so computer papers don't fall out i think

If I remember correctly, it was a regular folder with a special icon. The intention was that you could drag&drop it to some removable media to move between computers.

I guess MS envisioned it as a digital replacement for the physical suitcase of documents you'd bring to/from work.

Furthermore, this "digital replacement" strategy can be seen in other (now mostly defunct) MS programs such as that program that was bundled with windows 3.11 ( I think it was called wincard.exe) that mimiced a rolodex.

I'll take my MCSE now, thank you.

EDIT: Seems there was some sync stuff with it as well. I'll settle for some junior certification, thank you.

It was more than just a special icon for a folder, it had special behaviour too. Without looking it up (in the spirit of the meme), I seem to remember that it would automatically sync the files any time that you insert the floppy disk, kind of like having Dropbox but without the internet. The idea being that you would have files on your computer that you could take with you somewhere else (in your briefcase, on a floppy disk) and all instances of that briefcase would automatically sync the latest updates of the files without you having to manually copy them and work out which was the latest version of a file.
- It was more than just a special icon for a folder, it had special behaviour too.
  
  How much you bet that the code is still somewhere in explorer.exe?
  
  Wait, isn't this similiar to the homesyncd thing?
- I'd give you both the award.
I think it was very slightly more than a regular folder in that there was a sync wizard IIRC.

I think you set it up with a piece of removable media and then you could press the sync button when it was present to take the newest file from either the removable media or the local disk. I also vaguely remember a conflict resolution screen where if both copies had changed you could keep one, the other or both. I'm trying to remember if you could have a 3-point sync where you used the removable media as a way of keeping the briefcase on your home and work computers in sync, but I never used that feature if it did exist.

So yeah, It didn't do much more than just dragging and dropping (as I think the OS dialog had similar conflict resolution at least from windows 98ish) but the two way aspect was pretty useful.
- Yep - it kept files in sync.
  
  I never used it, though I always thought it was useful idea. Not sure how problematic it could be how did it handle collisions?)
The "digital replacement" nonsense is also why we now have "folders" instead of "directories". This thing gave me so many awkward flashbacks.
- Go back 40/50 years, and most people then thought of directories as an index (see telephone directory), and folders were thing that contained/were files within a filing cabinet.
  
  I still have a hard time calling them folders, it gives me a little eye twitch to say "folder", though I know the icon is a folder, and it makes it easier for the average person to grok.
- I completely changed my mind on this a bunch of years ago when I did a lot of work with LDAP. “Directory” may have seemed a good choice at the time, but now we have so many things which are directories and fit the IRL definition better, to look up information. Meanwhile “folders” fit the IRL definition better, for things that contain and organize files
Meanwhile apple tells you to put your removable media in the trash.
- That always bothered me, from the start.
  
  "Apple is more intuitive" oh really?
- Explain please?
Briefcase cased, so SyncThing could sync.
- Lol, nice.
  
  Offline Files is essentially the same functionality as the briefcase (no idea if it's the same code).
this "digital replacement" strategy

skeuomorphism
- TIL...
You mentioned wincard, but you didn't mention Bob. If you don't know about it, you should really look.
- I have a copy. So, so, so, so awful
I guess MS envisioned it as a digital replacement for the physical suitcase of documents you'd bring to/from work.

The whole computer was originally visualized as a digital office replacement. That's why you have the "desktop," like an actual desk top surface to work on. Files had icons that looked like papers, folders looked like the tan file folders you'd store in a filing cabinet. Plus a slew of other office-related parallels.

The briefcase was just a continuation of that digital theme. Office workers would bring their work files home in a briefcase to work on later, then bring back to the office the next day. Microsoft tried to digitally replicate that by creating a briefcase folder that would automatically sync your files to a floppy disk, so you didn't have to do it yourself. The Internet kinda ruined that concept, though. Now you can just email yourself files, text them to yourself on your phone, or store them in a cloud service to edit live on the site.

Specialty folder which did automatic syncing between devices.

When it felt like it
- True that.
Cloud syncing without a subscription? What is this, socialism?
- Wasn't even cloud. Just local device connected by cable. I know mystery how that worked. We kind of asked for dystopia thoug. I remember people complaining about having one extra cable.
- You did a dial up from home.
I remember the icon, but I never knew that was it's purpose.
- Unless you had pocket PC or PDA you never needed to touch it. And those were expensive business toys back in the day.
Oh! Today I learned that the briefcase was for. Thanks!
- You are welcome. Am not sure even people who had pocket PC used it. I had HP iPaq and that one came with it's own suite for syncing.

It was a zip file, essentially. You drag files into it, then you drag it to your usb memory stick and take it to work. At wprk, you drag it from the usb drive to your briefacse on the work computer and it updates with the newer copies. That's about as much as I remember.

This is before usb. It was a dialup synchronizer between your work pc and your home one so that you could keep working on that Word doc.
- Wow, I had definitely forgotten about briefcase. I remember clicking on it as a kid but don't specifically recall what happened. There was no work computer for my folks, my mom worked at home (essentially), so I'm pretty sure it did nothing. I do remember being unsure of its function. I was young though so I was unsure about much.
- I don’t think this was explicitly network connected? I’m fairly certain the original responder is mostly correct, except it would be a floppy disk instead of a USB drive.

MS OneDrive 0.1beta

Gpt4o the windows expert:

“ The meme references a somewhat obscure feature from older versions of Microsoft Windows called “Briefcase.” Here’s a brief explanation:

Windows Briefcase:

• Introduced in Windows 95 and present in several subsequent versions, the Briefcase was a special folder designed to help users keep files in sync between two locations, typically between a desktop and a laptop.

• You could create a Briefcase on your computer, add files to it, and then copy that Briefcase to another location, such as a floppy disk or another drive.

• When you made changes to the files on either location, you could use the Briefcase to update the files on both sides by synchronizing them. This feature was particularly useful in the era before widespread use of networked file sharing and cloud storage.

The meme humorously challenges a supposed “Windows expert” to explain this somewhat outdated and lesser-known feature, implying that true expertise includes knowledge of such old functionalities.”

OP specifically said "no cheating"!
- I didn’t say i had the answer. just passed it on :)
  
  For all i personally know this answer is completely made up, as is the danger with ai experts.
- Oh nooooo!!! A cheater good lord what is going to happen to them. How will they ever find peace knowing they've committed the worst of crimes.
Dang so it was sneakernet dropbox for Windows 95? That's honestly sick.

People don't like spending time with their family so they found a way to let you take your work home before high speed internet and hard drives you can put in your pocket.

It was a feature in Windows 98 that no one used so they discontinued it.

It deletes your files for no reason

I think we all ignored that.

I used this all the time with a portable drive in college. I could work on my personal computer (not a laptop), then finish working in the school computer lab and print stuff out.

I remember just trying this out when I was in school. The idea seemed interesting. It was a folder you could store on portable media like a floppy, a USB, or maybe even a CD-RW(to be crazy). I remember it was still in XP.

It basically worked like manual file syncing. It tried to automate how you'd work on something and keep a portable version of the files up to date.

I seemed to have much more luck just doing the copying myself though...my "briefcase" folder felt clunky and prone to losing files in the worst case, or just being generally confusing.

In my first briefcase I stored my MS Paint drawings. I got a new job and bought a bigger briefcase, and now I put my Linux isos in there.

Wait, Linux ISOs are bigger than Paint drawings? 😆
- They are if you get the organic kinds at the farmer’s market like I do

Wasn't it basically a portable "My Documents" folder? It would sync up online, right? Or at least was easier to copy to a floppy, cd, or USB drive? I never actually used it but I always assumed that's what it was for since it appeared in Windows once the Internet started being a major thing.

I actively used it to backup my art files onto USB, up until last year when it kept giving me error messages when I tried to update it, so I thought, screw it, manual drag and drop. I'm not sure if the amount or size of files got too big for it. Up till then, it was great for backups as it would automatically detect what had been updated and only transfer those files.