Note: This column has been updated to include a response from Kaspersky.

In the earliest days of the Web, I used to urge companies to force their developers to test all their sites on the slowest dial-up connections rather than on their enterprise T3 connections. My thinking was that if developers saw things through their users’ eyes, they would be more careful about making sure their sites were fast loading. That problem has gone away, but I have a similar message today about product updates and installations: Have your developers watch ordinary people using ordinary tech support try to install them.

As you can guess, this thought was prompted by a horrific user experience I just had to endure, this time at the virtual hands of Kaspersky. Kaspersky makes one of the industry’s best consumer-grade security packages. But you are probably going to want to pay someone else to install the product for you, because the process will have you considering homicidal acts.

After spending several hours of going through the process and getting nowhere with technical support in the guise of an ordinary consumer, I reached out to Kaspersky as a journalist and got connected to a very senior and helpful tech support person. It took him a few tries, but he eventually got the job done. And I have to wonder, If I weren’t a journalist, would I have ever finished the install? But let me go back and tell you how I got to that point.

The fun began when I received an automated notice that my key for Kaspersky was about to expire and that I should renew it. As a longtime fan of Kaspersky (once it’s up and running), I thought “Sure, why not? If I just give them my credit card and accept everything, I should be wrapped in about five minutes.” What can I say? It was early in the morning, before I had had my coffee. I am far too optimistic and naive at such moments.

The first thing I noticed was that there was no direct link in the email to accept the upgrade. That led me to scour the site for about 10 minutes before finding what I needed. It doesn’t help that Kaspersky’s constant product name changes made it challenging to know which product I wanted. Note that I wasn’t trying to upgrade the software, but merely to update the activation key, a.k.a. the license. Apparently, that required new software, but neither the email nor the site bothered to mention that.

No matter. After processing the payment for a two-year and three-device license, I tried to download the new software. That process began, but then it paused to tell me to uninstall the old version. Odd, given that most install programs do that directly and automatically. But if that’s what it takes, I’ll uninstall. The uninstall failed, however. A few Web searches found that this is a well-known issue with Kaspersky; some elements of the program just stay on the system despite an uninstall. Given that Kaspersky’s tech support site noted this in August 2013, one would think that it would have been fixed by now. (I have routinely accepted any Kaspersky patches and upgrades for several years.)

But I stayed on the ride. There was a special Kaspersky uninstall key, which Kaspersky tech support told me to install. They emailed me instructions. The instructions told me to go to a Kaspersky FTP site and download the tool. I went to the site and followed their instructions and used the provided FTP username and password. That combo worked initially, but the server asked for the password again and, that time, it rejected the credentials provided.

That’s when I finally gave up and spoke with the senior support person arranged for by Kaspersky corporate. He said that there was no reason to use the FTP site and that I could get the uninstall tool on the public-facing Kaspersky site. (Thanks, regular tech support.) That original email had also told me that, after I downloaded the uninstall tool, I’d need to boot into safe mode. The senior tech support person seemed surprised by that and said that that advice refers to a much older version of the tool. *Sigh!*

With the senior tech support person on the phone, we got the uninstall tool working and did a new download of the software — he helped me figure out the name change — and all seemed fine. Until …

Until a few hours later, when we tried installing the software on a second machine. Remember that this license was for three seats. The software refused, saying that we had exceeded the number of machines. (Math challenge: Since when is “one” more than “three”?) I called regular tech support (you’d think I’d have learned by now) and was told I had indeed exceeded the number of machines. How? Well, go to the Kaspersky site, a colleague was told by Kaspersky tech support, and it will tell you the machines the software is on.

I needed to log on to find this list, but there was no place on the homepage or any linked page that offered a place to log in. We eventually found a link deep within an old email that eventually took us to a place where we could log in.

After logging in, I discovered that there was no link on the site to display a list of all devices where the software thinks it has been installed. If the site does have the ability to display the machines it’s installed on, we never found it — and no one in regular tech support could find it, either. But tech support did confirm that we did pay for a three-device license for two years. Somehow, the system was displaying that it was a three-device license for one month. (That doesn’t explain anything, given that this all happened on the same day, so the “one-month” limit wasn’t a factor. But it’s a continuation of a pattern of conflicting messages.)

Tech support eventually concluded that I had seen the wrong key. Can they fix that? Nope, I was told by multiple tech support people. The sales team are the only people that can fix that. I was then transferred to sales. Most readers can guess what happened after a long wait in the sales queue: Sales said that they can’t help, but that tech support could. I then told sales that tech support said the opposite. Back I went to tech support. Rinse, wash, repeat.

My effort to get tech support and sales to agree to a conference call were unsuccessful. Eventually — that means five calls later — I was able to get someone in tech support to agree to try to fix the issue. Several hours later, I received an email that said, “You can now go ahead and try to reactivate your Kaspersky. We have already reset the activation code.” I did so, and the system seemed happy. Until we tried installing it on the second computer and the problem returned. Entertainingly, even the first computer was now saying that it was deactivating protections because we had exceeded the number of devices.

Software companies, of course, need to make their products powerful and effective. But if the installation and upgrade process is not made simple, problems are going to result. This is where you make your money. Please test it regularly and use external testers. And force them to get answers from the regular tech support team, accessed through normal channels. You’ll learn that there’s a lot more to software sales than the product itself.

Kaspersky responds:

“You ordered and paid 3-device license but 1-device license was delivered instead. It was caused by our internal system mistake. There was relatively short period of time when this system was down for maintenance and your purchase request came at that down time was redirected wrong way caused wrong type of license delivery. As a result you were able to install it successfully once but the second device installation failed as it was 1-device license. And resetting the license key by support engineer doesn’t help as it was still resetting to 1-device license. That’s why you faced the same issue with device count limit once again.”

— Alexander Voinov, head of Global Support, Kaspersky Lab