In the ongoing saga of my recovery from last weekend’s cycling accident, I’ve had a few bad mornings where I don’t want to get out of bed. Tonya and I had planned to spend Saturday at Chimney Bluffs State Park and stay overnight with friends in Rochester before driving on to Buffalo to run a cross-country race with our Finger Lakes Runners Club teams on Sunday. But when 9:30 AM rolled around and I was still in bed, feeling exhausted and dizzy, we pulled the plug on Saturday (<a href="https://www.youtube.com/<a href="https://comicvibe.com/how-to-watch-the-voice-season-30-premiere/” title=”How to Watch The Voice Season 30 Premiere”>watch?v=88nUwDG1roM” rel=”nofollow noopener” target=”_blank”>BPPV maneuvers helped with the vertigo later in the day, happily), and Tonya planned to carpool up to the race with the rest of our runners on Sunday.
The only silver lining in this adjustment to our weekend was that FedEx had proved incapable of delivering my iPhone 18 Pro on Friday as promised. The Apple Watch Series 12 had appeared on Friday, but there didn’t seem to be much point in trying to set it up with the iPhone 17 before leaving for the weekend.
So by Saturday mid-afternoon, when I felt better, I had a new iPhone and Apple Watch to activate. I wasn’t planning to write an article then, so I didn’t take careful notes, but after I got everything set up, I ran into enough interesting quirks that I felt they were worth sharing to alert others before they experience the same things.
Pairing a New Watch and New iPhone
The first question was the order in which I should activate these devices. I could connect the new Apple Watch Series 12 to my old iPhone 17, replacing my old Apple Watch Series 9, so that when I switched to the iPhone 18 Pro, the Series 12 would come along for the ride, since it would be included in the iPhone 18 Pro’s backup. I think that would have worked, but I ended up choosing a different path.
First, I unpaired my Series 9 from the iPhone 17, which triggered a backup. Then, I activated my iPhone 18 Pro and used the iPhone 17’s iCloud backup to restore it. Once I set up the iPhone 18 Pro, I paired the Series 12 with it and used the Series 9 backup to restore it. That worked flawlessly.
I have a vague feeling that the approach I chose—unpairing the old watch first, then setting up the new iPhone, and finally pairing the new watch—was more efficient and potentially less error-prone, but I have no definitive proof.
Transferring the eSIM
Since we recently switched from T-Mobile to US Mobile to cut costs, I was curious how my number would be transferred from the old iPhone 17 to the new iPhone 18 Pro. With major carriers, you specify that you want it to happen when you buy the iPhone, and it transfers during setup.
However, US Mobile was never mentioned during the purchase process, and when it came time to transfer the phone number, I was given a somewhat confusing choice: transfer from T-Mobile—my previous account, which was disabled but still associated with an eSIM in the iPhone 17—or scan a QR code.
It turned out to be extremely easy. I went to the US Mobile website, told it I was getting a new device, and it provided a QR code to scan during setup. Although the process wasn’t nearly as automatic as with a major carrier, it was easy enough. This is the sort of minor friction that’s worth $1000 in first-year savings for our three lines.
Choosing a Restoration Method
When setting up a new iPhone, you have several ways to transfer data from your old iPhone to the new one. Apple’s Quick Start gives you two choices, and there is a third option if your old iPhone isn’t available or Quick Start doesn’t work.
For Quick Start, put your old iPhone next to the new one, follow the on-screen instructions, and use it to scan the animation that appears on the new iPhone. When Quick Start asks how you want to transfer your data, you have two choices: iCloud or a direct transfer.
- Download from iCloud: Apple’s top choice is for you to restore from your old iPhone’s iCloud backup. This approach lets you start using the new iPhone while apps and data download in the background–Apple says it will take about 15 minutes before you can start using the phone. After you connect the new iPhone to Wi-Fi (which should happen automatically) and choose Download from iCloud, the process triggers another iCloud backup, even if you just made one. You want to restore from the latest backup, of course.
- Transfer from iPhone: The second option is to transfer your apps, data, and settings directly from the old iPhone, either wirelessly or with a wired connection—a wired connection can help if wireless migration proves unreliable, but there’s no way to know which will be faster. With a direct transfer, whether wired or wireless, both iPhones remain unavailable until the process finishes, which could take an hour or more. For wireless transfers, keep the phones close together and plugged in.
- Finder or iTunes: If you don’t have access to the old iPhone, or if Quick Start fails, you can set up the new iPhone manually, and then restore your old iPhone’s data from a backup saved to your Mac. Apple doesn’t even mention this approach in the interface, and I would use it as a last resort. When you get to the Transfer Apps & Data screen on the new iPhone, tap From Mac or PC, connect the new iPhone to your Mac, open a Finder window (or iTunes on macOS 10.14 Mojave or earlier), select the iPhone, click Restore Backup, and choose the appropriate backup.
Some years ago, I saw advice suggesting that transferring directly from the old iPhone would retain more app logins than restoring from iCloud, but in the last few years, I’ve had to re-authenticate to so many apps that I don’t think there’s much, if any, difference in this respect. Since I’m already backing up to iCloud and Apple positions iCloud restoration as the first choice, I went with that approach this time, and it worked well. It claimed it had 13.5 GB of apps and data to download, but it crunched through that fairly quickly while I did other things.
Google Account Update Chaos
For the most part, the post-update tasks went as I expected. One thing that did not was logging back into my Google account. I use Gmail, Google Contacts, and Google Calendar, and my Gmail account is set up separately in Settings > Apps > Mail > Mail Accounts so outgoing email uses my proper @tidbits.com return address rather than the underlying Gmail address. Plus, I have at least four email apps on my iPhone: Mail, Gmail, Mimestream (see “Why I Use Mimestream for Gmail,” 24 May 2023), and Avec (see “Taming Email Overload: Avec Makes iPhone Email Triage Almost Fun,” 16 July 2026).
I don’t know if any of those details are related, but after the iPhone 18 Pro finished restoring, it desperately wanted me to log in to my Google Account again. That’s not unreasonable, but I got multiple prompts to do so, interspersed with other prompts from other apps. I could only do one thing at a time, so by the time I got to logging into my Google Account again, I had already received at least four or five update requests. I assumed logging in once would satisfy all the requests, but that didn’t seem to be true, and I went through the process three or four times before I decided it was a waste of time and stopped.
In the end, I can’t really explain why this happened or whether it was actually necessary to log into my Google Account more than once, but if you use Gmail and other Google services, beware that you may get caught up in this flurry of prompts after setting up a new iPhone. My suspicion is that you can log in once and then cancel the rest, so try that if you find yourself in a similar situation. In the worst case, you’ll have to log in multiple times later.
Apple Pay Card Verification Rigmarole
The most annoying part of activating my new iPhone 18 Pro and Apple Watch Series 12 was setting up Apple Pay. Like many people, I have quite a few credit and debit cards in Apple Pay, and while the cards themselves transfer over, you have to verify ownership in multiple ways. There’s no rhyme or reason for which method a particular card uses, and some cards offer multiple choices. Worse, you may have to verify each card separately for both the iPhone and the Apple Watch. Be ready to:
- Enter the CVV number: Entering the three-digit CVV number seems to be the first step for verifying all payment cards, presumably because it helps prove that you have physical possession of the card. I recommend having all the cards in front of you when you start this process.
- Enter a code sent via SMS: Several of my cards could be verified by entering a code I received via text message, and at least one verified itself after receiving a text message without me having to enter a code at all.
- Enter a code sent via email: Other cards wanted to send codes via email, but for one, I never received them (and yes, I checked my spam folder). Unfortunately, by the time I realized they were going to Tonya’s account, I had used up the system’s patience and had to call someone to get the card verified.
- Verify with a phone call, like an animal: My most-used card forced me to fall back on an actual phone call to an actual person, so I had the pleasure of waiting on hold for 15 minutes before I could activate this card. At least iOS’s automatic Hold Assist meant I didn’t have to listen to the Muzak and constant interruptions while on hold. And the customer service person was nice.
- Verify in an app: We have a Capital One Visa card for the business and a personal Discover card. Since Capital One recently purchased Discover, I was able to activate both of them by running through a process in the Capital One app on the iPhone.
Apple could do more work here to standardize and improve the user experience.
Small iOS 27 Update
The iPhone 18 Pro shipped with iOS 27.0, of course, but it also prompted me to install an update during setup. I chose to delay the installation because I wasn’t sure how Software Update was configured regarding beta installs.
Interestingly, when I went back to Software Update after everything else was done, it offered iOS 27 again. I had been set to download public betas of iOS 27, but when I turned that off, Software Update still offered iOS 27.0, but this time, it was an unusual 892 MB download that promised only bug fixes. Whatever. I installed it and haven’t noticed any changes.
Time for a New iPhone Case
Because I am moving from an iPhone 17 to an iPhone 18 Pro, which has the camera plateau that debuted in the iPhone 17 Pro last year, I cannot reuse my Smartish Gripmunk case like I could when moving from the iPhone 16 Pro to the iPhone 17. I have ordered another GripMunk case with a custom photo, but let me know if you have another iPhone case that you think is particularly impressive and worth trying.
I know that some people are fine with case-less iPhones, and the iPhone 18 Pro is noticeably heavy even without a case, but its metal sides are just too slippery, and that’s doubly problematic now that my injured hands cannot grip tightly. The main level of our house has tile floors, and I am certain that dropping the iPhone onto the tile would destroy it–the tile has broken everything else that has fallen on it, including a large Wüsthof chef’s knife, without so much as suffering a scratch.
Apple One Offer
When writing about the recent Apple TV price hikes (see “Apple TV Subscriptions Jump from $12.99 to $14.99 Per Month,” 1 September 2026), I said I was waiting to see whether Apple would give me some free months when I bought my new iPhone. I have already taken advantage of at least one of these offers in the past, so I wasn’t actually expecting it, but indeed, in the iOS Settings app, there was an offer for 3 free months of Apple One. I’ve been a little too busy to take advantage of it, so perhaps there’s another gotcha, but if you are thinking about resubscribing to Apple TV for a little while, buying an iPhone may be a way to get a few free months.
