How-To: Successfully Installing SSH on the Apple iPhone with iTunes Restore and BlueDonkey

Although the iFuntastic application makes it super easy to put custom ringtones and customize the icons on the Apple iPhone, the current version has limitations, like not being able to add files to the Apple iPhone which is a necessary element for installing 3rd party applications. For advanced stuff like that, the Apple iPhone needs to be hacked to have things like SSH installed.

Using several different Wiki's and How-To's, we were able to do the SSH install without error, but we were not able to establish an SSH connection... the connection attempt would time out. So, we re-read the WIKI's, consulted the forums, did some Googling and tried again. Same result.

Not being the types to give up and taking it somewhat personally at this point, we looked for (and tried) alternate SSH installation method's. We tried different combinations of Restoring the Apple iPhone, along with ./jailbreak vs. iFunastic vs. iActivator, and all variations of step-by-step and "easy" SSH installs. Long story short, most methods worked without error but ultimately ended with the same result of being unable to connect... the connection attempt would time out.

We pressed on, and boy are we glad that we did! As luck would have it, during yet another iTunes->Restore for the Apple iPhone, we decided to try *not* synching the Apple iPhone after the restoration, basically keeping it as close as possible to the "out of the box" product Apple intended it to be. The Apple iPhone was activated, but we did not synch it and that made all the difference. Something about synching the data *before* installing SSH turned out to be the culprit behind not being able to establish a SSH connection.

The end result? Well, after the "clean" iTunes->Restore (the one where we didn't synch the data after activation), the SSH installation process completed without a hitch and we successfully established an SSH connection to our Apple iPhone. Given that we were already able to ./jailbreak and iPHUC, being able to SSH opened up the flood gates for Apple iPhone tweaks and customizations.

In hopes that our experience will help others, here are some items of note that we discovered along the way.
  • The ModMyiPhone iPhone Skinner web site rocks. Use the file it produces (an .IPB file) along with Install IPB to easily and fully customize the look of the Apple iPhone (MAC USERS: iPhone Skinner uses a lot of AJAX and does not work with Safari. Use Camino or Firefox.)
  • The Install IPB application works best with the Apple iPhone *after* the iPhone has been "freed from jail" using iFuntastic. It doesn't seem to work right using ./jailbreak or iActivator.
  • Whatever iPhone Skinner doesn't change, iFuntastic can (like the mail alert sound or battery icons, etc.)
  • iFuntastic cannot be used to install new applications.
  • There are several "quick and easy" install programs for SSH.
  • The various "easy" SSH installers seem to work best with ./jailbreak or iActivator vs. iFuntastic. Ultimately, we preferred the package put together by BlueDonkey, due to *not* requiring the use of ./jailbreak, iActivator, iFuntastic or anything else first.
  • Using BlueDonkey's SSH install package *immediately* after a "clean" iTunes-Restore is the magical combination for getting SSH installed on the Apple iPhone in a very simply way (iFuntastic, iActivator and iPHUC were all installed, we just didn't use them because BlueDonkey's package has all the bases covered. Of course, IMMV.)
  • The ModMyiPhone WIKI's are awesome, but they must be followed precisely. If you decide to take this route, be sure to take your time and focus, Danielson.
  • Once SSH is installed and you are able to successfully SSH into your iPhone, installing 3rd party applications and customizing the Apple iPhone are a cakewalk.
  • Don't forget to change the Root password, once SSH is installed (no need to be a walking exploit waiting to happen!)
  • Installing new applications works best with iActivator, iPHUC and SSH *but* using SCP to copy the application to the iPhone instead of iPHUC works even better than SSH and can be done directly from the Terminal without an active iPHUC or iPhoneInterface connection (SSH does need to be installed before SCP will work.) Pretty much everything else you might want to do is covered by iFuntastic.
A huge thanks to everyone who offered assistance along the way. Every little bit helped and ultimately got our Apple iPhone to the state of goodness we now enjoy. Hopefully, this collection of tidbits will help other people too. Trust us, it sure feels good when the kid gloves come off!