Forbidden Fruit? Why the Surface Pro 4 is better than the iPad Pro for litigators.

Happy New Year! This past week I got an email from a colleague of mine who asked some great questions about the Surface Pro line and how they stack up with Apple offerings. With their permission I decided to answer these questions for everyone’s benefit.

“Mr. Monteleone,

I wish you a happy holiday season and hope this email finds you in good health. I am writing because I am in the market for a new laptop and/or tablet device and wished to consult the resident expert. While I am historically a slave to the Apple, I saw your fancy Surface Pro commercial and am admittedly enticed. A few questions:

        What do you see as the primary advantages
disadvantages of Surface Pro v. iPad or MacBook?

        Are there any strong advantages to Surface Pro over Apple?

        Are there any notable differences between Surface Pro 3 and 4 worth the upgrade?

        Any notable differences between Surface Pro tablets and the laptops?

I am most interested in the prospected ability to write on a tablet and have that easily converted into text. Does that function work well on the Surface Pro? Do you use that very often and is it actually functional in notetaking in court?”

Well I think I can tackle this one!

Bottom Line

Surface Pro is a better device to make the transition from an analog lawyer to a digital attorney. It represents the best of how we used to do our work (pen) and the best of the future (flexible tablet computing devices that fit our workflow). When I set out to take the less paper route I started with the iPad. It didn’t do everything that I needed. I couldn’t multitask with multiple programs and instances of a single program running at once. Transferring files onto the device was a chore in the early days, and still relies on another PC to manage the files. I could only do one thing at a time, write notes, or review a document for a case never both. The iPad is a device that requires a full PC to do the content creation and organization, I wanted to have one device to create and consume, to handwrite and reference, a legal pad and trial notebook that was courtroom friendly. The Surface Pro line has brought my goal of a digital legal pad and trial notebook replacement to life. Let me tell you why.

What are the primary advantages and disadvantages of a Surface Pro v. iPad or MacBook? & Are there any strong advantages to Surface Pro over Apple?

I’ll roll the iPad Pro into this discussion too since the biggest difference in the iPad Air and MacBook offerings is the digital pen, a gap that is addressed in Apple’s larger iPad. While the digital pen is the first difference it isn’t the only one of course. Operating System and software available for that OS is also a huge consideration. Touch interface and the tablet form factor are a natural fit in the courtroom environment. Finally, I think another thing to consider is the type of work you want to accomplish and the current eco-system you currently do your digital work in.

The Pen

Let’s talk about the Pen. Digital ink is really my number one priority and it is no secret why I’ve preferred Microsoft’s offerings on an operating system level to the other choices (Apple, Android). Digital ink is incorporated at an OS level into Windows 10 (and 8.1) meaning that everywhere you can type something you can use the pen to write instead.

Windows 10 On-Screen Keyboard appears whenever you are prompted to enter text without a physical keyboard attached, or when you activate it on screen.

Instead of typing, you can use the on-screen keyboard to go into handwriting mode.

From here you handwrite the text you wish to enter and Windows 10 will convert your handwritten digital ink into typed out text.

This isn’t the only way the pen is integrated at a more fundamental level in Windows 10. It also works as a mouse replacement. The Surface Pro 4 Pen has left click (tap the screen) and right click (press the button on the barrel of the pen), allowing it to replace your mouse in situations where you can’t make use of one, namely in court when using the Surface Pro as a digital yellow pad, presentation device or trial binder using OneNote.

Here I am using the Surface Pro 3 Pen as a digital laser pointer with PowerPoint 2013 in court during a presentation.

Digital ink is a first class data citizen in Windows. You can run a search against handwritten digital ink and it will be found as if it were typed when using Microsoft OneNote. You can use digital ink to handwrite messages in Outlook, and Word, it can be used to annotate slides in PowerPoint live during presentations, and it can act as a pointing device in every other piece of software that Windows supports, which is the largest library of applications in any ecosystem. Using the pen or mouse you can select a block of handwritten text and copy and paste as if it were a paragraph of typed text, incredibly useful for litigators that want to quickly organize their handwritten notes. You can’t do that with a legal pad!

Microsoft OneNote converts freeform written digital ink into text. It is one of the reasons why the Surface Pro line and OneNote has become the foundation of the Modern Legal Pad.

Is the Surface Pro 4 Pen better than the Apple Pencil? For the purposes that lawyers will use it for I think the answer is yes. Most lawyers won’t be using the pen for artistic purposes, aside from some sketches for case preparation, and with that in mind the additional artist benefits of tilt-shading and seemingly lower latency (the amount lag time the digital cursor takes when following the pen as you drag it across the screen) that has been reported just don’t make up for the benefits that the Surface Pro pen has.

In addition to the features already mentioned, the Surface Pro 4 pen has an eraser just where you would expect to find it. That eraser is also a mutli-function button that can be used to launch OneNote (single click), take a screenshot (double click), or launch Cortana search (long hold). It is possible Microsoft will expand this capability in future updates like they did with the Surface Pro 3 pen, possibly allowing for configuration of the button in different ways. The Surface Pro 4 pen also comes with replaceable nibs (the writing tip or point of the pen itself) giving each user the option for a different feel when writing. The default option is a felt tipped point that makes writing on the glass screen of my Surface Pro 3 silent, and increases the traction making it feel more like writing on paper. The SP4 pen comes standard, and could be used on the SP3 and Surface 3 devices as well and it’s half the price of an Apple Pencil. For taking notes and preparing a case I think the balance tips to the Surface Pro 4 pen.

The Software

This is where the comparisons with the iPad will probably come to mind. Both are touch enabled devices, but only the iPad Pro and Surface line are equipped with digital pens, and this where I think the Surface line runs away with it from the iPad Pro perspective. A Surface is a full-fledged PC, it can do anything a normal PC desktop computing device can do, but it can be used as a digital writing tablet with OneNote. The iPad Pro can be a passable writing tablet with some of the writing apps, but I think the best software for lawyers that practice in court on the iPad is Microsoft’s OneNote; and OneNote is just better on a full PC.

I won’t go into the litany of reasons why OneNote is an absolutely amazing piece of software for lawyers again, suffice it to say I have come to center my practice on it.

OneNote isn’t the only benefit in terms of software. My law office is a Windows shop, we use PC’s and Office 365, our hardware pool is centered on Windows compatible devices and the accessories our IT department have for our use are also firmly based in the Windows world. While we have recently obtained a few iOS devices, our office doesn’t support those universally and there are no OSX devices services by our IT staff. So if one were to go the Apple route it would be almost entirely on your own.

This was the situation I found myself in when I first tried iOS as my main litigation platform. It was a struggle back then to even get files I needed onto my iOS device. Today that is a little easier with office support for OneDrive for Business but I’ve found that the iOS devices we do have in our office don’t behave as seamlessly as they do at home and that is a fundamental reason why I actually stopped looking to iOS. The lack of a file system in iOS also proved very frustrating. I’ve become so used to having files located in a folder on the device or cloud storage. In iOS this is mostly accomplished in each individual app. Having trouble getting a lot of files onto the iPad was a bad enough, not being able to find them all easily as my second problem.

Second reason is ironically the apps. The offerings in the App Store for lawyers are all islands of data each with their own wall around the information they use. Think of multi-program functionality, you can drag a file from a folder to a different folder or program that is running such as OneNote (desktop version, but you cannot do that in an app. Each one has its own copy of the data and they don’t share it very easily. That app model, where information was not organized on a system level was not what I had in mind for how I needed the iPad to work. I went through almost every single note taking app around and each of them had strengths and weaknesses to the point where a single one couldn’t do it all. Most lawyer apps I’ve seen since moving on from iOS take a small part of the puzzle and focus on that. None really take the place of a yellow pad (for handwritten notes) and trial notebook for preparation and use during trial at the same time. The fact that many of these apps recommend organizing your file on your PC first just reinforces my belief that a one device solution is better. Now, OneNote is available on iOS but even though I believe it is the BEST app for lawyers on iOS it can’t do it without help from a PC (or Mac). Since even OneNote is reliant on a desktop client to pre-configure the files for a trial notebook I wanted to cut out the middle man – in this case the iPad had to go.

I have said a few times that I could easily run my entire practice of law with Microsoft Office and Adobe Pro if I had to, and I stand by that. The caveat is that it’s the full desktop version of Microsoft Office including OneNote and Outlook, PowerPoint and Word etc. It’s using these full powered versions of the software that really makes a device like the Surface Pro shine. It gives you the form factor of a tablet and the power of a full PC.

For example in the full PC version of OneNote having multiple instances of OneNote running in multiple windows is a game changer. You can now have multiple pages open, even docked side by side if you like. All your notes, all your preparation and research all in one place. It’s easy to envision what you can do with this from a litigation perspective. One window is looking at the transcript, the other has your handwritten questions for the witness on the stand, and yet a third has copy of the exhibits you plan to use, all available at the click of a mouse button. Accomplishing the same thing in an iPad would require you to leave those pages and apps and go into a different one losing your place and taking your focus away from the information you have organized. The power of a full PC can increase your speed at getting things done, and your ability to call up information in high stress situations like a trial is vastly improved – and this can’t be done on an iPad.

The Hardware Accessories

It deserves mention that the iPad lacks USB support. That makes it very difficult to accomplish simple tasks that might not always crop up. Need to transfer a file quickly without an internet connection? What about printing to a non-network connected printer? How about HDMI projectors? You need an expensive set of adapters and connectors from Apple to accomplish these tasks. With a surface you need at most a mini-display to HDMI cable. How about wireless projection? With iPad you can only do this with an Apple TV. With the Surface you have several options including Microsoft’s Wireless Adapter, a Roku 3 or other third party adapter.

Did I mention that the Surface Pro can replace your desktop too? That really makes it a 3 in 1 device. Desktop, laptop and tablet. That is my current set up at work in our test program. The Surface Pro 3 I use for work has completely replaced my desktop, and it doubles as a secured home office work station when I need to work from home which, as any litigator knows, happens all too often. The docking station allows you to connect a large monitor, full size keyboard and mouse and multiple accessories. One accessory we use a lot that is fading away in the commercial technology world is a DVD/CD external drive. I have one of these at my desk to review digital files we receive on cases in that format. The iPad cannot do any of this, and while the MacBook can substitute as a desktop station and a laptop it cannot transition into the courtroom.

What about the MacBook?

Apple has made some fantastic devices, and the MacBook is no exception, but they have also made some very different design choices in terms of what devices they make. Apple makes a tablet, the iPad, and a PC, the MacBook, they do not and have said they will not make a hybrid device. This is in my opinion why the Surface Pro line of devices shines for lawyers, especially those that work in the close confines and limited space of a courtroom.

Since I don’t think an iPad is enough, I needed a full PC for my trial work. I loved the tablet form factor; being able to pick up the slate and scroll through with touch interface was intuitive and more convenient than a touch pad or mouse. The final piece was of course the pen to round out the Surface Pro device as the premier litigation tool that I believe it to be. The MacBook lacks ALL of those important features. You don’t have touch, you must use a touch pad or mouse, and it certainly doesn’t have a pen. In fact, Apple wants you to buy their other device to get all those features, but limits the litigator to an app store full of almost but not quite good enough apps. That is why I really think the MacBook is an also ran for a litigator in the courtroom.

The MacBook lacks the touch, pen, and tablet form factor of the Surface Pro line of devices. Using a laptop form factor in court is just awkward, a tablet PC is natural.


If you are coming from the Apple ecosystem there will be a sight learning curve. If you’ve only ever used OSX or iOS you will have to sit and learn Windows 10. It’s not as daunting a task as you might think. Any prior experience with Windows 7 or XP and you are more than halfway to the finish line in terms of familiarity with the operating system. The bigger hurdle is the learning curve for going towards a less paper “paperless” practice in general. However, if you want to make this change you will have to learn these new skills anyway, and in my opinion the Microsoft path is an easier choice.

You will have to take time to work with whichever hardware you wind up choosing. Using an iOS or OSX device for work isn’t as easy as it might appear. You have to do your homework on apps, and spend money on them. That is one reason why I didn’t like the iOS ecosystem for work, it does cost money for the software. Yes Office 365 also has a price tag, but it’s one I would be paying no matter what I use, and as I’ve found OneNote is still the best software for litigators and it is actually free. The App store on the other hand has a great many apps to purchase and use, some legal work apps cost as much as $90.00.

Price is a consideration. Top of the line Surface Pro 4 models will close in on $2,000.00 for a full set up (dock, keyboard, case and accessories) but so will a MacBook and iPad combination. I do think the Apple route requires both machines in the end. You will need a workstation class device to support the iPad, even the iPad Pro will need the benefits of a full PC/Mac to do the type of work we do when preparing for a trial.

Storage capacity is also a consideration. The Surface devices come as low as 64 GB (but really 128 GB is the minimum for a primary device) and as high as 1 TB of onboard memory, but it is SD card expandable, and you could plug in a USB hard drive as well. iOS devices come with a floor of 16 GB which is not going to cut it. Even the 64 GB version is probably too small to load all the apps and eventual files for multiple cases a 128 GB iPad is a bare minimum.

What about Microsoft’s notorious unreliability? In my experience with these devices since the dawn of Windows 8 I have had no outright catastrophic failures and no data loss (that sound you hear is me knocking on wood of course). I have had the occasional crash but a reboot has fixed the problem very quickly. Technology will fail from time to time, but the reliability of these modern operating systems has been very good in my experience. Users can be vigilant in making sure their devices keep working and I think a healthy separation between entertainment and work keeps a work device in better shape. Education about the easiest ways to defend against malicious attacks and software can go a long way to making sure your device is there when you need it.

Are there any noticeable differences between Surface Pro 3 and Pro 4?

I’ll start off with the conclusion; if you own a Surface Pro 3 get the Pro 4 keyboard with fingerprint reader and consider the Pro 4 pen. If you don’t already own a Surface Pro 3 go ahead and get the Pro 4. Now the why.

The Pro 3 and Pro 4 are the same size physically. They have the nearly the same dimensions but the Pro 4 has a slightly larger screen and is a bit thinner. Microsoft was able to thin out the bezels (that black border around the screen) to enlarge the touch screen size while keeping the same basic physical shape. The Pro 4 comes equipped with a Windows Hello camera for facial recognition sign-on. They also made some improvements underneath the screen for the pen. Also under the hood the Pro 4 has a Skylake Intel Core (and mobile) chipset which is two generations newer than those found in the Pro 3. The Pro 4 accessories are also improved, but the good news is these accessories will work with the Pro 3!

Let me start with the dock. This is an accessory you probably don’t need, but if you go for it, definitely get the Pro 4 dock. It will work with a SP3 but it offers much more flexibility in that you don’t have to remove your device from a protective case and can use the kickstand to its fullest extent while it stands in as a desktop workstation.

Second is the pen, this is a closer call for me. Bottom line, the SP4 Pen is more intuitive to use and has a better writing experience, the SP3 Pen might be more efficient for heavy users. The winner is the SP4 Pen, but if you are going to get the SP3 (or already own it, you don’t need to get the SP4 pen).

Finally the keyboard. The SP4 keyboard is much improved, and the slightly more expensive version with fingerprint reader gives new life to a SP3 which lacks the Windows Hello camera. If you are getting a SP4 you can skip the fingerprint reader if you like. Unlike the pen however, if you are the owner of an SP3 I do suggest getting the new keyboard with fingerprint reader.

Are there any differences between the Surface Pro and other laptops?

When a lawyer who spends a lot of time in court sits down to choose a PC device I think they have to first determine how they currently work to find out what the best fit for them will be. In my case, and I suspect many litigators, I used to have dozens of legal pads with notes, analysis, to-do lists, and outlines for every case spread around. To be precise, I did my best preparation and note taking with pen and paper. I wanted to translate that into a digital format I could search, annotate, and organize in a better way. Enter the Tablet PC. These devices have been around for a long time, but they are finally getting to the point where they are as powerful as traditional laptops and some workstations and thin enough to be a reasonable replacement for the yellow pad. When starting my search I look for a digital pen.

Digital pen equipped PC’s are available from several PC companies; Microsoft, Lenovo, Dell, HP, Toshiba, Vaio just to name some; and in a few different form factors. Most of these form factors are new hybrid style devices, whether they be foldable laptops like the Lenovo Yoga Pro line or HP Spectre 360 , or 2-in-1 devices like the Surface Pro line or Vaio Z-Canvas, or hybrids like the Surface Book where you can take the screen off of the keyboard and flip it to become a thick tablet. Finally there are smaller devices like the delightful Toshiba Encore Write 2 which is very thin if a bit underpowered for everyday use. Prices range from $300 to $2500 and beyond.

I’ll begin this by addressing the brand new Surface Book. A stunning device that almost bridges the gap between genuine laptop and hybrid tablet functionality. I think this is a wait and see device for lawyers right now for a few reasons.

First, the tablet portion when removed from the base only reports roughly 4 hours of battery time, that isn’t good enough. Second, the tablet portion doesn’t have any ports, meaning no USB, HDMI, or other accessory use when it’s detached. My first digital pen PC was the Lenovo Helix, a rip-and-flip hybrid device that suffered from a few flaws that made it less desirable for me. It got the job done, but was a little too heavy to take to court every day, and suffered from lower battery life than I’d like. It was remarkably similar to the Surface Book, but was smaller with a screen dimension size that didn’t lend itself to document work. What this means is the Surface Book is more laptop than tablet PC, and a litigator needs a Tablet PC that can become a laptop (or desktop) when needed.

So the form factor I look for is tablet PC first, laptop capability second. I do most of my work with the pen, the tablet has to be fully functional for me to consider it. Thankfully there are some PC designs that solve this problem, enter the foldable hybrids. The Yoga and Spectre 360 lines are very interesting, ultimately for me it is just a matter of preference. I don’t like my device to be that heavy, and I like to use a protective case instead of a laptop sleeve. That said, these devices equipped with a digital pen (and be careful in purchasing because not all models of these devices come with the correct technology to support a pen you have to make sure) are more than capable and a good choice if you want a little more laptop in your workflow.

The last style is thinner tablet PC which doesn’t really stand in as a laptop hybrid, but can add a keyboard in a pinch. These devices are generally powered by mobile processors and have less memory and RAM than the larger Surface Pro and HP Spectre 360 style hybrids. I think these are great as personal devices for handwriting notes, and as a backup machine on a budget.

My Recommendation

Tablet hybrid PC

If you own a Surface Pro 3 it’s not necessary to upgrade to Surface Pro 4 but consider getting the Surface Pro 4 Pen; and Surface Pro 4 Type Cover with Fingerprint ID

On a Budget?

Are you a lawyer, law student, or tech enthusiast in the market for a new device? Share your thoughts below!


7 thoughts on “Forbidden Fruit? Why the Surface Pro 4 is better than the iPad Pro for litigators.

  1. This was a great and informative article. I am a trial lawyer who started with PC and then converted my office to Apple. I just do not like TrialPad, and use sanction. Sanction will not run on a Mac device, and keynote and ppt are comparable. I also use office 365 for mac, but it works a little better on a PC,
    So my last few trials have been done on a cheap PC laptop. This is why I am looking at the surface pro 4. Thanks for great article
    Adam Sorrells
    Chico CA


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