I’ve used Windows long enough to understand how much it’s evolved. But because I use several other OSes, I’m reminded every once in a while that Windows 11 still doesn’t let me do a few perfectly normal things.

These limitations may not always feel like a total deal-breaker, but once you understand the extra steps they force on you, it’s impossible to stop wondering why they still exist.

Every file shows a size. Folders don’t.

The column File Explorer never added

Try this now: open File Explorer in Details view. Create a few folders and fill them with different files. Then include other files in the same directory as these new folders. Every file in the directory will report a size, but the folders will be blank.

It may feel like nothing, but when your SSD is almost full and you need to find the folder taking up the most space, something this simplebecomes more consequential. One would expect any regular user to be able to scan the list and have a perfect view of folder and file sizes, but no, not on Windows 11. File Explorer doesn’t include a “Size” column that totals folder contents. So if the goal is to sort by size, well, that only works on files.

If you actually want to get the number, you are forced into a couple of steps: right-click, select Properties, and wait for Windows to calculate the total. That’s something you’d expect a file manager to make easier to see. Having to take these few extra steps is unnecessary friction. So yes, Windows can calculate how much space that folder contains. That figure just won’t surface directly in the Details view.

Right next to this first limitation is a smaller version of the same thing. File Explorer displays sizes rounded to KB or MB. Without showing you the exact bytes, you’re getting a rounded value in the list, and you’re forced to leave the list (Details) view to see exact byte counts.

Windows still refuses perfectly valid names

Reserved words, stripped periods, and characters that never make it through

Create a new folder, then rename it to Report. and save it. Without any warning or notice, the folder name is saved as Report. If you name a folder with a trailing space, Windows silently removes the trailing space. But there are more. If you try creating a folder called CON or NUL, File Explorer will block it and display a pop-up notification: “The specified device name is invalid.”

Three separate rules lead to this kind of Windows behavior:

The obstacle here isn’t the filesystem itself. According to Microsoft’s documentation, NTFS can store names ending in a space or period. The restrictions are largely in the Windows shell and Win32 naming conventions used by everyday applications. Certain rules are enforced by Windows’ Save As window, as well as the rename dialog, which treat otherwise ordinary-looking names as either invalid or incomplete. Even after several decades, Windows’ standard file-management interfaces still don’t accept that ordinary-looking name.

Windows lifted its path limit. Most apps didn’t get the memo.

Long-path support needs two separate green lights

Try building a folder the way you’d typically organize your work. But this time, nest several folders like an actual project directory might look: Client → 2026 → Website Redesign → Assets → Approved → Final → High Resolution. At a certain point, your full path will exceed the old 260-character limit (MAX_PATH).

Windows no longer universally caps paths at 260 characters. That distinction often gets lost. The MAX_PATH restriction was removed for many common Win32 file and directory functions, provided long-path support is enabled and the application opts in. First, set LongPathsEnabled via the registry or Group Policy. Second, the application must declare itself long-path aware in its manifest.

Even when those conditions are met, that doesn’t mean every part of Windows, including File Explorer and every application in your workflow, will handle the longer path. You may have a perfectly reasonable nested structure that works fine, but as soon as an archive utility, sync client, development tool, or the next application in the workflow touches it, it can fail. You cannot always tell which application will break in advance.

The same mismatch in three different places

These are three different ways you face restrictions on Windows 11 for your everyday workflows. These three restrictions may look unrelated, but they all expose the same awkward gap: Windows’ user interface doesn’t always reflect the underlying system’s capabilities.