The great phone swap of 2026

I do this Information Technology thing for a living, and I just replaced my iPhone after more years than I should have kept it. Why, might you ask? Because I consider it to be a chore of epic proportions.

Phone vendors and wireless companies tout the ease of the switch, and I admit, it has gotten easier over time, especially with the presence of cloud-based backups, but it’s still an hours- or days-long ordeal.

This time, thankfully, I had a friend who loves Apple products more than any human probably should — but exactly how Steve Jobs envisioned people would — and he was more excited about my new phone than I was. He unboxed it with such great joy on his face while I prepped dinner for the evening. He even completed the upgrade steps on my behalf, but that’s the easy part.

The hard part is what happens after you pay the activation or upgrade fee (often around $35, depending on the carrier). What is that anyway? Seriously? Why should we have to pay to activate, electronically, a new phone on an existing service? Here’s my shout-out to the wireless companies to look at that practice!

The initial process was complete. Phone is ready. Make calls. Send texts. Then, bam! Security warnings. Passwords need to be entered. How many apps am I using anyway? Are all 68,897 of my photos truly there? How much access does this phone have to my life anyway? Oh, and now there’s artificial intelligence (AI) built into the interface of the new phone. What kind of security and guardrails do I need to put around that?

A realization that I had during the process was that my phone truly behaves as my “identity hub.” Every website, every app, every phone call to a business I work with wants to send a code to the phone, use the authenticator app, or use email to verify my identity.

As an IT professional, and more importantly, as someone with security certifications, I am thankful these multifactor authenticator (MFA) methods are in place to protect us, but with a new phone, moving the authenticator methods over became one of the most time-consuming pieces of the job. I’m not talking about the text messages; those are easy and happen when the phone activates on the cellular network. I’m talking about those authenticator apps, like Microsoft Authenticator or Authy, or any of the countless ones out there that hold our identities in their hands.

If I can offer any advice on the phone transition, make sure you plan for the authenticator app credentials to be backed up and restored or moved. Those are often tied to a device and do not move over to a new device ready to operate without intervention.

Granted, in my profession, I most likely have more credentials than the average human, but if you do not plan the move, I assure you that you’ll encounter a problem requiring tech support the first time you need to access work, banking, or productivity apps.

Other odd things happened with my phone switch.

If, by any chance, you read the first article in this column entitled “Did You Reboot?”, you’ll recall I spoke about the fact that I had even had to “reboot my car.”

That same SUV has a digital key that is stored in my phone’s wallet app. That “key” is linked to the physical key fob to prevent anyone from adding a digital key to their wallet for my vehicle. That key did not transfer with the phone move. The process to transfer, or more reasonably, re-add the digital key to the wallet, included needing both manufacturer’s key FOBs in the vehicle, along with the new mobile device, and for the vehicle to be parked and not in motion. While I understand the security of all of that, my mind starts cycling through the questions like “what would happen if one of the two manufacturer key fobs were lost?” and “when am I going to be able to track down the other key that happens to be with my spouse at work”?

Fortunately, the process was smooth to transfer the “key,” but that did not completely solve my problems as my SUV no longer recognized me as the driver and, therefore, my personal settings were not being applied to the car. A little AI goes a long way in quickly troubleshooting the cause of such issues, and I, thankfully, can say that the problems are all resolved.

Technology, huh? During this switch, I kept thinking about a line I once heard: “A goal without a plan is just a wish” (often attributed to Antoine de Saint-Exupery). That’s exactly what a phone upgrade becomes without a plan: a wish that everything will “just transfer.”

Before you start, take five minutes to list your critical logins, confirm how your authenticator apps will be restored, and make sure you still have access to recovery options. This transfer should be easy, but the pitfalls are numerous and predictable. With a little prep, those problems do not have to become a crisis.