diff --git a/Chattynator.toc b/Chattynator.toc
index a9bf8ac..cf2e850 100644
--- a/Chattynator.toc
+++ b/Chattynator.toc
@@ -28,6 +28,7 @@ Core/Objects.lua
 Core/Locales.lua
 Core/Constants.lua
 Core/Config.lua
+Core/EditBoxUndo.lua
 Core/Utilities.lua
 Core/HyperlinkHandler.xml
 Core/Fonts.lua
diff --git a/Core/Config.lua b/Core/Config.lua
index 7623606..e698819 100644
--- a/Core/Config.lua
+++ b/Core/Config.lua
@@ -109,6 +109,7 @@ local settings = {
   CLASS_COLORS = {key = "class_colors", default = true, refresh = {addonTable.Constants.RefreshReason.MessageModifier}},
   LINK_URLS = {key = "link_urls", default = true, refresh = {addonTable.Constants.RefreshReason.MessageModifier}},
   REDUCE_REDUNDANT_TEXT = {key = "reduce_redundant_text", default = false, refresh = {addonTable.Constants.RefreshReason.MessageModifier}},
+      EDIT_BOX_UNDO_HISTORY = {key = "edit_box_undo_history", default = 50},
 
   NEW_WHISPER_NEW_TAB = {key = "new_whisper_new_tab", default = 0},
   BUTTON_POSITION = {key = "button_position", default = "outside_left"},
diff --git a/Core/Dialogs.lua b/Core/Dialogs.lua
index 276112b..3ffea0c 100644
--- a/Core/Dialogs.lua
+++ b/Core/Dialogs.lua
@@ -46,6 +46,7 @@ function addonTable.Dialogs.ShowCopy(text)
     dialog.editBox:SetScript("OnEnterPressed", function()
       dialog:Hide()
     end)
+    addonTable.Core.EditBoxUndo.Attach(dialog.editBox)
 
     local okButton = CreateFrame("Button", nil, dialog, "UIPanelDynamicResizeButtonTemplate")
     okButton:SetText(DONE)
@@ -65,6 +66,7 @@ function addonTable.Dialogs.ShowCopy(text)
   dialog:Hide()
   dialog:Show()
   dialog.editBox:SetText(text)
+  addonTable.Core.EditBoxUndo.Reset(dialog.editBox)
   dialog.editBox:SetFocus()
   dialog.editBox:HighlightText()
 end
@@ -79,6 +81,7 @@ function addonTable.Dialogs.ShowEditBox(text, acceptText, cancelText, confirmCal
     dialog.editBox:SetAutoFocus(false)
     dialog.editBox:SetSize(200, 30)
     dialog.editBox:SetPoint("CENTER")
+    addonTable.Core.EditBoxUndo.Attach(dialog.editBox)
 
     dialog.acceptButton = CreateFrame("Button", nil, dialog, "UIPanelDynamicResizeButtonTemplate")
     dialog.cancelButton = CreateFrame("Button", nil, dialog, "UIPanelDynamicResizeButtonTemplate")
@@ -107,6 +110,7 @@ function addonTable.Dialogs.ShowEditBox(text, acceptText, cancelText, confirmCal
   dialog.acceptButton:SetScript("OnClick", function() confirmCallback(dialog.editBox:GetText()); dialog:Hide() end)
   dialog.editBox:SetScript("OnEnterPressed", function() confirmCallback(dialog.editBox:GetText()); dialog:Hide() end)
   dialog.editBox:SetText("")
+  addonTable.Core.EditBoxUndo.Reset(dialog.editBox)
 
   dialog:Show()
   dialog.editBox:SetFocus()
diff --git a/Core/EditBoxUndo.lua b/Core/EditBoxUndo.lua
new file mode 100644
index 0000000..9cdbbdc
--- /dev/null
+++ b/Core/EditBoxUndo.lua
@@ -0,0 +1,235 @@
+---@class addonTableChattynator
+local addonTable = select(2, ...)
+
+addonTable.Core.EditBoxUndo = {}
+
+local trackedEditBoxes = {}
+local defaultDebounceSeconds = 0.3
+
+local function NormalizeLimit(value)
+  value = tonumber(value) or 0
+  value = math.floor(value)
+  if value < 1 then
+    value = 1
+  end
+  return value
+end
+
+local function GetHistoryLimit()
+  return NormalizeLimit(addonTable.Config.Get(addonTable.Config.Options.EDIT_BOX_UNDO_HISTORY))
+end
+
+local function TrimHistory(state)
+  local overflow = #state.history - state.max
+  if overflow <= 0 then
+    return
+  end
+  for _ = 1, overflow do
+    table.remove(state.history, 1)
+  end
+  state.index = math.max(1, state.index - overflow)
+end
+
+local function ClearPending(state)
+  if state.pendingTimer then
+    state.pendingTimer:Cancel()
+    state.pendingTimer = nil
+  end
+  state.pendingText = nil
+  state.pendingCursor = nil
+end
+
+local function PushHistory(state, text, cursor)
+  local last = state.history[state.index]
+  if last and last.text == text then
+    return
+  end
+  for i = #state.history, state.index + 1, -1 do
+    table.remove(state.history, i)
+  end
+  table.insert(state.history, { text = text, cursor = cursor })
+  state.index = #state.history
+  TrimHistory(state)
+end
+
+local function FlushPending(state)
+  if not state.pendingText then
+    return
+  end
+  local text = state.pendingText
+  local cursor = state.pendingCursor
+  ClearPending(state)
+  PushHistory(state, text, cursor)
+end
+
+local function ScheduleCommit(state, text, cursor)
+  state.pendingText = text
+  state.pendingCursor = cursor
+  if state.pendingTimer then
+    state.pendingTimer:Cancel()
+  end
+  state.pendingTimer = C_Timer.NewTimer(state.debounceSeconds, function()
+    state.pendingTimer = nil
+    if state.pendingText then
+      local pendingText = state.pendingText
+      local pendingCursor = state.pendingCursor
+      state.pendingText = nil
+      state.pendingCursor = nil
+      PushHistory(state, pendingText, pendingCursor)
+    end
+  end)
+end
+
+local function ApplyEntry(editBox, state, entry)
+  state.ignore = true
+  editBox:SetText(entry.text)
+  local cursor = entry.cursor or #entry.text
+  if cursor > #entry.text then
+    cursor = #entry.text
+  end
+  editBox:SetCursorPosition(cursor)
+  state.ignore = false
+end
+
+local function Undo(editBox, state)
+  FlushPending(state)
+  if state.index <= 1 then
+    return false
+  end
+  state.index = state.index - 1
+  ApplyEntry(editBox, state, state.history[state.index])
+  return true
+end
+
+local function Redo(editBox, state)
+  FlushPending(state)
+  if state.index >= #state.history then
+    return false
+  end
+  state.index = state.index + 1
+  ApplyEntry(editBox, state, state.history[state.index])
+  return true
+end
+
+local function EnsureState(editBox, options)
+  if editBox.ChattynatorUndo then
+    return editBox.ChattynatorUndo
+  end
+  local state = {
+    history = {},
+    index = 0,
+    max = NormalizeLimit((options and options.max) or GetHistoryLimit()),
+    debounceSeconds = (options and options.debounceSeconds) or defaultDebounceSeconds,
+    pendingTimer = nil,
+    pendingText = nil,
+    pendingCursor = nil,
+    ignore = false,
+    hooked = false,
+  }
+  local text = editBox:GetText() or ""
+  local cursor = editBox:GetCursorPosition() or 0
+  if cursor > #text then
+    cursor = #text
+  end
+  state.history[1] = { text = text, cursor = cursor }
+  state.index = 1
+  editBox.ChattynatorUndo = state
+  trackedEditBoxes[editBox] = true
+  return state
+end
+
+local function CanEditBoxInput(editBox)
+  if C_ChatInfo and C_ChatInfo.InChatMessagingLockdown and C_ChatInfo.InChatMessagingLockdown() then
+    return false
+  end
+  return editBox:IsVisible()
+end
+
+function addonTable.Core.EditBoxUndo.Attach(editBox, options)
+  if not editBox then
+    return
+  end
+  local state = EnsureState(editBox, options)
+  if state.hooked then
+    return
+  end
+  state.hooked = true
+
+  editBox:HookScript("OnTextChanged", function(self)
+    if state.ignore then
+      return
+    end
+    local text = self:GetText() or ""
+    local last = state.history[state.index]
+    if last and last.text == text then
+      ClearPending(state)
+      return
+    end
+    local cursor = self:GetCursorPosition() or 0
+    if cursor > #text then
+      cursor = #text
+    end
+    ScheduleCommit(state, text, cursor)
+  end)
+
+  editBox:HookScript("OnEditFocusLost", function()
+    FlushPending(state)
+  end)
+
+  editBox:HookScript("OnHide", function()
+    FlushPending(state)
+  end)
+
+  editBox:HookScript("OnKeyDown", function(self, key)
+    if not CanEditBoxInput(self) then
+      return
+    end
+    if not IsControlKeyDown() or IsAltKeyDown() then
+      return
+    end
+    if key == "Z" then
+      if IsShiftKeyDown() then
+        Redo(self, state)
+      else
+        Undo(self, state)
+      end
+    elseif key == "Y" then
+      Redo(self, state)
+    end
+  end)
+end
+
+function addonTable.Core.EditBoxUndo.RefreshHistoryLimit()
+  local max = GetHistoryLimit()
+  for editBox in pairs(trackedEditBoxes) do
+    if editBox.ChattynatorUndo then
+      editBox.ChattynatorUndo.max = max
+      TrimHistory(editBox.ChattynatorUndo)
+    end
+  end
+end
+
+function addonTable.Core.EditBoxUndo.Reset(editBox)
+  if not editBox or not editBox.ChattynatorUndo then
+    return
+  end
+  local state = editBox.ChattynatorUndo
+  ClearPending(state)
+  state.history = {}
+  state.index = 1
+  local text = editBox:GetText() or ""
+  local cursor = editBox:GetCursorPosition() or 0
+  if cursor > #text then
+    cursor = #text
+  end
+  state.history[1] = { text = text, cursor = cursor }
+end
+
+function addonTable.Core.EditBoxUndo.Initialize()
+  addonTable.CallbackRegistry:RegisterCallback("SettingChanged", function(_, settingName)
+    if settingName == addonTable.Config.Options.EDIT_BOX_UNDO_HISTORY then
+      addonTable.Core.EditBoxUndo.RefreshHistoryLimit()
+    end
+  end)
+  addonTable.Core.EditBoxUndo.Attach(ChatFrame1EditBox)
+end
diff --git a/Core/Initialize.lua b/Core/Initialize.lua
index 44eb886..82a498f 100644
--- a/Core/Initialize.lua
+++ b/Core/Initialize.lua
@@ -199,6 +199,7 @@ function addonTable.Core.Initialize()
 
   addonTable.Core.ApplyOverrides()
   addonTable.Core.InitializeChatCommandLogging()
+  addonTable.Core.EditBoxUndo.Initialize()
   addonTable.Modifiers.InitializeShortenChannels()
   addonTable.Modifiers.InitializeClassColors()
   addonTable.Modifiers.InitializeURLs()
diff --git a/CustomiseDialog/Main.lua b/CustomiseDialog/Main.lua
index c3031ba..0104560 100644
--- a/CustomiseDialog/Main.lua
+++ b/CustomiseDialog/Main.lua
@@ -329,6 +329,14 @@ local function SetupLayout(parent)
   end
   table.insert(allFrames, editBoxPositionDropdown)
 
+  local editBoxUndoHistory
+  editBoxUndoHistory = addonTable.CustomiseDialog.Components.GetSlider(container, addonTable.Locales.EDIT_BOX_UNDO_HISTORY, 1, 200, "%s", function()
+    addonTable.Config.Set(addonTable.Config.Options.EDIT_BOX_UNDO_HISTORY, editBoxUndoHistory:GetValue())
+  end)
+  editBoxUndoHistory.option = addonTable.Config.Options.EDIT_BOX_UNDO_HISTORY
+  editBoxUndoHistory:SetPoint("TOP", allFrames[#allFrames], "BOTTOM", 0, -30)
+  table.insert(allFrames, editBoxUndoHistory)
+
   local newWhispersNewTab = addonTable.CustomiseDialog.Components.GetCheckbox(container, addonTable.Locales.NEW_WHISPERS_TO_NEW_TAB, 28, function(state)
     addonTable.Config.Set(addonTable.Config.Options.NEW_WHISPER_NEW_TAB, state and 1 or 0)
   end)
diff --git a/Locales.lua b/Locales.lua
index 2ed8f43..ef449ae 100644
--- a/Locales.lua
+++ b/Locales.lua
@@ -63,6 +63,7 @@ L["LINK"] = "Link"
 L["SHOW_COMBAT_LOG"] = "Show Combat Log"
 L["LOCK_CHAT"] = "Lock chat"
 L["EDIT_BOX_POSITION"] = "Edit box position"
+L["EDIT_BOX_UNDO_HISTORY"] = "Undo history size"
 L["BOTTOM"] = "Bottom"
 L["TOP"] = "Top"
 L["SHOW_TABS"] = "Show tabs"