Easily Transferring Large Files over the Internet

Sending someone large files isn’t as easy as attaching them to an email. If you’ve ever tried that, you’ll remember the cryptic “Mailer Daemon / Postmaster Failure” notice you received shortly after. This notice means the email didn’t go through and was dropped. Why? Because many email providers have limits on their attachment size. Go over that limit and your email will be dropped.

How then are you supposed to send a large file to someone? What if they are three time zones away, or in another country? You’ll still use the internet, but you won’t be using email.

Transferring Files Indirectly:

Indirect transfers are when you go through an intermediary (third party) service. They also mean that both parties don’t have to be online at the same time. There’s a few decent services out there for this:

Using Gmail:

Yes, I know that I said we wouldn’t use email but just so you know, Gmail has a 25 MB message limit. If your data can be easily broken into chunks less than 25 MB, or your idea of a large file is only 10MB, you can use Gmail. Since Google gives a large amount of storage space in your account, this might be a simple option for you. The downside is, if you have a lot to send – don’t send a barrage of 25MB emails.

Emailing files with DropSend or YouSendIt:

A simple way to directly email someone a large file (up to 2GB) without installing anything is via DropSend or YouSendIt. What’s nice about DropSend is that you can send up to 5 files a month (2GB max) for free and its really simple to use. If you want to send more or have online storage, you’ll have to pay for one of their service plans. YouSendIt works similarly except the free plan lets you transfer up to 100MB and has a monthly 1GB cap – no 5 transfer per month limit.

For an additional fee you can also password protect your transfer with YouSendIt but if you’re transferring sensitive data, you should save your cash and send it in an encrypted and password-protected container instead.

Sharing folders with Dropbox:

Dropbox is great for syncing files between computers but you can also share files with Dropbox. You can choose who has access to the shared folder and can revoke it (and the files) at any time. You can see changes is real time – if someone you’re working with changes the file, you’ll see the change. There’s also undo history if you need to go back.

To set up sharing with Dropbox:

1. Log into the Dropbox website.

2. Click on the Sharing tab and share a folder. You can either create a new folder or share an existing one.

3. Invite people to your share.

4. When they accept, your shared folder will appear in their Dropbox!

Transferring Files Directly:

Direct transfers are when you send a file directly to someone else’s computer. They have to be online for this and it could be tough if the connection is slow but there’s no intermediary to deal with.

Skype / MSN / AOL / iChat:

Many instant messenger programs allow you to send files directly to someone. The downside is that you both have to be connected for the transfer – it’s not asynchronous like email. Also, speeds can not be guaranteed. I’ve seen small (under 1MB) .JPG family photos take an extremely long time to transfer via Skype.


Most businesses that deal with large files like publishers, printers, design houses and studios, have a dedicated FTP site for file transfers. Its fast (depending on your connection), easy to do and can be very secure if you use SFTP. The downside is that setting up a dedicated FTP/SFTP server isn’t something for a beginner. If you want to set up something similar on your Mac at home, use AFP/SMB.

AFP / SMB Sharing:

Using AFP (Apple File Sharing) or SMB (Windows File Sharing) is a much easier (and dangerous) way to quickly and directly transfer files. There’s no server to set up, SSH keys to mess with or poor connection issues like with Skype / AOL / MSN. However, if done wrong, you’ll be creating a serious security risk on your Mac.

You do not want the general internet accessing your shared folders!

If you choose to use AFP / SMB over the internet you will need your real internet IP. Go to www.whatismyip.com to quickly find it. You will also need to open up ports on your router / firewall.

To keep your Mac secure:

1. Password protect your shared folder. Do not share it openly and anonymously. Use a decent password.

2. The minute your transfer is complete, close the firewall ports and turn off file sharing.

Really Really Large Files:

Let’s say you’ve got hundreds of gigabytes of data to transfer, or even a terabyte or more. If you’re dealing with hours of raw HD video footage, this amount of data is pretty normal.

With a standard home connection, this could take days if not weeks. The fastest way to transfer this to someone is to send a Hard Drive via Fed Ex / UPS / USPS to them. Or if they are close enough, drive it on over.

Just make sure any sensitive data is encrypted. Use delivery tracking, pack it in an anti-static bag and make sure you have a backup in case the drive gets lost.

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