The Email Attachment Problem and How We're Not Solving It


Last weekend, my mother-in-law, a recent Mac convert, sent an email out to family with 111 photos embedded in the message. Yes, one hundred and eleven. My synagogue has been trying to save postage fees by emailing out the monthly bulletin…a PDF file that has averaged 3-6MB in size every month. My inbox is always overflowing with attachments from my co-workers.

Still I have to wonder…is this a problem that really needs solving?

This isn’t about the 75 MB video file. Even the novice knows that email won’t work for sending files that big. The challenge lies in the smaller, but still-too-bulky-for-email type files–photos, audio, PDFs, etc. The space-filling stuff folks attach to email without thinking twice.

Aside from the disk space and bandwidth considerations, we all know what’s wrong with all these attachments: Multiple versions of the same files floating all over the place; No way to know who has and has not opened the attachment; No way to control who can forward the file.

Lately, there’s been a proliferation of web apps looking to solve the email file problem. This week alone we saw the launch of Zector and Topicr, joining the field already crowded by services like Box, Dropbox, YouSendIt and many more.

Yet none of these solutions has emerged as a clear winner. In fact, it seems many of these services solve one problem while they create others. Users have to maintain yet another web application (or many new applications if files are sent/received from different services), learn a new interface or two, maybe install some software, and they have to trust their data to an unknown 3rd party. So with that, folks still attach files to email with reckless abandon. It’s frankly easier to click that paperclip right in the email application than install and maintain software or visit a new site.

How are you sending around larger files? Take our GigaOm poll below and then let us know your thoughts in the comments. Are you seeing the same resistance to these file attachment/sharing services in the “real world” that I am?



You should try using LeapFILE.

Although it is a web based service like those of YSI and dropbox, LeapFILE’s products and services are more business oriented with enhanced security features and options, but just as easy to use as regular email clients. Also LeapFILE just annouced the official release of Desktop and Outlook Plugin that would work seamlessly with Microsoft office applications.

You can also send directly through the Desktop client without having to open up your email or a new web browser. Check out the website for more information:


I always try to suggest people who send big attachments to use something like (which I adopted because of its being simple).
But still many people know e-mail only, they seem to completely miss the “web side” of the net.

Lawrence Salberg

You missed Zenbe which has completely solved the very problem you lament. The email attachment problem is no longer. They are still in private beta (I think) but you must try it. I haven’t posted a full review on my blog yet, but I’m referring to it as “the Gmail killer”.

Next problem?


I can’t remember how many times a large Word doc got screwed up because multiple versions of the same file were floating around through email. We used the OnStage File Vaults feature to solve this problem. I use a “free” version of these web-type softwares to exchange files with family. It drives me crazy when my inbox gets clogged up with a million photos.

Jeff Barson

Er… you’re all invited to open up a free Sendside Account: No spam. No Phishing. Free files up to 100MB, unlimited for business. ProfileLink,and it works with your existing email address. Best of all it’s free – which is a terrific price.


It’s not the attachments that bother me so much as the people who CC my email address to a million people I don’t know.

Emails with stupid animated gifs I can delete, but spam and potential viruses from having my email address passed around to every man and his dog bothers me no end.


Even better? You can kill the idea of ‘attaching files with reckless abandon’ altogether by collaborating online. I know sending attachments is a tough habit to break, but I think those days are numbered. As we shift towards online sharing, storage, collaboration for everyhting (documents, photos, video, etc)- all you should have to do is send your friends/family/coworkers a url the file or an invitation to a collaboration folder where they can participate in the sharing.

Take good care,



I’m torn on this actually.

For many, many, many years I was unapologetically opposed to most attachments over, say, 40k. I had a small hard drive, I kept my mail archives on my computer, I hated big bloated mail archives. I had procmail set up to reject messages with attachments over a certain size (I think 500k was my limit, I forget now).

Since converting to GMail I’m a little more tolerant of the practice. In fact it’s sometimes nice to have newsletter and such at my fingertips in my GMail. There are pluses to attachments.

However I still respect others. I never send pictures, instead I pay $20 a year for an extra 10 GB of storage on Picasaweb. Almost every ISP on the planet offers space for a website. I stick PDF files and whatnot there for people to download.


This is solving the wrong problem – the real solution is for people to move more of their workflow and interactions to web apps, particularly wikis and blogs. Once people get used to attaching a file to a wiki page, particularly for less transient files, they really like it – and their friends can use RSS etc to pick up on the new postings.

This is a cultural change but email’s real downside is not full inboxes, but the flurry of inefficient communication that can’t be turned into shared knowledge.

Judi Sohn

I’m relieved that I’m not the only one who has thrown hands up in defeat. WWD will of course continue looking for file sharing nirvana because, well, that’s what we do. But I’m not hopeful that any outside-the-inbox solution will prove to be worth the hassle of changing mindsets.

It’s like the gorgeous, new car with all the best features is parked a mile up the hill…so folks will continue to ride around in their beat-up jalopy that gets them from Point A to Point B and nothing more simply because it’s parked outside their door. :-)

Tammy Lenski

I use No software to download. No account to create. If you can type and click, you can upload and download. Elegantly simple, I must say (and no, I’m just a fan, not affiliated with them). For me, problem solved.


For many (most?) people, email is the only program they use for file transfer. And it is one of their primary filing systems. I’ve given up trying to get my users to change to other file transfer methods. Fortunately disk space and bandwidth gets cheaper every year.

When we dumped Exchange for a Unix based email system, several years ago, I changed their storage limit from 100MB to unlimited and their attachment size limit to 25MB. They’re happy, which means I’m happy. And so is our storage vendor.


moved to gmail (so no more cleaning), if I get an office attachment I need to read I use the “view as html” option, If its something important I use “Open as google spreadsheet/doc”. For pictures: I dont event bother anymore (or if important I move them to my home server) and the Preview in osx just opens pdf’s instantly.

I dont have office installed anymore and my workflow just spreads around in the office (complains on office/windows and outlook)


My clients are generally not very tech savvy. They resist learning Basecamp, Central Desktop, and Google Docs just to work with me. And FTP? You gotta be kidding.

None of their other peers are doing it, so the learning curve seems steep to them.

YouSendIt is awesome, particularly with the Outlook plugin.


The problem with most of these web services for online file storage and transfer is they require the recipient to have an account on the service as well, or sign up for an account just to receive the file you want to share with them. One more web app to sign up for and give your information too, and then remember for the next time you may or may not have to use them.

We have settled on using Its not free – some would even say they’re pricey – but I can share a large file(s) with someone and they simply receive a link by e-mail which will let them download the file(s) without having to sign up or give any information to I do give the recipient’s e-mail address in order to send the link, but I have never heard of any abuse of this. (currently free beta) seems to have a similar capability, but they also have a limitation of sharing only one file at a time – i.e. your recipient gets a separate e-mail with a link for each file you are sharing, which can end up being troublesome on its own.

Jeffrey McManus

Getting fifteen versions of a Powerpoint show attached to emails is one thing, getting a hundred “me too” comments on one of those versions is another. Email is great for brief communication but it sucks as a workflow platform.

This problem is why we developed


Well your synagogue could post the pdf on their website and inform members that it was available and include the hyperlink in the e-mail so they just had to click it.

I have used yousendit but the limit to one file at a time is akward. Why not allow a folder? (I’m merely a G.I.T (geek in training )so I may not realize any tech limitations.

But how do you limit your friends and family from sending all the attachments is beyond me.

Rob Grayson

This issue would bother me a lot less if Google would introduce into Gmail the ability to remove attachments from e-mails (i.e. save e-mails without attachments).


Lately I have used as my choice and it’s what I have encouraged clients to use as well. I have even set up something similar on my own server. I like the idea behind dropbox but as you said it’s something addition people have to install.

Within my own company and work we use Basecamp from 37 signals as a solution for not only sharing files but for also allowing customers to view project progress.

If I had my choice, resources and influence I would totally revamp the way e-mail and file transfer works. We hear a lot about Web 2.0 but sadly e-mail seems to be stuck a a .9 beta release. Currently e-mail and file transfer solutions seem to be an ununified kludge.

I would do the following;

1.) Combine e-mail and ftp servers into a unified solution

2.) Make security a top and required priority. Hardly anyone uses security measures with e-mail like signing or encryption and it’s too annoying to encourage others to adopt security measures even if you are gung ho about it.

3.) Maybe adopt something like a Basecamp solution for friends and family as well a business associates.

Those are my ideas.

Joel Falconer

Since moving to Gmail, attachments don’t bother me so much as long as they’re solicited. While I was using POP, different story! Gmail lets me find out what the files are, then delete or download – POP doesn’t, so you might download 50mb only to trash it.

The file attachment services really haven’t jumped out at me as useful enough to sign up.

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