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How to Email Large Attachments - fixedByVonnie

How to Email Large Attachments

Low file size limits for attachments is one of the biggest annoyances I have with email.

Almost every email server restricts email attachments to 10MB.  Even the best ones only raise the ceiling to 25MB but even 25MBs isn’t capacious enough for most practical needs.  Moreover, when you send a 25MB email attachment your email message can actually end up being 30% larger because of something called Multipurpose Internet Mail Extensions better known as MIME encoding.

MIME has nothing to do with speechless people acting out stories through body motions.   No no no, that’s a Mime artist.  MIME as it applies to email, is an internet standard that define how messages must be formatted so they can travel between email systems.  For example, if you copy and paste a photo into the body of an email message, then your recipient’s email software needs to know how to display that picture.  MIME makes it happen but sometimes errors happen too.

Emails that are rejected because the attachment was too large may barf out an error such as:

System Undeliverable, message size exceeds outgoing message size limits


This message is larger than the current system limit or the recipient's mailbox is full.  Create a shorter message body or remove attachments and try sending it again.

Ack, I hate those.

So what can we do?  We’ll there are really two options and the first is less favorable than the second but I’ll mention it anyway because it is useful in some cases.

  1. Send a multi-part archive
  2. Use a free cloud storage service

1. Sending Multi-Part Archives

This is just a fancy way of saying, “Hey, I want to break my big attachment into smaller chunks and then email each chunk one at a time”

I could have said that, but hey, it doesn’t seem as alluring.

The problem with multi-part archives is pretty obvious; for one it’s annoying and two, we’ll it’s annoying.

Who wants to go through the arduous process of segmenting an attachment? And if you don’t want to do that, what makes you think the person you’re sending the attachment too is going to feel elated reassembling the whole thing?  And God forbid if you have to email your 100MB photo album to your future father in law.  This method simply isn’t practical (and you should shouldn’t piss off your future father in law with a million bite sized email attachments).

But hey, if you must, here’s how to segment your attachments using a free, high quality, open source, file archiver called 7-Zip. (It’s like WinZip but free)

  1. Download and Install 7-Zip.
  2. Corral all the files you need to email into one folder.  Select them all, right-click the selection, mouse to 7-Zip and click Add to archive.Using 7-zip to add to archive
  3. In the Add to Archive window you only need to change four settings which I’ve highlighted below: Archive name, Archive formatCompression Level, and Split to Volumes, bytes.  Make sure the Archive name makes sense, I’m zipping my 311 Album so I named mine 311 – The Best Of.  Also, change the Archive format from 7z to ZIP and change the compression level to Maximum but not Ultra because depending on your system it may lock it up.  Finally, make sure Split to Volumes is set to a little less than the maximum upload limit of most email providers.  Since 10MB is a common upload maximum, I set mine to 9MB.7-zip add to archive settings
  4. When you’ve adjusted the settings, click OK and a window with a progress bar jumps on the screen.  Depending on how many files you need to compress this could take a while.
    7-zip hard at work compressing
  5. When it finishes compressing your stuff, go back to the folder that has your files and notice all the smaller files with the Archive name you configured in step 3.  If you look at the file sizes you’ll see they’re all within the 10MB boundary.  Now you can email each attachment individually and hope the person you’re emailing doesn’t kill you for all the work you’re making them do.  The recipient will need archiving software like 7-zip to open these files.  They can right-click them and open with 7-Zip, Winrar, WinZip or whatever program they use to extract compressed archives.Multi-Part Archive Done

2. Using a free cloud service provider

The smart way to send large email attachments is to use a free cloud service provider.  The drawback of course is that you have to signup for a new account and that’s one more password you have to remember; however, the benefits eclipse this minor inconvenience.   Cloud providers such as Shared.com, Sharefest.me and HighTail (formerly YouSendit) let you email the recipient a direct link to your downloads.  You create a free account on the website, upload your attachment and then share it via an email link.  In most cases, the recipient doesn’t even have to be a member of your cloud provider to access the shared file.

Sending email attachments with Yousendit (Hightail)

HighTail makes it easy to send attachments up to 50MB.


Shared.com gives you a 100MB of free space.


And Sharefest is the new kid on the block.  Technically speaking it isn’t really a cloud service since it uses peer-to-peer networks to send file links.

The nice thing about Sharefest is that there is no registration, it’s super easy to use (just drag files into the main window), and has a huge 1GB file limit.

The Bottom Line

When it comes to sending large attachments, the cloud is your best friend.   Sites such as Hightail let you share files with a single click.  Other such as Shared give you 100GB of free storage and let you share access with friends and family.  Finally, Sharefest is the most innovative and doesn’t even require a sign-up.  Just go to the site and start sharing.  It’s really that easy.

What cloud service providers do you prefer? Let me know in the comments!  Thanks



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