Updates All Around


Guy surrounded by techIt seems like ever computer or computer-like device I have received significant updates in the past couple of days. The 8 security updates for my Windows 7 PCs and VMs were the least time-consuming updates, much to my surprise. Apple released iOS 5 today so the last couple of days have seen related updates from apps to operating systems. Let’s not forget all those iPhone/iPad apps that have been updated in the last few days. With new iPhones arriving on Friday (or before) I figured I better work on upgrading my phone as soon as possible, or wait a week.¬†All this motivated to me finally upgrade my desktop Mac Mini to Lion.

Mac Mini To Lion

I’ll start with the quick and easy upgrade. My MacBook Air is already running Lion so I knew all the apps that mattered would work. I did allow time to get Synergy working again as I figured it would break. It kept right on working and Synergy was sharing my mouse/keyboard between my desktops – Mac Mini and Windows 7 PC. I installed Lion from the DMG file I extracted from my original Lion install rather than from the App Store.

The Lion install downgraded iTunes so I wouldn’t open after Lion was installed. I got an error that the library was an older version. Running software update allowed me to install the latest iTunes. It also presented the latest Lion update 10.7.2 which required a reboot. Once I installed those I was all set.

The iCloud configuration was presented after the 10.7.2 install but I ignored it for now since I wasn’t ready to tackle moving from MobileMe,

iPhone Upgrade to iOS 5

The upgrade to iOS 5 on my iPhone was more problematic. The upgrade sounded scary and complicated – a backup and restore that could take an hour or more according to the dialogs. The “upgrade” seemed more like a complete wipe and re-install as it included a backup and restore.

I upgraded shortly after I saw it was available (about 1PM ET) and received a “internal error” just before the restore part of the installation. The error implied old software or a security setting as the cause, but I suspected it was overloaded Apple servers. My software was already up to date so I removed backup encryption (since the error was just before the restore phase) and removed the passcode from the iPhone. It failed again one more time but then worked. At least it didn’t do the download each time but used the cache copy. Once the upgrade started it took just under 90 minutes to finish, including a very long sync after the restore.

iPad2 Upgrade to iOS 5

I tried the iPad 2 upgrade after the phone finished. I received a different error, but again right before the restore. Right after the progress message that it’s verifying the restore with Apple I received the error that the update server could not be contacted. By this time I’d seen enough blog posts and tweets to know it was in fact an Apple server load issue so I didn’t bother trying again. This is where I upgraded the Mac Mini to Lion, since it’s also my iTunes computer I wouldn’t be compelled to waste time trying the iPad upgrade.

I tried the upgrade several hours later and it went right through but also taking about 90 minutes. Although it seemed to be the luck of the draw as a second iPad upgrade after this failed with the same error.

Preparing For iCloud

All these updates were to enable iCloud in the Apple world. Despite that I’ve yet to enable iCloud on anything, First off, I have little confidence that the iCloud introduction will be problem free. Apple’s history with MobileMe and .Mac does little to inspire confidence, although the optimist would say they learned from their mistakes. I don’t use MobileMe for much, but what I do use it for doesn’t get migrated to iCloud. Namely syncing Transmit favorites, Text Expander snippets and OmniFocus data.

OmniFocus has their own sync service, OmniSync, which is in beta. I had used it months ago and had problems and OmniFocus syncing became my main driver for getting MobileMe. Despite this I decided to move back to it, mainly because I knew I had regular and reliable OmniFocus backups. This was actually more problematic than I thought. First off, I synced all my devices so they all had the same data. Then when I setup my first Mac to sync with OmniSync it failed silently so it was time to troubleshoot.

I went out to the OmniSync website and changed the password. The Mac setup didn’t prompt for a password so I though it might be wrong. I also deleted the registered devices (which hadn’t synced in months).This time it did prompt for the password and then it told me it was going to replace everything on the Mac with the server data – not at all what I wanted. I thought this might be a bad message so did a backup then did the sync. Yup, all my data was replaced with the really old data, So it was time for a restore. Then within the OmniFocus for Mac menu I found “File -> Replace Server Database” and that did the trick, uploading my data. For the other Macs and devices I let the server data update OmniFocus. Interestingly, the iPhone and iPad prompted to ask whether I wanted to use the local or server data, while the Mac software just takes the server data.

As for transmit and Text Expander I decided to go with Dropbox since both supported using it. I had cancelled Dropbox awhile back but signed back up for the free 2GB account. I don’t plan to expand my Dropbox usage, but for now this seems to be the best solution. The setup was simple enough as both apps have settings for Dropbox syncing, no hacking required.


It took about 8 hours (including breaks), but I got all my iDevices upgraded to iOS 5 and got my desktop Mac Mini up to Lion. Now that everything is upgraded I can finally start looking at what all these updates bring me. First off I’ll enable iCloud. While I don’t trust it will be smooth, I don’t have anything critical that will depend upon it. There’s still one older iPad left to upgrade but there’s no hurry and I’ll try again once things settle down.

Anyone actually using the new features? Is it going to be worth the trouble?

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