diff --git a/lua/oil/adapters/trash/freedesktop.lua b/lua/oil/adapters/trash/freedesktop.lua
index 07e8a7f..c669730 100644
--- a/lua/oil/adapters/trash/freedesktop.lua
+++ b/lua/oil/adapters/trash/freedesktop.lua
@@ -151,7 +151,7 @@ end
 ---@field info_file string
 ---@field original_path string
 ---@field deletion_date number
----@field stat uv_fs_t
+---@field stat uv.aliases.fs_stat_table
 
 ---@param info_file string
 ---@param cb fun(err?: string, info?: oil.TrashInfo)
@@ -596,8 +596,7 @@ M.perform_action = function(action, cb)
         if err then
           cb(err)
         else
-          ---@diagnostic disable-next-line: undefined-field
-          local stat_type = trash_info.stat.type
+          local stat_type = trash_info.stat.type or "unknown"
           fs.recursive_copy(stat_type, path, trash_info.trash_file, vim.schedule_wrap(cb))
         end
       end)
@@ -625,8 +624,7 @@ M.delete_to_trash = function(path, cb)
     if err then
       cb(err)
     else
-      ---@diagnostic disable-next-line: undefined-field
-      local stat_type = trash_info.stat.type
+      local stat_type = trash_info.stat.type or "unknown"
       fs.recursive_move(stat_type, path, trash_info.trash_file, vim.schedule_wrap(cb))
     end
   end)
diff --git a/lua/oil/adapters/trash/mac.lua b/lua/oil/adapters/trash/mac.lua
index 8b2d33a..66cf4c1 100644
--- a/lua/oil/adapters/trash/mac.lua
+++ b/lua/oil/adapters/trash/mac.lua
@@ -224,7 +224,6 @@ M.delete_to_trash = function(path, cb)
       end
 
       local stat_type = src_stat.type
-      ---@cast stat_type oil.EntryType
       fs.recursive_move(stat_type, path, dest, vim.schedule_wrap(cb))
     end)
   )
diff --git a/lua/oil/fs.lua b/lua/oil/fs.lua
index ac216a1..a9ae10c 100644
--- a/lua/oil/fs.lua
+++ b/lua/oil/fs.lua
@@ -1,3 +1,4 @@
+local log = require("oil.log")
 local M = {}
 
 local uv = vim.uv or vim.loop
@@ -245,6 +246,37 @@ M.recursive_delete = function(entry_type, path, cb)
   end, 10000)
 end
 
+---Move the undofile for the file at src_path to dest_path
+---@param src_path string
+---@param dest_path string
+---@param copy boolean
+local move_undofile = vim.schedule_wrap(function(src_path, dest_path, copy)
+  local undofile = vim.fn.undofile(src_path)
+  uv.fs_stat(
+    undofile,
+    vim.schedule_wrap(function(stat_err)
+      if stat_err then
+        -- undofile doesn't exist
+        return
+      end
+      local dest_undofile = vim.fn.undofile(dest_path)
+      if copy then
+        uv.fs_copyfile(src_path, dest_path, function(err)
+          if err then
+            log.warn("Error copying undofile %s: %s", undofile, err)
+          end
+        end)
+      else
+        uv.fs_rename(undofile, dest_undofile, function(err)
+          if err then
+            log.warn("Error moving undofile %s: %s", undofile, err)
+          end
+        end)
+      end
+    end)
+  )
+end)
+
 ---@param entry_type oil.EntryType
 ---@param src_path string
 ---@param dest_path string
@@ -262,6 +294,7 @@ M.recursive_copy = function(entry_type, src_path, dest_path, cb)
   end
   if entry_type ~= "directory" then
     uv.fs_copyfile(src_path, dest_path, { excl = true }, cb)
+    move_undofile(src_path, dest_path, true)
     return
   end
   uv.fs_stat(src_path, function(stat_err, src_stat)
@@ -333,6 +366,9 @@ M.recursive_move = function(entry_type, src_path, dest_path, cb)
         end
       end)
     else
+      if entry_type ~= "directory" then
+        move_undofile(src_path, dest_path, false)
+      end
       cb()
     end
   end)
diff --git a/lua/oil/util.lua b/lua/oil/util.lua
index 707aa24..7be1d5e 100644
--- a/lua/oil/util.lua
+++ b/lua/oil/util.lua
@@ -195,6 +195,18 @@ M.rename_buffer = function(src_bufnr, dest_buf_name)
       -- Try to delete, but don't if the buffer has changes
       pcall(vim.api.nvim_buf_delete, src_bufnr, {})
     end
+    -- Renaming a buffer won't load the undo file, so we need to do that manually
+    if vim.bo[dest_bufnr].undofile then
+      vim.api.nvim_buf_call(dest_bufnr, function()
+        vim.cmd.rundo({
+          args = { vim.fn.undofile(dest_buf_name) },
+          magic = { file = false, bar = false },
+          mods = {
+            emsg_silent = true,
+          },
+        })
+      end)
+    end
   end)
   return true
 end