File Sharing with an iPad: Ugh!

| Ted Landau's User Friendly View

The iWork apps are a weathervane for predicting the future direction of the iPad. Many analysts are predicting that the iPad is destined to replace traditional laptop computers over time. If so, the iPad will almost certainly need better content creation capabilities than it now has. The iWork apps are currently the premiere content creation software for the iPad. So it pays to take a close look at how they work.

In that regard, I want to focus on only one aspect of these apps today: file sharing. For now, file sharing is a nearly essential feature of these apps. It is how you transfer iWork documents from your Mac to your iPad — and vice versa. It is also necessary for printing any documents created or modified on your iPad. The day may come when such transfers are of trivial importance, as you will be doing all your work (even printing) directly from an iPad. You may not even own a Mac anymore. But that day is not yet here.

Unfortunately, file sharing via iWork apps on the iPad is a major kludge. The feature works, but not with the sort of user interface that we have come to expect from Apple.

Duplicate documents from iWork apps on your iPad

The first thing you should know is that the iWork apps have no Save command. Documents are “auto-saved” about every 30 seconds automatically. This means you need to be careful when working with an existing iWork document: although there is an Undo command, you may be unable to revert back to an earlier state of a document if you have made too many changes. To preserve the ability to revert to an earlier version of a document, you should duplicate the document before you begin working on it. To do so:

1. In Pages, go to the My Documents view. (To keep things simple, I am going to use Pages in the examples here. Keynote and Numbers work similarly, except for minor name changes. For example, My Documents in Pages becomes My Presentations in Keynote.)

2. You will see a graphic “list” of all of the documents that Pages knows about and can open. Swipe the screen to rotate through the list until the document you want occupies the center highlighted position.

3. Tap the + icon at the bottom of the display (Figure 1).

4. Tap the Duplicate Document button from the menu that pops up.

Figure 1

                      Figure 1

Export a document from iWork apps on your iPad (Part 1)

Now let’s get down to the business of file sharing. Suppose you want to transfer a Pages document from your iPad to your Mac. To do so:

1. From Pages’ My Documents, center the document you want to transfer.

2. Tap the Sharing (arrow) icon at the bottom of the display (Figure 2). A menu with three options pops up: Send via Mail, Share via, and Export.

You can email a document to yourself or copy a document to — and later access the document from your Mac. However, these options are primarily useful for sharing a document with other users. Especially if you expect to be sharing a document back and forth between your Mac and your iPad, these are not convenient methods. In fact, the iWork apps on the iPad cannot import documents from at all; is useful only for exporting from the iPad. For these reasons, the best choice for file sharing between your iPad and your Mac is the Export command. The one potential advantage of the other two options is that they allow wireless transfers; the Export command requires a USB connection.

3. Tap the Export command. In Pages, you have the option to export the document as a Pages, PDF or Word file (Figure 3). If you attempt to Export a document with the same name as one already on this list, you are asked whether you want to replace the existing document with the one you are exporting.

A pleasant surprise here is that the iPad does not have to be connected to a Mac to use the Export command. The app stores the exported document in a folder location that is contained within the app package itself. It will be accessible to your Mac the next time your iPad and Mac link up.

Figure 2 Figure 3

                      Figure 2                                                          Figure 3

The Import Document list

Tap the folder icon in the upper right of Pages’ My Documents display (Figure 4 to right). This brings up a popover called Import Document (Figure 5). It contains a list of all the documents you have selected to Export from the iPad as well as (as you will soon see) all the documents you have selected to Import from the Mac.Figure 4

The files in My Documents and in Import Document are completely independent. That is, when a document is exported to Import Document (as confusing as this nomenclature may sound), a copy of the file is placed there. The original document remains in the My Documents list. If you delete the original from My Documents, the copy in Import Document remains. Conversely, if you delete the file listed in Import Document (as you can do by tapping the Edit button in the upper right of the popover), the version in My Documents remains intact. Modifications made to the content of one copy have no effect on the other.

Figure 5

                         Figure 5

Export a document from iWork apps on your iPad (Part 2)

Once you have completed the Export step, you are ready to access the document from your Mac. To do so:

1. Connect your iPad to your Mac, via the Dock Connector USB cable.

2. Launch iTunes and go to the Apps tab for your iPad. Scroll down to the File Sharing section at the bottom of the window (Figure 6).

3. From the left column of the File Sharing section, select the app from which you exported the desired document (Pages, in the example here).

4. From the right column, select the document you want to transfer. Click the Save to… button. Alternatively, you can drag the desired document to any Finder location.

Conveniently, you can select multiple documents at once. This means if you have a number of documents to transfer, you can do it all in one step. This contrasts to the limitation of the Pages app on the iPad: Each document must be individually exported from My Documents; there is no way to export more than one at a time.

5. The last step is to wait. There will be a several second lag, as iTunes prepares to do the transfer. Finally, iTunes initiates a sync and the selected documents are copied to your Mac.

This sync is restricted to copying the selected documents; a full sync (which includes a backup, copying new apps, etc.) does not occur. This helps save time when using file sharing. In fact, if you instead selected the Sync button, no transfer of shared documents occurs. File Sharing transfers only happen via the steps just listed.

Figure 6

                                          Figure 6

Import a document from your Mac to iWork apps on your iPad

To go in the reverse direction, importing a document from your Mac to the iPad, do the following:

1. Connect the iPad to your Mac and go to the File Sharing section in iTunes, as previously described.

2. Click the Add… button, locate the document you want to transfer and click Choose. Alternatively, you can drag the document(s) you want to transfer to the File Sharing list for the desired app. If you select to place a document with the same name as one already in the list, it will ask if you want to replace the existing copy.

To delete documents from iTunes’ File Sharing list, select the name of the document and hit the Delete key on your Mac’s keyboard.

As far as I can tell, you can place any type of document in the File Sharing list for a given app. However, only documents compatible with the app will later show up in the Import Document display on your iPad. Although apparently not implemented in the iWork apps, an Apple developer document claims that a user accessible “document interaction controller (on the iPad) provides options for previewing the contents of such files in place or opening it in another application.”

When done, you can disconnect the iPad from the Mac.

3. Launch the relevant app (Pages in the example here) on your iPad and go to the Import Document list (as described above).

4. Tap the name of the document in Import Document; this imports it into the My Documents list. It is now available to open and modify. If there is already a document with the same name in My Documents, a copy of the document (with a number appended to its name) is imported. Importing does not replace an existing document. If you only want one copy of the document, you can delete the older copy before or after importing the newer one.

[Update: If you instead decide to email a Pages document to yourself and open it as an attachment in Mail on the iPad, an “Open in Pages” button appears. This allows you to import the document into the Pages app.]

What’s wrong with this picture?

Let’s review how to export a document (such as a Pages file) from a MacBook to an iMac:

1. Assuming both Macs are on the same local wireless network, locate and select the MacBook in the Shared section of the left-hand column of a Finder window on your Mac. If you have previously done this successfully (having entered the needed account name and password), the connection should be automatic.

2. From the mounted MacBook, navigate to where the document you want to export is located and drag it to the desired location on your iMac. Done!

Compared to the simplicity of this Mac-to-Mac transfer, the iPad-to-Mac transfer is a labyrinth of restrictions and complications. If you expect to transfer the same document between an iPad and a Mac multiple times, I can guarantee you will be grumbling before too long.

It gets worse. There is no way to share the same document with more than one iPad app. For example, a Word document imported to Pages cannot be accessed by any other iPad app, even other apps that can open Word documents. The only work-around is to import the document twice, once for each app. Further, if you ever delete an app from your iPad, any documents stored with that app are deleted as well. Thus, to make sure your documents are preserved, copy them to your Mac before deleting the relevant iPad app. Shared files are included in a Sync backup of your iPad (at least that what this Apple support article claims), but they are not accessible for a restore of specific files.

What can be done to fix all this?

Assuming I’ve convinced you that file sharing via iWork apps need fixing, what should the fix be?

For starters, Apple could permit iPad apps to both export documents to and import documents from a MobileMe iDisk. This would make it much easier to shuttle files back and forth between a Mac and an iPad.

Even if Apple insists on maintaining the current USB-based Export command, Apple could improve how it works. In fact, Apple did implement a better method in earlier beta versions of iPhone OS 3.2. As I reported previously, Apple planned for file sharing to work via a Shared directory which would “mount on the desktop when the device is connected to a computer.” Users would be able to “modify the contents of this directory freely by copying files out, deleting files, or dragging new files in.” This would work completely independently of iTunes. As seen in the figure posted here, Apple intended to enable this feature via a File Sharing option in Settings > General of the iPad. All of this was dropped from the release version.

I doubt that this Shared directory would have allowed multiple apps to access the same document, but it would still be a huge improvement over the current interface design.

Not all of the clunkiness of file sharing in iWork apps are absolutely required for iPad apps. For example, GoodReader for the iPad, a third-party app that offers file sharing support, doesn’t use a separate Export command or a separate Import Document listing. All documents in GoodReader’s My Documents list automatically show up in iTunes’ File Sharing — and all documents added to the GoodReader item in iTunes’ File Sharing are automatically added to GoodReader’s My Documents on the iPad. GoodReader also uses a Save command for documents modified from the app itself — as opposed to iWork’s auto-save.

Why, oh why?

At this point, you may be asking: Why did Apple ever allow this file sharing implementation to see the light of day? Only Apple can say for sure. But I’d be willing to bet that it all stems from Apple’s obsessive desire to keep the iPhone OS as closed as possible (a topic I have written about extensively before; check out this article for one recent example). One way Apple does this is by, as much as possible, forcing all iPad-Mac interactions to go through iTunes. Eventually, if the iPad is to truly become an laptop replacement, I believe this will have to change. The iPad will increasingly need to be able to bypass iTunes. Hopefully, Apple agrees.

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Ted -
You’d totally nailed it. The nature of syncing documents, spreadsheets and presentations is a horrible labyrinth. Is apple serious? Using iTunes as a needle’s eye to get user stuff on and off the iPad? Fine for iPod related music, podcasts, etc. Terrible for documents, etc. Even the present implementation of iWork is horrible. No transparent syncing aka “Dropbox”.
So now there’s MobileMe, iWork and iTunes competing for the same space. Utterly confusing. Three solutions that don’t work transparently or elegantly. Apple can do better than this.

Ted Landau

Macworld’s just-posted look at iWork apps adds one notable point about file-sharing that I did not mention:

When importing from a Mac, “some document elements may be lost in translation. For example, if you import a Keynote presentation from your Mac to your iPad, it?ll lose any recorded or embedded audio, object groups, presenter notes, and 3D charts. If the iPad app doesn?t have one of the fonts used in the original, it?ll substitute it with one that matches it closely; if a match is not found, it?ll use Helvetica. When you first open the imported document, the app will show you a list of the changes.”


Good report Ted. It’s mind-boggling why Apple is so tight on file sharing. I hope iPhone OS4 opens things up a little… I hope but have little confidence.

Every company builds a natural level of expectation from their consumers by the quality of their products and service; think AT&T, Microsoft, Ford, and so on. Apple’s consumer base expect aesthetics, high-performance, and ease-of-use. Even as the Apple consumer base is growing significantly, I hear people feeling cagey about moving to the Apple platform quoting proprietary and closed systems. A few years ago I could confidently banish their worries but these days, I too am growing concerned about Apple’s controlling nature.


One of the main reasons I’d get an iPad is for iWork, but this wonky file sharing system sounds utterly and completely abysmal. Apple, please allow Dropbox (and other third parties) access to iWork files so that they can straighten out this mess.

Lee Dronick

If the iPad app doesn?t have one of the fonts used in the original, it?ll substitute it with one that matches it closely

Does the iPad use the same fonts as the iPhone? Being the same OS I am sure that they both come with the same fonts, but do you know if fonts can be added to the iPad.

Follow up question. Does a PDF display embedded fonts or does it substitute with system fonts?

Thanks for the this article. I am going to be doing tech support for the wife when she gets her iPad 3G


You do know that if you go yo in Safari on the iPad and select a document, you have the option to open it in the iWork app that’s appropriate. So accessing is quite easy.



This is my problem exactly!

The iPad is hamstrung with the iPhone OS 3.2 non-file system. I’m hoping that the Thursday announcement on iPhone 4.0 will ADD A FINDER in the near future to the iPad. This anti-Finder trend is ridiculous! I’ve not seen any great idea that does a better job of handling stored data. This is actually more important to fix than 3rd party application multitasking. The GoodReader you mentioned and Air Sharing applications both add wireless connections to the Mac Finder as a Shared server connections. Unfortunately they have to work with the iPad’s non-Finder system, so the shared connection hangs-up if their application is not alive and in the file handling mode. If the iPad had a real Finder, synchronization could happen in the background and all iPad apps would have access to all the data whenever they needed it. The iPhone OS does system multitasking now and could handle a real Finder.


Great article, Ted - this definitely puts its finger on a sticking point with what is essentially a hybrid computer/portable media device.

Seriously, who’da thunk we’d be syncing every stinkin’ file on a satellite computer to its main machine, with decade-old jukebox software. I know Apple is a huge proponent for making computing as simple as possible, but as iPods (and now the iPad) have evolved from music players to mobile computers, just seems like that way of syncing is a bit of a lazy solution on their part.

I’m sure we’ll see the iPad evolve in the next few years, but right now I’m not convinced that they’re desirable for much in the way of productivity until Apple addresses 1. a more flexible way of syncing files between machines, 2. a way to move files to & from the iPad w/out tethering to iTunes or a cloud service (ie. USB mini-jack or SD card slot, possibly), 3. a realistic way to manage files on the thing.

In the meantime, I look at it as a super-cool way to consume media, but not for creation.


Sounds a little stupidly designed. I know there has been talk of coming access to files shared on the local network. I hope that happens. Why not have file sharing by bluetooth too and smooth integration with and MobileMe? Files exported to and imported from any of these should automatically be tracked the same as local files when they are available.

I think an actual finder, as far as a hierarchical file-system, is a bad idea but you should be able to browse files compatible with the app. Files created by the app should be unlocked as well as previously unlocked files. Other compatible files should as easy to unlock as clicking on them and confirming. Being able to tag files by a keyword and filter based on keywords, creation and modification date, creation app, etc is a good idea.

Time Machine integration for backup would be great.


While I agree with your ire about the clunkiness of the whole process of file sharing, I did want to challenge the premise in your introduction and conclusion: that is, the iPad is NOT intended to replace a laptop or traditional computer. It was not created for this purpose. Apple explicitly stated it serves a different purpose.

Whatever we may desperately wish the iPad would be, we can’t judge based on those wishful assumptions. Anyone who judges the iPad as a laptop replacement is going to be disappointed because that is not what Apple created. It is simply not intended as a general content creation device. It is primarily designed to consume content.


Does anyone know if AirSharing HD would make this easier?


Why did you dismiss the email option for moving the file between iPad and Mac?

Ted Landau

the iPad is NOT intended to replace a laptop or traditional computer. It was not created for this purpose. Apple explicitly stated it serves a different purpose.

I understand this. And I was not suggesting that we judge the current iPad by this standard. But there is a lot of speculation about a future iPad playing a different role. I don’t believe this is just wishful thinking. Apple would never say this, because it doesn’t talk about unannounced products, especially one that may be three years away, but I believe this is their hoped for direction for the iPad. I guess we’ll have to wait and see.

Ted Landau

Why did you dismiss the email option for moving the file between iPad and Mac?

I view having to email an attachment to myself to move from iPad to Mac ? and email it back to myself and receive it on the original device to move in the other direction ? to just be too clunky to be the primary way for file sharing.

Maybe that’s just me. But that’s the reason for the dismissal.


Actually, I *am* intended to replace my MBP with my iPad as my primary computer (blogging about it at so this is a bfd for me.

It was the first ‘uh-oh’ moment for me and my plans when i realized the inelegance (and difficulty) of such simple, otherwise routine actions.

I’m still going to brave it…but I really hope they announce better on Thursday.


Maintaining tight control might be one reason for the convoluted file-sync-via-iTunes approach.  But I think that there is an even more practical reason… housekeeping/cleanup.  Delete an app, all data (configuration info and content) gets deleted as well.  There are obvious limitations to that approach as was cited in the article (a one-to-one mapping of data file to app, duplicate copies are required to associate the file with multiple apps).

As for why Apple allowed the iPad to roll out with this method… I don’t know, but I assume that it is because it was the only thing that they could do with the current iPhone OS architecture at the time.  We’ll see if things improve with 4.0.

Mike Roberts

Replacing your laptop with an iPad would be like replacing your truck with a set of rollerskates. Just because both have wheels and let you move around doesn’t mean they are meant to be used in the same situations.

The iPad is meant mainly as a web-browsing tablet and content-delivery system, but Apple’s attempts to keep the system as closed as possible (and manufacturing costs down) end up hurting it even in those limited roles.

Even if Apple suddenly decided to make it an open platform (which I believe they will be forced to do sooner or later, if they want to sell to a broader reange of users), it simply does not have the hardware specifications to be a viable content-creation platform.

I wouldn’t be too surprised if Apple used the iPad experience to design a ThinkPad-style MacBook in the future, maybe with an iPhone OS style interface for OSX when it’s in tablet mode. And *that* might be a real winner.


This is a great post on a really important topic. I got a chance to try a couple of ipads, and I something I tried just didn’t work at all. I placed a winword DOC file on a web server and also emailed it to myself before visiting with the ipads. I could view the DOC file by loading up gmail or just on the web: fine. (A surprising amount of formatting was gone - e.g. it appeared as single rather than double spaced.)

But more interesting was the “Open in pages” button that appears when you view a DOC file through Safari: this button did nothing at all. I tried on two different units.

Yes, I did try just going into pages and looking in the import document list—I think I figured out how to try this, and didn’t see the doc there.

Was something wrong with the two units I tried? Or is there a really broken feature on the ipad?

Anyone have any success doing this?

Is there any reason to hope for improvement on the file-sync front?


Am I the only one that thought “Google Docs” all the way through reading this?  Not only is syncing not an issue at all (things get saved to the cloud, easily accessed from anywhere) but it is also multi-player (more than one person can edit a document at the same time).

Better yet, you probably can use it already on an iPad (since it is in javascript).  I don’t own one, so I haven’t verified this, but if anyone wanted to send me one, I would be glad to test it smile


Nope, I hear that ipad cannot do google docs editing:

J Dodd

Are there perhaps some DRM implications from forcing sharing through iTunes here?


There are some other possibilities: Download the mobile me app from the app store. I hope it gets updated soon for the iPad. But nevertheless you can share a doument that exists on iDisk to the cloud and eMail it to you. Open it in Mail on iPad. That works well. So you don’t have to prepare your files that you wish to work with on the iPad and load them up from your desktop machine in the first place.

Someone of you asked of imbedded movies in a keynote presentation. Those survive the synch process just fine.

Abhi Beckert

Actually, I *am* intended to replace my MBP with my iPad as my primary computer (blogging about it at so this is a bfd for me.

Why? If it’s your primary computer, you will rarely if ever need to sync.


What, it doesn’t run Windows 7 either!  It’s been out almost a year now, er, well, almost a week ... what a piece of ....


Are you certain that the MobileMe iDisk does not adress your concerns?  It certainly appears to work fine on my ipod touch…

Ted Landau

Are you certain that the MobileMe iDisk does not adress your concerns??

As far as I can tell, I cannot import a Pages document from the iDisk app to Pages.

greg Huddleston

You are 100% correct about this wacky complex to iPad file interaction. (I just figured out how to get Keynote to export last evening).

The lack of ‘some’ file/folder interactions on iPad makes it harder not easier…

As another example:  Photos cannot make a ‘folder’ album on the iPad device nor more photos between albums (if one gets into wrong album by mistake) you cannot just drag a photo to the right album.  Nutty that in a touch screen device you cant move around the photos via ‘touch’.

Keep the good advice coming & perhaps our beloved Apple will relax these annoyances a bit with upcoming iPad s/w updates.

Best GH

Anony Cowa

You’re kind of all missing it.

The iPad isn’t meant to replace a laptop.

You can get an iPad for $500-800, or a mac book for $1000.

Apple would be competing with themselves. They’re facing a Microsoft-like split.


Follow up question. Does a PDF display embedded fonts or does it substitute with system fonts?

The PDF hould display embedded fonts (at least that is what happens on Macs and WIndows machines).



@brianiv jk is right—because Mobile Safari does not implement ContentEditable (Rich text/HTML editing), you are stuck with two choices for word processing:

1) type code into plain textareas on the web
2) use Pages, Notes, or some other native app and email the files to yourself

If you do a lot of composing for or on the web, these options suck, and the iPad becomes inferior to a $400 netbook. Let’s hope MobileSafari learns how to edit rich text soon!


This is an obvious deficiency… the argument that the ipad was not designed to do this, its only a web browsing content consuming fun loving lap sitting pad… is to ignore that Apple itself gives us the work programs Pages, Numbers, and Keynote.  Apple is promoting it as a productivity machine as well as the above.  All we are saying is that the apps are just the first step in the promise of the pad, a reasonable file system is needed too.  Let’s just call it like it is.  Apple dropped the ball on that one.  Hopefully future versions.


I agree. Apple needs to focus efforts on file sharing and also allow more flexibility and openess with files/applications. Forcing to go through itunes is not a good long term solution. Apple should work to update the iphone and ipad, or at least ipad system to allowing better file storage/sharing/manipulations. For those on the fence wishing to replace their laptop, this may be the deciding factor. lets keep the pressure on Apple!

Mark Simonson

One little point: You don’t have to explicitly sync to copy documents to and from the iPad. If it’s already connected to your computer (say, for charging), when you add a document to the iTunes pane, it will immediately be copied to the iPad and immediately shows up with the associated app. Sort of a mini-sync.

Dan Hamilton


Air Sharing HD is the best solution out there.

I basically allows you to access your iPad as a wireless drive from your computer. You can transfer files to and from the iPad to Air Sharing’s workspace.

When you open a spreadsheet, word processing, or presenetation document in Air Sharing, if you have Pages, Keynote or Numbers installed, you have the option to open the doc in the appropriate program.

You can also transfer files to and from Mobile Me, and more.

If you want to get any work done in the iPad, it’s an essential app.

Daniel Dilger

The ideal way to work with documents on iPad is to mail them to yourself or to people you work with.

This seems very “unsophisticated” to IT types, but it’s how normal people think to use documents. You can open iWork/Office (but not RTF/Text) documents right from Mail, and then work on them in the iWork apps and mail them back out.

I didn’t really see a problem in exporting files to sync through iTunes, but it seemed like more of a hassle, and I didn’t see why there wasn’t a wireless file share (I was imagining iPad would have a Bonjour file share on it).

Until then, if you know how to use Mail, you know how to get files on and off your iPad fastest and easiest.

My experience with was that it doesn’t work yet.


The ideal way to work with documents on iPad is to mail them to yourself or to people you work with.

This seems very ?unsophisticated? to IT types, but it?s how normal people think to use documents.

“Ideal in the sense that that’s pretty much your only option. I disagree about what most people perceive as the norm - any human who has used a desktop in the past 30 years has at least a basic understanding of how a file system works- the current method for iPad is inflexible and counter-productive.


In the above section “Export a document from iWork apps on your iPad (Part 1)” in step 2 it was said that the iPad cannot import documents from, but in a recent email to Steve Jobs, this feature was confirmed. From
“The reader asked if there was a way he could transfer his Google Docs to his iPad through or iDisk. Jobs’ reply? “Yes.”“

Mark Simonson

You can send and retrieve documents from iWork dot com, but you can only send within the iWork apps. To retrieve, you must go to iWork dot com in Safari. So it is possible to use iWork dot com with the iPad, albeit clumsily.

One thing I notice is that when you upload a doc back to iWork dot com from the iPad, it asks if you want to replace it, since it has the same name. And it does replace it. Going the other direction, if you download a doc and it has the same name as a doc that’s already in “My Documents” on the iPad, a number is appended to the name (“Whatever” becomes “Whatever 1”), and you now have two copies of the same doc with different names on the iPad. If you want to avoid this, you have to first delete the local iPad copy of the doc before downloading it from iWork.

So, iWork dot com works, but it’s just as complicated as the USB/iTunes method.

Mark Simonson

After playing around with this a bit, I’ve come up with a relatively easy way to round-trip a document between an iPad and a Mac using iWork dot com:

1. Create an iWork document on the iPad.

2. Go to “My Documents” screen and use the “Share via” command at the bottom.

3. Delete the document from the iPad. (You may want to verify that it uploaded successfully first.)

4. On your Mac, go to iWork dot com a browser.

5. Download the document.

6. Open it and make some changes.

7. Upload to iWork dot com (using the button in the iWork toolbar), replacing the copy that’s there when asked.

8. Delete the local copy. (Again, you may want to verify that it uploaded successfully first.)

8. On the iPad, go to iWork dot com in Safari.

9. Download the Pages document and tap the button at the top right to open it in the appropriate iWork app.


The key thing is to delete the local copy after uploading to iWork dot com, whichever direction you’re going. That way, you don’t have to worry about having out-of-sync duplicates or other version problems. It works basically like the “New Transported Man” trick in “The Prestige”. Not sure if it’s better than simply emailing the documents, but it works.

Ted Landau

So, iWork dot com works, but it?s just as complicated as the USB/iTunes method.

Yup. That’s the essence of the problem. I’m looking for a solution that at least comes close to how easy it is to do file sharing between two Macs. Nothing I have tried meets this criterion for me. I admit, however, that some of the alternatives suggested in comments here are better than the ridiculous iTunes method that Apple came up with.


Definitely broken.

Surprising and annoying, considering the original iPod had disk mode back in 2001.

Surely Apple could easily fix this problem if it wanted to… right?

Sherman Wilcox

Actually, I was thinking PasteBot as I read this. I wonder if the folks who produced that nifty app are at work on a better way to transfer from Mac to iPad.


I have a feeling this data center they’re currently building has something to do with MobileMe and it may not be about media-streaming, solely or at all, but about syncing capabilities between MacOS and iPhoneOS.

The current file handling for the iPad is so screamingly not Apple-like that they have to have something in queue which is not yet ready to be released but might be revealed, say, with iPhoneOS4.1 this fall?

Let’s just hope so. Can’t be their aim to literarily push their users into GoogleDocs (as soon as it works on the iPad).

Lee Dronick

I have a feeling this data center they?re currently building has something to do with MobileMe and it may not be about media-streaming, solely or at all, but about syncing capabilities between MacOS and iPhoneOS.

That is quite possible. As long as we can synch locally then I personally wouldn’t be concerned.

iPad <> Mac Sync via

Have had success transferring Keynote & Pages docs back and forth via using the following.

Just took a Keynote presentation I made on the iPad with two movies imbedded and used the “Share via” option > then opened iWork with my web browser on my Mac after the file uploaded and downloaded the Keynote file to my desktop. > Then opened the file on my desktop with Keynote made a change in the file, saved it as rev 1 and uploaded it from Keynote on the Mac to > Then opened Safari on my iPad went to signed in found the file, hit download, after download a button on the top right asked me if I wanted to open the file in Keynote, said yes and iPad Keynote opened with the revised file.

Seems simple enough to me


Personally, I hope this question ushers in the demise of file & folder browsing altogether.

While an iPad Finder sounds like a great idea at first, requiring the user to manage individual files on the device is really a step backwards.  File management is truly a complete waste of time, especially on mobile devices. The user should be thinking “which is the best photo for my presentation?” not “Where is that jpeg again? Oh, here it is… maybe I should move it from my desktop to the images folder because I don’t need it very often. I’ll make a new folder inside images called ‘For presentations’.”

If Apple ran with direct file copying via USB (as seen in the iPad developer previews) then iPads would be stuck with the same cumbersome file/folder metaphor that “real” computers are stuck with.

The best way out of this file-sync quandry would be for an iPhone OS service to invisibly manage access to all data on the device. For example, when the user pushes or pulls any file into the iPhone/iPad (via itunes, email attachment, web download, idisk, whatever) the OS file management service grabs it.

The file service examines the new file, says “Okay, this is a .docx file. I know what to do with .docx files. Let’s share this with Pages, MS Word Mobile, and PDF Maker. Oh right, and the user wants me to sync .docx files, so let’s copy this to mobileme right away and then watch for changes. And since this file just arrived, we’ll let the user find it under ‘new arrivals’ as well as ‘word processing.’”

When the user pops into Pages or Open Office for iPad, there’s a list of files, or better yet call them work items. Here’s where you can organize or rename your work items. Group them into projects or contexts if necessary, so for example certain movie clips and text objects fall under the name of a specific project.

Basically think of the existing media browser concept and expand it to all types of data. The trick is to design that file-management service in a way that offers users a multitude of convenient transfer options.

I’ll bet my landlady’s refrigerator this is the direction Apple’s headed.


Apple has to do a better job here.

Add to the confusion the role of the iDisk for users with a mobile me account.

If I store files from my laptop onto my iDisk, they should be available to me on my iPad, right…


I can use the iDisk application on the iPad. I can see the files. But if I want to open a presentation in Keynote, I need to make that presentation a shared file, and then I need to send an email to myself with the link to the location of the shared file.

THEN, I can open this file on my iPad. Great.

Now if I change the file… no way to get it back to myself, except to email it to myself. If I change it on my computer, I need to remember to put it back on the iDisk so the new version is available to me on the iPad.

I was at the Apple store today, the rep I spoke with suggested installing VPN server software on my laptop, and then connecting to my laptop via VPN from my iPad.

This does not represent a simple solution!


Obviously, the solution is to wirelessly allow transfer of any document on the iPad to a shared folder on the Mac and vice versa. Or better open up the filesystem and let the iPad be mounted as a volume.


I was at the Apple store today, the rep I spoke with suggested installing VPN server software on my laptop, and then connecting to my laptop via VPN from my iPad.

Hah. That’s also the workaround for watching Hulu and using other Flash-based content: use a VNC client to connect to a desktop Mac via Screen Sharing.

It’s not as bad as it sounds, but it’s not that great either. For one thing, a desktop doesn’t really understand touch events.


I am having such a bitch of a time working with this sucky file sharing. I thought because i could do word processing on iPad this would not be an issue. I love this gadget but I cannot really use for day to day if this does not change. So to me this is really a big iPhone and nothing else.


Can’t find the File Sharing section on my iTunes??

What can i do??


So to me this is really a big iPhone and nothing else.

So you can make phone calls on yours? How?

Lee Dronick

So you can make phone calls on yours? How?

From what I understand you can use Skype, but the big iPhone phrase is a troll talking point. At least over at CNET


Am I the only one that thought ?Google Docs? all the way through reading this?? Not only is syncing not an issue at all (things get saved to the cloud, easily accessed from anywhere) but it is also multi-player (more than one person can edit a document at the same time).

Interesting point, which had me thinking:

1) Apple’s current syncing solution is so terrible that it almost seems like a stop-gap until they reveal a bigger plan.

2) What if that bigger plan is to move everyone towards the cloud…THEIR cloud, me[dot]com/iWork[dot]com?

3) Everyone seems to think they’re investing in that data center in order to implement a new music-selling model, but what if they’re gearing up to put all Mac, iPod Touch, iPhone, and iPad owners on Me[dot]com?

4) With their recent divorce from google, we mostly assume that Google is the one that is now capitalizing on things they’ve learned from Apple, which I suppose is a fair assumption given Google’s entry into the smartphone and OS markets. However, there’s no way Apple didn’t learn quite a great deal from Google’s operations as well. Me[dot]com isn’t that dissimilar from Gmail, what with the email service, cloud-based hard drive, and a slow roll-out of web apps like iWork[dot]com.

5) Am I the only one who finds it strange that Apple, despite making money hands over fist, is essentially crippling adoption of Me[dot]com by charging that pesky $100 annual fee? Yes, no one’s gonna turn away an extra/easy dime, but we’re talking about a company that essentially gives away it’s OS and production suite. So, what if they’re using that fee as a way to manage the flood gates of growth? Sort of like their version of an invite-only program.

6) To that end, it seems perfectly reasonable that Apple is still trying to fine tune its understanding of these web services, put its processes in place, setup the necessary backend hardware, then one day Steve Jobs unleashes his plot to supplant Google and move Apple into the next stage by:

a) Making Me[dot]com FREE to all existing and registered Mac users.
b) Bundling a FREE Me[dot]com account with every Mac, iPod, iPhone, iPad, and even aTV purchase.
c) Then using me[dot]com to undermine gmail.
d) Then using iWork[dot]com to undermine googledocs, which wouldn’t have as tight an integration with people’s hardware as iWork does.
e) Then using it’s new iAd framework to push wares. This would be a breeze because no other company has as many customer credit card information on record and ready to capitalize on their apple-verse buying trends.
f) And last but not least, using that massive hoard of cash to do the only thing they feel they can’t quite accomplish from scratch/within, buyout a ‘major’ search player like Yahoo, which would strike directly at the heart of Google.


Lee Dronick

Am I the only one who finds it strange that Apple, despite making money hands over fist, is essentially crippling adoption of Me[dot]com by charging that pesky $100 annual fee? Yes, no one?s gonna turn away an extra/easy dime, but we?re talking about a company that essentially gives away it?s OS and production suite. So, what if they?re using that fee as a way to manage the flood gates of growth? Sort of like their version of an invite-only program.

Do we have any numbers of how many users have a MobileMe account, beyond the free period? We have and use a family plan, but in talking to other Mac users I don’t find too many who even have a single account.

Would I like to see a cheaper annual fee? Yes

Would Apple sell more subscriptions if the annual fee was cheaper? Maybe. We use it a lot for synching our iPhones and Macs, but it is also used to share photos. However, free social networks such as facebook have photo albums and I am thinking that they take subscribers from MobileMe.

I wonder if Apple does have some big plans for MobileMe in regards to the data center being built in North Carolina.

Gianni Catalfamo

Totally so. Maybe we should all write a nice email to El Jobso
asking for a Finder on the iPad


I totally agree with you about this big limitation of the iPad. As a long time Mac only user (since 1986), and one who has never used an iPhone or Touch, my iPad is a totally new paradigm for me and a confusing one at that. I’ve download and played with 83 app (only 3 games). The only ones I use regularly are reference apps and book-readers. Even Safari is a hassle. I do not find content creation easy enough on my iPad to make it my primary choice and I don’t even need to share documents with others. A laptop is so much better. The reasons are mainly the ones you mentioned. I want total access to the OS.

The answer to all of this is of course JailBreaking.


This problem is killing the iPad for me. I can’t believe there isn’t a solution to integrate the iPad into document workflow.

I mainly use pages and keynote, save all doc’s to drop box and edit them on various client machines. I’ve tried to use airshare HD and transmit to sync file between MacBook and iPad, but the doc’s can’t be accessed by pages on the iPad.

As I’ve only got the wifi iPad I need a physical copy of the doc’s on the iPad to edit and then a solution to sync the changed doc’s back to the iPad.

Has anybody go ant idea’s?

Samatha Lewis

Hi Ted

A very informative post.  I’ve just spent the last few days getting my head around the functionality of an iPad my 89 year-old mother bought.  I’ve worked on Macs for nearly a decade and have an iPhone - so I didn’t have those initial cross-platform problems that pc users might have.  But I’d have to say, getting my head around Pages still took quite some time.  Your article is very well laid out and very informative.

We bought an iPad for Mum because she’s an avid reader - but word processing was also an important feature for her.  It sure would make life a hell of a lot easier if Apple went down the path you’re suggesting as the file sharing is quite cumbersome.

Like the dreaded DRM issue with eBooks, manufacturers will have to stop and think of the consumer for a change if they want to keep everyone on board and increase market share.




Thank you for writing this article. I am a university student and I have been doing my class notes in pages for the past two and a half years of my studies. When I saw the pages app on the release of the iPad I was really excited - so much so that I sold my MacBook Pro (which I had been meaning to in any case) and bought the iPad instead of a smaller Mac laptop.

My first gripe was that I couldn’t access my iDisk files from the pages app, but I overcame that by downloading quick office pro which I find works the best for iDisk integration. The problem is that this app can’t edit pages documents, but it does let you open iDisk documents in the iPad pages app. It also let’s you save documents back to the iDisk. The absolute ball breaker? Pages won’t let you open the document in any other app. So once you get your pages documents into the pages app (wirelessly), they are stuck there. My workflow is simple and I’m sure many others who pay for mobile me do exactly the same. So why has apple crippled their device? They have literally broken the iPads kneecaps and left it in the middle of a busy road. I simply do not understand the logic of it!

james Houston

I have IOS9 ipad and i usually remote access from my ipad to home cameras and laptop, i usually use purevpn ( source: ) but the problem is that i can’t afford this one and i need suggestion for more ipad vpn.

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