t- sixth bullet
+      TEXT
+
+      vim.edit filename
+      vim.normal 'GA'
+      vim.feedkeys '\<cr>'
+      vim.type 'seventh bullet'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<C-d>'
+      vim.type 'eighth bullet'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<C-d>'
+      vim.type 'ninth bullet'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<C-d>'
+      vim.type 'tenth bullet'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<C-d>'
+      vim.feedkeys '\<C-d>'
+      vim.type 'eleventh bullet'
+      vim.write
+
+      file_contents = IO.read(filename)
+
+      expect(file_contents).to eq normalize_string_indent(<<-TEXT)
+          # Hello there
+          I. this is the first bullet
+          \tA. second bullet
+          \t\t1. third bullet
+          \t\t\ta. fourth bullet
+          \t\t\t\ti. fifth bullet
+          \t\t\t\t\t- sixth bullet
+          \t\t\t\t\t- seventh bullet
+          \t\t\t\tii. eighth bullet
+          \t\t\tb. ninth bullet
+          \t\t2. tenth bullet
+          II. eleventh bullet
+
+      TEXT
+    end
+
+    it 'restarts numbering with multiple outlines' do
+      filename = "#{SecureRandom.hex(6)}.txt"
+      write_file(filename, <<-TEXT)
+          # Hello there
+          I. this is the first bullet
+          \tA. second bullet
+          \t\t1. third bullet
+      TEXT
+
+      vim.edit filename
+      vim.normal 'GA'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<cr>'
+      vim.type 'A. first bullet'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<C-t>'
+      vim.type 'second bullet'
+      vim.feedkeys '\<cr>'
+      vim.type 'third bullet'
+      vim.feedkeys '\<C-t>'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<cr>'
+      vim.type '1. first bullet'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<C-t>'
+      vim.type 'second bullet'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<C-t>'
+      vim.type 'third bullet'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<cr>'
+      vim.type '- first bullet'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<C-t>'
+      vim.type 'second bullet'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<C-t>'
+      vim.type 'third bullet'
+      vim.write
+
+      file_contents = IO.read(filename)
+
+      expect(file_contents).to eq normalize_string_indent(<<-TEXT)
+          # Hello there
+          I. this is the first bullet
+          \tA. second bullet
+          \t\t1. third bullet
+
+          A. first bullet
+          \t1. second bullet
+          \t\ta. third bullet
+
+          1. first bullet
+          \ta. second bullet
+          \t\ti. third bullet
+
+          - first bullet
+          \t* second bullet
+          \t\t+ third bullet
+
+      TEXT
+    end
+
+    it 'works with custom outline level definitions' do
+      filename = "#{SecureRandom.hex(6)}.txt"
+      write_file(filename, <<-TEXT)
+          # Hello there
+      TEXT
+
+      vim.edit filename
+      vim.command "let g:bullets_outline_levels=['num','ABC','std*']"
+      vim.normal 'GA'
+      vim.feedkeys '\<cr>'
+      vim.type '1. first bullet'
+      vim.feedkeys '\<cr>'
+      vim.type 'second bullet'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<C-t>'
+      vim.type 'third bullet'
+      vim.feedkeys '\<cr>'
+      vim.type 'fourth bullet'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<C-t>'
+      vim.type 'fifth bullet'
+      vim.feedkeys '\<cr>'
+      vim.type 'sixth bullet'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<C-t>'
+      vim.type 'not a bullet'
+      vim.feedkeys '\<cr>'
+      vim.type 'seventh bullet'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<C-d>'
+      vim.type 'eighth bullet'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<C-d>'
+      vim.type 'ninth bullet'
+      vim.feedkeys '\<cr>'
+      vim.type 'tenth bullet'
+
+      vim.write
+
+      file_contents = IO.read(filename)
+
+      expect(file_contents).to eq normalize_string_indent(<<-TEXT)
+          # Hello there
+          1. first bullet
+          2. second bullet
+          \tA. third bullet
+          \tB. fourth bullet
+          \t\t* fifth bullet
+          \t\t* sixth bullet
+          \t\t\tnot a bullet
+          \t\t* seventh bullet
+          \tC. eighth bullet
+          3. ninth bullet
+          4. tenth bullet
+
+      TEXT
+    end
+
+    it 'promotes and demotes from different starting levels' do
+      filename = "#{SecureRandom.hex(6)}.txt"
+      write_file(filename, <<-TEXT)
+          # Hello there
+          1. this is the first bullet
+          2. second bullet
+      TEXT
+
+      vim.edit filename
+      vim.normal 'GA'
+      vim.feedkeys '\<C-t>'
+      vim.feedkeys '\<cr>'
+      vim.type 'third bullet'
+      vim.normal '3hi'
+      vim.feedkeys '\<C-t>'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<esc>'
+      vim.feedkeys '>>'
+      vim.type 'astandard bullet'
+      vim.feedkeys '\<cr>'
+      vim.type 'fourth bullet'
+      vim.feedkeys '\<cr>'
+      vim.type 'fifth bullet'
+      vim.feedkeys '\<C-d>'
+      vim.feedkeys '\<C-d>'
+      vim.feedkeys '\<esc>'
+      vim.feedkeys '<<'
+      vim.feedkeys 'i\<C-t>'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<cr>'
+      vim.type '+ sixth bullet'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<C-t>'
+      vim.type 'not a bullet'
+      vim.feedkeys '\<cr>'
+      vim.type 'seventh bullet'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<cr>'
+      vim.type '* eighth bullet'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<C-t>'
+      vim.type 'ninth bullet'
+
+      vim.write
+
+      file_contents = IO.read(filename)
+
+      expect(file_contents).to eq normalize_string_indent(<<-TEXT)
+          # Hello there
+          1. this is the first bullet
+          \ta. second bullet
+          \t\ti. third bullet
+          \t\t\t- standard bullet
+          \t\t\t- fourth bullet
+          \tb. fifth bullet
+
+          + sixth bullet
+          \tnot a bullet
+          + seventh bullet
+
+          * eighth bullet
+          \t+ ninth bullet
+
+      TEXT
+    end
+
+    it 'does not nest below defined levels' do
+      filename = "#{SecureRandom.hex(6)}.txt"
+      write_file(filename, <<-TEXT)
+          # Hello there
+          I. this is the first bullet
+          \tA. second bullet
+          \t\t1. third bullet
+          \t\t\ta. fourth bullet
+          \t\t\t\ti. fifth bullet
+          \t\t\t\tii. sixth bullet
+          \t\t\t\t\t- seventh bullet
+          \t\t\t\t\t\t* eighth bullet
+          \t\t\t\t\t\t\t+ ninth bullet
+      TEXT
+
+      vim.edit filename
+      vim.normal 'GA'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<C-t>'
+      vim.type 'not a bullet'
+      vim.feedkeys '\<cr>'
+      vim.type 'tenth bullet'
+      vim.write
+
+      file_contents = IO.read(filename)
+
+      expect(file_contents).to eq normalize_string_indent(<<-TEXT)
+          # Hello there
+          I. this is the first bullet
+          \tA. second bullet
+          \t\t1. third bullet
+          \t\t\ta. fourth bullet
+          \t\t\t\ti. fifth bullet
+          \t\t\t\tii. sixth bullet
+          \t\t\t\t\t- seventh bullet
+          \t\t\t\t\t\t* eighth bullet
+          \t\t\t\t\t\t\t+ ninth bullet
+          \t\t\t\t\t\t\t\tnot a bullet
+          \t\t\t\t\t\t\t+ tenth bullet
+
+      TEXT
+    end
+
+    it 'removes bullet when promoting top level bullet' do
+      filename = "#{SecureRandom.hex(6)}.txt"
+      write_file(filename, <<-TEXT)
+          # Hello there
+          A. this is the first bullet
+
+          I. second bullet
+          \tA. third bullet
+      TEXT
+
+      vim.edit filename
+      vim.normal 'j'
+      vim.feedkeys '<<'
+      vim.normal '3ji'
+      vim.feedkeys '\<C-d>'
+      vim.feedkeys '\<C-d>'
+      vim.write
+
+      file_contents = IO.read(filename)
+
+      expect(file_contents).to eq normalize_string_indent(<<-TEXT)
+          # Hello there
+          this is the first bullet
+
+          I. second bullet
+          third bullet
+
+      TEXT
+    end
+
+    it 'handle standard bullets when they are not in outline list' do
+      filename = "#{SecureRandom.hex(6)}.txt"
+      write_file(filename, <<-TEXT)
+          # Hello there
+          1. this is the first bullet
+          \t- standard bullet
+      TEXT
+
+      vim.edit filename
+      vim.command "let g:bullets_outline_levels=['num','ABC']"
+      vim.normal 'GA'
+      vim.feedkeys '\<cr>'
+      vim.type 'second standard bullet'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<C-d>'
+      vim.type 'second bullet'
+      vim.feedkeys '\<cr>'
+      vim.type 'third bullet'
+      vim.write
+
+      file_contents = IO.read(filename)
+
+      expect(file_contents).to eq normalize_string_indent(<<-TEXT)
+          # Hello there
+          1. this is the first bullet
+          \t- standard bullet
+          \t- second standard bullet
+          2. second bullet
+          3. third bullet
+
+      TEXT
+    end
+
+    it 'adds new nested bullets with correct alpha/roman numerals' do
+      filename = "#{SecureRandom.hex(6)}.txt"
+      write_file(filename, <<-TEXT)
+          # Hello there
+          I. this is the first bullet
+
+          \tA. second bullet
+
+          \tB. third bullet
+
+          \tC. fourth bullet
+      TEXT
+
+      vim.edit filename
+      vim.command 'let g:bullets_line_spacing=2'
+      vim.normal 'GA'
+      vim.feedkeys '\<cr>'
+      vim.type 'fifth bullet'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<C-d>'
+      vim.type 'sixth bullet'
+      vim.feedkeys '\<cr>'
+      vim.type 'seventh bullet'
+      vim.feedkeys '\<cr>'
+      vim.type 'eighth bullet'
+      vim.feedkeys '\<C-t>'
+      vim.feedkeys '\<cr>'
+      vim.type 'ninth bullet'
+      vim.feedkeys '\<C-t>'
+      vim.feedkeys '\<cr>'
+      vim.type 'tenth bullet'
+      vim.feedkeys '\<C-t>'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<C-t>'
+      vim.type 'eleventh bullet'
+      vim.feedkeys '\<cr>'
+      vim.type 'twelfth bullet'
+      vim.feedkeys '\<cr>'
+      vim.type 'thirteenth bullet'
+      vim.feedkeys '\<C-t>'
+      vim.feedkeys '\<cr>'
+      vim.type 'fourteenth bullet'
+      vim.feedkeys '\<cr>'
+      vim.type 'fifteenth bullet'
+      vim.feedkeys '\<C-d>'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<C-d>'
+      vim.type 'sixteenth bullet'
+      vim.feedkeys '\<cr>'
+      vim.normal 'dd'
+      vim.insert '				wrapped line'
+      vim.feedkeys '\<cr>'
+      vim.type 'seventeenth bullet'
+      vim.feedkeys '\<cr>'
+      vim.normal 'dd'
+      vim.insert '				wrapped line'
+      vim.feedkeys '\<cr>'
+      vim.type 'eighteenth bullet'
+      vim.write
+
+      file_contents = IO.read(filename)
+
+      expect(file_contents).to eq normalize_string_indent(<<-TEXT)
+          # Hello there
+          I. this is the first bullet
+
+          \tA. second bullet
+
+          \tB. third bullet
+
+          \tC. fourth bullet
+
+          \tD. fifth bullet
+
+          II. sixth bullet
+
+          III. seventh bullet
+
+          \tA. eighth bullet
+
+          \t\t1. ninth bullet
+
+          \t\t\ta. tenth bullet
+
+          \t\t\t\ti. eleventh bullet
+
+          \t\t\t\tii. twelfth bullet
+
+          \t\t\t\t\t- thirteenth bullet
+
+          \t\t\t\t\t- fourteenth bullet
+
+          \t\t\t\tiii. fifteenth bullet
+
+          \t\t\tb. sixteenth bullet
+          \t\t\t\twrapped line
+
+          \t\t\tc. seventeenth bullet
+          \t\t\t\twrapped line
+
+          \t\t\td. eighteenth bullet
+
+      TEXT
+    end
+
+    it 'add and change bullets with multiple line spacing and wrapped lines' do
+      filename = "#{SecureRandom.hex(6)}.txt"
+      write_file(filename, <<-TEXT)
+          # Hello there
+          I. this is the first bullet
+      TEXT
+
+      vim.edit filename
+      vim.command 'let g:bullets_line_spacing=2'
+      vim.normal 'GA'
+      vim.feedkeys '\<cr>'
+      vim.type 'second bullet'
+      vim.feedkeys '\<cr>'
+      vim.feedkeys '\<C-t>'
+      vim.type 'third bullet'
+      vim.feedkeys '\<cr>'
+      vim.normal 'dd'
+      vim.insert '	wrapped bullet'
+      vim.feedkeys '\<cr>'
+      vim.type 'fourth bullet'
+      vim.write
+
+      file_contents = IO.read(filename)
+
+      expect(file_contents).to eq normalize_string_indent(<<-TEXT)
+          # Hello there
+          I. this is the first bullet
+
+          II. second bullet
+
+          \tA. third bullet
+          \twrapped bullet
+
+          \tB. fourth bullet
+
+      TEXT
+    end
+  end
+end