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iPad Pro Day Three: Document Management

[fa icon="calendar"] 02-Dec-2015 08:30:00 / by Eddie Vassallo

Eddie Vassallo

As you know, most of my posts thusfar have been super-sunny, cheery, and lots of love and rainbows for the iPad Pro. And yeah, by and large it has really replaced my 2015 Retina MacBook for most everyday business tasks. 

But there are still some headaches. And here's the first big one.

Document management.

I actually (innocently) believed the Dropbox app for iPad would solve most of my document issues. I was so cocky about this, that I quickly set up a new folder in Dropbox called - eloquently - 'iPad Pro Desktop', made a shortcut for my iMac, and was certain document sharing and management would be smooth sailing from there. 


My thinking was - if I have a clearly delineated Dropbox folder I can synch between my iPad Pro and iMac, I could simply put all 'desktop' files there, add any email attachments I want to hang onto, and easily upload or move them. 

Boy was I wrong.

First off, Dropbox isn't even optimised for the iPad Pro - and seriously, what's up with that? The usual upscaling issue abound, and it's really like navigating a 12.9-inch iPhone App to even find my new folder, much less my documents. And I could live with all that if the folder actually did what I needed it to do - namely allow me to dip into and out of it, attaching and uploading files as needed.

But I quickly realised that moving files OUT of Dropbox was a complete joke.

To demonstrate, here's my use case:

1) I receive an email with an attached PDF invoice from a partner

2) I would like to upload said invoice to our Xero Accounting System 

3) Job done

Sounds simple, right? Well it took me almost 2 hours to figure out how to do this efficeintly on the iPad. 

Thanks to Apple's lack of a desktop or file system of any kind (outside of drag/drop from iTunes and maybe iCloud for iWork documents - which let's face it, absolutely no one is using), I first tried saving the PDF Invoice attachment from my email app to my Dropbox folder using the iOS 9 share feature.

So far so good. 

I then jumped into Safari and went to the Xero Web site to set up the the Invoice info. Swell. However, things started going wrong quickly when I attempted to upload the PDF:


See what's happening there? The file is greyed out, unavialable, totally immobile. Basically you cannot upload anything but images from Dropbox.

Yeah. Images only. Painful.

So after a lot of messing around, I gave up and decided to go with what was given to me - images only. So I then concocted the following ridiculous workaround:

1) Open attachment from mail

2) Choose to save to Dropbox

3) Open Dropbox and download said file to the app

4) Open the file in Dropbox

5) Take a screenshot of the PDF

6) Upload image/screenshot of PDF to Xero site

Yeah. Ridiculous, right? And that wasted an hour of faffing to even get that far. I actually thought I would be stuck with that workflow if I ever wanted to upload a file type other than a photo - to any Web site or easily attach to an email. 

I was just about resigned to this monstrosity of a workflow, when the heavens opened and I discovered Documents 5 by Readdle. Seriously, if you own an iPad Pro (or any iPad really) you need to stop reading this post, and download this app. It's a lifesaver, and really, is the app Apple should have built and shipped natively with the iPad Pro. documents.png

How this device could cater to the business user without an app like this is beyond me. It's that good, and has completely elimated the silly Dropbox workaround listed above. Not only does it have a number of sharing options to allow you add any document, but it connects seamlessly to Dropbox itself - meaning that Dropbox icon you see on my homescreen above will soon be tucked away in a folder on my second screen. I simply won't need to use it anymore.

So back to my use case. All I wanted to do (you can tell my frustration here, right?) is upload a PDF file to a web site from an email attachment. Without a real desktop, this is enormously difficult. But with the Documents 5 app, all I had to do was the following:

1) Open attachment from email

2) Save to Documents 5 

3) Go to Web site and choose to upload from Documents 5




For some, even having to do all this sounds silly - and makes the case for the iPad as a substandard business device. But to be honest, this isn't that much more difficult to doing the same workflow on a normal computer. I suppose it's all based on your point of view. That said, this small 'issue' was set to drive me back to my MacBook at a frightening speed, if I couldn't figure out - and quick. 

Now with Readdle's fabulous Documents app aboard, I'm ready to get back in the saddle, and continue this little iPad Pro adventure.

Bravo, Readdle!


Topics: iOS

Eddie Vassallo

Written by Eddie Vassallo

Eddie is Founder & CEO of Entropy, former Head of Mobile for Discovery Channel, regular Guest Contributor on GigaOm and has been featured on Daring Fireball, CNN, and Strategy Eye.