diff --git a/README.md b/README.md
index 140b6e79..38818be3 100644
--- a/README.md
+++ b/README.md
@@ -40,6 +40,7 @@ on a function, press `<Leader>d`, jump quickly through `TODO` items using
     + [`g:doge_mapping_comment_jump_forward`](#gdoge_mapping_comment_jump_forward)
     + [`g:doge_mapping_comment_jump_backward`](#gdoge_mapping_comment_jump_backward)
     + [`g:doge_comment_interactive`](#gdoge_comment_interactive)
+    + [`g:doge_comment_jump_wrap`](#gdoge_comment_jump_wrap)
 - [Commands](#commands)
     + [`:DogeGenerate`](#dogegenerate)
 - [Help](#help)
@@ -164,6 +165,12 @@ Default: `1`
 
 Jumps interactively through all `TODO` items in the generated comment.
 
+### `g:doge_comment_jump_wrap`
+
+Default: `1`
+
+Continue to cycle among placeholders when reaching the start or end.
+
 # Commands
 
 ### `:DogeGenerate`
diff --git a/autoload/doge/comment.vim b/autoload/doge/comment.vim
index b4efd0d9..640c0cb3 100644
--- a/autoload/doge/comment.vim
+++ b/autoload/doge/comment.vim
@@ -5,9 +5,20 @@ let s:comment_placeholder = doge#helpers#placeholder()
 
 " vint: next-line -ProhibitUnusedVariable
 function! s:jump_forward() abort
-  let l:wrap = g:doge_comment_jump_wrap ? 'w' : 'W'
+  let l:wrap = g:doge_comment_jump_wrap == v:true ? 'w' : 'W'
   let l:next_pos = search(s:comment_placeholder, 'n' . l:wrap)
 
+  if l:next_pos != 0
+        \ && l:next_pos > b:doge_interactive['lnum_comment_end_pos']
+        \ && g:doge_comment_jump_wrap == v:true
+        \ && mode() ==# 's'
+    " If we have more TODO items below the comment then we'll go back to the
+    " start position of the comment so we can continue to cycle. This option is
+    " a 2nd solution besides the 'w' or 'W' being used in the initial search()
+    " function (called at the top of this function).
+    return "\<Esc>:" . b:doge_interactive['lnum_comment_start_pos'] . "\<CR>/" . s:comment_placeholder . "\<CR>:silent! noh\<CR>gno\<C-g>"
+  endif
+
   " Check if the next pos we want to jump to is still inside the comment.
   if l:next_pos != 0 && l:next_pos <= b:doge_interactive['lnum_comment_end_pos']
     if mode() ==# 'i'
@@ -29,9 +40,20 @@ endfunction
 
 " vint: next-line -ProhibitUnusedVariable
 function! s:jump_backward() abort
-  let l:wrap = g:doge_comment_jump_wrap ? 'w' : 'W'
+  let l:wrap = g:doge_comment_jump_wrap == v:true ? 'w' : 'W'
   let l:prev_pos = search(s:comment_placeholder, 'bn' . l:wrap)
 
+  if l:prev_pos != 0
+        \ && l:prev_pos < b:doge_interactive['lnum_comment_start_pos']
+        \ && g:doge_comment_jump_wrap == v:true
+        \ && mode() ==# 's'
+    " If we have more TODO items above the comment then we'll go forward to the
+    " end position of the comment so we can continue to cycle. This option is
+    " a 2nd solution besides the 'w' or 'W' being used in the initial search()
+    " function (called at the top of this function).
+    return "\<Esc>:" . b:doge_interactive['lnum_comment_end_pos'] . "\<CR>?" . s:comment_placeholder . "\<CR>:silent! noh\<CR>gno\<C-g>"
+  endif
+
   " Check if the prev pos we want to jump to is still inside the comment.
   if l:prev_pos != 0 && l:prev_pos >= b:doge_interactive['lnum_comment_start_pos']
     if mode() ==# 'i'
diff --git a/doc/doge.txt b/doc/doge.txt
index 1deadeb9..2b0ec32e 100644
--- a/doc/doge.txt
+++ b/doc/doge.txt
@@ -34,6 +34,11 @@ Whether or not to enable built-in mappings.
 
 The mapping to trigger DoGe.
 
+                                                    *g:doge_comment_jump_wrap*
+(Default: 1)
+
+Continue to cycle among placeholders when reaching the start or end.
+
                                          *g:doge_mapping_comment_jump_forward*
 (Default: '<Tab>')
 
@@ -51,12 +56,6 @@ The mapping to jump backward to the previous TODO item in a comment. Requires
 
 Jumps interactively through all TODO items in the generated comment.
 
-                                                    *g:doge_comment_jump_wrap*
-(Default: 0)
-
-Cycle among placeholders when reaching the last one (or first one if jumping
-backwards).
-
 ==============================================================================
 COMMANDS                                                       *doge-commands*
 
diff --git a/doc/tags b/doc/tags
index dec030f0..a62c7d8d 100644
--- a/doc/tags
+++ b/doc/tags
@@ -7,6 +7,7 @@ doge#generate()	doge.txt	/*doge#generate()*
 doge#helpers#count()	doge.txt	/*doge#helpers#count()*
 doge#helpers#keyseq()	doge.txt	/*doge#helpers#keyseq()*
 doge#helpers#placeholder()	doge.txt	/*doge#helpers#placeholder()*
+doge#helpers#trim()	doge.txt	/*doge#helpers#trim()*
 doge#indent#add()	doge.txt	/*doge#indent#add()*
 doge#token#extract()	doge.txt	/*doge#token#extract()*
 doge#token#replace()	doge.txt	/*doge#token#replace()*
diff --git a/plugin/doge.vim b/plugin/doge.vim
index c6977199..c13f93d5 100644
--- a/plugin/doge.vim
+++ b/plugin/doge.vim
@@ -68,15 +68,6 @@ if !exists('g:doge_mapping')
   let g:doge_mapping = '<Leader>d'
 endif
 
-if !exists('g:doge_comment_jump_wrap')
-  ""
-  " (Default: 0)
-  "
-  " Cycle among placeholders when reaching last one (or first if jumping
-  " backward)
-  let g:doge_comment_jump_wrap = 0
-endif
-
 if !exists('g:doge_mapping_comment_jump_forward')
   ""
   " (Default: '<Tab>')
@@ -103,6 +94,14 @@ if !exists('g:doge_comment_interactive')
   let g:doge_comment_interactive = 1
 endif
 
+if !exists('g:doge_comment_jump_wrap')
+  ""
+  " (Default: 1)
+  "
+  " Continue to cycle among placeholders when reaching the start or end.
+  let g:doge_comment_jump_wrap = 1
+endif
+
 nnoremap <Plug>(doge-generate) :call doge#generate()<CR>
 nnoremap <expr> <Plug>(doge-comment-jump-forward) doge#comment#jump('forward')
 nnoremap <expr> <Plug>(doge-comment-jump-backward) doge#comment#jump('backward')
diff --git a/test/vimrc b/test/vimrc
index 2659980a..cf29280c 100644
--- a/test/vimrc
+++ b/test/vimrc
@@ -11,6 +11,9 @@ endif
 " Since the <Leader> key is not an easy way for Vader we'll use <C-d>.
 let g:doge_mapping = '<C-d>'
 
+" Disable the continues comment cyling since this breaks existing tests.
+let g:doge_comment_jump_wrap = 0
+
 " Disable interactive mode in tests, because it will break existing tests and we
 " want to test this manually.
 let g:doge_comment_interactive = 0