I’m a Lawyer, should I get an iPhone? | Part One

Posted on March 19, 2010 | by Derrick

After getting involved in a “Blackberry versus iPhone” thread on LinkedIn, I thought it might make sense to write a series of posts about my experience transitioning to the iPhone after being a Blackberry user for as long as they’ve existed.  This is not meant to be a comprehensive comparison of every feature.  If you want that, there are lots of reviews out there.  I also realize that these aren’t the only two options.  Android is starting to become a player, and you’ve also got your Palm Pre and what not, but most lawyers I know use a Blackberry, and many of those that do wish they could switch to an iPhone.  Part One will focus on email and isn’t particularly lawyer-specific, but once I get to applications, you’ll see a definite emphasis on the legal industry.  One disclaimer – the last Blackberry I actively used was a Curve, so if some of their newer features make certain of these points moot, I apologize in advance.  My understanding is that the OS hasn’t changed drastically with the newer devices, but please feel free to comment on any inconsistencies you see.  Here we go.

Email Configuration

The Blackberry is unmatched as an email device.  Let’s get that out of the way right now.  If you want the ultimate email solution, and you don’t care about anything else, then don’t even bother with the iPhone.  If you care at least a little bit about other features, then keep reading.

The iPhone has several different methods of email retrieval.  I have tried nearly all of them, and the only one I can really tolerate requires setting up your primary mail account to access an Exchange server.


Exchange is a centralized server that hosts your email, calendar and contacts.  No matter how you access your information, changes are made on the server, so when you access it again from somewhere else, the changes are instantly seen.  Add a contact, send an email, remove a calendar event on your iPhone; you will see the results next time you open Outlook.  All of this is synchronized and managed wirelessly.

Depending on a variety of factors, this option could cost you a little extra.  AT&T (or Apple, who knows…) wants you to pay an additional service fee in order to hit an Exchange server.  I have two points of reference to provide on this issue.  First, while I was still accessing email at my previous employer – I set up an Exchange account using my webmail credentials, and it seemed to work fine without having any extra services added to my AT&T account.

My second experience is with Google Apps and Google Sync.  At Core, we use Google as the backbone of our email system, and Google Sync acts as an Exchange server of some sort and does a great job of syncing email, calendar and contacts.

If neither of these options work, and you do have an Exchange account at your firm, you might be stuck with an extra $15 charge on your bill.  If your firm doesn’t use Exchange, keep reading.


I’m not going to get into this option too much for a couple of reasons.  Unless your firm is Mac-based, you probably aren’t going to be set up to use MobileMe.  And if you aren’t Mac-based at home, and you don’t want to pay $100 a year, and you don’t want to primarily use a new email address, then this is not a great solution for business.  Now after reading that rave review, if you still want to read up on it, go here.


These options are great for personal email accounts, but generally not business-oriented.  So I will skip them as well.  As I mentioned before, we do use Google as our company email server, but it works best to configure it as an Exchange server.

Other (IMAP / POP3)

If you don’t have an Exchange server managing everything, then things start to get a little trickier.

First, let me provide an overly simplified explanation of email protocols.  You’ve probably seen the term POP or POP3 before.  Back in the day, this was the primary way to access your email.  Lots of people today still configure their email clients to access email via POP or Post Office Protocol.  How it works is not really relevant (thank goodness, because I have no idea), but the bottom line is that your email application always downloads ALL messages that reside on the server.  If you have 50 emails out there, it will download the content of all fifty of them when you hit “Send and Receive”, whether you want to read them all or not.  Those emails then live on your local computer, and unless you previously checked the box in Outlook that says “Leave Messages on Server”, they ONLY reside on your local computer and are no longer on the server.   Even if you do check that box, each new computer you use to download messages has no knowledge of what has been previously downloaded, so it thinks everything on the server is new.  And, when you send an email from that local computer, it only resides in the “Sent Items” folder of that computer.

IMAP, on the other hand, is more like a portal into the server.  When you see a list of messages configured via IMAP, you are essentially looking at those messages on the server (or a downloaded list of those messages, not the messages themselves).  Only the messages you choose to read are fully downloaded or loaded into memory.  And with IMAP, when you read a message, it is tagged on the server as being read.  If you then access the account from another computer, you will immediately know what has been read and what hasn’t.  In this way, it behaves a bit like Exchange – but only for email.  Also, with an IMAP account, items you send from a local computer generally show up in the server’s “Sent Items” folder – depending on your configuration.  Now considering that you are constantly hitting the server, it can be a little frustrating if you aren’t on a stable internet connection during an entire session of reviewing messages.  Since you only download what you are accessing at the moment, the local computer polls the server each time it needs to open a new message.

As I said, this is all oversimplified, and there are features such as caching that can affect what resides on the server versus the local computer.  But generally, I think that about covers the basic initial configuration options.  Next I’ll discuss retrieving mail from these various servers.

Push or Fetch?

There are two ways to retrieve mail from a server on the iPhone.  “Push” or “Fetch”.  In simple terms, a Push service notifies you immediately when an email hits the server.  Alternatively, a Fetch service polls the email server at specified intervals to determine if there are any new messages.  For a variety of reasons, a Push configuration is far superior, but there are two main reasons that I consider it the only way to go.  On a non-jailbroken iPhone (more on that in a later post), the shortest interval you can set to check for new messages is 15 minutes.  That may not seem like a long time, but for business, that can be an eternity when you are in a crunch.  Secondly, the process of polling the server every 15 minutes – whether you have any new messages to check or not – is a drain on the battery.  So, I consider it a lose/lose option.

An Exchange server supports Push.  It pushes emails, contacts and calendar updates, and it’s great.  Any of the “Other” iPhone mail configuration options that are suitable for business are Fetch-based.  Not so good.  However, there is a workaround if you are stuck without an Exchange server. There are several apps on the Apple App Store that can be configured to serve as a middle-man to push new email notifications to your iPhone.  Why the iPhone isn’t set up to do this by default is beyond me, but whatever.  These apps work by allowing you to forward a copy of your emails to a throwaway email address that does nothing more than push notifications to an app on your iPhone.  The app I like is creatively titled “Pushmail”, and sits on my iPhone ready to notify me when I receive a message on one of my personal accounts.  To configure this, I accessed my gmail settings page and configured all incoming mail to also forward a copy to [myusername]@dopushmail.com, then when a new mail gets forwarded to that address, it pings my iPhone.  As a result, I know to open up the webmail link on my phone and have it check for new mail.  But using this configuration, I can have Fetch completely turned off on my iPhone, thus saving valuable battery power.

One important thing to note here is that a Blackberry that does not interface with a BES (Blackberry Enterprise Server), would be faced with some of these same issues.  It is just rare for a firm to deploy a lot of Blackberrys without a BES because it really handicaps the device.  Without a BES, the Blackberry works most like the iPhone’s Mobile Me option, but without the $99 subscription fee.


The iPhone email application is pretty nice if you don’t try to make it do too much.  Those of you that are used to the Blackberry mail program will notice several key differences.  First, the Blackberry has the ability to combine multiple accounts into one inbox.  The iPhone can’t do that.  Secondly, your Blackberry can show both sent and received mail in that same inbox.  The iPhone can’t do that either.  Thirdly, if you do decide to split your accounts into separate icons on your Blackberry, it is very easy to jump from viewing one account to the other.  On the iPhone, it is an annoying process to back out of the current account you are viewing, then drill back down into another one.

In light of these differences, I have had the best luck setting up only one account in the iPhone’s native mail application.  I use it to access my work account and that’s it.  If you have multiple accounts you want to check, I recommend using a separate personal application for that mail service (Yahoo, Gmail, etc), or by accessing it via webmail on the iPhone’s web browser.  By splitting things up this way, your iPhone mail app is always focused on the correct account, ready to go as soon as you open it.

The iPhone interface is slick.  Reading email is a very pleasant experience and feels like you are viewing it on a computer.  As with a Blackberry, default attachment viewing can be hit or miss.  Frankly, I can’t really remember what works by default and what requires 3rd-party apps, but I am able to view PDFs and most Office files pretty well on my iPhone.  There are numerous apps out there for viewing and editing various file types, and I think a former Blackberry user would be at least as pleased as they were with the Blackberry functionality.  And considering the screen size of the iPhone, and the ability to switch to landscape mode, you have plenty of screen real estate to view that spreadsheet.


On the merits of email alone, I don’t think the iPhone has enough going for it to make it worth the switch.  I find it perfectly acceptable, but it certainly doesn’t break any new ground, and if anything, adds a few annoyances.  Typing is another factor, but I will focus on the keyboard in another post.

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