An Apple customer on the phone with customer service.
Image: Marcus Aurelius

After authoring technical articles for two decades, I sometimes sense a problem or issue I’m experiencing will become the subject of an article. That’s just what occurred on a Friday evening a few weeks ago.

Hours after Apple reported a courier picked up my paid purchase and said the package was out for delivery, I contacted Apple customer service via text to share concerns the delivery window Apple promised had come and gone 90 minutes earlier. The customer service representative told me not to worry: “It should be there on or before Today [sic] 16:30-18:30.” When I noted the time was now 19:58, I was told: “We do assure that you will receive your order within the said date within within [sic] today.”

SEE: iCloud vs. OneDrive: Which is best for Mac, iPad and iPhone users? (free PDF) (TechRepublic)

I added that I was particularly concerned now because clicking Apple’s shipment tracking link directed me to an Uber message stating the order had been canceled. Regardless, Apple’s representative insisted there were “no worries about the delivery” because “our order management team is making sure that you’ll receive your order within the day” and “Its [sic] just that sometime [sic] we are having a hard time booking grab [sic] thats [sic] why we do hope for your understanding.”

That’s when I lost faith and suspected I was beginning an odyssey that would not end well. The courier had already had the package in its possession for several hours, at that point, and my residence is only 10 or 15 minutes from the Apple Store with traffic. I was particularly disappointed because Apple rightfully owns a reputation for quality customer service, yet this was not the first time I’d experienced trouble with an Apple order. In this case, I’d chosen Apple’s Delivers From Store Today option ( Figure A ).

Figure A

Apple purchases can often be delivered to you the same day you place an order using its courier delivery option.
Apple purchases can often be delivered to you the same day you place an order using its courier delivery option.

A few years ago I failed to answer the door when Apple’s contracted courier delivered an iPhone. That mistake was on me, but unfortunately the package was returned to Apple, and they canceled the order. There was no option to just swing by an Apple Store or courier location to retrieve the box, nor was there an option to attempt a second delivery.

Subsequently I found myself in a frustrated and prolonged battle negotiating between my cellular provider and Apple, as each blamed the other for locking the authorization needed to migrate the corresponding telephone line following the canceled order. The trouble prevented me from being able to place a replacement order for several weeks.

To be fair, I should note that not all of my Apple delivery orders go bad. A business equipment order for multiple products I placed some 18 months ago delivered on time and without a single error.

This was not to be the case with my Friday evening order. Despite repeatedly being assured the product would be delivered that day, and despite the fact I never left my house while steadfastly keeping a watchful eye out for the courier, the package never arrived.

I contacted Apple customer service the next morning, again by text, only to experience a suddenly disconnected chat when I began asking specific questions regarding exactly what went wrong. I then called Apple and spoke to a cheerful customer service representative named Stacy who, while trying earnestly to assist, provided information that conflicted with the text-based customer service representative and even Apple’s own IVR system. Ultimately, I had to cancel that order, wait for a refund, then repeat the purchase.

What should you do when experiencing Apple order issues?

The Apple order issues I’ve experienced offer multiple lessons. What could I have done differently?

Visit your local Apple Store

For starters, I could have just completed the orders in person at my local Apple Store. I’m confident visiting the local store would have eliminated the errors I experienced.

Sometimes delivery to your home or business just makes more sense, but beware when choosing that option. Make sure you don’t miss a delivery, and diligently monitor the shipment’s progress.

I suspect communication issues are arising between Apple and its delivery partner, as I received differing information from Apple representatives regarding this latest shipment’s status the very next day after the package was supposedly returned to the Apple Store. I never did receive an answer as to what went wrong with this specific order, despite my politely asking repeatedly both by text and voice call.

Buying in-store ensures you have faces and names, people with whom you can meet to review an order’s errors or issues, and enables you to make any needed adjustments. These staff members may help you avoid other errors, too, by pointing out configuration adjustments or accessories you may have overlooked.

If you are purchasing equipment for business use, consider building a relationship with a store’s manager or sales staff, too. Taking time upfront to explain your budget and the purpose of your purchase enables the local store’s team to understand your needs while also creating relationships you can draw from should an order encounter trouble.

Call instead of text

Another lesson is to avoid text-based support when troubleshooting order and delivery errors. Grammatical issues introduced additional confusion, and the text-based representatives failed to make obvious connections — such as the fact the product was supposed to be delivered by 6:30pm, which had come and gone 90 minutes earlier. Worse, the chat-based representative then discounted my concerns when I requested assistance just before 8:00pm.

The courier had held my package for hours according to Apple’s shipping information at that point. I suspect text-based customer service representatives manage multiple cases simultaneously, which likely distracts their attention. I also suspect resolving order and delivery issues requires the representative to properly learn and appreciate the facts of the case, and having to manage multiple cases simultaneously likely doesn’t help.

Calling an Apple customer service representative helps ensure you receive what at least feels like an employee’s undivided attention. I have always found Apple’s telephone- and store-based customer service staff professional, engaged and committed to assisting both my personal computing and professional business needs. Working with a phone-based representative with whom you can conduct a meaningful conversation — a task that’s much more difficult using just a chat interface — pays dividends when conflicting information arises ( Figure B ).

Figure B

Calling a phone-based representative may better assist navigating complexities that text-based customer support may struggle to understand or resolve.
Calling a phone-based representative may better assist navigating complexities that text-based customer support may struggle to understand or resolve.

Keep your order information handy, and troubleshoot yourself

Another step to take when troubleshooting an Apple order is to keep your order information at your fingerprints. Whether contacting text- or phone-based assistance or visiting an Apple Store in person to resolve a problem, the order number will prove critical in obtaining help. The individual on record for making a purchase should be the person who conducts any troubleshooting for an order. Delegating the task to a subordinate will only complicate matters, especially as other information may be required to obtain additional assistance.

Remain calm when frustrated

When trouble does arise, stick to facts. Resist temptation to take offense or become angry. Avoid using adjectives and adverbs and just state actualities: Try saying “I have not received my order” instead of “I’ve been waiting forever and I haven’t so much as received a single package yet.”

Ensure you provide actual dates and times and accurately describe delays succinctly. Sticking to essential information assists the customer service representative in isolating the trouble and determining the best way to proceed; don’t make the episode more difficult by including extraneous and unnecessary information.

Sometimes that’s harder than others. I admit to having made a frustrated joke suggesting maybe the delivery driver was enjoying my purchase instead of delivering it while seeking assistance with my recent order. But I would have been wiser avoiding such distractions.

It’s important to remain civil. When troubleshooting an order failure or other issue, maintain your composure. Be calm and polite, refrain from using profanity and remember the person to whom you’re speaking deserves respect and professionalism regardless of the nature or trouble the order failure may be causing.

Whenever I’ve seen people lose their cool or I’ve behaved rashly, the situations almost always become more complicated, and there’s little reason for the other party to want to help you other than the fact it might be their job.

On a happier note, read about Apple recently debuting new and enhanced watches, iPhones and AirPods , and a recap of its Fall 2022 event .