iPad Secure transfer of docs PC to iPad?

Ruffian829

macrumors 6502
Original poster
Jun 17, 2008
319
2
I work for a government agency and am looking for a secure way to transfer documents from a PC to an iPad. I realize that I can email documents but it would be nice if there was a better, more efficient way to do this. Cloud service is unlikely to be approved for this purpose so I need something other than the norm: Dropbox, icloud, etc.

There is wireless in the office but the PCs don't have wireless built in, so the devices are not on the same network.

Any apps that will do this? Any suggestions?

TIA
 

Night Spring

macrumors G5
Jul 17, 2008
13,074
5,173
Are you allowed to install iTunes on a work PC and connect your iPad to it with a USB cable? Or are you looking for a wireless solution?
 

scaredpoet

macrumors 604
Apr 6, 2007
6,627
342
The above is pretty much the most "secure" way to do it with the requirements you're describing. You install iTunes on a PC or Mac, plug a USB sync cable between the PC and the iPad, and you drop the PDF files into iTunes under "Books." The PDFs will then appear in the iBooks app on your iPad after you sync them.

I put "secure" in quotes because I've found that there's a lot of superstition in government IT practices that don't always make a lot of sense. For instance, for all the attention paid to the "security" in transferring the PDFs to the iPad, what method was used to get these super-sensitive PDFs to the PC in the first place? My guess is a departmental LAN, which unless they're using Windows 8, likely runs over an unencrypted SMB file sharing network.
 

Ruffian829

macrumors 6502
Original poster
Jun 17, 2008
319
2
The above is pretty much the most "secure" way to do it with the requirements you're describing. You install iTunes on a PC or Mac, plug a USB sync cable between the PC and the iPad, and you drop the PDF files into iTunes under "Books." The PDFs will then appear in the iBooks app on your iPad after you sync them.

I put "secure" in quotes because I've found that there's a lot of superstition in government IT practices that don't always make a lot of sense. For instance, for all the attention paid to the "security" in transferring the PDFs to the iPad, what method was used to get these super-sensitive PDFs to the PC in the first place? My guess is a departmental LAN, which unless they're using Windows 8, likely runs over an unencrypted SMB file sharing network.
Is there a way to move a document in a form that isn't a PDF? Like if I get MS Word on the ipad can I move that via iTunes? I dont want to be stuck with only PDF documents if they are still in the editing phase...

And I totally agree about things being "secure" or not. I'm not sure what we are using (re: LAN?) as I'm not that well versed on these IT issues... but, for example, my ipad isn't required to have a password on it until I get my email account server set up. Then all the sudden I need an extensive password just to turn the ipad on. However, its not like its not possible for someone to hack into or access our exchange email on the web app without this ridiculous password.

A friend asked if I couldn't get a wireless USB type thing for the desktop, and then be able to transfer documents wirelessly from the ipad to the desktop via some app (as then they'd be on the same network). The state absolutely will not let us use any could service that has servers (or something) that are out of the country. So apparently, no dropbox, icloud, etc.

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There are some apps that double as a file server that you can access from the web. You turn it on and off as needed, and send your documents that way.
How does this work, exactly? If the document is uploaded to a site where it can then be downloaded I'm not sure it'll be allowed...
 

Night Spring

macrumors G5
Jul 17, 2008
13,074
5,173
Is there a way to move a document in a form that isn't a PDF? Like if I get MS Word on the ipad can I move that via iTunes? I dont want to be stuck with only PDF documents if they are still in the editing phase...
Yes, iTunes can be used to move documents in any format you want. You just need an app on the iPad that can open those formats.


How does this work, exactly? If the document is uploaded to a site where it can then be downloaded I'm not sure it'll be allowed...
Some apps lets you remote into your computer over the internet and browse and transfer files to and from the iPad. Whether or not this works will depend on the setup at your work.
 

Jessica Lares

macrumors G3
Oct 31, 2009
9,274
781
Near Dallas, Texas, USA
Some apps lets you remote into your computer over the internet and browse and transfer files to and from the iPad. Whether or not this works will depend on the setup at your work.
He wants to send files TO the iPad though.

How does this work, exactly? If the document is uploaded to a site where it can then be downloaded I'm not sure it'll be allowed...
The way the web server works is that the app gives you a link to go to, which is simply the IP address of your phone. You go to that link on any web browser, and it'll give you a way to upload something, like you normally would on.. Let's say... this message board.

The only thing that would be vulnerable is pretty much your phone (although the only thing someone could do is just upload a file).
 

Night Spring

macrumors G5
Jul 17, 2008
13,074
5,173

jlc1978

macrumors 68030
Aug 14, 2009
2,700
1,044
I work for a government agency and am looking for a secure way to transfer documents from a PC to an iPad. I realize that I can email documents but it would be nice if there was a better, more efficient way to do this. Cloud service is unlikely to be approved for this purpose so I need something other than the norm: Dropbox, icloud, etc.

There is wireless in the office but the PCs don't have wireless built in, so the devices are not on the same network.

Any apps that will do this? Any suggestions?

TIA
Email is probably the most secure and actually not that bad of an option. You have access to the docs and can delete them, providing a bit of security, and download again later if needed.

Depending on the IT org you may or may not be able to install iTunes as was recommended.

Another option, if you want to avoid using a PC, is a wireless usb stick, such as Sandisks. You transfer the files to it, assuming your security allow you to use non-approved usb devices, the wirelessly to the iPad.

If they provide secure gov't issue usb drives, such as Ironkey, you could use that so you maintain document security up to the point where you put them on an iPad.

Here is something else to consider:

Once the doc are on your iPad they are essentially insecure. Depending what is in the docs you could very well cause a security breach.

I've worked with an agency that let us use iPads/iPhones but we had to enable remote wipe via Outlook's web interface.

My advice - check with your IT security person to be sure you aren't committing a violation. The convince of an iPad isn't worth the hassle.
 

scaredpoet

macrumors 604
Apr 6, 2007
6,627
342
Email is probably the most secure and actually not that bad of an option. You have access to the docs and can delete them, providing a bit of security, and download again later if needed.
I would have to think that if an organization is saying that cloud-based storage of these documents is a security risk, they might think the same is true of e-mail. And in reality, e-mail is probably far less secure than any other cloud service that is dedicated strictly to access-controlled file storage.

But then, lack of knowledge of these things is unfortunately endemic in a lot of government IT departments, so they may (erroneously) think that e-mail is in fact, okay.

Depending on the IT org you may or may not be able to install iTunes as was recommended.

Another option, if you want to avoid using a PC, is a wireless usb stick, such as Sandisks. You transfer the files to it, assuming your security allow you to use non-approved usb devices, the wirelessly to the iPad.
Quite a few organizations who are hyper sensitive about security have imposed restrictions on their workstations which disable all use of USB mass storage devices. Something to be aware of.

Once the doc are on your iPad they are essentially insecure. Depending what is in the docs you could very well cause a security breach.
I would have to disagree with this. The storage system on all currently-supported iOS devices is AES-128 encrypted, provided a lock code is enabled. To access these files, an attacker would need physical access to the device, and either have knowledge of the lock code, or physical access to a computer which the iPad's owner has allowed the iPad to trust for syncing and data transfer purposes.

Of course, a lot of this security is dependent on the user taking steps to make sure that the security features are in fact utilized. But the same would be true if the files were on, say, a laptop, or printed out and stuffed in a briefcase. If the user manages to lose those things, or an attacker gains access to them, then the files are of course compromised.

I've worked with an agency that let us use iPads/iPhones but we had to enable remote wipe via Outlook's web interface.
There's also this capability, which increases security. Passcodes of a specific length and composition can also be enforced.
 

960design

macrumors 68030
Apr 17, 2012
2,987
937
Destin, FL
My advice - check with your IT security person to be sure you aren't committing a violation. The convince of an iPad isn't worth the hassle.
Or you could contact a mobile learning analyst ( like me ) for assistance in ensuring you iPads ( mobile devices ) are setup properly.
 

whooleytoo

macrumors 604
Aug 2, 2002
6,572
654
Cork, Ireland.
I would have to think that if an organization is saying that cloud-based storage of these documents is a security risk, they might think the same is true of e-mail. And in reality, e-mail is probably far less secure than any other cloud service that is dedicated strictly to access-controlled file storage.

But then, lack of knowledge of these things is unfortunately endemic in a lot of government IT departments, so they may (erroneously) think that e-mail is in fact, okay.
It's weird.. email - unless you encrypt the files before sending - has no security whatsoever. You're just sending files in the clear. A cloud solution, used wisely, is far more secure, yet they are often taboo in enterprise environments.

Once, we had to go through a lengthy, exhaustive security audit from a large client as we would be handling a lot of PII data. We spent weeks sending them data on our security team, how we responded to new malware threats, how we managed our site certificates etc. Once we passed - they emailed the data to us! Zero security.

Anyway, back on topic: if the OP can't sync via iTunes and using a cloud service isn't permitted, perhaps you could set up a local web site with the files in question and access it on the iPad? I think that should work if the files are typical document formats (pdf, Word etc.) though I haven't checked if Safari on iOS gives you a Save to iBooks option.
 

Night Spring

macrumors G5
Jul 17, 2008
13,074
5,173
I think that should work if the files are typical document formats (pdf, Word etc.) though I haven't checked if Safari on iOS gives you a Save to iBooks option.
Yes, it does. I often save PDFs from websites to iBooks through Safari.
 

jlc1978

macrumors 68030
Aug 14, 2009
2,700
1,044
Or you could contact a mobile learning analyst ( like me ) for assistance in ensuring you iPads ( mobile devices ) are setup properly.
Setup properly is irrelevant if the organization does not allow the use of mobile devices. No matter how it is setup it is a security violation if the rules do not allow their use; hence the need to verify acceptability.
 

Ruffian829

macrumors 6502
Original poster
Jun 17, 2008
319
2
Email is probably the most secure and actually not that bad of an option. You have access to the docs and can delete them, providing a bit of security, and download again later if needed.

This is less than ideal for many reasons- I end up with many versions of the same document, split between the ipad and the computer. I would like to just end the document to the ipad to work on it from home, bring it back and send it back to the computer. But, I'm not sure if that is even possible even if it were not for the government restrictions?

Also some of the files are very large and need to be emailed in separate emails, clogs up my email and takes up space on the mail server until I get around to deleting all the attachments. We are not supposed to delete emails permanently.


Depending on the IT org you may or may not be able to install iTunes as was recommended.

I have yet to receive an answer on if I can do this or not yet.

Another option, if you want to avoid using a PC, is a wireless usb stick, such as Sandisks. You transfer the files to it, assuming your security allow you to use non-approved usb devices, the wirelessly to the iPad.

If they provide secure gov't issue usb drives, such as Ironkey, you could use that so you maintain document security up to the point where you put them on an iPad.

I am not sure if this is allowed, I am going to look into it as it seems promising. I know we can use encrypted USBs to transfer documents, but a normal USB obviously doesn't help with the ipad issue.

Here is something else to consider:

Once the doc are on your iPad they are essentially insecure. Depending what is in the docs you could very well cause a security breach.

I've worked with an agency that let us use iPads/iPhones but we had to enable remote wipe via Outlook's web interface.

This is enabled

My advice - check with your IT security person to be sure you aren't committing a violation. The convince of an iPad isn't worth the hassle.
It is a work issued iPad. It has a ridiculous password (as required).


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Setup properly is irrelevant if the organization does not allow the use of mobile devices. No matter how it is setup it is a security violation if the rules do not allow their use; hence the need to verify acceptability.
I'm not sure why this wasn't obvious, but the use of mobile devices is permitted and in fact the iPad I am using was given to me by the agency to use. It is work issued and owned. I didn't just go ahead on my own and start putting documents on an unapproved device.
 

Night Spring

macrumors G5
Jul 17, 2008
13,074
5,173
I would like to just end the document to the ipad to work on it from home, bring it back and send it back to the computer.
Sending files back and forth between the iPad and the computer means there will always be at least two copies of the files, one on the iPad and one on the computer, and you have to make sure to copy it back to the same location on your computer when you bring it back. Then remember to delete the copy on the iPad, because if you don't, most iPad apps will create a second copy of the file on the iPad the next time you transfer the file from computer to iPad -- it won't simply overwrite the old file.

The simplest way to do what you want is to use a cloud based service like OneDrive, Google docs, or Apple's iWork, which all allow you to keep a copy of your documents in the cloud, and edit it from whichever device you happen to be using. Since this is a work issued iPad, you should probably just talk to the IT department. If they mean for you to use this iPad to get work done, it's up to them to figure out how to set things up so you can get work done while complying with the work security requirements.
 

Ruffian829

macrumors 6502
Original poster
Jun 17, 2008
319
2
Sending files back and forth between the iPad and the computer means there will always be at least two copies of the files, one on the iPad and one on the computer, and you have to make sure to copy it back to the same location on your computer when you bring it back. Then remember to delete the copy on the iPad, because if you don't, most iPad apps will create a second copy of the file on the iPad the next time you transfer the file from computer to iPad -- it won't simply overwrite the old file.

The simplest way to do what you want is to use a cloud based service like OneDrive, Google docs, or Apple's iWork, which all allow you to keep a copy of your documents in the cloud, and edit it from whichever device you happen to be using. Since this is a work issued iPad, you should probably just talk to the IT department. If they mean for you to use this iPad to get work done, it's up to them to figure out how to set things up so you can get work done while complying with the work security requirements.
I figured that might be the case re:file transfer. Still doesn't leave email as a great option IMO. But it might be the only option I guess.

I was told "no" to Dropbox, one drive, etc. We are not allowed to have non-public documents stored on a server like that, I guess. There are some weird restrictions where the state won't let us use services that have servers outside of the US. They'd prefer we use services with servers inside the state but they "accept" that that might not be possible.

Our IT department is... Well let's say there was a reason I turned to you all. They are not experienced at all with iPads (despite the fact that they chose iPads for the agency vs surfaces or the like even though our desktops are windows and Microsoft based) and they are not great at figuring these things out. I won't even get into the issues that came up because every iPad is on the same iCloud account and everyone's calendars, notes, safari pages, etc were syncing....
 

Night Spring

macrumors G5
Jul 17, 2008
13,074
5,173
Sorry to hear your IT department isn't competent. Without good IT support, it does sound like emailing documents back and forth might be your only option. :(
 

JoArmstrong

macrumors newbie
Jan 12, 2018
1
0
get2Clouds is your solution and is so easy to use, you don't need an IT department.

get2Clouds automatically encrypts your files before they are synced with the cloud. You can sync up to three devices so you can see documents on your PC, iPad and smartphone.

The app is free and available on Windows, iOS and Android. Send secure large file transfers, chat in an E2E messenger and prevent unauthorised access to your private information.
 

sparksd

macrumors 68040
Jun 7, 2015
3,511
2,305
Seattle WA
Setup properly is irrelevant if the organization does not allow the use of mobile devices. No matter how it is setup it is a security violation if the rules do not allow their use; hence the need to verify acceptability.
Yes. He should absolutely contact his own IT organization and management to ensure that whatever he does, it's explicitly authorized and he's not breaking organization rules.
 
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