Dave Weiss thought he’d done everything right with his iPhone trade-in. He sent his old phone back to Apple, expecting a smooth transaction and a $160 store credit. 

But what followed was a two-month odyssey of unanswered calls, dead-end tracking updates, and a lost device that left him phoneless — until he asked my advocacy team for help.  

“Apple shipped it to me, UPS lost it — but I was the one paying the price,” he says. 

Weiss’ case raises critical questions for anyone shipping high-value items:  

• Who’s responsible when a package is lost during a trade-in?  
• What should you do when a company stops responding to your claims?  
• How can you escalate a problem effectively — and get results?

Let’s unwrap Weiss’ saga — and what it means for you.  

“I’m stuck”

Weiss initiated a trade-in through Apple’s website, and he says he followed Apple’s instructions to the letter. He shipped his iPhone using the prepaid UPS label provided by the company. 

But a few weeks later, his tracking number froze at the “on the way” message. 

Apple later claimed that his old phone failed inspection, and sent it back to him. But the old phone never arrived.  

Over the next 8 weeks, Weiss made five calls to Apple, emailed CEO Tim Cook, and contacted corporate relations. Each time, promises of investigations led nowhere. 

“I’m stuck,” he says.

Apple advertises its trade-in program as an easy way to upgrade your phone, and for most customers, it is. But it doesn’t prominently say that the program depends on the cooperation of UPS and that your device could fail an inspection. Or that you be without a smartphone for weeks or even months when something goes sideways.

I suppose if it did, fewer people might upgrade their iPhones. But anyway, here we are. Weiss still didn’t have his phone, and that’s when his case landed on my desk.

Who’s responsible when a trade-in gets lost?

If a company provides the shipping label, it’s the shipper of record, not you. Under UPS’ terms, the party that pays for the label (Apple) must file claims for lost packages. 

Consumers often assume they’re on the hook because they dropped off the box. But liability falls on the company that arranged the shipment.  

Weiss’ ordeal highlights a common loophole: Many companies outsource trade-ins to third parties, creating confusion over responsibility. Apple’s trade-in terms initially suggested Weiss might be liable if the device was “damaged in transit,” but its own label contract with UPS negated that.  

That’s one reason you should always screenshot the shipping label’s terms before sending items. If a retailer claims you’re responsible for loss, remind it that its label — and its contract — controls liability.  

Another thing you should do: Take a picture of the intact phone you’re trading in. Power it up. Take a picture. Flip it over and take a picture of the other side. That way, you have evidence that you sent an undamaged phone back to Apple, or whichever company you’re working with on the trade-in.

I’ve had too many cases like this, and unfortunately, consumers often pay a high price for failing to document their trade-in. 

What if a company ghosts you after a trade-in? 

Weiss’ paper trail, including call logs and emails to executives, was key to his case. Without documentation, companies can claim they never heard from you. A timeline proves you’ve followed their process.  

Apple’s silence after multiple escalations isn’t unusual. Large companies often rely on automated systems to flag “high-risk” cases, like repeated complaints. And unfortunately, it sets you to “ignore.” (Paradoxically, persistence can bury your claim deeper.) 

After two unproductive contacts, consider switching channels. Weiss’ pivot from calls to executive emails (and later, media advocacy) forced Apple to manually review his case. Use platforms like LinkedIn or registered mail to break through automated systems.

That being said, there’s no perfect way to get a company’s attention. There are stories of Tim Cook personally answering his email, which is why I publish it on my site. But more often than not, he probably forwards the message to an assistant, who then re-inserts it into Apple’s customer service system — which may then continue ignoring you. 

But the bottom line is, Apple couldn’t just refuse to send him the promised credit. It either needed to send him his old phone or give him the credit.   

Here’s the $160 resolution — and what It means for you

Within 24 hours of my contacting Apple on Weiss’ behalf, he received an apology and a $160 credit. 

“Wow, I don’t know how you did it, but you accomplished in a day what I couldn’t in weeks,” Weiss said. “Thank you so much for your help, Christopher.”

But this case isn’t just about a refund. It’s a blueprint for navigating opaque corporate systems.  

Companies count on consumers giving up. But there’s always someone higher to contact. Document everything, escalate strategically, and never assume a “closed” case is truly closed.  

Remember, when a trade-in vanishes, the shipper — not you — has to fix it. And if it won’t? Sometimes, all it takes is reaching the right person.