Advice welcomed on switching from 2008 iMac to new iMac

This is my first posting and I guess there is an answer somewhere but I can't find it! Here goes:

I bought a new iMac in 2008 after 20+ years with MS and have been fairly happy with it. The OS was upgraded as required and is now 10.8.5 Mountain Lion.

However I have ordered a new 27-in iMac Retina model and am not sure how to make the transfer of data, programs, etc from the old machine to the new. I use an external WD My Book for Time Machine back-ups.

Should I upgrade my old machine's OS to the latest version before switching? What is the most reliable method of moving my programs and files from one machine to the other?

Any help will be most appreciated, thanks in anticipation!

I don't think anything special is required. Connect the new machine to the old machine by Ethernet or USB cable (Thunderbolt if both machines have it, though you may need to buy a cable for that). Thunderbolt would be the fastest, followed by Ethernet, followed by Firewire if both machines have it, followed by USB. It's helpful to ensure that all your third-party software is up to date, of course.

The important thing is to connect them by whatever method you choose BEFORE you turn on the new iMac! Then start up Migration Assistant on the old machine (its in the Utility folder) THEN turn on the new iMac. Naturally it will automatically start with its setup routine, and about halfway through will ask you if you want to transfer your stuff from the old machine to the new one, and should automatically pick up however the old machine is connected. You also have the option of simply using your Time Machine external hard drive if you prefer, but unless its on USB3 it will be pretty slow, but at least the option is there.

That's pretty much it. Migration Assistant will replicate your old Mac's settings, and move over everything that is compatible with the new machine (and let you know at the end if there were things that were not compatible -- coming from Mountain Lion this really should not be an issue). It works remarkably well but needs to be left alone until it completes, then you finish running the setup and your old account and programs and documents and stuff are all on the new Mac as though they always have been, in all the right places.

Thank you so much Chas-m, your instructions are very clear and most reassuring and the 12 minute gap in my posting and your response is sensationally brilliant! This forum is a wonderful resource so thanks also to all concerned in running it.

I will post a message when the switch-over is made.

Mac to new Mac transfer hanging

My new iMac Retina 27-in arrived this morning, intended as a replacement for a 2008 vintage 24-in model now using Mountain Lion.

Following advice from Chas_m and others I have started the transfer process using Migration Assistant with the two machines connected by an Ethernet cable. All proceeded as detailed with the message, in both screens that my files would take 3 hours to be transferred. All went well until the final minute since when the there has been no progress for more than hour. The message on-screen indicates one minute to go but it hangs there.

I have tried unplugging the Ethernet cable for a couple of seconds but it makes no difference - the 'one minute to go' message has been on the screens for what seems an age.

Any help in solving this problem will be gratefully received!

Unplugging that ethernet cable was a grave mistake. You should've just waited -- The process does sometimes hang towards the end as the verification stage takes place, but usually resolves itself. By breaking the connection, you will probably need to start again.

Migration Assistant: Message v Outcome conflict

Mea culpa Chas-m, my head is bowed albeit waiting for more than an hour for conclusion of an action that both screens state will be 'about a minute' is perhaps an indication that the Migration Assistant's messages could be more helpful.

However, I fully accept your admonition; I have been stupid but now what do I do? Is it possible to simply switch-off both machines and then start from scratch again?

Your advice will be gratefully welcomed - with thanks too for your toleration.

Successful transfer, thank you! - but missing emails

Despite having briefly broken the port-to-port Ethernet connection between my 2008 24-in iMac and the new Retina model the transfer continued without having to be restarted, much to my surprise, and the new machine has been in service for a couple of days. The migration took a long time - more than 18 hours - but it was a relief to boot up the new machine and start using it in earnest. I am happy to reiterate my thanks for this excellent forum and particularly the sound and clear advice from Chas_m.

There is something else that is puzzling me: my Mail folders and messages cannot be found. A friend advised me to look in the user's Library/Mail folder but no such folder can be found on my 2008 Mac nor the new machine. I have pored over various books but could not find advice leading to a solution.

Any suggestions on how to proceed will be most welcome.

Thanks again!

The important thing is to connect them by whatever method you choose BEFORE you turn on the new iMac! Then start up Migration Assistant on the old machine (its in the Utility folder) THEN turn on the new iMac. Naturally it will automatically start with its setup routine, and about halfway through will ask you if you want to transfer your stuff from the old machine to the new one, and should automatically pick up however the old machine is connected. You also have the option of simply using your Time Machine external hard drive if you prefer, but unless its on USB3 it will be pretty slow, but at least the option is there.

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I want to point out that I disagree with chas regarding the speed of transfer using Time Machine vs by ethernet cable. I have found the Time Machine (even USB 2) method to be faster and it also will transfer everything including your mail and mail boxes. As you found out, the Migration Assistant is not a guaranty that everything will transfer over properly.

Do you have a recent Time Machine backup of your old iMac? If you do, you can manually recover all your mail and its folders and mailboxes.