Troubleshooting iMac to MacBook Air: A Personal Experience

April 17, 2026

You’d think it is easy to upgrade your computer gear. Just buy a new computer, plug it in, and that’s it. Well, let me share our experience replacing an old iMac. Not to give you the conclusion of our story, but just to say that it took us one week to get the new MacBook Air functional, while using words not appropriate in polite company.

It began when Kathy’s 14-year-old iMac couldn’t load the Revenue Canada files needed to prepare taxes. We tried her 2-year-old iPad, which easily downloaded them, but it wasn’t suitable for doing taxes. The iMac had security issues, so I suggested that it was time for a new computer.

The first question was whether she wanted another 28-inch iMac. She decided to switch to a smaller one, perhaps a laptop. Since she was using Apple devices, we went to the Apple store to shop. She insisted that we get someone knowledgeable to set up her new computer and migrate the info from the old to the new device.

I said, ” Sure, let’s have someone do the entire installation, and the geniuses at the Apple store will do it for us.” Entering the store, a pleasant lady asked what we were there for and, upon learning that we’d like to buy a laptop, called another person to help us.

The young gentleman who came to assist us was very personable and provided the choices for screen size, color, and data storage on the computer. Once Kathy selected her choices, the salesman wrote up the order and brought out the selection from the back and led us to a table where another genius helped us start the computer and enter the date, time, email, and other basic information.

When finished with the initial tasks, I asked, “How do you transfer the data from the old iMac?” The fourth person, replacing the previous helper who went on her lunchtime, explained that we could do it at home, or bring in our mammoth 28inch iMac from home, and they would do it. Then he checked with the geniuses in the back, who advised that our iMac is too old to migrate its content to the new shiny MacBook Air. The explanation, if I understood it, was that they would download the iMac’s content to a storage device and then upload it to the new laptop, except that they did not have the appropriate storage device, or our iMac was too old for the task.

Instead, they advised us to call Apple support to do it ourselves. Ok, so we went home, and the first thing was to hook up the laptop to our internet service. And then the trouble started. We discovered that Apple, of course, has iCloud installed for its email system, but Kathy uses Gmail, which is not installed on an Apple device. So, we tried to install the Gmail program. And we tried and tried and tried again to no avail. No password that we knew was accepted.

Ended up calling Apple support and talked with a very courteous woman who advised us to go through the same steps we just did a dozen times to no avail. She concluded that it was a Google issue, not an Apple issue, so we should talk to Google.

I started with a Google chatbot, which, or should I say who, asked a dozen questions, very courteously in a mellifluous tone, and then decided to refer me to an actual person. The final instruction from the bot was to sign on a plan to pay five dollars, refundable, I was told, before I could talk to a real person. When I read the fine print on the plan, I discovered it would cost $90 a month, with cancellation at any time. I do not like signing up for these plans. I sometimes forget how many plans I have until I notice the charges on my VISA card, and then I have to hunt down the account to cancel it. So I just exited the chatbot.

My next line of attack was to have someone come to our house. She showed up late. After she tried to follow the instructions to install Gmail, just as we did before, and was unsuccessful, as we were, she left, suggesting that we figure out our passwords and have her come back for another visit.

We still needed help, so I left messages with a couple of service outfits. Surprisingly, many of these technical shops opened at 10am and closed at 3pm. I thought private industry would be more diligent and work longer hours.

Then I found one shop that had a timetable for making appointments online, and, more surprisingly, there were empty time slots for the same day. The tech expert at the store explained that Google had locked us out because we had tried to change the password 5 times. But he suggested that using our home internet service would recognize our Google account, and we could change the password there. He came to our house, came up with a new password, and started migrating data from the old iMac to the MacBook Air. It took all night to complete the migration.

It was a frustrating experience finding expert service and taking time to be present to answer questions about passwords. (Needed Face ID or fingerprint ID every time you logged in to either computer, or a password for the device, for your Apple account, and for Google). I had a steady supply of coffee and offered some to the tech expert, but he did not drink coffee or tea. He was from Mumbai; coffee or tea may not be a popular drink there.