Well, I’m not exactly what you’d call an early adopter, and I’ve only recently rediscovered a place in my heart for Apple based computing devices.

That said, there was a lot of internal debate an struggle when it came time for me to upgrade from my Cingular 8525 HTC/Phone/PDA device. Initially, I was convinced that I wanted the newest HTC the Fuze, since it was a logical upgrade from what I had. But there was just soooo much hype about the iPhone, I had to give it a fair shake. Fortunately, my sister and brother-in-law each got one a few weeks before my wife and I were due to upgrade. I got a real good chance to check them out. After seeing the HUGE amount of apps, and overall support that existed for them, the choice was easy. Sign me up, I’m a lemming..

I’ve had my iPhone for two and a half weeks, and I’ve made a lot of changes, tweaked a lot of configuration, and jailbroke the device. The rest of this post will serve to document that for my own sake should I ever have to recover the device, but also to hopefully shed some light on why you might jailbreak your phone, and what apps a techie like me finds useful.

Read more after the break…

Freedom for your phone.

Jailbreaking was a topic I couldn’t find a satisfying answer to when I started researching it.  I knew that it would give me a greater degree of control over the device, that it would allow me to install software that wasn’t offically endorsed by Apple, and that it would give me access to the innards of the device… Metaphorically speaking.  I also knew that I’d feel weak if I didn’t do it.  But that aside I couldn’t think of a compelling reason to do it, nor did I see any "killer app" that would persuade me to jailbreak if I hadn’t already made the choice based on my status in the geek community.

That said, I won’t presume to know why jailbreaking your phone appeals to you.  Instead I’m going to very thoroughly outline what jailbreaking my phone accomplished for me.

SSH The "killer app"

Apps from Cydia: OpenSSH & Insomnia

My primary computer at home runs Gentoo Linux.  Now I do dual boot to Vista because there is stuff that I have to run windows for (iTunes to sync the phone namely), but I rarely fire her up and choose the Vista option.  That said, the ability to connect to my iPhone, over WiFi using SSH is the killer app for me.  I can access the entire file structure, transfer files to and from the device, and all sorts of other good stuff.

I’m using this SSH connection to sync my iPhone’s music library with Amarok.  Now this isn’t a totally seamless proposal.  The first step is to mount your iPhone’s file system as a directory on your linux box.  You can see a fairly good outline of that here.  Then, you also have to tweak a file to tell your iPhone that the library Amarok uploaded uses a previous version of the iTunes database.  You can read about this in Amarok’s on Wiki under the Devices with Firmware 2.x section of Media Devices.  Still very cool.

The Insomnia app simply makes the phone not go to sleep after a period of inactivity.  It’ll still shut the screen off to save power, but it keeps the WiFi powered up, and SSHD running.  This allows me to stay connected via SSH without diddling the screen or something to keep my connection alive.

Sync your calendar and contacts

 Apps from Cydia: NemusSync

You may know that I use GooSync to keep up my contacts and appointments on my calendar.  The AppStore has a few apps from Synthesis AG that’ll use SyncML to sync your contacts, todo list, and calendar with your iPhone.  With that said, the calendar part does not sync with your iPhones built in calendar.  Instead it maintains it’s own calendar and syncs all your appointments to that.

That’s fine and all, and I still use their app to sync my contacts, but I wasn’t too keen on the limitation of syncing my calendar.  Enter NemusSync it properly communicates with the built in calendar.  There are limitations of course.  For instance, all it does is sync the calendar, though the author has plans to sync todo items, and contacts in a future version.  More vexing however is that it is a manual sync.  You have to go into the app, and click a button to sync up.  I’ve actually worked out a solution for that, but that’s for another article.

Springboard customization and organization

Apps from Cydia: BossPrefs, Categories, Five Icon Dock, iBlank, QuickGold, WeatherIcon

Once you start adding a bunch of apps to your iPhone it can get cluttered in a hurry.  The screen which contains all the icons for your apps has been dubbed the "Springboard" by Apple, and the list of apps above all contribute in one way or another to keeping it clutter free.

Five Icon Dock

This should be fairly self explanatory, but it’s pretty handy.  It allows you to squeeze 5 icons down in the dock instead of just 4.

BossPrefs

BossPrefs, aside from having a lot of great functionality has a Hide Icon functionality that’s quite handy.  It’ll make any icon on your springboard disappear!  Now this is only really useful in combination with something that allows you to still access that app.  That’s where Categories, and QuickGold come in.  Read on to see how!

Categories

Categories allows you to have folders on your springboard.  Once you’ve selected one of these folders, you’ll be presented with a whole new screen with the apps that are in that category presented.  I’ll admit that I had some trouble with this app, and I don’t use it a ton.  But it does help to de-clutter the Springboard in a major way

QuickGold

QuickGold is quite possibly the most used application on my whole phone.  It does what the Google app for iPhone does, and more.  Basically, when you’re on the first page of your springboard and you press the home button, a search function pops up.  As you type, it searches and presents all sorts of stuff that matches the search.  Applications, contacts, web bookmarks, SMS conversations, web clips, safari history, and more.  You can configure what items get searched, and it holds the last 6 recently launched apps in a queue for you to easily click on without searching.

Primarily, I use this to get to apps which I’ve hidden, or buried too deep with Categories.  Needless to say, a SUPER useful app.

iBlank

iBlank creates a transparent icon on your springboard which you can use to make a custom layout if you want.  To be honest, I thought this was cool when I loaded it, but haven’t really used it since the first couple days I had the phone, and I’ve deleted most of the blank icons I’d created.

WeatherIcon

Are you sick of seeing sunny, and 72 degrees when you look at the weather icon?  This simple app replaces that icon with your actual weather conditions, as configured in the weather app.  Extraordinarily simple little customization, and something that Apple should have done to begin with.

Utilities Apple Forgot

Apps from Cydia: Backgrounder, Clippy, Docs, iRealSMS, LockCalendar, Notifier, Safari Download Plug-In

Backgrounder is AWESOME!  Got some app you want to run in the background while you do something else?  Backgrounder does that.  The main thing I use it for is Pandora.  I get to listen to my Pandora radio station while I do other stuff on the phone, like play games or text!

Clippy is the clipboard that Apple forgot, and is purportedly working on for a future update.  There is another solution called hClipboard which is evidently quite good as well, but I found and installed clippy first and it’s met all my needs.

Docs..  Pretty simple, it allows you to open all sorts of document types including Microsoft Word and PDF’s.  Can’t live without it!

iRealSMS is one of the very few apps I’ve paid for, and I think it’s TOTALLY worth every penny.  It’s a replacement SMS app that adds several cool features, and most importantly for me a landscape keyboard.  They have a trial period, I encourage you to check it out.

LockCalendar allows you to see your upcoming appointments superimposed over the lock screen.  Very handy to be able to see your schedule at a glance this way.

Notifier shows missed calls, new emails, new SMS messages, and other useful bits up in your status bar just next to the battery.  I find it very handy.

Safari Download Plug-In.  Speaks for itself, allows you to download files with Safari.  Sweet. 

Total visual customization

Apps from Cydia: WinterBoard, WbApp

Some of the items I’ve talked about before require Winterboard.  Winterboard in short is the total UI customization tool for the iPhone.  It allows you to change your icons, fonts, wallpapers, colors…  Pretty much everything about how the UI is drawn can be tweaked with Winterboard.

There are several total customization themes you can download through Cydia, or pieces you can change.  Right now, I’ve hidden all of the labels for my apps on the spring board, made my status bar and dock transparent, and changed my lock screen slider to a can of Mt. Dew.  This is just scratching the surface of what you can do with Winterboard.

WbApp provides some configuration tools for Winterboard, quite handy for themes that support it.

Okay, I think that’s enough for now.  Obviously there is a lot you can do with a jailbroken iPhone and this isn’t an exhaustive list of even the stuff I have loaded, but it should give you a good feel for why you might want to make the leap to jailbreak your phone.  I know I’m glad I did.