diff --git a/CHANGELOG.md b/CHANGELOG.md
index b585ed0e2..832c76419 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -11,6 +11,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 - Added `opts.follow_img_func` option for customizing how to handle image paths.
 - Added better handling for undefined template fields, which will now be prompted for.
+- Added  :ObsidianToggleCheckboxReverse  command. This command goes in reverse order compared to the :ObsidianToggleCheckbox.
 
 ### Changed
 
diff --git a/README.md b/README.md
index d5d382b62..58c3fc3a4 100644
--- a/README.md
+++ b/README.md
@@ -86,6 +86,8 @@ _Keep in mind this plugin is not meant to replace Obsidian, but to complement it
 
 - `:ObsidianToggleCheckbox` to cycle through checkbox options.
 
+- `:ObsidianToggleCheckboxReverse` to cycle through checkbox options in a reverse order.
+
 - `:ObsidianNewFromTemplate [TITLE]` to create a new note from a template in the templates folder. Selecting from a list using your preferred picker.
   This command has one optional argument: the title of the new note.
 
diff --git a/lua/obsidian/commands/init.lua b/lua/obsidian/commands/init.lua
index f31eaf8ea..d52778d90 100644
--- a/lua/obsidian/commands/init.lua
+++ b/lua/obsidian/commands/init.lua
@@ -4,6 +4,7 @@ local iter = require("obsidian.itertools").iter
 local command_lookups = {
   ObsidianCheck = "obsidian.commands.check",
   ObsidianToggleCheckbox = "obsidian.commands.toggle_checkbox",
+  ObsidianToggleCheckboxReverse = "obsidian.commands.toggle_checkbox_reverse",
   ObsidianToday = "obsidian.commands.today",
   ObsidianYesterday = "obsidian.commands.yesterday",
   ObsidianTomorrow = "obsidian.commands.tomorrow",
@@ -170,6 +171,8 @@ M.register("ObsidianFollowLink", { opts = { nargs = "?", desc = "Follow referenc
 
 M.register("ObsidianToggleCheckbox", { opts = { nargs = 0, desc = "Toggle checkbox" } })
 
+M.register("ObsidianToggleCheckboxReverse", { opts = { nargs = 0, desc = "Toggle checkbox in reverse order" } })
+
 M.register("ObsidianWorkspace", { opts = { nargs = "?", desc = "Check or switch workspace" } })
 
 M.register(
diff --git a/lua/obsidian/commands/toggle_checkbox_reverse.lua b/lua/obsidian/commands/toggle_checkbox_reverse.lua
new file mode 100644
index 000000000..39fc249f1
--- /dev/null
+++ b/lua/obsidian/commands/toggle_checkbox_reverse.lua
@@ -0,0 +1,10 @@
+local toggle_checkbox = require("obsidian.util").toggle_checkbox
+
+---@param client obsidian.Client
+return function(client)
+  local checkboxes = vim.tbl_keys(client.opts.ui.checkboxes)
+  table.sort(checkboxes, function(a, b)
+    return (client.opts.ui.checkboxes[a].order or 1000) > (client.opts.ui.checkboxes[b].order or 1000)
+  end)
+  toggle_checkbox(checkboxes)
+end