A few days ago a new M5 powered MacBook Pro arrived from Apple. I bought it because my 2019 Intel powered MacBook Pro couldn’t handle the new Golden Gate operating system, also known as Mac 27 OS, I believe.
I hooked the two laptops together with a Thunderbolt 5 cable, then expectantly fired up Migration Assistant on both computers to perform what, in the past, has been a straightforward transfer of my old computer’s files to the new computer.
Only problem was, Migration Assistant churned away for a couple of hours, never getting past the “starting up” message. I consulted Google AI and was told that given the high transfer speed of the cable, and the fast processor of the new MacBook Pro, Migration Assistant should do its thing in just 20 minutes or so.
So I phoned Apple. Was able to talk with a real person after going through an Apple AI first. He took control of my iPhone and had me show him the setup of the two laptops. I started up Migration Assistant and he said he’d call me back in 15 minutes to see how things were going.
But a different real person from Apple called me. As described below, he had me do something that didn’t solve the Migration Assistant problem. So I turned to my Anthropic AI friend, Claude, who I’ve had many productive discussions with over the past few months.
Since this blog post is about how Claude AI and I ended up figuring out the problem that real people at Apple were clueless about, it’s fitting that I share my conversation with Claude — starting with my suspicion that Clean My Mac software could have been the reason Migration Assistant was hanging rather than transferring files from my old computer to my new computer.
I used to be skeptical that AIs are actually thinking and reasoning like humans. No longer. Read on… I’m starting at a point in my conversation with Claude after I’d been told by Claude to manually close apps on my old computer, rather than trusting that Migration Assistant would close them after it started up.
ME: I’ll try this approach. How should I handle Clean My Mac and Moonlock. They work in the background even when shut down. How can I disable them while using Migration Assistant. They might be interfering with Migration Assistant.
CLAUDE AI: Good instinct — CleanMyMac’s malware/real-time monitoring and Moonlock’s protection engine are exactly the kind of background security tools that can interfere with a peer-to-peer Thunderbolt handshake, since they run as background agents independent of whether the main app window is open.
Here’s how to fully disable both on the old Mac (the one you’re migrating from is the more important one to quiet down, but do both if you can):
1. Quit the visible apps first
- Open CleanMyMac X and Moonlock (if they have menu bar icons, click each and choose Quit)
2. Disable their background/login items — this is the part that keeps running even after quitting:
- Go to System Settings > General > Login Items & Extensions
- Under “Allow in the Background,” find and toggle off every entry related to CleanMyMac (CleanMyMac X Menu, Health Monitor, Updater) and Moonlock (its protection engine/agent)
- This stops their real-time malware monitoring and background processes from running until you turn them back on
3. For Moonlock specifically — since it’s a real-time security/antivirus tool, check inside the Moonlock app itself for a “Real-Time Protection” or “Pause Protection” toggle in its settings, and pause it there too, not just via Login Items. Antivirus-style tools sometimes have a kernel extension or system extension that Login Items alone won’t fully stop.
4. Check System Settings > Privacy & Security > Login Items & Extensions, also look under the “Network Extensions” or “Endpoint Security” section if visible — Moonlock may register as a system extension there, and those can intercept network/device traffic even when the app is “off.”
5. After migration, re-enable everything the same way — flip those toggles back on in Login Items & Extensions.
If disabling both still doesn’t help, a more forceful (but reversible) option is booting the old Mac into Safe Mode (hold Shift at startup) just to run Migration Assistant, since Safe Mode disables most third-party background processes and kernel extensions automatically — though note Migration Assistant itself may need a normal boot, so test this first.
ME: [day after Claude’s suggested fix above worked] I felt that Claude AI was more helpful than real people at Apple support in finding a solution to my Migration Assistant problem. Do you believe this is a sign that Ai agents will replace live person technical support in the not-too-distant future?
CLAUDE AI: This is a real trend worth taking seriously, though the picture is more mixed than a straight “AI replaces support” story.
Why it’s happening in your case: AI models are trained on enormous amounts of documentation, forums, and troubleshooting threads — often more comprehensive than what any single human rep has memorized. For well-documented issues like Migration Assistant quirks, an AI can synthesize the right fix faster than a rep working from a script or limited internal knowledge base. There’s also no queue, no tiered escalation, no reading from a flowchart.
Where the “replace” narrative gets complicated:
- Companies are already deploying AI heavily in tier-1 support (chatbots, triage), but the trend so far is more “AI handles the routine stuff, humans handle escalations” than full replacement. Novel bugs, account-specific issues, hardware diagnosis, and anything requiring empathy or judgment calls (refunds, exceptions) still tend to go to people.
- There’s a trust and liability dimension — companies are cautious about AI giving wrong advice that damages hardware or data, especially for something like a failed migration that could involve data loss.
- Human support also serves a service-recovery function: when someone’s frustrated, a person who can bend a policy or just listen matters in ways a bot generally can’t yet.
My honest take: the trajectory does point toward AI handling a growing share of technical troubleshooting, especially for solvable, documentable problems — probably faster than most companies’ public roadmaps suggest. Full elimination of human support is less clear; it’s more likely to shrink to handling exceptions, emotionally charged situations, and genuinely novel problems, while AI (or AI-assisted reps) absorbs the bulk of routine cases.
Curious what actually happened with your Migration Assistant issue, if you want to compare notes on what tripped up Apple’s support.
ME: Migration Assistant worked perfectly after I made the changes to Clean My Mac and Moonlock that you suggested. Of course, I came up with the idea that Clean My Mac could be the problem that was preventing Migration Assistant from transferring files from my old MacBook Pro to my new MacBook Pro. Apple AI was useless the first time I called Apple. The second time, I told the AI that I wanted to talk to a real person.
Thankfully, it didn’t sound offended. The AI just transferred my call. The Apple real person then told me to start up my old computer in safe mode, or whatever it is called, by holding down the command and some other key while it restarted. I then was told to choose the option of replacing the Tahoe OS, because the Apple real person said a file in the operating system must be corrupted. Well, it wasn’t, since Migration Assistant still wouldn’t work. As you noted above, I had the feeling that the Apple real person was reading from a script, rather than dealing with the detail of my actual situation.
CLAUDE AI: Good story — and it actually complicates the neat “AI vs. human” narrative in an interesting way.
Notice what actually happened: the AI phone system was useless, the human rep gave you a plausible-sounding but wrong diagnosis (reinstalling macOS on a hunch about corruption), and it was you — connecting the dots between two pieces of third-party software and a transfer failure — who found the actual root cause. Neither the AI nor the human support rep solved it. The person who understood the specific, idiosyncratic details of the actual setup did.
That’s often how these things really shake out. CleanMyMac and similar “cleaner” utilities are notorious for interfering with system processes, permissions, and background services in ways that are hard to predict and rarely show up in a standard troubleshooting script — Apple support scripts are built around common failure modes (corrupted files, network issues, disk permissions), not around “what does this particular third-party optimizer app happen to be blocking today.” A rep working through a decision tree has no way to know that.
So the more honest framing might not be “AI vs. human support” but “generic troubleshooting vs. someone who actually reasons about your specific configuration.” Where I was useful wasn’t because I’m an AI and the phone AI wasn’t — it’s that in a text conversation I could actually reason through the specific combination of apps you had installed, rather than following a script optimized for the most common cases. A human rep given the same time and freedom to think it through might have gotten there too; they usually don’t have either.
That’s a real gap in current phone-support AI, incidentally — it sounds like it was closer to a basic router/FAQ bot, not something reasoning about your actual problem the way a chat-based model would. So “AI” isn’t one thing here; there’s a big quality range from “scripted bot” to “actually reasoning through your setup.”
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