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How to Upgrade to iOS 5 and iCloud: Tips & Tricks


Posted October 19, 2011 by Tom Slayton

While there is an abundance of iOS 5 upgrade guides available on the internet, they rarely address the small issues that can drive you crazy. After spending the weekend upgrading the 6 iOS devices in my household, I thought I would share with you what I learned.

The Installation

  1. Make sure that both your computer operating system and iTunes are running the latest versions. This is an often overlooked step that can make the rest of the upgrade process painful and rocky. Trust me; take the time to do this first.

  2. When you plug in your device, you will most likely be greeted with a notification that iOS 5 is available for download. You will also be given a choice to either “download and install” or “download only”. I recommend choosing the download only option so you can use the time it takes to retrieve the file from Apple’s servers to sync your device.

  3. Once the update has been downloaded and your device has finished syncing, it’s time for the installation. Simply press the update button and you’re off and running. Be advised, however, that the full upgrade process can take several hours, depending on how many apps/songs/movies/etc. are installed on your device. You will NOT be able to interrupt the process once it begins.

iTunes screen shot

Wireless Sync

  1. Once the update is complete, you are free to unplug your device. However, one of the best features of iOS 5 is the ability to sync your devices wirelessly. This is truly a revolutionary feature, and one that you most likely don’t want to miss out on (assuming you have a WiFi network). To enable it, leave your iPhone/iPod/iPad connected to your computer when the upgrade is complete, navigate to the summary page of the device being upgraded and check the following box: “Sync over WiFi” I also recommend selecting: “Sync only checked songs and videos” if you have a large library. This next part is important: click the “apply” button in the lower right corner. Your device will sync one last time, and when it’s done you can unplug it. You will then notice that your device is still listed in the column on the left. Clicking on it will reveal that you can add songs/videos/apps to it as you always have; except, of course, now you can do it without plugging it in first.

  2. If, like most of us, if you have not yet fully embraced the Cloud and are still using a computer running iTunes to store your media, I recommend backing up your device to your computer rather than iCloud. It will be faster, easier to retrieve, and you won’t run afoul of data caps from your ISP.

  3. If your device disappears from iTunes at this point, or simply doesn’t sync (both of these things happened to me), restart both your device and your computer.

  4. If you don’t like or recognize the name of the computer your device is syncing with on the iTunes Wifi Sync pane (Settings àGeneral àiTunes Wifi Sync), you can change that on a Mac by navigating to the Sharing pane within System Preferences.

  5. Important: Your device must be plugged in to a power source or it will not sync (although it may back-up)!


  1. When you start your iPhone/iPad/iPod for the first time after upgrading, you will be greeted by a series of iCloud setup screens. Here, you will be given the opportunity to use your current Apple ID for iCloud or get a new email address. It will be much simpler if you just use your existing email address, however, I wanted to retain my old Mobileme email address so I opted to use that one for iCloud.

  2. If you decide that you want a new email address (or are a recovering Mobileme subscriber), please be aware that you will most likely have to re-enter your Apple ID in the App Store settings screen on your iDevice as it may have been replaced with the one you just created for iCloud. Once you have both correctly set, there should be no further issues. However, forgetting to check the email address associated with the App Store could result in some future puzzlement when you try to buy apps. If you’re wondering why I don’t suggest using your Mobileme address as your Apple ID, it’s because Apple doesn’t let you. You see, when you signed-up for Mobileme, Apple cleverly created you a new Apple ID using your Mobileme email address. If you are new to the iTunes Store, this is not a problem. However, if you have already purchased anything under another email address, you are pretty much stuck with it because Apple does not let you merge accounts.



iTunes screen shot



  1. A great new feature of iOS 5 is the ability to send free text messages to anybody who is also running iOS 5. This feature works great once you get it set up, however, setting it up isn’t as straightforward as it should be. First, navigate to the Messages pane within the Settings App and make sure iMessage is enabled.  That was the easy part.

  2. Next, you will need to associate an Apple ID with iMessage. Tap on the “Receive At” button and enter an Apple ID. Feel free to use your iTunes or iCloud email address (if different); either will work. However… Do you remember the part about migrated Mobileme email addresses being a pain? Well, you will feel it here too because you won’t be able to use your newly transferred address unless you also use that email address as your iMessage Apple ID. This frustrated me because I use both email addresses to communicate daily, and wanted both of them associated with iMessage.

  3. You will know if iMessage is being used because the text bubbles within the messaging app will be blue. If you are using SMS through your carrier they will be green.  I initially had some difficulty getting iMessage kickstarted for some reason. My solution was to navigate to the contact sheet for the individual I was trying to communicate with, and tapping “Send Message” button. This initiated a new conversation using iMessage rather than simply tacking the message onto my existing conversation. Give this a try if your texts don’t turn blue.

  4. Remember, iMessage only works if both the sender and the recipient are using iOS 5 AND they have enabled iMessage on their device.

iPhone screen shot


  1. Photostream is a way to sync your photos across all of your devices, including your computer. It is disabled by default. To enable it, navigate to the iCloud pane with the Settings App and select it. It achieves this wondrous feat by uploading all of your photos to iCloud and downloading them to your linked devices when you are connected to Wifi.

  2. If you inadvertently upload pictures that you wish you hadn’t, do not despair. Turn off Photostream on all devices and then log into Once there, click on your name, click on “Advanced,” and select “Reset Photo Stream.” You will be given the opportunity to first download all photos in the stream in case you have any there that you want to keep. When you enable Photostream on your devices, you will find that all of your photos that were once languishing in iCloud are now gone.

iPhone screen shot


Now you're ready to enjoy your iPhone, iPad or iPod Touch running iOS 5!


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