‘Tis the season for my annual iPhone Upgrade Program membership to kick in. This year I moved from a purple iPhone 14 Pro (256GB) to a blue titanium iPhone 15 Pro Max (256GB). The notification and pre-order process went smoothly, as I received a timely upgrade email and also had the correct information populated in the Apple Store app on the older phone. It’s nice that this has all worked without major issues for several years now.

The UPS delivery person brought the new phone to our house on Friday and I decided to do the phone-to-phone transfer process again instead of restoring from the iCloud backup (which I also ran manually on the old phone immediately before starting – just in case). The time estimate displayed laughingly said it would take 10-15 minutes, but I needed to let the process run overnight. Even then, it didn’t download all the apps to the new phone until I hit the continue button Saturday morning.

Despite the long setup time, big kudos to the team at Apple that is responsible for engineering this upgrade process. Trying to create a process that works reliably for millions of customers with a basically infinite number of combinations just blows my mind. Here are some examples from my particular setup:

• All of my Apple Wallet items transferred seamlessly (with the process to add my Wings Credit Union debit card now all online with no need to call them like before) – Apple Card, tickets, Science Museum membership card
• All photo, music, iMessage and health data just worked on the new phone (did need to sign-in to MyChart to restore that app)
• My third party calendar app Fantastical asked me to sign in again, but then all the correct calendar data appeared
• All my favorite third-party games data transferred with no issues this time: Two Dots, Lightning Link, Star Wars Card Trader and Words with Friends
• Password management didn’t skip a beat – 1Password transferred over after a sign-in on the new phone and all of the iCloud password management worked as expected
• My 2FA accounts in Google Authenticator did not automatically transfer, but the export/import process via the double QR scanning worked great (make sure you don’t erase your old device until you do this)
• Didn’t experience any of the software update issues I had read about – the setup process started by first telling me I needed to update to iOS 17.0.2 before transferring data from the old phone
• Re-pairing with my Apple Watch was much smoother this time (and was part of the upgrade process and not something I needed to handle manually)
• I had to reauthorize the new phone for CarPlay in my Honda Civic, but after that everything just worked as before (needed a new USB-A to USB-C cable)

I wasn’t entirely sure I wanted to go back to the larger size again, but really, really wanted the 5x optical zoom lens only available on the Pro Max. So far it fits OK in my pocket and the in-hand feel and overall weight are much better than I expected. The build quality of the iPhone Pro models continues to be on par with the excellent MacBook line of laptops – I really don’t want to use anything else.

Hopefully I can go more than a week without scratching the screen or dropping it on the floor (yes, I’m still a no-case, no-screencover daredevil)…

No shortage of opinions on today’s Apple Event, but here are my immediate action items:

• Will move from my 14 Pro to the 15 Pro Max via the iPhone Upgrade Program on Friday (256GB Blue Titanium)
• Still want an Ultra 2, but don’t like the new bands – will stick with my Series 5 for now (and might actually prefer a Series 9 with a Nike band)
• Need to find out the pricing on the new iCloud+ 6TB and 12TB storage tiers (and how that ties in with Apple One) – rumor is $30/month and $60/month
• AirPods Pro cases get USB-C on September 22, but I will still probably wait for the 2nd edition of AirPods Max

Thinking iPhone 15 Pro Max this time (if the camera rumors are true). Would also go for an Apple Watch Ultra 2 if that’s released. Need to do something about my semi-broken AirPods too…

Now that the WWDC news has faded (and resurrected again today with the new beta releases and SDK), I’ve started to think about what my next purchases will be. I’m super fortunate to have great working gear right now, so there is no big rush on anything. Apple hardware just lasts such a long time: my home office iMac is from 2017 and my Apple Watch is a Series 5, which was released in 2019. I use both daily and they still work great.

My laptop, tablet and phone are all newer and also get heavy daily use. Thanks to the iPhone Upgrade Program, I do tend to turn in phones every year for the newest model. My only decision this year will be if I want to move back up to the larger screen or not. If the best camera ends up being exclusive to the Max, I’ll probably do a 256GB Pro Max.

If I were to order a new work laptop today, I’d go with the new 15-inch MacBook Air. $1499 for the base 8/512 model is a great value. A fully loaded 24/2TB model goes for $2499, which is what I’d get for a personal use laptop. My 2021 14-inch MacBook Pro will likely last a long, long time, though. I mainly use my iPad Pro for watching video on the treadmill, so I don’t see needing a new tablet anytime soon either (same goes for our AppleTV units).

I’ll reserve all opinions on the Vision Pro until the developers go wild and I get a chance to see if my specific optical prescription will even work with the custom inserts. My initial reaction was overall positive (and much different than I expected from the rumors), but also that I probably wouldn’t want one right away. The reality is that I’ve thought that about most of the recent platform additions, but ended up buying all of them in the end (most on launch day too).

Outside of the next phone, though, here are my top 3 wish list purchases: 1) Apple Watch Ultra with Black/Gray Trail Loop, 2) the next version of the AirPods Max and 3) the next version of the iMac…

Schrader valves are the old “traditional” style, while Presta valves are the newer, thinner ones. Thought I needed these $6 adapters, but turns out my fancy bike pump works with both, as long as you loosen the Presta valve core first. Looking forward to riding in the warm weather this week…