diff --git a/runtime/doc/lua.txt b/runtime/doc/lua.txt
index 1d561bdbe4..e9ceb47d3e 100644
--- a/runtime/doc/lua.txt
+++ b/runtime/doc/lua.txt
@@ -722,6 +722,10 @@ vim.schedule({fn})                                            *vim.schedule()*
     Parameters: ~
       • {fn}  (`fun()`)
 
+    Return (multiple): ~
+        (`nil`) result
+        (`string?`) err Error message if scheduling failed, `nil` otherwise.
+
 vim.str_utf_end({str}, {index})                            *vim.str_utf_end()*
     Gets the distance (in bytes) from the last byte of the codepoint
     (character) that {index} points to.
@@ -1272,7 +1276,7 @@ vim.defer_fn({fn}, {timeout})                                 *vim.defer_fn()*
     Defers calling {fn} until {timeout} ms passes.
 
     Use to do a one-shot timer that calls {fn} Note: The {fn} is
-    |vim.schedule_wrap()|ped automatically, so API functions are safe to call.
+    |vim.schedule()|d automatically, so API functions are safe to call.
 
     Parameters: ~
       • {fn}       (`function`) Callback to call once `timeout` expires
diff --git a/runtime/lua/vim/_core/editor.lua b/runtime/lua/vim/_core/editor.lua
index 963d67dbde..fb1d154f22 100644
--- a/runtime/lua/vim/_core/editor.lua
+++ b/runtime/lua/vim/_core/editor.lua
@@ -509,25 +509,28 @@ end
 --- Defers calling {fn} until {timeout} ms passes.
 ---
 --- Use to do a one-shot timer that calls {fn}
---- Note: The {fn} is |vim.schedule_wrap()|ped automatically, so API functions are
+--- Note: The {fn} is |vim.schedule()|d automatically, so API functions are
 --- safe to call.
 ---@param fn function Callback to call once `timeout` expires
 ---@param timeout integer Number of milliseconds to wait before calling `fn`
 ---@return table timer luv timer object
 function vim.defer_fn(fn, timeout)
   vim.validate('fn', fn, 'callable', true)
+
   local timer = assert(vim.uv.new_timer())
-  timer:start(
-    timeout,
-    0,
-    vim.schedule_wrap(function()
+  timer:start(timeout, 0, function()
+    local _, err = vim.schedule(function()
       if not timer:is_closing() then
         timer:close()
       end
 
       fn()
     end)
-  )
+
+    if err then
+      timer:close()
+    end
+  end)
 
   return timer
 end
diff --git a/runtime/lua/vim/_meta/builtin.lua b/runtime/lua/vim/_meta/builtin.lua
index 35398ecfcc..d1910eaf09 100644
--- a/runtime/lua/vim/_meta/builtin.lua
+++ b/runtime/lua/vim/_meta/builtin.lua
@@ -178,6 +178,8 @@ function vim.iconv(str, from, to, opts) end
 --- Schedules {fn} to be invoked soon by the main event-loop. Useful
 --- to avoid |textlock| or other temporary restrictions.
 --- @param fn fun()
+--- @return nil result
+--- @return string? err Error message if scheduling failed, `nil` otherwise.
 function vim.schedule(fn) end
 
 --- Waits up to `time` milliseconds, until `callback` returns `true` (success). Executes
diff --git a/src/nvim/lua/executor.c b/src/nvim/lua/executor.c
index 78d4515057..b76244cc2d 100644
--- a/src/nvim/lua/executor.c
+++ b/src/nvim/lua/executor.c
@@ -407,17 +407,20 @@ static int nlua_schedule(lua_State *const lstate)
     return lua_error(lstate);
   }
 
+  lua_pushnil(lstate);
   // If main_loop is closing don't schedule tasks to run in the future,
   // otherwise any refs allocated here will not be cleaned up.
   if (main_loop.closing) {
-    return 0;
+    lua_pushliteral(lstate, "main loop is closing");
+    return 2;
   }
 
   LuaRef cb = nlua_ref_global(lstate, 1);
   // Pass along UI event handler to disable on error.
   multiqueue_put(main_loop.events, nlua_schedule_event, (void *)(ptrdiff_t)cb,
                  (void *)(ptrdiff_t)ui_event_ns_id);
-  return 0;
+  lua_pushnil(lstate);
+  return 2;
 }
 
 // Dummy timer callback. Used by f_wait().
diff --git a/test/functional/lua/vim_spec.lua b/test/functional/lua/vim_spec.lua
index c752be128a..e31c215817 100644
--- a/test/functional/lua/vim_spec.lua
+++ b/test/functional/lua/vim_spec.lua
@@ -1786,6 +1786,24 @@ describe('lua stdlib', function()
     eq(true, exec_lua [[return vim.g.test]])
   end)
 
+  it('nested vim.defer_fn does not leak handles on exit #19727', function()
+    n.expect_exit(exec_lua, function()
+      vim.defer_fn(function()
+        vim.defer_fn(function()
+          vim.defer_fn(function() end, 0)
+        end, 0)
+      end, 0)
+      vim.cmd('qall')
+    end)
+  end)
+
+  it('vim.defer_fn with timeout does not leak handles on exit', function()
+    n.expect_exit(exec_lua, function()
+      vim.defer_fn(function() end, 50)
+      vim.cmd('qall')
+    end)
+  end)
+
   describe('vim.region', function()
     it('charwise', function()
       insert(dedent([[
diff --git a/test/functional/testnvim.lua b/test/functional/testnvim.lua
index 75c48f36a6..c9cbc472e3 100644
--- a/test/functional/testnvim.lua
+++ b/test/functional/testnvim.lua
@@ -510,8 +510,8 @@ function M.new_session(keep, ...)
     end
     if delta > 500 then
       print(
-        ('Nvim session %s took %d milliseconds to exit\n'):format(test_id, delta)
-          .. 'This indicates a likely problem with the test even if it passed!\n'
+        ('\nNvim session %s took %d milliseconds to exit\n'):format(test_id, delta)
+          .. 'This indicates a likely problem with the test even if it passed!'
       )
       io.stdout:flush()
     end