Apple rolled out the much-anticipated iOS 5 upgrade on Wednesday, bringing a bevy of helpful new features for music fans. However, the upgrade process is not going smoothly for everyone.
Here’s what happened the first two times I tried to update my iPhone 4 to Apple’s new iOS 5 operating system on Wednesday:

The same thing is happening to at least five of my friends. Others report that they installed the update in minutes with no problem. At this point, there’s no way to know how widespread the problem is, although there certainly is one. (Please let me know if it’s happening to you.)
After the second fail, I followed each of Apple’s recommendations:
1. Yes, I have the latest version of iTunes (10.5).
2. I updated a bunch of unrelated programs including iPhoto and Safari, on Apple’s recommendation, and restarted my computer as required.
3. I disconnected other USB devices. (During the first fail, I had an iPad plugged in.)
4. I don’t have any weird security settings, although my router was not made by Apple.
5. I restarted my computer (again).
Once again, the “Backing up ‘iPhone’” progress meter made scant progress, even after over twenty minutes:
Lo and behold, we encountered a third fail, even after exhausting Apple’s list of suggestions:
At least this time Apple gives us an error number, which yields the following suggestion:
If the steps listed in Error 3000-3999 do not resolve the issue, and you are using a Mac, you may be able to resolve an error 3004 by quitting iTunes and using the following command at the command line: dscacheutil -flushcache
Command line? I do remember encountering a similar cache flushing issue with a blogging tool at one point, but this is clearly not the “ready for primetime” experience we expect from Apple — and it’s even more frightening that the problem only seems to affect Macs.
We’re going to try that suggestion, and will keep updating this story as things progress. Even if it works, Apple’s iOS 5 upgrade process appears to be a pretty serious fail in some cases — one we have corroborated with multiple other iPhone users.
For now, my iPhone is bricked:
And my only option is to restore the iPhone to factory settings, losing all contacts. I have no choice but to trust that Apple will later be able to give me my contacts back… and right now, I don’t have a lot of trust in the process:
I bit the bullet and allowed Apple, which doesn’t have a lot of my trust right now, to delete everything on my phone. Then iTunes told me that Apple’s servers are down. This is bad.
Apple’s servers came back up, but error 3004 strikes again:
I tried the command line trick that Apple recommends for error 3004 for a second time:
My iPhone is still bricked. I’ll let the following screenshots speak for themselves.
Ready:
Set:
Caveat emptor.
Update: My iPhone became bricked — as in it couldn’t boot up, and iTunes couldn’t recognize it. If that happens to you too, follow the below directions from Apple, then keep trying to Restore your iPhone until you can then install iOS 5. I just tried it and while iTunes failed (for the umpteenth time) to restore my iPhone, at least it lets iTunes recognize your iPhone, which is a start. Here’s how to make iTunes recognize your iPhone again, so that you at least have a fighting chance of unbricking your iPhone (thanks for the suggestion, Josh Newman):
1. Disconnect the USB cable from the iPhone or iPod touch, but leave the other end of the cable connected to your computer’s USB port.
2. Turn off the device: Press and hold the Sleep/Wake button for a few seconds until the red slider appears, then slide the slider. Wait for the the iPhone or iPod touch to turn off.
▪ If you cannot turn off the device using the slider, press and hold the Sleep/Wake and Home buttons at the same time. When the device turns off, release the Sleep/Wake and Home buttons.
3. While pressing and holding the Home button, reconnect the USB cable to iPhone. When you reconnect the USB cable to iPhone, the device should power on.
Note: If you see the screen pictured below, let the device charge for at least ten minutes to ensure the battery has some charge and then start with step 2 again.
4. Continue holding the Home button until you see the “Connect to iTunes” screen. When this screen appears you can release the Home button:
5. If necessary, open iTunes. You should see the following “recovery mode” alert:
6. Use iTunes to restore the device.
However, be forewarned — just because iTunes can recognize your iPhone is no guarantee that Apple’s servers will be up to the task of upgrading your iPhone. Even after following these instructions, I ended up here once again:
Update 7:30pm ET: Apple’s iOS 5 servers are still down or too busy to serve the update. My iPhone remains in limbo:
7:54pm ET: Restore is finally in progress. I started this process about six hours ago:
8:11pm ET: It’s alive. Sort of.
8:14pm ET: It’s restoring my apps. I had over 250:
8:31pm ET: The iPhone is usable again, and iCloud is installing (there wasn’t enough storage in the free 5GB iCloud to back up my 32GB iPhone 4 for free, but that’s a different story):
9:08pm ET: Apps almost restored (it finished shortly thereafter):
Now for the iPad.
10:40pm ET:
11:56pm ET:
8:34am ET: The iPad update seems to be going a lot smoother this morning. The install didn’t happen last night, but the iOS 5 installer for iPad downloaded in about ten minutes this morning. It’s restoring the apps:
Our iPad upgrade failed too, although not as badly: See part two of this 22-hour saga.











