Act Now to Secure Your iOS Device

This article originally appeared on the Affinity Consulting blog on legal technology.

On Friday, February 21st, Apple released a seemingly innocuous update to their iOS operating system, update 7.0.6. You should be forgiven for not thinking much of this. Most 0.0.x updates fix minor bugs addressing specific user situations. For example, 7.0.5 was not even released to iOS users outside of China since the fixes and updates in that release were Chinese-specific. Update 7.0.6 is dramatically different from previous 0.0.x updates.

Despite the minor-update version number, iOS 7.0.6 fixes a critical flaw in iOS security related to accessing secure websites, like your bank. If you're running any version of iOS 7 prior to 7.0.6 or a version of iOS 6 prior to 6.1.6, this bug effects your iPhone and iPad. The respective updates are free and can be applied directly from your iDevice by going to Settings > General > Software Update. Download and install any available updates.

Background on the Flaw

You should apply the update; no question about it. If you're interested in the background of what the flaw means, keep reading.

The flaw existing in iOS prior to 7.0.6 and 6.1.6 effects how the operating system and apps handle secure connections over https connections; again, like your bank, online shopping, secure email, etc. These https connections rely on protocols called SSL and TLS. When your device reaches out to make a secure connection with a web service, the service and your device perform what programmers call a "handshake" to negotiate how they're going to talk to one another. The iOS flaw allows a nefarious third party to intercept your communication with the web service and read all of the traffic going each way. In security parlance, this is called a "man in the middle" attack because the bad actor inserts himself into the middle of your conversation for purposes of stealing passwords or other confidential data.

If you'd like more technical details on the vulnerability, here are some excellent resources:

Final Note

For those of you who, in addition to using iPhones and iPads, also use Macs, there's an additional bit of bad news. The same flaw that iOS suffers also exists in Mac OS 10.9 Mavericks, the latest release of Apple's operating system. Versions of Mac OS prior to 10.9 are unaffected. There is also a patch for Mac OS, update 10.9.2, which addresses this vulnerability. You should apply it as soon as possible. For those not updating immediately, it's our advice for users of 10.9 and 10.9.1 to rely on Chrome or FireFox instead of Safari for web browsing, and to avoid unsecured wireless networks (although that last bit is always and everywhere good advice).

Being Thankful for Fellow Mac-Loving Attorneys

This article originally appeared on the Affinity Consulting November 2013 newsletter on legal technology.

Having just wrapped up a week of conferences in Florida, I'm happy to be back home in Ohio. Although, of course, it was pleasant to escape late fall temperatures and spend time in Ft. Lauderdale and Orlando, at Disney World. The first of my two conferences was mostly work, training default services law firms on case management software. But the second, MILOfest, which I mentioned in August's column, was a fun and festive opportunity to meet with fellow Mac-loving attorneys, and learn some new tips, tricks, and software. I thought an excellent article would be to recap some of the cool things from the conference and encourage you to mark your calendars for next October.

Mac Power Users

Katie Floyd, of Mac Power Users fame, gave two excellent talks. The first highlighted her life as a Mac-using attorney in a firm that is otherwise all PC. The impetus for her bringing a Mac to the office was her desire to use OmniFocus to manage both her personal and work projects. She was fortunate in that she worked in a relatively small firm (seven attorneys) and served as the unofficial IT director. In her setup discussions, she talked about how to get Spotlight to index network drives (a terminal command: mdutil /Volumes/volumename -i on), the use of a Hazel rule to record completed OmniFocus tasks in Day One, and how to use your TextExpander snippets on Windows with a tool called Breevy, if you're stuck on a PC sometimes.

Katie's second talk focused on advanced use of Evernote as her "everything bucket" for notes, webpages, and other "paperish" things that she wants to store. In addition to storing text notes, searchable text and pdf documents, Katie demonstrated how she used Evernote to track her home-building project. She scanned in everything from blueprints to paint can lids (for future color-matching) into Evernote. And since Evernote syncs to any mainstream device, she could pull that information up anytime, anywhere, such as when the contract put the window frames in the wrong place in her guest bedroom. Katie pulled up the blueprints right on her iPad and showed him how the physical building did not match the plans. Per Katie's recommendation, the best starting point for the Evernote newbie is Brett Kelly's Evernote Essentials book.

Acrobat Deep-Dive

One of the presentations I felt was particularly helpful, and wish had been longer was Justin Kahn's dive into Adobe Acrobat. Justin has years of experience using Acrobat in the most advanced ways. He's not only a real-life magician (the card tricks at Thursday's dinner were amazing), but he's an Acrobat magician too. Justin's talk started with basic tips (like using the advanced "search" by hitting Shift+Command+F versus the simple "find" dropdown you get by hitting Command+F) and moved swiftly to more "Ph.D" level topics like the relative merits of OCRing with "searchable image" versus "Clearscan". His preference is generally for "searchable image" for its smaller file size, but "Clearscan" if you intend to copy and paste text from the PDF into a word processor. Finally, for additional information on Acrobat's capabilities and "how to" demos, Justin recommended Adobe TV's Acrobat videos.

The Legal Business

Macs are the reason MILOfest exists, but the conference doesn't just focus on cool tools, programs, and websites, although it has its share of those. It also focuses on the business of law and the practice of law. To that end, we had a couple of fascinating presentations on attracting business and working in growing practice areas.

Mark Merenda of Smart Marketing presented on how to attractive websites and how to draw people to your firm. Make sure your website focuses on people, not abstractions. Your site should have videos because the number one activity on the Internet is watching videos. But, be sure to post a transcript as well since search engines cannot index videos. Videos are popular because most people view reading as work whereas watching is entertainment. Videos should be the "welcome mat" for your site.

The three most important pages on a website are the videos, the "meet the team" or "about" page, and directions to your office. In Mark's experience, people who hire an attorney are generally not qualified to judge an attorney's competence. They will hire you because they like you. If you have the choice between being a great marketer and a great attorney, be a great marketer. You can always hire attorneys. There are plenty of brilliant attorneys who need jobs.

In conclusion, Mark said that if you're not happy with your site's ability to draw in business, try something new. Life rewards action and ruthlessly punishes inaction. Every inch of a website is someplace to be creative.

On the last day of the conference, Steve Riley of Atticus discussed guiding your practice into profitable, growing markets. He began by discussing shocking statistics. In 1968 there were 168,000 lawyers in America. Today there are 1,250,000. In Washington D.C., there is one attorney for every 25 people. The proliferation of lawyers is driven by law schools which, after football programs, are the most profitable part of most universities. According to the Wall Street Journal, in the 2011 class of law school graduates, only 50% had a job utilizing their degree. The "do it yourself" LegalZoom does $125 million per year. A foreclosure firm is now hiring associate attorneys in Panama to do American foreclosure work. Pretty shocking stuff.

To compete with this market, Steve encouraged us to narrow your niche of practice to avoid being commoditized, where technology and automation can compete on price. Second, create experiences that clients appreciate. Anytime you can improve a commodity product, you're moving closer to something unique and valuable. Use technology strategically, such as document assembly, because you want lawyers being face-to-face with clients, not spending their days drafting documents in front of a computer. Build a referral portfolio where, ideally, at least 100 attorneys see you as the go-to guy for a particular niche. Try to build recurring revenue streams so that overhead and payroll can be met by this revenue, freeing you from thinking month-to-month and focus on long-term growth. Finally, look for new practice areas. Steve mentioned a story about two granddaughters who spent $25,000 fighting over a deceased grandma's pie plate. It might sound ridiculous, but digital profiles like Facebook pages are the pie plates of the future.


In addition to those presentations I described, we had many fabulous Mac tips and tools talks including: Mitch Adel & Bob Kueppers of Cooper, Adel & Associates discussing their experience of running a 45-employee law firm on Macs; Brett Burney on iCloud; Randy Juip on Keynote presentations; Mark Metzger on 1Password; and Larry Staton on powerful automation and macros using Hazel and Keyboard Maestro. Not to mention Disney World and beautiful weather. It was a blast.

Next year's MILOfest is set for October 23-25, 2014. Mark your calendars!

Avoiding Some Scary Internet Problems

This article originally appeared on the Affinity Consulting October 2013 newsletter on legal technology.

As Mac users, we're accustomed to ignoring most of the scary IT stories that surface in the Windows' world. Fundamental weaknesses like viruses, root kits, and even device driver conflicts are scarce to non-existent on the Mac. Thank god. But, that doesn't mean that we're immune to all computer-related hauntings. Let's tackle a couple of those this October.

Plugins Be Gone

We Mac and Windows users share the same Internet. And, despite the Web's reduced dependence on third-party plugins to display content, most users still have a few core plugins that they install in Safari, or their browser of choice. These are Flash, Acrobat Reader, and Java. As Apple, and particularly Microsoft, work diligently to harden their respective operating systems from intrusion, hackers have started to look at third-party programs for ways to invade and infect your computer.

Adobe Reader

It's worth noting that none of these three programs come installed by default on your Mac. If you open a new Mac out-of-the-box, and never install these three plugins, you're as safe as can be from the potential pitfalls of these add-ins. In lieu of Adobe's admittedly bloated Reader program, every Mac comes with Apple's own PDF reader and light editor, Preview. For day-to-day use, and certainly for reading PDFs on the Internet, Preview is more than capable. It's regularly updated by Apple. It also, honestly, has fewer features (such as the inability to execute Javascript) that make it less vulnerable than Adobe's Reader. Unless you can name a reason that you need Adobe's Reader over Preview, in which case you have or someone in your IT organization has hopefully made an informed choice, there's no need to install Reader. If you do need it, Adobe releases patches and security updates at least quarterly, and sometimes more often if critical vulnerabilities are exposed in the intervening time. To ensure that you're running the most current version of Adobe Reader (11.04. as of this writing), launch Reader and then click on Help > Check for Updates. If there's an update for your version, Reader will download and install it.

Adobe Flash

After PDF reading, the most common plugin legal professionals might need is Adobe's Flash. Since this plugin also comes from Adobe, you have a similar likelihood for vulnerabilities and the same quarterly security patch schedule. Thankfully, in large part because of the rise of iOS and Android mobile devices, none of which run Flash, this plugin is gradually being supplanted by HTML5 technologies, which are built in to all modern browsers including Safari on the Mac and iOS. However, you will still encounter this plugin for websites on Macs. Depending on your philosophical stance on Flash, you can take one of two approaches.

The first is to download and install Flash in your browser of choice, and then make sure to check regularly for updates (System Preferences > Flash), or check the option that lets Flash check for updates regularly on its own. This method is the simplest and most straight-forward. The second option is to not install Flash in Safari (or Firefox), but to download Google's Chrome browser and use it exclusively for sites requiring Flash. Chrome's installation includes a Flash viewer that is sandboxed within Chrome, and which Google updates automatically as it updates Chrome itself. You can still view the overwhelming majority of sites in Safari, and install extensions like YouTube5 for Flash-heavy websites that still require Flash despite working perfectly fine as HTML sites when accessed by mobile browsers.

The second method - Google Chrome for Flash-only sites - is the one I use and prefer, but it does require a conscious choice to use two browsers; Safari or Firefox for general purpose browsing and Chrome for Flash-requiring websites. Using this approach means tolerating those times when you land on a website in Safari, where it doesn't work properly, and then copy the web address, launch Chrome, and paste the address there. If you can become accustomed to this approach, it is safer and, if you're using a laptop, you may see improved battery life because Flash is known to be a battery drain.


Recently, we've seen no end to Java vulnerabilities. The current release, version 7, was launched in July 2001, and has seen 40 patch cycles. These subsequent releases include fixes for 30 vulnerabilities in update 9 in October 2012, 50 vulnerabilities in update 13 in February 2013, and 42 in update 21 in April, and 40 more in update 25 in June. One could make two arguably contradictory arguments at this point: 1) Java is patched and updated often, and 2) If Java 7 has been out for more than two years and their still patching 25 vulnerabilities in month 23 after the release, how many more remain undiscovered.

I tend to lean in favor of the second view, and avoid installing Java if I can. That being said, Java can play two roles on your Mac. The first, and relatively safer one, is as part of a desktop application used for strictly desktop purposes. An example of this would be NeoOffice, an open-source office suite. There are other desktop programs that require Java. Installing it for those purposes is fine.

What you want to avoid is installing Java and letting it be active in Safari or your web browser of choice. If you've determined that you need Java installed, and have installed it from, make sure to go to Safari > Preferences > Security, and uncheck "Allow Java". This will allow you to use desktop apps that require Java without exposing this plugin to the Internet.


Hopefully this article protects your browser and computer from some of the scary parts of the Internet. Feel free to reach out if you have questions.

Fresh Apple Season is Upon Us

This article originally appeared on the Affinity Consulting September 2013 newsletter on legal technology.

One of the best things about using Apple products is that, as a consumer-centric company, they understand the value of making a marketing splash heading into the Christmas season. At June's Worldwide Developers Conference, we were teased we many new products for fall. Now it's nearly time for those products to reach our hands.

What's New

This fall, Apple will release new versions of Mac OS X and iOS. In addition to software, we're likely to see new MacBook Pros based on Intel's latest Haswell) microprocessors, with battery life similar to the 12 hours observed in the new MacBook Airs. We should also see the completely redesigned Mac Pro which, while undeniably stylish, innovative, and powerful, is also undoubtedly overkill for what legal professionals do. This is probably a good thing given that its rumored starting price is "guestimated" at north of $3,500. All of these Mac introductions don't include the new iPhones, rumored to be revealed on September 10, and new iPads and iPad minis. And, of course, revised iPods, if you are among the few who care.

Lets Focus on Software

The primary excitement, assuming you're not in the market for new hardware, should focus on the revisions to iOS and Mac OS X. Fortunately, these are also the two cheapest things you can acquire from Apple this fall. As has been true for all iOS releases for iPhone and iPad, iOS 7 will be free. The only requirement is that your iDevice is sufficiently new to run it. Check the bottom of this page to see if your iDevice made the cut. With the new version of Mac OS X, named Mavericks, after a surfing spot) in California, no pricing or system requirements have been announced. However, given past releases, I would expect a price of about $20, and that most Macs that run Mountain Lion can run Mavericks.

iOS' New Features

iOS 7 is the first version of Apple's mobile OS overseen by its famed designer Jonathan Ive. The man responsible for Apple's hardware look is now also in charge of software appearance. Therefore, iOS features an entirely new look. All of the icons have a "flatter" appearance and the entire user interface is more colorful and brighter than before. The system has more whitespace and interface elements (buttons, etc.) aren't as "heavy" in appearance.

In addition to the new visual appearance, Apple has also added many new features to make your iDevice more useful and fun:

  • Control Center - This does for system functions (WiFi, Bluetooth, Lock Screen, Time, etc.) what notification center did for pop-ups in iOS 4. The Control Center is an easy swipe-up from the bottom of the screen to access these often-used functions.
  • Improved Multitasking - Application switching is now much more visual. You can swipe through running applications horizontally and close them by swiping upwards on the screen. In the background, applications group their data requests so that the iDevice only has to fire up the cellular radio one time and bulk-download data updates for multiple apps at once. Ultimately, this translates into less battery drain and therefore longer battery life.
  • Camera / Photos - Apple has added filters to the camera app, so that you can change the image straight from the built-in camera without relying on an external app. Regarding photos, they've also added new sorting features so that the Photos app automatically divides pics by collections.
  • AirDrop - This is a really cool feature. It allows you to share content with other nearby iDevices over Bluetooth. The setup is automatic, and there's no physical connection or even "bumping", ala the recent Samsung commercials.
  • Safari - In addition to faster performance, and improved image handling, Safari now has the ability to store passwords in iCloud, which sync back to any Mac running the Mavericks version of OS X. It also has the ability to create secure passwords, so you no longer have an excuse to use "password" as your website passwords. Please stop doing that even if you don't upgrade to iOS 7.
  • The App Store - It gets the simplest, but nicest upgrade that you can think of: apps will automatically upgrade themselves in the background. No more constant number badges on the app icon. Maybe we can thank John McCain for this feature.

Mac OS X Mavericks New Features

The changes to Mavericks are not as fundamental as those to iOS 7. If you think about this, it make sense given that desktop operating systems are approaching 30 years old versus just six for iOS. But, there are some new features to celebrate:

  • Calendar - This application has finally been rethought and no longer has the hideous and stupid leather color scheme. You can now schedule "travel time" automatically before appointments, and have the system calculate that time to your destination. Relying on the new Maps app in Mavericks, the Calendar app can show you the location of your calendar event and the weather forecast for that location.
  • iCloud Keychain - I mentioned this under the "Safari" description for iOS 7, but it is also integrated into Mavericks. Your passwords and other information you store in Keychain syncs automatically between all your Apple products.
  • Multiple Displays - Anyone who has used Macs with multiple displays has probably experienced the same nuisance. When you make a single app fullscreen, it turns the "subordinate" display into a linen black background. You can't use it for anything. Apple has finally fixed that in Mavericks. Now you can have multiple apps running fullscreen, one on each monitor. And each monitor can have its own menubar at the top, so there's no more turning from one monitor with the app to another with the menubar. Its sort of a dull thing to describe, but this is one of those "sleeper" features that you'll use every day if you have multiple monitors.
  • Finder - The Finder, one of the few features of Mac OS that everyone uses everyday, has a couple of excellent enhancements. First, you can have a tabbed view on Finder windows, just like you do now with your web browser. Second, you can now add "tags" to individual files. The idea of tags is not new, and we've had labels in the Finder for years. But now, in addition to using labels to color file names, you can now "tag" files in the save dialog box, i.e. "Smith Proposal", to multiple file types in different applications. And the number of different tags you can have is limitless.

As I said, no pricing has been announced, but the last updates to Mac OS X have been very affordable as operating systems go - about $20 through the Mac App Store.


As you can see, the fall will be an exciting time to be a Mac user and iOS aficionado. The new hardware should be excellent, but the coolest new features will come for virtually free on your existing hardware.

If you have any questions about these or any of Apple's upcoming releases, please give me a call at (614) 602-5491 or email at

Meet Fellow Mac Lawyers

This article originally appeared on the Affinity Consulting August 2013 newsletter on legal technology.

In the Beginning

Much like Apple's other businesses, Mac sales have grown remarkably in recent years. At first it was the "halo effect" of folks buying first an iPod and then a Mac. Then came the iPhone and the iPad, both of which spurred additional Mac sales. Previous Windows-only bastions fell as employees demanded IT departments adapt to Apple products. At some firms, this change was motivated by "C-level" employees demanding that company email work with their new devices. At others, "bring your own device" policies drove platform variety into the mainstream. This device variety was further enabled by cloud computing and other platform-agnostic technologies.

The Office Today

I think it's fair to say that today's office is very different from the 1990s. In the legal environment, we see the rise of web-based case-management software like RocketMatter, Clio, and even old-line firms like Amicus Attorney going into the cloud. None of these solutions requires more than a web browser to access case data. All work perfectly well with Safari on the Mac. And that's just one example of flexible computing in the modern law office.

But without knowing the available resources, you're left to wonder what your Mac can do in a formerly PC-centric environment. That's what I'm going to share with you today.

Socialize Your Mac to the Law Firm

The first thing to know is that you are neither the first nor the only attorney working on a Mac. There are many networking resources out there to help you maximize your Mac in your law practice.

1) The first resource I recommend is the Macs In Law Office Google Group. This group operates as a traditional listserv (for those of you who've been on the Internet long enough to remember such things). You can subscribe to receive either every message sent to the group or just daily summaries of the topics discussed. This community is an excellent resource to address your Mac concerns, ask about Mac-specific case management apps, like Daylite, or just which scanner or printer work best in a Mac office environment.

2) A second great resource are the blogs and Twitter feeds that cater to Mac-using attorneys. These are, of course, free to all, and serve as a tremendous resource for innovative Mac tools in the law office. Two of my favorites are David Sparks' blog, MacSparky, and Ben Stevens' blog, The Mac Lawyer.

David not only practices full time in California and maintains a lively Mac law office blog, but he has also published three iBooks on Mac technology, including launching your paperless office and using Mac OS X 10.8, Mountain Lion, more effectively. He also hosts a weekly Mac office podcast, Mac Power Users.

Ben, also a full time attorney, is a frequent author and presenter on the subject of using Macs in law. A great place to start is his 2012 ABA article, The Fine Art of Practicing Law on a Mac.

3) Many (most?) of we Mac-using attorneys also rely on iOS devices. If that crowd includes you, avail yourself of Jeff Richardson's iPhone J.D. blog. He reviews both products and legal-specific apps, giving detailed usage scenarios where the product or app makes sense, and whether it lives up to the marketers' hype.

4) Finally, meeting other users on the Internet is helpful and convenient, but it doesn't always make up for personal, face-to-face contact with fellow Mac-using lawyers. Given the rising popularity of Macs in legal offices, and the hard work of recent ABA TechShow planners, the country's largest technology event for lawyers includes a full "Mac track" on effectively using your Mac to practice law. If you're not able to attend the annual April show in Chicago, or prefer something warmer and more relaxing than Chicago in Spring, I highly recommend the much more intimate, and thoroughly enjoyable MILOfest Conference.

MILOfest is an outgrowth of the MILO listserv I mentioned above, and the brainchild of MILO member, and practicing New Jersey attorney, Victor Medina. This conference, now in its fifth year, is coming up in October at Disney World in Florida. The conference is affordable as legal conferences go, $700 if you register before September 24th. In addition to the opportunity to learn from and socialize with Mac legal enthusiasts, you also gain reduced fee hotel and tickets to Disney in the heart of a Florida Fall. Take a look at the schedule and see if the topics interest you.


Hopefully this article provided you with some useful social networking resources to better use Macs in the your law office. As always, if you have questions or want additional information, feel free to contact me. And I hope to see you at MILOfest this October.