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Joy & frustration (mostly frustration) in upgrading Apple Macs to Lion, iCloud

June 18, 2012

In recent days, my Apple computers have brought me both great joy and great frustration.

Interestingly, those two things have gone hand in hand. I could not have had one without the other.

First: Why the great joy? Because I have been required to flip back through 25 years worth of data and virtually see my life flash before my eyes. I got my first Apple Macintosh computer in 1987 and saved much of the writing, spreadsheets, drawings, databases and messages I created and received over the years. I’ve been able to see my life from my post-college work years through getting married and having kids. I’ve been able to revisit letters and instant message logs and e-mails from colleagues, friends, and family members. I’ve been particularly fortunate to find and read messages from my younger brother, Andy—messages I forgot entirely—that make me laugh as if we were still in the moment. And since Andy died of ALS in 2010, it makes these pieces of digital memorabilia all the more valuable.

But while it’s great to be nostalgic and great to find these forgotten gems, why have I spent so much time living in the past instead of using my Mac to be  productive?

I have spent the time because I need to update many of these files in my archives. And why do I need to do that? Because Apple is updating an online service I have relied on for a dozen years, one that provides me my primary e-mail address. I’m currently using MobileMe and I need to update to the new service called iCloud. But to update to that, I need to update all my computers to the current operating system, OS X Lion. And under Lion, many of my old files will not open properly, which requires this massive file update/trip down memory lane. I have one computer—my main computer that contains 25 years worth of archives—that is running the previous system, OS X Snow Leopard.

Oh, and one more thing: I need to have this all updated by June 30. On or after that day, MobileMe will be discontinued and I’ll lose my e-mail address and the services I rely on. But if I update too soon, before all my old files are updated to be used with Apple’s modern operating system, I will lose some files, be unable to open (or easily open) others and some would be turned into unreadable binary hash.

It is a dilemma: Lose the e-mail and online services. Or possibly lose (or lose easy access to) a portion of a quarter century worth of memories.

And let me be clear: I knew this deadline was coming for more than a year. Apple announced the end of the MobileMe service more than a year ago. In fact, former Apple CEO Steve Jobs himself announced the end of the program. It should be somewhat a testament to MobileMe that it outlived Jobs himself.

And let me be more clear than that: I could read the writing on the walls even years before that. I knew that some of the programs I was using were not going to be supported by Apple indefinitely. They had stopped updating them, they had declared them unsupported, they had replaced them with newer, but in my opinion, paler substitutes.

And let me be even more clear: For many years, I have been preparing for this day. I would even say I was an early bird to finding alternate programs and methods that, had I waited a couple years, I might have saved money by buying less expensive software developed later that suited my needs as well or better.

However, with only about a fortnight to go to the deadline, I still am not able to make the transition.

Well, then, you say, shouldn’t you be working tirelessly night and day making sure you can make that transition instead of writing a whiny blog post? Yes, I should and I would, except that the main computer of which I speak is right now in the shop getting a new hard drive.

This repair break gives me a moment to pause and reflect—and complain.

Let me just say this so you don’t unnecessarily panic on my behalf—as soon as I get my Mac back with its new hard drive, I will be able almost immediately to finally upgrade my machine to Lion and begin the process to convert to iCloud. Barring unforeseen circumstances—such as a delay in getting the hard drive installed or another failure on the 4-year-old machine—I should be up and running with Lion and iCloud in less than 24 hours after I get my Mac back.

However, I did hours and hours of work converting old or incompatible files in recent weeks and months to get ready for that. It was only after all that work was done, as I was doing final preparations for upgrading to Lion, that I ran a hardware test and discovered my hard drive was failing and needed to be replaced.

For all the ease of use that Apple has touted over the years, converting to Lion and iCloud should not be so hard nor so mysterious nor so fraught with peril. While I consider myself a somewhat advanced user, I have often been perplexed at what the upgrade would require; I’m not sure it has been spelled out in enough detail. And I think there is a strong possibility that even those people who think they’ve taken all possible precautions, may end up either losing valuable data or losing the ability to easily access it through the upgrade process.

Now, my problem may come from the fact that I’m a legacy Apple user. I am not among the majority of Apple users who have bought devices and software recently. They will have few problems, since their files and applications are modern and are completely compatible with Lion and iCloud.

Let me run through a chronology, so you can better understand the problems I’m dealing with:

1987: I bought my first Macintosh, a Macintosh Plus. It had a tiny 9-inch diagonal black-and-white screen and no internal hard drive. You loaded applications and stored files by using the single floppy drive slot. Every time you wanted to save a simple change to a word processing document, you had to swap disks in and out of the drive. It was a major pain in the ass. But since we didn’t know any better, it was magical and tremendous. I created most of my files—word processing documents—with an early version of Microsoft Word. 

1989: I began to use a Macintosh for work as a newspaper reporter, creating information graphics that had become popular at the time. These were created with Apple’s MacDraw program. Today, this program would not be considered advanced enough for kindergarteners to use. But then, it’s what was being peddled to newspapers to help make them look more like USA Today. At home, I used MacDraw to create my own greeting cards. Oh, yeah, in 1990, I also used it to make a program for our wedding ceremony.

Through the 1990s: I continued at newspapers, making more graphics, still with MacDraw, even though more advanced drawing programs became available. I upgraded Microsoft Word right along and eventually added Microsoft Excel for spreadsheets. At some point, when I got a new Macintosh computer, it came bundled with a program called AppleWorks, also known in various incarnations as ClarisWorks.

This, without question, was the greatest single application ever created for the Macintosh platform. It was the Swiss Army knife of computer programs—it could do it all. It was a word processing program, a drawing program, a spreadsheet program, and even had a database program, back when most people didn’t even know what that meant. It did more than that, too—it was a floor wax and a dessert topping. But seriously, even though I was a fan and a heavy user of this program, I didn’t even use it for all its capabilities. On top of this, AppleWorks was a consumer-level program—it was intended for everybody and was easy to learn and use. Just about every time I touched my Macintosh, I was using either Appleworks or Microsoft Word.

Around 2000, Apple introduced a new online service called iTools, which later morphed into something called .Mac, then became MobileMe and finally, last year, became iCloud. All the services provided something slightly different each time they were renamed, but at its core, they gave users an e-mail address and provided services to synchronize calendars, contacts, web bookmarks and other features among Macs and later, iPhones, iPads, and iPod touches. I was one of the first in line to sign up for iTools and received an e-mail address ending in “” This has not only been my primary e-mail address ever since, it also earns me a measure of respect when dealing with others in the know about Apple. That’s because Apple discontinued the “” e-mail suffix in 2008 with the introduction of MobileMe, replacing it with an “” suffix. Existing customers were allowed to keep their “mac” e-mail address along with their “me” address. But if you use your “mac” e-mail address when dealing with Apple Store employees, for example, they’ll almost always treat you differently because they know you are a longtime Apple user, very likely more experienced and knowledgeable than they are.

In 2001, Apple introduced a new operating system—OS X (say “oh ess ten.”) The first released version of this was named Cheetah and each version since has been named after a big cat. I didn’t begin using this new operating system until 2004. Instead, I stuck with an older computer running OS 9 for several years. Making the transition from OS 9 to OS X was hard, but I was able to do it because a lot of older OS 9 programs would still run in OS X. For example, AppleWorks still worked.

In 2006, Apple changed the internal workings of its computers, transitioning from Power PC to Intel processors. This made computers run better and more efficiently. But it also meant some things were left behind. Now, with Intel processors, programs written to run in OS 9, that were previously able to run on OS X with Power PC computers, would no longer run. Programs that were not rewritten for Intel would have to run under a translator called Rosetta. While some claimed this slowed their favorite programs down, I never had a problem with it. Long story short: AppleWorks still worked.

However, by this time, I could see time was running out for my Rosetta applications like AppleWorks, which had not been updated since 2004 and would not be sold after 2007.

AppleWorks was seemingly abandoned when Mac users could easily go elsewhere for the functions AppleWorks provided. Microsoft, in particular, offered Word and Excel, programs that in many ways were superior for word processing and spreadsheets than anything Apple had to offer. Other companies produced drawing programs that left AppleWorks’ drawing program in the dust. But the problem with these other programs was that they were more complex and not well integrated together.

While I had Microsoft Word and Excel, I resisted using them. For one thing, they didn’t run well on my computer. And frankly, I did not like giving Microsoft—Apple’s enemy at the time—my business. Also, because of antagonism between Microsoft and Apple, I feared Microsoft might at any time pull support for its products, which could possibly result in being unable to open old files. It seemed a better bet to me to use AppleWorks. Even though it was discontinued, I figured Apple would always provide a way to keep that namesake program working indefinitely. Turns out, I was completely wrong about that.

I gave up hope that AppleWorks would finally be updated in 2005, when Apple released a new program called iWork, that included a word processor called Pages and a presentation package called Keynote. Pages in particular was anemic, did not have the same capabilities or ambitions as the “old” AppleWorks word processing program had. It wasn’t until 2008 that iWork contained a spreadsheet program called Numbers. To be fair, these programs now do some things that AppleWorks was not capable of doing, but the iWork package did have some shortcomings.

For one thing, there was no database program in iWork and never has been. In fact, for a long time, there was no feasible way to replace AppleWorks’ database program. For years, there was no good consumer level program that could do what AppleWorks did for databases as easily, as well, and as inexpensively. When I shopped for an alternative in about 2005, the only choice really was FileMaker Pro, produced by a subsidiary of Apple. But this was a $300 piece of software intended for professional use. It wasn’t until 2008 that the same company put out a consumer-level database program, Bento, that sold for around $50.

I had a lot of databases I created. I wanted to keep using them into the future. So I knew I had to switch. For me, the only alternative at the time was FileMaker, so I bought it. And it remains the most expensive software I ever bought. But that move did future-proof me. The databases I converted from AppleWorks to FileMaker Pro still work under Lion.

The other major application I had that had not been updated for Intel and was running under the Rosetta translator was Quicken, on which I keep track of the family’s finances. Intuit, the company that makes Quicken, had a reputation for being indifferent to the Mac platform and slow on the draw to provide useful updates. At some point, it appeared Intuit had given up on the Mac, ceasing Quicken for Mac development altogether—yet there was no viable alternative in the marketplace. Eventually, as the Mac grew in popularity and market share, several software companies came along to fill the niche for financial tracking software. I spent about a week doing nothing but giving some a try, but found them all wanting. I’m sure they are better now, but at the time I decided to resume using Quicken, even though I felt like I was jumping off a life raft and back into a sinking ship.

Finally, Intuit announced they would produce a version of Quicken that was written for Intel machines and would not require the Rosetta translator. This new version, Quicken Essentials for Mac, was a watered down, backward-step version of the product. It was improved a bit over time, but the Rosetta version still has features the new Intel version does not.

With time running out for Rosetta, I did not want to be caught unprepared, so I eventually moved from the Rosetta-version Quicken 2006 to the Intel-ready Quicken Essentials for Mac. It does some things better than the Rosetta version and many other things not quite so well. I viewed it as the best solution at the time. (Since that decision, Intuit released a version of the old Quicken that will run natively on Intel. But since I had already planned ahead and got their new software, I didn’t want to spend the time and energy to move back to the old/new software.)

Probably about 2007 or 2008, I stopped using AppleWorks on a daily basis. I did everything I could to keep myself from launching the application so beloved to me to create new files. If there were AppleWorks files I was using on a daily basis, I begrudgingly converted them from AppleWorks to something else, often with mixed results. Yet, I still had nearly two decades of AppleWorks writings, drawings, spreadsheets and databases on my hard drive. To convert them all or to make sure they would still be compatible with other software was simply not a task I had time for. So I put it off.

In June 2011, Apple announced its new online service called iCloud. It was launched in the fall of 2011. MobileMe users were given time to get their affairs in order—we had until June 30, 2012, at which point MobileMe will end. At about the same time, in July 2011, Apple released their new operating system, OS X Lion. The previous version of the operating system, OS X Snow Leopard, still contained the Rosetta translator, which allowed older programs (with PowerPC technology and not updated for the Intel processors) to keep working. This new operating system, Lion, would not include Rosetta. That meant that the old PowerPC programs would no longer run with the new operating system. Oh, and one more thing: iCloud requires Lion, so if you want to have iCloud, you must abandon your PowerPC applications.

This, at long last, was the end of the road for PowerPC and Rosetta apps. No more would programs like AppleWorks run on modern machines.

This, of course, while being a shame, is also a terrible inconvenience. Plus, we users of programs like AppleWorks have had to put up with the condescending attitude of new users who wonder why we can’t “get a life” and move on. The thing is, we do have a life and it is largely recorded and stored in files that only AppleWorks can properly open.

So what to do? Well, in my free time in the past year, I have made sure the applications I want to use into the future are not just updated to work with Intel and Lion and iCloud, but that they are actively being developed. I upgraded a secondary computer from Snow Leopard to Lion and was able to test which files could open and which ones could not.

Now, I felt I spent a lot of time and research knowing exactly which files would need to be updated. But I was taken by surprise. And I realize now had I not gone through to see what would open in Lion, I may have lost easy access to some important things.

Interestingly, I was able to open most really old files, from 1987. But I had a lot of trouble successfully opening files—especially Microsoft Word files from the mid-1990s to the mid-2000s. Often when I tried opening files created with previous versions of Word in a modern version of Word on Lion, I would get nothing but mishmash—no text whatsoever. I had to go through, file-by-file and save a new version of each document in a more modern format. That way, the files would open perfectly in Lion with formatting and everything correct.

It is possible that those documents were created in a PowerPC version of Word. I don’t know. And it’s possible there were other ways to convert them. I don’t know that, either. I knew it had to get done and I knew there was a deadline. I found a technique to save them and did it.

My heart sunk when I  found that some the files that would not open under Lion also did not open under Snow Leopard. For example, I would get errors when trying to open older AppleWorks word processing documents. This was discouraging because it meant that I failed to update documents years ago. 

But there was a solution: I had a 2002 Apple iBook laptop that still ran OS 9. I hadn’t booted it up in maybe 6 years. Would it still run? Yes! Even though two subsequent OS X Macs of mine had died, this one still ran. And yes, it turned out that this computer had those AppleWorks documents on them. They had been created with a previous version of AppleWorks, so I was able to update them on the old iBook, copy them to a flash drive, and find that I could now open these on my iMac running Snow Leopard. And it turned out, they would also launch perfectly in Lion using Apple’s Pages application.

I was similarly discouraged when I discovered that the years of graphics I created would not open in Lion. It also seemed that I had failed to check them over the years and some would not even open in Snow Leopard. However, Macworld magazine introduced me to a program called EazyDraw that not only opened my more recent AppleWorks drawing program files, it also rescued ancient MacDraw drawings, such as the program I created for our wedding.

So why bother converting all these files? Obviously, some of them, you haven’t looked at for five or more years, so why go to the trouble? Are you some kind of packrat? Well, yes, I am a packrat, but I do find it valuable to be able to look up old information, old notes and messages. I went to the trouble of creating or receiving and reading these things, wouldn’t it be nice to keep them all usable?

But on the other hand, these things I’m saving, in the long run, are not that old. In many cases, I’m looking at a file created only five years ago that I need to convert to keep using. That seems wrong. I’m all for moving forward and keeping technology on the cutting edge and I just can’t buy into the arguments that modern computers will be compromised too much by allowing translator technology like Rosetta to remain active. I’ve spent the greater part of the past month converting old documents so I can keep accessing them—what has been compromised is my time. 

Features are constantly added to make computers and operating systems and services like iCloud better and easier to use. Apple and other tech companies are always pushing forward. I don’t have Lion installed yet and already the next Mac OS, Mountain Lion, is scheduled to be released next month. While I do my best to follow technology and especially Apple technology closely, this is all getting a bit too much even for me. On my iPhone, apps constantly require updating. On the Mac, software and firmware needs my attention. I’m finding myself spending more time being a computer administrator and less time getting things done. Plus, in this rush of updates, we are forgetting a past that really is not that far past.

It’s great the computers get better and faster and more capable and easier to use all the time. And as features are added to make computers better, a great feature to add would be to make sure computers have the capability to be easily backwards compatible. Because to do otherwise, is not only a great inconvenience, but a potential great loss of data. And memories.

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