Amazon seems to be a well-oiled machine that magically delivers any of its millions of products to us in a day and sometimes in just a few hours. But there are a few questions that have recently surfaced that makes me question the company’s operations. And the deeper I dig, the less I really know.
This week I was searching on Amazon using my iPhone for a costume to purchase for a Halloween party and found one I liked for $49.95. I went to show my wife on her computer and the very same item was $44.95. The seller was the same company, but the delivery time was four days rather than one. The difference was I had not signed into my Prime account on her computer and Amazon assumed I was not a member. Wasn’t Prime supposed to offer free shipping and the best prices? Apparently not.
I did some online searches and apparently my experience was not unusual. I came across a discussion on Reddit where someone was trying to buy an iPad case, logged into Amazon, and the price was $11.99. When he checked the same page in an incognito window to mask his identity, the price dropped to $9.99. Same product, same seller, same reviews. Only the cost changed.
Apparently this is quite widespread. Amazon’s pricing system is built around the Buy Box, the bright button we all click without thinking. But the Buy Box isn’t always about the lowest price. Instead, Amazon’s algorithms weigh factors like shipping speed, Prime eligibility, warehouse location, and seller reliability. For Prime members, the platform often prioritizes speed. Amazon will happily serve up an item that costs a few dollars more if it means it lands on our doorstep tomorrow.
From Amazon’s perspective, this is supposed to be a feature, not a bug. Customers value convenience, and Amazon wants to keep us hooked on fast delivery. From our perspective, though, it can feel like being charged extra for loyalty. That $5 markup on the costume may not seem like much, but across millions of transactions, it adds up. And this doesn’t seem right: You pay $139 a year for Prime and get higher prices!
It’s also possible that Amazon is also practicing dynamic pricing, the strategy airlines use when your ticket price depends on who you are, when you book, and where you sit. In the case of Amazon, it’s a much more complex operation than just an open marketplace offering the same price to everyone and special delivery benefits to Prime members.
I tried contacting their customer service to learn more about the pricing discrpency, but they appeared to to be totally in the dark. Their response was to offer a credit to make the issue go away. While their customer agents seem well trained to be very generous with refunds and returns, I don’t think they have visibility into the the company’s policies or operations.
When it comes to Amazon’s logistics the agents have little idea where your package actually is. If a delivery is late or seems lost in transit, the scripted responses are the same: “It’s on its way,” “Check back tomorrow,” or “Wait until the estimated delivery window passes.” The reality is that Amazon relies on a web of third-party couriers, contract drivers, and regional warehouses. Once a package leaves Amazon’s own trucks, visibility can drop to almost zero.
On one hand, Amazon can be a logistics miracle, capable of getting toothpaste to your doorstep in four hours. But from my experience, when something goes wrong, customer service agents are left guessing. They don’t have the granular tracking that FedEx or UPS can provide, and the “guaranteed delivery dates” that lure us into clicking and paying a premium for quick delivery can quickly unravel into apologies and refunds. For a company that prides itself on convenience, this lack of transparency seems to be one of their weakest links.
My friend Joe Brancatelli (biztravel.com) related his Amazon experience when he recently placed an order. He was waiting for a promised 11am delivery the next day. Without notice, they rescheduled the order to arrive at 6pm a day later. The stated reason was that the order was late arriving to a nearby location, New Windsor, N.Y., eight miles from his home. He wondered why it would take another 31 hours to deliver if it’s just eight miles away.
Then he received a second email saying the package was “running late” with no promise of a delivery date at all. In the middle of the night at 3 am, Joe checked the package status on Amazon and it said his package recently arrived at New Windsor at 1:30 am, contradicting what they told him the day before. The package arrived soon after at 4:40 am
Clearly their delivery information is opaque and often wrong. It’s telling you (and probably the chat and phone agents) stuff that simply is not true. So there is no way to know when/if your packages will arrive on time or at all. And, of course, with the system lying about the actual state of things, it’s impossible to do real service recovery because the agents you’re talking to don’t know where anything is.
One of my recent orders was supposed to arrive on a Monday, two days after ordering it. When Monday came and went without a delivery, I checked their site and it said the package was taking longer than expected and if it didn’t arrive within the next two days, I could cancel the order. Two days later, with no sign of the package, I canceled it and received this cryptic message: “Your package is returning to Amazon because of one of the following reasons: Damaged in-transit, carrier could not locate your address, or refused by the recipient.” That’s quite a wide range of excuses.
So what can you do to protect yourself—on price and reliability?
- Look beyond the item marked Prime. Scroll down to “Other Sellers on Amazon.” You’ll often find the same product—identical in every way—for less.
- Compare logged-in and logged-out views. Check the same listing in incognito mode or signed out. The difference might surprise you.
- Think about shipping needs. If you don’t need something tomorrow, you might save by choosing the slower, cheaper offer.
- Use tracking tools. Sites like CamelCamelCamel let you see price histories. You’ll quickly spot if the Amazon discount is real or not.
- Don’t forget competitors. Target, Best Buy, and Walmart often match Amazon, especially for mainstream products.
- Contact customer service early. If a package looks stuck, push for a refund or replacement sooner rather than later.
Amazon counts on our impulse to click “Buy Now” without checking. But you don’t have to pay the loyalty tax—or endure endless waiting for packages that may never arrive. Its vaunted logistics network is sometimes more illusion than precision.
The irony is that Amazon built its empire on being the place with the best prices. Today, it’s the place with the best convenience. That’s fine, as long as you know what you’re paying for—and sometimes, that’s not just the product, but the privilege of hoping it actually arrives when promised.
Joe has found he gets better service from Walmart+, their version of Amazon Prime. Deliveries come from local stores and are more predictable. The Amex Platinum card offers a free membership in Walmart+. Here’s a summary of how they compare.
| Feature | Walmart+ Perk | How It Compares / What’s Unique |
|---|---|---|
| Subscription cost | $98/year or $12.95/month. | Slightly cheaper than Prime’s $139/year. Month-to-month are close in price. |
| Free delivery / shipping | Unlimited free delivery from Walmart stores, sometimes same-day for many items. Minimum often $35. | Prime offers free shipping with fewer minimums, often free 1- or 2-day shipping without a high threshold. |
| Grocery delivery | Included, especially for Walmart groceries. Same-day delivery from local Walmart in many areas. | Prime has strengths here via Amazon Fresh / Whole Foods / Prime Now; but availability depends on location. |
| Fuel discounts | Members get discounts at Walmart, Murphy USA, Murphy Express gas stations (and some others), e.g. 5¢‐per‐gallon off. | Prime doesn’t offer fuel discounts as a core benefit. This is a differentiator for Walmart+. |
| In-store convenience | “Scan & Go” using the Walmart app (scan items, skip lines), mobile checkout, etc. | Prime has physical-benefits via Whole Foods discounts and/or Amazon stores, but doesn’t have this kind of scan/checkout convenience in many everyday grocery/retail stores. |
| Entertainment / streaming | Includes a Paramount+ Essential plan (with ads) for Walmart+ members. | Prime gives more in entertainment: Prime Video, Prime Music, Prime Reading, etc. Walmart+ is more limited here. |
| Additional perks / deals | Discounts at places like Burger King, auto-care perks at Walmart, free returns, exclusive deals. | Prime has its own set of deals (Whole Foods discounts, etc.), but Walmart+ is focusing more on everyday savings (fuel, in-store ease, grocery) rather than heavy entertainment or global reach. |
