iOS 7 wants: Better email attachment handling

iOS 7 wants: Better email attachment handling

Almost 6 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.

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 have to 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 Facebook, email clients like Gmail and Sparrow, and the official Twitter app and Tweetbot.

Some of these are more elegant than others, but all of them are more discoverable. And that's still only for photos and videos. What about files?

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 app, add Kevin as the recipient, add the subject "trip", paste in the dates, then--

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

"Um..."

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--

Shit. 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 shit. 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.

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 is that Apple forgot a cardinal principle of design: unreasonable simplicity sometimes leads to inane levels of complexity.

Apple already uses a blue + button to add contacts. Something like that could work for attachments as well. (I did a mockup along those lines for a pre-iOS 6 article on higher hanging fruit, but I'll update it below.)Tapping the attachment button could bring up a Share Sheet that includes the Photos icon, so you could attach photos as normal, but also any other app icon that contains documents. Tapping an icon would bring up a list view of all the files associated with that app. It's a bit overwrought, but it fits with the existing iOS constructs, including the binding of files to apps, and has the advantage of familiarity-as-a-feature.

Depending on how many file-capable apps are installed, it could create a very dense Share Sheet. It also still requires the user remember which app contains which file.

That's why, for the last couple of years, I've been asking for a simple, flat document repository for iOS -- a Files app that works the same way as the Photos app (or Passbook app for that matter). A Files app for iOS would remove unnecessary cognitive load from users and solve a wide swathe of current usability problems with iOS, including email attachments.

With a document repository, any user 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, increasing simplicity at the same time.

Rene Ritchie

Editor-in-Chief of iMore, co-host of Iterate, Debug, ZEN and TECH, MacBreak Weekly. Cook, grappler, photon wrangler. Follow him on Twitter, App.net, Google+.

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There are 36 comments. Add yours.

bcuz421 says:

Organidoc is the best app I have come across for sending multiple files.

Dev from tipb says:

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 Mail.app to compete. Even if Mail.app 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.

Rene Ritchie says:

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.

acwyau says:

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.

Michael Mi says:

Yes, the shortcoming you described is really a problem for making email with attachment, so hope that apple can see this and improve

jhulgan says:

This should be functional for iMessage as well.

Solublepeter says:

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 http://itunes.apple.com/us/app/mailshot-pro-group-email-done/id445996226... 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.

RogerL says:

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

C Rogers says:

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).

cardfan says:

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.

geggyta516#AC says:

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.

Bazza1 says:

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.

j7469 says:

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.

iSRS says:

Agreed. Think we need an OoO trigger. Good idea.

Easy-G says:

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.

lamonicaj says:

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!

ArgonNJ#CB says:

Apple is too busy suing people to be worried about this.

Corfy says:

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.

Ipheuria says:

how do I +1 this? god iOS 7 better be a hell of a lot more than iOS 6 brought.

avyj says:

Here is a full feature email client app with attachments handling and cloud services integration :

https://itunes.apple.com/us/app/group-email!-mail-client-attachments/id3...

Note: we are the developers

rkevwill says:

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.

1776_1865_RIP says:

Why stop there? For their seventh attempt perhaps they could include a real file system so we can access files in multiple programs...

admirer_of_you says:

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.

SierraRomeo says:

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 photo.app or in the iPhoto.app !
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

Jfmartin67 says:

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. http://myios7wishlist.tumblr.com

piggypigs says:

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.

Dean Cobb says:

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..

ArgonNJ#CB says:

But the teen girls love it

Bizlaw says:

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.

dougierydal says:

Agree - I have to do this alot, I use the app 'Groups' and it excellent (costs US$5)

Jfmartin67 says:

This document repository is a much need space in iOS that really needs to be fixed somehow... http://myios7wishlist.tumblr.com.

dougierydal says:

I would like to see the Unified Inbox colour coded, so at a glance I could see which emails are from which account (ie work, personal etc). This could be very subtle, for example in the form of a small coloured dot, or very obvious where the entire email is coloured. This would definately help my work flow...

CurVoOlicO says:

All you guys say is you want iPhone to do what Blackberry does for years and now Androids do as well.
I had different Blackberry devices and some experiences with a Samsung Galaxy S2.
Now i got an iPhone and i'm shocked with how this can be possible. I found this article because I went like crazy googling and looking for answers to this attachment problem.
It's simply unbelievable!

khurtwilliams says:

Convenience is the enemy of security. Start poking holes in the sandbox and pretty soon it's useless. Let's stop trying to make out mobile devices behave just like our desktop.

igrar#IM says:

Hi Rene, that's a great idea you've put forward...I also think why on the earth iCloud is not integrated with the Mail.app meaning why I cannot access iCloud from the Mail.app.

But I have found an elegant solution: http://www.getseedapp.com an elegant FREE app which is integrated with the DropBox, so you can attach any file in your DropBox while composing/replying to an email. The only downside it does not support Exchange, only IMAP.

Greg Aldridge says:

Apple is slipping. Can they maintain their market position without Steve Jobs? This is but one of several annoying problems on a list of tasks that I can't perform from my iPhone or iPad. Half the time when someone sends me an email with a a critical attachment that I need to forward, and I select "include" attachment, the next recipient gets the email without the attachment. For best results, repeat one or two more times. Forwarding links with embedded videos is also problematic. People receive the link, but the embedded videos don't arrive. I can spell and predictive spelling is horrible on iOS. iOS7 has been a cluster. A colleague in the next office got on the waiting list to replace his aging company phone with a 5S. A friend stopped by with a new 5S, my colleague looked at it for 5 minutes and was so unimpressed he cancelled his order. My iPhone is 2.5 years old and I'm waiting for the battery to begin to fade. But unless there is a new iPhone sooner than September of 2014, I'll probably go in a different direction. Time is money and I can't do the time, regardless of price.