How to Send Folder on Outlook: Why Most People Do It the Hard Way

You’re staring at a folder full of PDFs, images, or project logs. You try to drag that entire folder into a new email, and Outlook just... stares back. Or worse, it starts attaching every single file individually, cluttering up the draft until it looks like a digital junk drawer. It’s annoying. Honestly, it’s one of those tiny technical hurdles that makes you want to toss your laptop out a window.

The truth is, Outlook—whether you’re using the classic desktop app, the "New Outlook," or the web version—doesn't actually have a "Send Folder" button. It’s not there. Microsoft never built it. To learn how to send folder on outlook, you have to understand that the software sees a folder as a container, not a file. You can't send a container; you can only send what's inside.

But don't worry. There are ways around this that don't involve clicking "Attach File" fifty times.

The Zipping Hack Everyone Should Know

If you want to move a folder through an email pipe, you have to trick the system into thinking that folder is a single file. This is where compression comes in. Most people call it "Zipping."

When you zip a folder, you're essentially vacuum-sealing it. It shrinks the size (usually) and turns the whole directory into a single .zip file. Outlook loves .zip files. It handles them like any other attachment.

On a Windows machine, you just right-click the folder, hover over "Compress to ZIP file" (on Windows 11) or "Send to" > "Compressed (zipped) folder" (on older versions). If you’re a Mac user, it’s even easier—right-click and hit "Compress."

Once you have that shiny new zip file, you just drag it into your Outlook message. Done. The recipient gets everything in one neat package, and they just have to double-click to unpack it. It’s clean. It’s professional. It saves you from the embarrassment of sending sixteen separate emails because you forgot one document in the sub-folder.

Dealing with the "File Too Large" Nightmare

Here is the catch. Outlook has a strict attachment limit. For most Microsoft 365 accounts, it’s 20MB or 25MB. Some enterprise setups allow more, but generally, if your folder has a bunch of high-res photos or a few video clips, that zip file is going to be too big.

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You’ll get that dreaded pop-up: "The file you’re attaching is bigger than the server allows."

When this happens, zipping isn't enough. You need to pivot.

Using OneDrive for the Heavy Lifting

Since Microsoft owns both Outlook and OneDrive, they’ve made them work together, though sometimes the interface feels a bit clunky. Instead of attaching the folder, you’re going to share a link to it.

Think of it like this: instead of trying to shove a physical filing cabinet through a mail slot, you’re just handing the person the keys to the office.

1. Go to your OneDrive (usually found at onedrive.live.com or via the little blue cloud icon in your taskbar).
2. Upload the entire folder there. You can literally just drag the folder from your desktop into the browser window.
3. Once it’s uploaded, right-click the folder and select "Share."
4. You can choose to "Copy Link" or enter the person's email address directly.

If you do this within the Outlook desktop app, sometimes it’ll automatically suggest uploading to OneDrive when it sees a large file. My advice? Don't wait for it to suggest it. Control the process yourself. By sharing a link, you avoid the "bounced email" headache, and you can even set a password or an expiration date on the folder if the data is sensitive.

The "New Outlook" vs. Classic Outlook Dilemma

Microsoft is currently in this weird transition phase where they are pushing everyone toward the "New Outlook." It’s basically a web wrapper. If you’re using this version, the process of how to send folder on outlook feels a bit different.

In the New Outlook, when you click the paperclip icon (Attach), you’ll see an option for "Upload and share." This automatically puts the folder into your OneDrive and sticks a pretty little link box into the body of your email. It looks a lot more modern than a raw URL string.

However, if you're a die-hard fan of the Classic Outlook (the one with the "File" tab in the top left), you might find the integration a bit more rigid. In the classic version, I still recommend the manual zip method for anything under 20MB. It’s just more reliable for the person on the other end who might not have a Microsoft account to view shared links.

What About SharePoint?

For those in a corporate environment, you aren't just sending a folder; you're often collaborating on one. If your company uses SharePoint, don't even bother with attachments.

Open the folder in SharePoint, click the "Share" button at the top, and grab the link. When you paste that link into Outlook, it usually resolves into the name of the folder automatically. This is the "pro" way to do it because it ensures everyone is looking at the same version of the files. No more "Final_v2_REVISED_actual_final.docx" confusion.

Common Mistakes to Avoid

One mistake I see constantly: people try to "Attach" a shortcut.

You know those little icons on your desktop with the tiny arrow in the corner? That’s not the folder. That’s just a pointer. If you attach a shortcut to an email and send it, the recipient will get a file that's only a few kilobytes big. When they click it, it’ll tell them the file path doesn't exist. To them, it looks like you sent a broken file. To you, it’s a waste of time. Always make sure you are grabbing the actual folder from your C:\Users\Documents or wherever it lives.

Another tip? Check the contents of your folder before you zip it. Hidden files, like .DS_Store on Mac or temporary Word "lock" files, can get sucked into the zip. It's not a huge deal, but it makes the folder look messy when the recipient opens it. Clean it up first.

Actionable Steps for Your Next Email

Stop fighting with the attachment button. If you need to send a folder right now, follow this logic:

• Is the folder small (less than 20MB)? Right-click it, compress it to a ZIP file, and drag that zip into Outlook. It’s the fastest way for everyone involved.
• Is it a massive folder (hundreds of MBs or GBs)? Upload it to OneDrive or Google Drive. Generate a "View Only" link. Paste that link into your Outlook email.
• Are you sending it to a coworker? Use the SharePoint "Share" feature. It keeps the file permissions internal and secure.
• Is it sensitive data? Use the OneDrive "Protect" feature. Send the folder as a link, but set a password and send that password via a different app (like Teams or a text message).

Sending a folder doesn't have to be a multi-step saga. Once you realize Outlook wants files, not directories, you can just give it what it wants and get back to your actual work.