I spent a good chunk of the last four days figuring out how to back up and transfer the data from an overloaded iPhone 8 to a new iPhone 13 for a loved one. Every step in the process took about ten times more pondering and about three hours more time than I anticipated. So while it’s fresh on my mind, here’s an exhaustingly specific account of the steps I took in hopes that it may help someone stuck in a similar situation some day.

NOTE: How-to articles on this site are provided for educational purposes only. I’m doing my best to describe my experiences, but I do not guarantee or warrant the accuracy, appropriateness, completeness, safety or usefulness of any article. If you attempt any of these procedures, you do so at your own risk. And please, always back up everything before trying any repair, update, or transfer.

The Scope of the Job

The phone I needed to back up contained a huge number of photos and voice memos that had to be archived in a useable, searchable way. I knew that creating a backup of the iPhone via iTunes (as it works in Mac OS High Sierra or Mojave) or via the Finder (as it works with later Mac operating systems) wouldn’t create a searchable folder that you could pull individual files from. So I needed to figure out different ways of archiving that would give access to photos and voice memos as useable files. Then I needed to back up the entire phone via iTunes in order to safeguard everything on it and enable an easy transfer of its data and settings to the new phone.

Step One: Setting Up a Backup Computer

The original phone had a 256 GB hard drive and was almost completely full, which meant it was too big to be backed up onto its owner’s computer any longer. Annoyingly, Apple does not make it easy to save iTunes backups of iPhones onto external hard drives. So I had to clear a massive amount of room on the internal drive of a different computer that could become a dedicated backup and archive machine.

Fortunately, after upgrading to a new computer last year, I’d hung onto my old 2013 Macbook Air. I set up a new user (creatively named Backup) on that Macbook Air to establish a clean space free of my old data and dedicated to archiving. Then I logged back in under my original user name so I could see all my old documents and data. I’d backed up and ported this computer’s data to my new laptop last year. But on the off chance that I’d missed anything back then, I obsessively backed up the computer’s files once again to an external hard drive. And then I began deleting.

Step Two: Clearing Enough Space

If you’re like me, you’ve got documents scattered all over your computer. Some prime areas to look for them include the Downloads folder (often full of giant installer files and other big downloads), the Documents folder (which I seldom use intentionally, but programs sometimes save files here unbeknownst to me), and the Desktop (because yes, I’m Gen X, so I have loads of files and folders strewn all over my virtual and physical desktops).

But many of the biggest files on our computers are stashed away in folders most of us never open. To ruthlessly make space, I needed to root around a little more deeply.

The Photos Library linked to the Apple Photos app can be found in Users > My User Name > Pictures. As it turns out, you can move that Photos Library file to anywhere else on your computer or to an external drive, click on it to open Photos, and Photos will recognize that as your new library. So I copied the library to an external drive, tested it by opening Photos by clicking on it, then deleted the original file from the laptop’s hard drive. (Of course I’d already transferred these photos to my new laptop last year, so I didn’t technically need to save another copy of that photo library, but when it comes to historically and personally vital documents like photographs, I never take any chances.)

iTunes media can be found in Users > UserName > Music > iTunes > iTunes Media. The big categories here are Movies, Music, Podcasts, and TV Shows. I backed up all the media files inside those folders onto an external hard drive, then deleted them from the laptop. When I open iTunes again, I can see the icons of those files and could download them again from Apple if I’d originally bought them through the iTunes store. But this computer will be a dedicated backup machine, so I won’t be downloading my own music here again.

Email was a tricker challenge, and I haven’t really figured it out. I had multiple IMAP email accounts on this computer. I went to Mail > Accounts, and one at a time, highlighted each of those IMAP accounts and clicked the “minus” button to remove them. This, I was assured by helpful folks on Mastodon, would simply stop this computer from connecting to those accounts without removing the emails from the server. Apple’s own instructions say that once an IMAP account is disabled, its associated emails will be removed from the computer. And when I deleted accounts, their associated emails and email boxes disappeared from the listings in Apple Mail. But I did not regain any hard drive space, even after deleting accounts that had 20,000 emails in them. I do have a considerable chunk of archived email stored on this computer that appears in the “On My Mac” section of the Apple Mail window. But the removal of the IMAP accounts should have increased hard drive space. I still haven’t figured out what the problem is. There’s a massive folder labeled V5 in Users > Username > Library > Mail, which presumably contains all the “On My Mac” mail and the undeleted IMAP mail, but the subfolders inside have nonsense names, so I don’t have any confidence that I can determine what to keep and what to delete there.

If I wanted to start from scratch, I could just delete all the email — I transferred it all to my new laptop last year and it’s also presumably duplicated in an old Time Machine back up of this old laptop. But I erred on the side of caution and left it alone for now. Something to figure out on some other day!

Next I tackled my Dropbox folders, which contained huge amounts of data. I had a terrible fear of deleting things from the laptop the wrong way and triggering the deletion all of my Dropbox files from the Dropbox servers. So I followed these instructions to unlink the computer from Dropbox. This meant that Dropbox would no longer connect to its folder on the laptop. I then quit Dropbox entirely JUST TO BE SURE. Then I copied the entire Dropbox folder to an external hard drive so I’d have a backup JUST IN CASE. Then I moved the Dropbox folder on the laptop to the desktop of the laptop, which was probably unnecessary but felt like a good thing to do just in case Dropbox somehow reactivated itself and went looking for the folder in its regular place.

Then I went through a long and laborious process of deleting individual files and folders. Even though all this data was now living in five different places (a Time Machine backup of this laptop, a Time Machine backup of my new laptop, my new laptop itself, the Dropbox servers, and the Dropbox folder backup I’d just put on an external hard drive), I was still nervous about deleting files containing irreplaceable family photos. So I deleted all of the non-heirloom files — and still needed more space. So on Day Three of the process, I finally backed the family data up to yet ANOTHER external hard drive and deleted the Dropbox folder entirely from the old laptop.

Step Three: Backing Up Photos from the iPhone

Given how much space I’d cleared, I figured I could back up the photos from the phone through the Photos app to the computer’s hard drive. But I was wrong — the computer gave me an error message, saying I didn’t have enough room. So I followed Apple’s official instructions and moved the Photo Library to an external hard drive. In a more rational world, you’d be able to go through a menu and select a folder for the Photos app to create a new library. But instead, you have to move (or copy) the existing Photo Library to wherever you want it to live, then click on it to open the Photos app, which will then recognize this new Photo Library in its new location as the one it will use. Long story short, I moved the library to an external hard drive, plugged in the phone, and started backing up the photos.

Unfortunately, with tens of thousands of photos, the process can get a little weird. I went to sleep and woke up in the morning to discover that only half of the photos had been transferred. An error message said that thousands were unreadable or had missing metadata. I contained my panic and started individually selecting files to be transferred. I discovered a handful of photos triggered that error message, but the vast majority were fine and backed up properly. But I couldn’t trust the computer to handle all of them at once, so I transferred them in batches of a few hundred, working on a comic book script in between each download. This took long hours. But it worked, and in the end I had a giant Photo Library on an external hard drive that was linked to the Photos app on the computer.

Step Four: Backing Up the Whole Phone

Now I had to back up the entire phone. The archive computer was running High Sierra, an older Mac OS, and the phone was running iOS 16, the newest iPhone OS. This is apparently not a fantastic combination. When I plugged the phone into the computer, iTunes wouldn’t recognize it. It gave me a vague error message saying “A software update is required to connect to phone.” I didn’t click on the update link because I wasn’t sure if it would upgrade the phone or the computer, and I knew the phone had virtually no space and was too old to risk upgrading. So I ludicrously went through the laborious process of upgrading the computer from High Sierra to Mojave, which I was pretty sure would take care of the problem. An hour or so later, I plugged the phone into the upgraded computer… and got the same error message.

I did some Googling and found a page that assured me that clicking the link in the error message would just upgrade the computer, not the phone. So I unplugged the phone and clicked the link, fully expecting to be taken to the App Store for an update to Big Sur, the latest operating system compatible with this computer. But instead, the computer just worked for a little while, apparently downloading and installing a small patch, and when it was done, iTunes recognized the iPhone!

I rolled my eyes at myself, realizing I probably could have skipped updating to Mojave if I’d had the wherewithal to do some research and click on that software update link earlier. But whatever; I was ready to back up the phone! Which I did, using the iTunes tools! But I didn’t notice until it was too late that the backup was automatically set to “Encrypted.” I didn’t worry too much; I had a record of the last encryption password I’d used on this computer. Of course that came back to bite me — more on this in a bit!

The backup took a little over an hour. Interestingly, the backed up file (which lives at Users > Username > Library > Application Support > MobileSync > Backup) was just 150 GB or so. The phone’s nearly full hard drive was 256 GB, so that tells me about 100 GB on the phone are system files that iTunes doesn’t back up. A bit of valuable information in case you’re trying to judge how much hard drive space you’ll need for the backup.

It’s worth noting that Apple’s backup protocols introduce an annoying redundancy and inefficiency regarding photos. I couldn’t find any way to exclude photos from the iTunes backup process. So if you’ve downloaded your photos to the Photos app and then backed up your phone through iTunes, you’re doubling the space taken up by your photos. That’s fine in terms of safety — I like redundancy in essential data! But it can turn into a big headache when it comes to making enough space on a machine for other things.

Step Five: Setting Up the New Phone and Transferring the Data

Now, finally, the fun part! Which of course turned out to be not so fun. I fired up the new phone, an iPhone 13! The system’s pretty darn advanced now and your new phone can wirelessly nab the information needed to get up and running from your old phone. The new phone flashes a weird, round, swirly image that your old phone reads — this serves as a security key that allows your old phone to transfer its number and some of its essential operating data over to the new phone. You’re also given the option to transfer the entirety of your data — presumably your music and messages and emails and photos, etcetera. But there’s no option to selectively pick and choose what data to transfer, and the owner did not want to transfer all their photos over. So we cancelled this process in hopes that we could get more options by plugging the phone into the computer and completing the transfer via iTunes.

Alas, that wasn’t the case. iTunes doesn’t give you the ability to transfer data to a new phone selectively — your music but not your photos, for example. It’s all or nothing! Since we wanted all the email and messages and whatnot to be ported over seamlessly, we decided to transfer everything and just delete the photos manually from the phone later. So we told iTunes to start the process… and it asked for the password to unlock the encrypted backup. I cheerfully typed in the last password I’d used for this… and it didn’t work!

So now I had another conundrum that took hours to figure out. After trying a bunch of variations of the password, none of which worked, I decided to back up the original phone to a different computer and start over. But when I got to the key moment, I saw that the “encrypted” button for the backup was still checked, and when I tried to uncheck it, I got that pop up asking for the password. In short, once you’ve made an encrypted backup of an iPhone, the phone remembers and tells iTunes to ask you for that password again whenever you goof around with backups, even if you’re on a different computer.

I then spent hours trying to figure out alternate ways of backing up the phone and transferring data to the new phone. I figured I could wipe the new phone and start over, this time using the easy start option to transfer data from one phone to the other wirelessly. But I got nervous — what if something went wrong and the data on the original phone was damaged? I wanted to have a working, accessible backup of the essential data before I tried the transfer.

I considered using PhoneView, a third party backup program, which I’d installed on my new laptop. But after a little experimenting, I realized that the program wouldn’t separate out any data it backed up from the old phone into a clearly marked file that I could then transfer to the archive laptop. Instead, the data would be confusingly co-mingled with the data from previous backups I’d made of my own phone, which wouldn’t be acceptable.

I considered backing up the old phone’s Voice Messages through iTunes. But I wasn’t a thousand percent sure what would happen when I pressed “Sync.” Was there any chance that instead of being transferred to the archive computer’s iTunes program, the messages would be overwritten or erased from the original phone? I’m certain that’s not the way the program should work. But since I didn’t have a working backup of the entire iPhone, I felt nervous pressing that blue button.

So I did more pondering and researching and agonizing, and I strongly considered following these emergency steps to reset the old phone to erase the backup password. But that terrified me, because it goes against my grain to change anything about the original device I’m trying to back up for fear of screwing it up before I’ve backed it up.

In the middle of this, it finally dawned on me that the password I’d been trying to use to unlock the archive was the password associated with MY phone, not the phone of the person I was trying to help! And when I did some searching through my password storage program, I found a note with a password from the last time I helped the owner of the phone. And that password WORKED, unlocking the encrypted iPhone archive!

Back in business, I plugged the iPhone into the archive computer and hit the “Restore Backup” button, as per these instructions. I held my breath a bit, because “Restore Backup” is weirdly vague — it implies the backup on the computer will be restored or affected in some way, when all we’re doing is using data from that backup to populate a new phone. The button really should read “Restore FROM Backup” for clarity.

Despite my anxiety and copy editor’s annoyance, the process worked, and in about an hour, the new phone was functioning properly with all the data of the old phone!

Step Six: Dealing with Voice Memos

Now that I knew I had a working backup and I’d successfully transferred all the data to the new phone, I felt much safer trying to sync the Voice Memos on the old phone to iTunes for archiving. But when I gave it a shot, I got a pop up telling me that the phone could only be synched via iTunes with one computer at a time and that it was already synched with a different computer. It also told me that if I proceeded, any songs that had not been downloaded through the iTunes Music Store would be deleted. I still don’t understand all of this. I’m not sure if non-iTunes songs would be deleted from the computer or the phone or both. And I believe this all has something to do with iTunes in iCloud, but I haven’t done the research to figure it all out. Instead, I immediately backed away because I didn’t want to do anything that might damage, delete, or change files on the original phone.

After half an hour of research, I settled on transferring the Voice Memo files from the iPhone to the laptop via AirDrop. I followed the instructions at idownloadblog.com, which showed a handy way to send multiple files to AirDrop at once. If you click the “Edit” button, you’ll be able to select multiple files, then click the Share button to send. I’m always nervous pressing an “Edit” button on anything I don’t want to actually edit, but it worked without a hitch.

After several rounds of exporting, I successfully transferred all the Voice Memo files to the laptop and breathed a big sigh of relief. But I quickly noticed that the “Creation date” metadata was wrong. That field seemed to have been overwritten with a later “Modified” date, so there was no way to correctly arrange the files on the laptop according to the date they were actually recorded. The files showed up on the iPhone in the Voice Memo app with the correct creation date, so I knew the data must be in there somewhere.

After another search, I discovered Fireebok’s Meta Media app, which claimed to have the ability to replace the “Creation date” with the actual “Recording date.” That seemed to be exactly what I needed, so I ponied up $19.99 for the app through Apple’s App Store and… it worked exactly as described!

After I imported the files into Meta Media and selected the command to replace the Creation date with the Recording date, the app created duplicate files with the corrected metadata in a separate folder, leaving the original files untouched and unedited. That seems like a great system to avoid destroying original data by accident. But it does eat up hard drive space since you’re duplicating the audio files in their entirety. If you use this program, I also highly recommend working from duplicate files of your originals anyway, because if you hit “save” after changing the dates, it will overwrite the metadata on the files you uploaded.

In the end, my work flow was a little ridiculous — I created duplicate files of the originals, uploaded those duplicates into the program, used the “Copy Shooting/Recording date to Creation date” command under “Quick Action” to change the dates and create the new corrected files, then deleted the duplicates I’d uploaded into the program, keeping just the originals and the corrected files.

Another quirk was that if the creation date on a file was actually accurate and had not been replaced with a modified date, the metadata apparently didn’t contain a separate “recording date.” So the program would replace the accurate creation date with today’s date and time, which obviously wasn’t the correct recording date. I only had that happen with a few files and replaced those manually with dupes of the correct originals. It was more complicated than I would have liked, but it worked out and I was happy.

The only other small hitch is that the recording dates are logged in UTC time, a.k.a Coordinated Universal Time, which is five hours off from New York time. I imagine there might be a way to make that time stamp conform to whatever time zone you’re in, but I’m not quite up for the extra work in figuring that out, and I figure UTC time is actually the most specific and accurate record you could have anyway. As long as you know the time in UTC, you can make the adjustment and know exactly when the recording was made.

Step Seven: Cleaning up the New Phone

Since iTunes annoyingly did not give me the chance to pick and choose what data I transferred to the new phone, my next job will be to remove the photos from the Photo app on the new phone, as per the owner’s request. I remember tackling this job on my own phone back in August 2021.

There are two tricks here, according to this article. The first is to mass select photos for deletion by dragging your finger across the photos instead of selecting them individually. The second is to check the “Recently Deleted” section to tell the phone to really delete the photos you just deleted. Whew!

Conclusions

And there you have it! An incredibly simple process made incredibly complicated due to the huge size of the files involved and the hinky way Mac iOS devices interface with Mac desktops. It really shouldn’t have been this hard and time consuming to back up a phone and transfer useable data to a desktop and to a new phone. I think about the millions of people who don’t have the time or interest to go through all of these steps and who might just lose gigabytes of photos, videos, emails, texts, and voice recordings as a result. Every new phone purchased increases the risks of losing priceless personal memories and cultural history. I wish I had a solution for all of that on a macro level. I can only hope that on a micro level, writing all this down might help someone else figure out how to preserve the personal memories and history they cherish.

Just switched webhosts for GregPak.com and now I’m testing things out. Everybody seeing this?

Glenn Fleishman recently posted a list of software problems he’s been encountering in his Macs. The post resonated with me — for about two or three years now, I’ve had the sense that problems with my Apple computers are constantly increasing. I’m not about to switch — I’ve been using Macs since 1985 and have gotten myself pretty locked into the ecosystem. I also essentially owe much of my career to Macs — the advent of cheap digital video editing with Final Cut Pro made it possible for me to make the majority of my shorts and my feature film “Robot Stories.” And the introduction of the iPad has enabled digital comic distribution to develop as an actual business that helps pay my rent. So yes, I’m grateful to and very appreciative of Apple products and generally very comfortable using them.

But that doesn’t mean everything shouldn’t work better. The company’s made a lot of hay over the idea that “It just works.” But increasingly, it doesn’t. So here’s my list of problems, and here’s to hoping the company’s paying attention and working on improvements.

• The whole file system of iOS seems overly complicated. I understand the system isn’t built for my specific needs. But I want to be able to plug an iPad into a computer and see a hard drive pop up on the desktop that I can move files to and from. And I want to be able to access those files with any app that can read them on my iPad. Instead, I have to figure out how each separate app uploads files — and I have to upload the same file separately to different apps if I want to view it in different apps. This seems wasteful of both user time and space on the device.
• The rollout of Final Cut Pro X and the lack of support for FCP 7 makes no sense to me as a pro user. I’ve stuck with FCP 7, like every other filmmaker I know because FCP 7 has all the features I need and because I have fifteen years of edited films that I CANNOT OPEN with FCP X. But I know eventually Apple will release an OS that I have to upgrade to in order to do my other work that isn’t compatible with FCP 7. And that’s going to be a terrible day. The writing is already on the wall — since upgrading to Yosemite, I can’t export from FCP 7 to QuickTime. I have to export via Compressor — which works, so at least there’s a workaround. But it’s a sign of things to come, and I don’t like it.
• Apple hardware has become increasingly difficult to fix/upgrade at home. I was pretty easily able to upgrade many parts of my old Pismo or even my black Macbook back in the day. Much more difficult to do anything with any current hardware.
• Searching in the Apple Mail program is a disaster. I admit — I have a HUGE number of emails in my program. But doesn’t everyone? For about a year now, using the search function to find anything in Mail frequently takes up to a minute. Since upgrading to Yosemite, it’s improved for me a bit. But it still can take many long seconds to complete a search. And sometimes it doesn’t complete the search ever — I have to clear out the search terms and try again to get a response.
• I’ve had similar problems just using the Finder to search my computer. Searches used to be instantaneous. Now they can take a few seconds or what feels like a full minute.
• Image Capture fails if I’ve kept it open and done other things between sets of scans. Upon returning to do a second set of scans, it typically loses its connection to the scanner and sometimes the entire computer has to be restarted for it to recognize it again.
• For the first time ever, Preview started giving me trouble, taking forever to open and scroll through a document that was only 25 mb in size. This happened after I upgraded to Yosemite and after I’d been working with a pdf with fields you could fill in. I’ve finished what I needed to do with that document and haven’t had trouble again.
• Every time I start up my computer, I get a message saying Text Expander wants to open up System Preferences so I can give it permission to work on my computer. I have already given Text Expander permission. But this dialogue box comes up anyway.
• Mac Pro frequently doesn’t recognize USB drives it recognized moments before. The drive in question is a Lexar USB 3.0 drive.

I’ll update this post as I discover/remember additional problems.