iOS 8 wants: Better file attachment handling

Almost 8 years after it was introduced, you still can't attach files to emails in iOS. While iOS 6 has introduced a method to attach photos and videos to in-progress emails, it suffers from poor discoverability, and only works with content from the Photos app. If you want to attach any other file to an email, it's a usability disaster. That's because iOS has an ImagePicker but no broader DocumentsPicker, so it can't handle a broader range of attachments. So why is that such a bad thing?

The current method for adding photo or video attachments to in-progress emails is done via the same pop-up menu originally introduced in IOS 3 for cut, copy, and paste. You tap the screen to get the popup, tap a tiny, obscure arrow button to get more options, and then tap to add the attachment.

An easy to find, easy to use attachment button would be simpler. It's a solution employed by third-party apps like Gmail. Maybe a paperclip is obscure as well, but it's discoverable.

Emailing, and including files as attachments in email, is a common task and something that takes only a few seconds on the Mac with OS X. Trying to attach a non-photo or video file on an iPhone or iPad with iOS takes an annoying amount of time and causes an unreasonable amount of frustration. Here's some blog-theater by way of example:

"Hey, Rene, can you email me the dates for that trip?"

"Sure, Kevin." I grab my iPhone, open the [Mail](/mail "Apple Mail app for iOS and OS X) app, add Kevin as the recipient, add the subject "Trip", paste in the dates, then--

"Could you also attach that outline for discussion topics?"


My only option now is to copy the contents of the email, trash it, go to the app I wrote the topics in, find the file, tap share, tap email, add Kevin again, add the subject again, paste in the dates again--

Crap. I deleted the app I wrote the topics in. A hotter, newer app came out and I started using that instead, and even though both use iCloud, neither has any idea the other exists so... I re-download the old app and pray the data is either still there, or magically comes back from the cloud.

"And those two PDF files about that thing?"

Double crap. Both those PDF files are in different PDF apps, one in a simple reader, the other one in an app that supports annotation. Now I have to send the discussion topics from one app, and each of the PDF files from their apps. That's three separate emails, and nothing approaching a thread.

Oh, wait. I have copies in Dropbox. I can share from Dropbox... Only no, each file is in a different directory and I can only share from one directory at a time! I'm back to three separate emails again!

Now Kevin is laughing his ass off at me and asking me to tell him again how the iPhone is easy to use, and I want to punch things.

And the reason for all this goes back to the violation of a cardinal principle of design: the attempt to keep things simple can ultimately cause ridiculous levels of complexity.

Apple already uses a blue + button to add contacts. They already use a gray camera icon in Messages. Something like that could work for attachments as well. Especially if, as I've been asking for the last 4 years, iOS added a DocumentsPicker controller that works the same way the current ImagePicker controller works.

A DocumentsPicker controller for iOS would remove unnecessary cognitive load from users and solve a wide swathe of current usability problems with iOS, including email attachments. Any file could be attached to any in-progress email, without the need for a Share Sheet, or for the user to remember app ownership. And it would do so in a way that's consistent with how iOS already works and increasing simplicity at the same time.

And it would make iOS more powerful without alienating the mainstream user base Apple is so good at embracing.

Note: This post was originally written prior to the announcement of iOS 7 but has been updated for iOS 8.

Rene Ritchie

Rene Ritchie is one of the most respected Apple analysts in the business, reaching a combined audience of over 40 million readers a month. His YouTube channel, Vector, has over 90 thousand subscribers and 14 million views and his podcasts, including Debug, have been downloaded over 20 million times. He also regularly co-hosts MacBreak Weekly for the TWiT network and co-hosted CES Live! and Talk Mobile. Based in Montreal, Rene is a former director of product marketing, web developer, and graphic designer. He's authored several books and appeared on numerous television and radio segments to discuss Apple and the technology industry. When not working, he likes to cook, grapple, and spend time with his friends and family.

  • Organidoc is the best app I have come across for sending multiple files.
  • Or...Apple could just allow a user to set another mail application as the default, and Sparrow would get you 95% of the way there, perhaps spurring Apple to improve their own to compete. Even if does not compete for sales per se against Sparrow et al, an open, level playing field would almost assuredly lead to *somebody* getting you that last 5% faster that the status quo is doing.
  • Sparrow has a paper clip attachment button, but unless/until Apple makes some form of document repo, Sparrow is still stuck with only pics/vids as attachments.
  • Boxer and Evomail both allow Dropbox and Box document attachments. Acompli allows attachments of files in your email and Mailbox allows attachments from Dropbox. Here's your problem, you're asking for too much. iOS blows, and Apple are their own worst enemy. They create these apps, I believe, for the sole purpose of fucking with us. I don't think anyone at Apple uses any of their own apps. Why would they when they've created this great device that's so much better when running other apps outside of Apple apps? As soon as Apple realizes that they are their own worst enemy and stop putting tons of restrictions in place, they'll be able to compete in the "next" market. Because at their current pace, if they don't, someone will come along and make a better mobile OS that allows you and I to do exactly what we want with our device. Right now we are so limited by what Apple chooses to let us do. When that new device comes, it will be like a magical awakening and we'll see all we've been capable of accomplishing but couldn't before because Apple wouldn't let us...and then we'll watch porn on that new device. But seriously. iOS needs a complete overhaul from the ground up. It's bloated and ass backwards and creates a roadblock in front of every alleyway we want to go down because traffic is so congested. It reminds me of those old Apple commercials making fun of John the "PC" guy. Go back and look at all of those and you'll see Apple now does everything it used to make fun of Windows for. P.S. Stop using iCloud, that's your main problem. It's stupid.
  • Agree. He's asking for too much. Just ditch the iPhone and get a Galaxy S5, HTC One M8, Xperia Z2, Galaxy Note 3 (if you can deal with the size), Nexus 5, or Moto X and be more productive. If you still want an iOS device... That's what the iPod Touch is for. So you don't have to punish yourself with using the iPhone as a daily driver, should productivity be a high priority. The TW/Sense email apps poop all over on the iPhone. The disparity is so huge, it's as if Apple had an intern create this app (and the Calendar) in like 1 or 2 afternoons and then forgot about it, save for the forgettable touchup here and there...
  • It's a money thing. You can have your cake, but you have to pay extra for the proper utensils to eat it. The market will correct, in the meantime, buy a Samsung.
  • This is the number 1 reason that I jailbreak. AnyAttach puts a paper clip in the message that links to your photos or Dropbox, and lets you attach multiple files. I send a lot of attachments, so I carry around a jailbroken iPad 1 just to do this.
  • Yes, the shortcoming you described is really a problem for making email with attachment, so hope that apple can see this and improve
  • This should be functional for iMessage as well.
  • It seems frustrating, but its a result of sandboxing each app's documents. I think most users would send out a few separate emails in practice. You can at least FORWARD an email containing lots of attachments to a group with our best-selling "MailShot Pro" app It creates a special "contact" that contains your group, which you can use from Mail, so it's the only group email app that can do this. Peter
    Disclosure, I am the developer of MailShot and may benefit from its sale.
    We only post on a forum when it's relevant to the discussion.
  • I so hope Jony I've reads this post now he has software responsibility. No Files app is the reason I'm seriously considering jumping ship away from iOS. I am a data-centric guy and miss the productivity I had with my Treo
  • Have you thought about an HTC One Mini (Android)? Same size as iPhone, with larger screen, and all the file attachments your mailserver will allow (via a real file-system). Build quality the same too. I only mention this because you said you liked your Treo, and I came from Treo to iPhone, to HTC Android phones (currently Galaxy Note 2, though). I keep waiting for Apple to add that functionality, but after 7 releases of the OS, I think they are unlikely to. Unfortunately, iPhones are too far behind in terms of the functionality I have come to rely on in Android phones, for it to be a good match for me. It's a shame too, because their build quality is quite good (well, except for the iPhone 5c, of course).
  • I agree with you here. I found myself always jailbreaking to to have this feature that I used on a daily basis in the office. Waiting for a jailbreak to be released wouldn't cut it anymore. As iOS will always have a place in my heart, I did try out Android 2 years ago and loved the file system. Today, my Note 3 is my daily driver because of the ability to attach files in your file directory and the in-app ability to 'share via' across your apps. In the beginning, I did find it difficult to give it a chance and learn. This is not for everyone. Posted via iMore App
  • The BlackBerry 10 phones do all this with ease and intutivity. BB10's email sends anything you want at the max size my server will allow from your SD card, phone memory, Dropbox... And you wouldnt have to leave the app your in to do so. I'm just sayin
  • Correct, same with Windows phones. The benefit from Android was I had more options to choose from: (manufacturer, screen size, camera, launcher). Posted via iMore App
  • This is why I will be returning to Android in all likely hood when my contract ends in July. As much as I want the Z30, its a VZW exclusive, so Android it is. I'll be honest, of the two iphones and the GS3 i have had since I left my 9630 behind, the GS3 handled my needs the best. The only thing that gives me hesitation,is my wife is required to use an iPhone by her university and we tend tend to travel a bit. Its been so much easier to have one charging cable in all our cars/bags.
  • The best work around for me when I had an ipad was using Logmein for those things. I still prefer to think of phones and tablets as extensions or remotes for your laptop or desktop. Although file attachment is something you'd think would be basic, the more you add to iOS, the more it becomes something complex for users. We should still push the idea that a Mac or PC should be your central hub. My PC's are left running 24/7.
  • R.I.P. LogMeIn! Your change from a purchased app to a subscription model made you dead to me. We used to be pals! Your selfishness brought collateral damage along with it, and basically killed the usefulness of my pc and it too is now dead to me. It's ok though, I'm learning to cope, and I'm a much stronger person now because of it! Sent from the iMore App
  • GoodReader is a good option for this. But it would be better if we had a native File Repo like Renee said. I'm surprised more people haven't written about this.
  • It never occurred to me that Apple would have made such a grievous lapse as to not include attachments as part of their Mail app when I moved from BlackBerry a couple of years ago. While I long maintained that the iPhone was nothing more than a content delivery device for the iTunes Store, this discovery was a surprise and hardly argues for the device (or the iPad) to be taken seriously as a business device. I 'get' that Apple has a certain neurosis about users gaining access to files with the iOS, but I also note that the Mail program has gained access to the Photos app (though, as Rene points out, neither gracefully or obviously), so in-keeping with trying to leverage as much profit / user-dependence on their products as possible, perhaps allowing Mail to access onboard iWork files (so you gotta purchase Pages, Numbers, etc) and/or your iCloud files? Rene's mockups above are great and the solutions he offers incredibly obvious - so clearly not a route Apple would take. They seem more fixated at present on embedding new useless / Beta apps into the iOS.
  • Why stop at just adding attachments? The lack of being able to turn on out of office replies kills me as a frequent traveler. Also would like to be able to request read receipts but that not a deal breaker.
  • Agreed. Think we need an OoO trigger. Good idea.
  • This is perhaps my biggest grievance with iOS. Attachment problems are a great use-case, but, a traditional files and folders management system (not likely), or as Rene says, a "Files app" is needed.
  • Aside from document attachment, I would LOVE to be able to have an HTML signature!!! I shouldn't have to jailbreak just to get that basic functionality!
  • Apple is too busy suing people to be worried about this.
  • Yes please! All I want is the ability to send attachments to the groups I've created on my device. Is it really that hard? Until this happens the iOS just feels somewhat crippled.
  • how do I +1 this? god iOS 7 better be a hell of a lot more than iOS 6 brought.
  • NOT for STANDARD business work, and then why would you intentionally exclude a while segment of people with a crippling platform and never address it ?
  • Here is a full feature email client app with attachments handling and cloud services integration :!-mail-client-attachments/id3... Note: we are the developers
  • Yes, it should be included in the iOS. However, you can use Docs to go, to send office docs, or paste in docs to go, and send from there. Not elegant, but effective.
  • Why stop there? For their seventh attempt perhaps they could include a real file system so we can access files in multiple programs...
  • I would like that. And I'm seriously ready for a complete overhaul to the typing and autocorrect. Would love to see something along the lines of android typing w word choice. With that extra touch of finesse apple usually puts on its products.
  • Hi René, I do agree with most of your article except for the bit about the file repository.
    I know how it makes sense to us, coming from years of desktop computing to see this as the solution, but i think we have to force ourselves beyond that and forget the filesystem.
    A file repository is a file system. Apple will never go back to that. We have to think in terms of apps instead of files.
    If you want to access a file, you're supposed to know which app it belongs to. But i can see the problem here for similar file types.
    Example, a photo which resides in the or in the !
    Or a PDF you saved in iBooks or in PDF Expert... But still. I don't think Apple will go the file repository way... I do agree though that we need a system in which sharing files between apps is simplified.
    That's a glaring omission and potential problem of iOS. If sharing file types between apps is made easy and Apple solves it without compromising security and app sandboxing, it may well be the answer we are all looking for ! We can still use an app centric approach, but see all the files the chosen app is able to open.
    Too much to ask for ? Jean-Luc
  • Apple can get rid of the file system as we know it but still... a document repository of some sort should be available to the user... call it whatever you want... I'm certainly going to link to this article as this is an area of much needed improvements for iOS7.
  • I think the app centric file system is a total failure and iFruity definitely didn't think it through on this. First of all, it creates all sorts of unnecessary duplicates of files and when it is huge files it creates more than a hassle, it actually eats up a lot of storage space. Secondly, you also hit on the main weakness, though you did not recognise it as such. And that is that the USER must REMEMBER which files was used and saved in which apps .. and which version is the latest one. Do you really expect a user to remember all these things at the snap of a finger? Thirdly .. god forbid if you want to delete an app and migrate to another app. There really isn't any easy way to migrate your files from one app to the other. And if you delete an app for whatever reason, ALL the files associated with it will be gone as well. If they want to insist on this silly app centric system, which are all CON and no Pro, they should at least 1) work out some common sharing and editing rights between apps that access similar files.
    2) Have universal rights for common apps such a mail clients etc.
    3) have a common repository for apps that have access to such files, so that they do not create unnecessary duplicates.
  • I think we need a complete iOS 7 revamp.. Like someone pointed out to me iOS is nothing more then a gloried app drawer... Nothing special about it at all.. Infaxct the os feels very dated and almost primitive these days..
  • But the teen girls love it
  • I was thinking the same thing. It's basically Palm's old OS with a bunch of apps on the screen that can't interact with each other. I feel like iOS is de-evolving with every new iteration.
  • Another big issue is being able to select a group from Contacts to send an email to. It's ridiculous that I can't have my mobile device send an email to a group of people, such as a baseball team I coach to notify parents that practice is cancelled, etc.
  • Agree - I have to do this alot, I use the app 'Groups' and it excellent (costs US$5)
  • This document repository is a much need space in iOS that really needs to be fixed somehow...
  • I would like to see the Unified Inbox colour coded,