Ask HN: Have you ever worked on a product that was killed by technical debt?

There are multiple cases of "killed by technical debt".

There's the case of mysterious and unsolvable breakage. The product simply stops working, and the team is unable to get it working again, period. This can happen with really ancient legacy products where the original team is gone, or young products that are written badly by inadequate teams.

There's the case of unpleasantness. A product is so difficult and slow to work on that the company simply loses interest in it, and shuts it down rather than suffering through more maintenance. This does not happen with products that are highly successful business-wise, no matter how bad the suffering, so it's really a business failure rather than a technical one.

There's real antiquation. The product is dependent on a product of an outside vendor that is no longer available/maintained. I've dealt with this on a mainframe replacement, and it was horrible. I've also dealt with this in Java, and it was plenty painful there too.

And finally, there's replacement. A product is replaced (or intended to be replaced) by a new product that does more or less the same thing, only this time with a smart new team, in a hip new language, and by the gods, this time it's not going to be stupid and suck like that piece of crap the morons on the old team built! Most of these projects fail before they ever replace the old, working code, so I'm not sure this counts as technical debt failure.

Yes and no.

The project wasn't killed specifically because "you have technical debt". It was killed because there was no way for anyone to be effective with the combination of poor undocumented code.

"We need to change the email message that goes out when someone registers". This took a team of (4?) people 5 calendar days to change. As a contractor, I had to vpn in to one system, then remote desktop over another vpn to another system. Building web apps, these dev systems were not allowed to talk to the internet at all, so things like pulling external dependencies (security libraries, templating libraries, etc) was impossible - pretty much everything was handrolled, largely due to this restriction.

The last big killer was that the system was not passing accessibility audits. Trying to determine where to make a change to any single element would take minutes to hours, vs seconds to minutes you'd normally expect. Much of the 'templates' used were the result of a SQL statement joining 12 tables (html_meta, html_form, html_link, html_grid, etc) and complex concat()s, so adding a page or making a change might take an hour to track down the appropriate collection of tables, then figure out a SQL script to run, then send it to the person who had permissions to make updates to the SQL, then wait and see.

Did the technical debt itself kill the project? Technically no, but the inability to do anything productive in a reasonable amount of time forced the project to shut down.

I was CTO of a company that had a two-week outage due to technical debt. I didn't sleep much for any of it. We fixed it, and we'd lost about 30% of our subscriber base in that period. The company took on new funding to survive, invested that in a new set of products, and shuttered the old stuff just to stay afloat.

I am currently working in a business where there is a nearly 8-year old Rails app (600+ models, 250+ controllers, 400+ libraries, LOC around 60k), that sits at the heart of everything we do.

The company is struggling to grow and believes the cause is that engineering is slow. We have asked to refactor this code base multiple times, and point to the technical debt as the cause features that should take a day to implement taking between 3-4 weeks, typically.

It is only recently that the penny has finally dropped and they've realised if they don't invest in replacing this thing (there is too much technical debt to fix, we're calling bankruptcy and moving to a brand new architecture piecemeal), the business is likely to fail within 1-2 years.

That means my current employer is likely to go bust because of technical debt within 2 years max unless we become really good at fixing this.

We are optimistic.

We have to be, right?

Knight Capital lost $465 million in 45 minutes caused (at least in part) by technical debt and poor development practices.

Summary: http://pythonsweetness.tumblr.com/post/64740079543/how-to-lo...

It happened to me twice. The first time was in a start-up at the beginning of the century, we were developing an electronic health record and we had outsourced the database abstraction layer to a company in Greece. In the beginning things went fine but after a while the development of the DAL went slower and slower and it became unstable as well. Eventually the word came out: the main developer of the DAL framework had left the company and, according to the Greek CEO, she had been 'too smart' which meant that nobody understood her code. They had tried adding features but that had made things only worse and the DAL had started to crash randomly. We tried to take over the framework by ourselves but it was written in Eiffel and the code was a horrible entangled mess. Eventually we rewrote it in Java but, being a start-up, we lost too much precious time already and eventually went almost bankrupt and were bought up by a competitor.

The second time was in a small company whose product was a search engine for consumers. The web layer was written in a mixture of JSF, JQuery and Ajax. While that combination already slowed down development on the front end, the main problem was the performance of JSF on the server. Because JSF is rendered on the backend, it placed a massive load on our server for certain heavily used pages and we just couldn't scale any further. Skipping JSF for a framework that was rendered on the front-end would be the solution but that was a massive refactor for which the company just didn't have enough resources. Eventually the company had to skip their search product and change their business model to a more community based website.

I've worked in the industry as a developer for 12 years and I can't remember any.

I do remember a competitor dying of not releasing their big refactored next version soon enough, and running out of cash.

Spolski tells it better than me:

https://www.joelonsoftware.com/2000/04/06/things-you-should-...

The closest I've come was a Rails project I inherited from a star developer who had just left the company. It was a B2B project that involved importing large Excel spreadsheets of various different formats into a standardized database for itemized review.

The code was pretty sloppy, but didn't deviate much from standard Rails idioms. Not many people on the team understood Rails well enough to read it, but I did. Bug reports were constantly flooding in. I suggested taking a sprint to build up an integration test suite and then letting loose on the backlog.

We did build up a sufficient test suite in one sprint. But the bug reports never slowed. By the time we had the confidence to truly start tackling bugs at speed, the battle had been lost. We had been so busy writing tests that we forgot to manage the bug tracker. The impression was that we were overwhelmed and unable to make progress. The project was swiftly closed.

People remembered that codebase as an exemplar of sloppy code and technical debt, but that's not the lesson I took from it. I had seen, and others would see later, much worse. The lesson I took was that perceptions are as important to manage as results.

The last place I worked at will die because it will take them years to migrate from Oracle to postgres due to "technical debt" (the codebase is coupled with the database to a hilarious degree; business logic in triggers, huge plsql packages, plain sql queries in the java codebase, halfassed homerolled ORM). They're not getting as many new customers as they could because, for various reasons, the Oracle licensing terms are now unacceptable for the new customers they have been in contact with over the last two years.

That's the most concrete reason I can come up with why the technical debt will kill them, but there's plenty of vaguer reasons why it's been killing them for the past 5 years and will finish them off over the next 5. The attrition rate have been around 20% a year since I joined. For most of the time I worked there they compensated somewhat by hiring new people. Word has gotten around though, and they've run out of qualified candidates willing to work on their mess. Hell, we even had a couple of gifted hires leave after a month or two while shaking their heads.

My current workplaces main product is using the same tech, is the same size (loc) and has the same functionality of the other company, but serving a different market. They did the oracle to postgres migration in 2 months. 2 MAN months, one guy.

New workplace: 15ish developers, serving the same amount of customers, doing similar revenue, making stable releases every week

Old workplace: 80 developers at its peak, doing non-hotfix releases around every 3 months. Just a mess in every way. Mostly stemmed from the codebase and the architectural choices that had been made along the way.

ITA software is a good example of a company that succeeded due to the collective technical debt across their competitors.

Though they only really succeeded on the shopping part. They didn't ever get to a credible booking engine that anyone would buy. Which may point to something other than tech debt being the biggest barrier to modernizing an airline reservation system.

How about: All Of Them

Every failed product/project I've worked on in my professional career, which had full intent to ship from the start, was killed by technical debt. It's usually indirect, but it's always the root cause.

It takes many forms:

* Too buggy to ship, due to a creaky old code base being over-stretched to a product with too high reliability/experience expectations.

* Product form factor, efficiency, user experience not good enough to sell well, due to spaghetti code base which couldn't be whittled down to removable pieces. Result: large runtime, more expensive, less efficient hardware.

* Existing old codebase deemed too bad to ship a product, requiring a rewrite-from-scratch, but timescale too long to make any sense -> product killed.

It's difficult to elaborate more while maintaining some discretion about exact companies and projects. The general point is: technical debt isn't just some fuzzy intangible issue — it indirectly creates enormous costs in people and time, can affect the physical form products take on, and impact the user experience. Products always get started without taking this debt into account, but when it's finally realized, it can change basic features, and then it kills them.

Products are designed with faulty assumptions about what existing resources can be applied to them.

I'm currently working on the reincarnation of a project that was killed by technical debt -- TWICE.

The original codebase was about 20 years old. It was control code for something best described as an industrial robot. Written for the last 20 years by greybeards who knew a lot about the manufacturing process, and were reasonably good at getting a product out the door.

But the whole thing was riddled with #ifdefs for this customer or that, or one batch of machines or another. All long forgotten, written by people who had since left, or been pensioned. It was in dire need of improvement and extension, but it would have been superhuman to inject new features into this rat's nest. Plus their electronics supplier was discontinuing the control electronics the system was designed for. The UI also looked like it had been designed by German engineers in the 1980s. Which was the case.

So they made the defensible decision to start from scratch. A team of engineers was to develop an brand new machine, with all new electronics and all new code. They got to work -- and had to scrap the new software about three years in. It was just utterly misdesigned, and riddled with bugs. It featured wonderful WTFs like the embedded realtime code depending on the Qt libraries.

I observed its instability myself: it would just spontaneously crash every five minutes, sometimes just while idling. Once the project lead was on holiday, the programmers revolted, went to the head of the company, and the project lead found himself without a project on his return. Whee.

Now we've started from scratch again, and have at least succeeded in making different mistakes this time around. Fingers crossed, this might end up working.

I have seen a product getting killed by trying to resolve technical debt. The refactor took nine months and in the end didn't work better.

I am a big fan of constant refactoring on a small scale but I am very skeptical of large refactoring of a whole project. You may end up with something that's just different but not really better.

I did work on a project that was Rails 3, and for various reasons, it can never be upgraded without basically rebuilding the entire system. They keep hoping for an exit that will simply never happen because who would buy a rotting system like that? I think myself and only a few other devs there understood the situation. Its not like sales or the CEO fully understood.

I am working on a project now that bears some study.

I built this extranet app for a Fortune-class / NYSE company in 2001. They were a Lotus Domino shop so for that and various other reasons the extranet was deployed in Domino. The initial rollout was considered quite successful, but it was definitely "v1" code, and I'm being really generous with the code quality. Plus, Domino.

The application was considered a stopgap until the shop had become fully Microsoft-centric, at which point it was expected to be migrated to .NET. That was expected to be in ~5 years.

The result was that no investment was made into the app for over fifteen years. Every now an then an enhancement would be needed, and a contractor would be called up to bolt on a feature in shockingly slipshod manner (this app is much too complex for the average Domino dev). But no technical debt was ever cleaned up, because "meh, we're going to replace that app by 2007."

2007 was 10 years ago. In the meantime two projects to replace the app were spun up and killed. The app is finally being retired this year. I was called up at the 11th hour to jump back in (15 years later) to help support the thing through the conversion, as the one existing Domino dev they had on staff finally (wisely) jumped ship.

I cannot even begin to describe the state of this app.... it's a case study in "how to not manage IT."

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Another recent client was a content-creation shop (think glossy magazines). Their outgoing sr dev had deployed a CMS that nobody had (or has) ever heard of. This CMS was originally developed during the glory days of XML. Believe it or not, the app worked by loading all of the CMS content into a single in-memory XML document. This was probably OK for a brochure site, but this was a site with hundreds of thousands of pages of content. As a result the application required a server with 64GB of RAM just to launch. Also - launching the app took about ten minutes after the server OS was loaded. And there was no server farm, just the one server. If the app was ever stopped, it would stay down for at minimum 10 minutes.

I came in to fill in temporarily and to try to find someone to staff the position permanently. Even with a competitive salary, nobody qualified wanted the job.

Meanwhile, the same company also had a set of blogs that they managed in WordPress....

I worked for a startup that had basically the right idea but proper execution took so long we ran out of runway. The first iteration of the product was built in an extremely haphazard, cowboy way - and took months, if not years, to refactor into something stable, usable and crash-proof. By the time the product was operational, the company was bankrupt. We simply hemorrhaged money until we bled to death.

As someone else pointed out - technological debt is not a cause per se; it's an indication of some deeper problem - usually of human, not technological, nature.

Kind of, but not really. When I complain about that product I almost always complain about marketing, intransigent leadership, etc. Ostensibly technical debt killed the product, but technical debt is almost always a symptom not a cause. Technical debt can get out of control, but you have to wonder how it got to be that way.

It seems everybody here is suggesting that they have worked on products that were killed by technical debt.

I'm going to take a different stance and suggest it is very difficult for a product to be killed by technical debt.

I'm working on a product now which has huge technical debt requiring a full re-write, but we have customers who love the product, so we just keep the old version going while building the new version.

Let's assume we are talking about a single product company here, to make the discussion simpler and not get bogged down by larger corporate issues and it lets us focus on the case where the product is what is paying the bills (assuming we're talking commercial products here).

Let's look at a few examples.

The product has some customers, but it is difficult to add new customers due to some technical debt issue and the lifetime customer value for your target market does not cover the cost of re-developing your product and continuing operations. Ok, you're probably dead.

You've got some customers, and you can't sell more, but the lifetime customer value is greater than the cost of re-engineering the system. You've got some bad times ahead, but there is a path. So technical debt doesn't kill you.

You've got technical debt, and you don't have many users, you want to add features but can't because of technical debt. Did technical debt kill the product? Or was it killed by a lack of market? You don't know that the new features would have saved it, all you know is that what existed did not make enough to keep you going, so that can't really be blamed on the technical debt.

Technical debt can be costly, but rarely fatal. It's great not to have it, it can make it difficult to keep good people (I lost 2 amazing devs partly because they hated the old code-base we inherited, but they also had amazing opportunities).

Yes. Technical debt rendered it difficult to create features, and difficult to hire. The project dragged on as engineers came, tried to refactor and then left. I didn't stay.

My understanding is that it was never released, so all of the money the company put into the project was wasted.

This is maybe different from what people normally consider 'technical debt'. I don't mean just code aesthetics but also bugs, redundant code, and bad abstractions.

Projects rarely die because of technical debt. Instead, it becomes ridiculously expensive and difficult to add new features. But the software itself can remain in use for decades, gradually decaying and rarely adapting to changes in the business environment. Eventually either the software gets thrown out and replaced with something new, or the company is no longer able to compete.

I've seen this play out probably close to a dozen times now, at different employers and consulting clients.

Technical debt is not a thing that kills products. Shit-ass management kills products. Technical debt may or may not be a symptom of shit-ass management.

I'm currently watching this happen to a product from the outside. The company I work for has an ERP system from the late 80s, written in COBOL for the HP 3000 series computers. At the time, it was probably an excellent system; however, over the years it's had modernizations tacked on with no regard to actually improving the core system. Some examples:

* In the early 2000s, they added support for Windows NT to the product. Unfortunately, they did this with an MPE compatibility layer that means the entire thing still thinks it's running on an HP 3000, so controlling it programatically means writing MPE job streams.

* It was originally written to store data in COBOL records. When they added support for SQL databases, they apparently just copy-pasted the schema verbatim from the COBOL copybook format. This means the database has no foreign keys, FLAGS columns all over the place (including tables where you have to JOIN ON SUBSTRING), and, most egregiously, a table with ITEMNO_001, ITEMNO_002, ITEMNO_003, PRICE_001, PRICE_002, PRICE_003 and so on, which has to be queried three times and UNIONed to get the data out.

* Printing packing lists requires not only a specific model of printer, but also an extra several-hundred-dollar chip to be installed in that printer. I'm told that this chip's sole function is to enable barcode printing.

I have no insight into what goes on inside the company that makes this thing, but it certainly looks to me like they have a severe case of technical debt. Any bug fixes generally take 4-6 weeks in the best case scenario, and frequently either don't fix the bug or introduce new ones instead. Their only customers are the ones that have been using the system for so long that they're stuck with the system, and can't switch--in fact, many of them are still running HP 3000 systems, which HP has been trying to end-of-life since at least 2006.

The end result of this is that the product is dying a slow, agonizing death of attrition. I think the only reason it still exists at all is because the company that makes it is stuck with support contracts that haven't expired yet.

I had a chance to ship the first Tower Defense game for iOS. The OS X game I was porting had some crippling performance problems that were incredibly hard to track down.

The problem was two-fold:

1. The relevant tools (Unity3D) were extremely immature and the problem was quite diffuse. No profiler, poor quality of generated code, tiny caches, etc.

2. A problem in string-handling code that was quite diffuse throughout the game. As near as I can tell, it was blowing out the tiny CPU cache hundreds of times per frame.

On desktop, this code was a complete non-issue. On the puny little ARM on the iPhone? It was the difference between having dozens of towers and 50 enemies in play vs half a dozen towers and less than a dozen enemies in play. The impact on game dynamics, and need to re-balance everything by itself would add weeks to the shipping schedule.

There were plenty of other things that needed to be scaled WAY back of course: Switching from 3D to 2D to get vertex count and draw call count down. Completely rebuilding the entire UI. Revamping the pathfinding and suffix caching to not play havoc with the CPU cache. Moving from a 24x24 grid to a 12x12 grid. All of that combined helped a LOT, but not nearly enough.

The string manipulation was for a hierarchical property system that let me parameterize all sorts of attributes for enemies/spells/towers/projectiles in a set of text files. Ultimately, I had over-engineered on the assumption that I would be tweaking many more things -- with much greater frequency -- than I wound up actually tweaking.

Had I ripped most of it out and just had local properties on each prefab that I assigned manually, I might've hit that market opportunity. Finding that that was the cause was a multi-month project because of how interwoven it was with everything else. Hell, it would've been fine, had a not over-generalized it into a shared component on each prefab that the other components inquired with to get property values. But I did. And it took me vastly too long to identify it was the major problem it was.

Opportunity missed, and that was the final nail in the coffin for my fledgling game studio.

Technical debt won't necessarily kill a project, but over time it will reduce the speed at which you iterate and ship software. That loss of speed does kill companies, young and old.

I wouldn't say, killed, but severely burdened? Limited by technical debt? Sure.

One application was a web application built in C++ in the 90's. It didn't have the STL, it implemented everything from XML parsing to PDF rendering from scratch. It stored all data in XML files on the file system. It was a single-threaded CGI application. And it was the core product of the small business that created it.

There was no series-B/C/D/E that was going to appear so we could hire more developers and re-write everything or develop a new, superior product, etc. This is where I learned how to maintain and extend legacy software. I spent hours pouring over Michael Feathers' book. We did manage to extend and breath new life into the system. We wrapped the old code in Python, wrote a tonne of integration and unit tests on every change, wrote some code to sync data to a database alongside the XML file storage scheme it used. We even got to a place where we started replacing code paths from the Python API with functionally-equivalent (as far as our test suite was concerned) code written in nice, clean Python (and gained some features along the way thanks to Python's nice libraries!).

We kept the lights on without having to spend too much time hacking on undocumented, untested C++ code and without trying to just re-write everything. It was much more difficult to make progress than a typical greenfield project in a dynamic language but that would've cost more upfront without a clear payoff... so we did what we had to do.

Another company? Well they decided to use a document-based data storage system as the source of truth in a hot-new micro services architecture that was going to save everything... only there was no schema validation and their use cases were killing performance in some scenarios. Random breakages cause by changes at a distance. It hasn't killed their business but it has limited their options.

Our product, a large-scale enterprise software, is slowly getting killed. It's old and it's rather unusable (by the users). Plus, for "backward compatibility", it supports dozens of strange configurations. It's dragged down by so much technical debt (functions longer than 3000 lines with 60 parameters!) that every small changes requires so much time.

We're slowly killing (i.e. no big new developments, but only maintenance for existing customers) and abandoning it. And luckily we're not rewriting it. :-)

I think implementations are more often killed by technical debt rather than products or brands tbh.

Although at that point I wouldn't call it technical debt. If you've a million lines of spaghetti code, then you've a million lines of spaghetti code not technical debt. I.e. a camel is a camel. It's not a horse with technical debt.

Two examples I can recall. First time was an embedded application for a smallish (2-3 SW developers total in the company) firm. The code was, by my estimation, initially developed by a real talented senior guy. It at one time did what it was meant to do pretty well, and adhered to sound (at the time) best practices. Well Mr. Senior Guy ended up leaving for whatever reason, and since then, a string of less senior folks were brought in one by one to burn out maintaining the system throughout the years. And by "maintain" I mean "toss in every feature under the sun that the CEO asked for, whether or not it made sense and whether or not the rest of the system kept working". Every little thing that might get one potential customer to say yes was bolted on hastily and shipped as soon as it could compile. Just get it to work by any means and ship it. I was brought in as one of this long string of people. By the time I came, the CEO was frustrated that the system could not be added to quickly enough anymore, and that core functionality would fail in the field more and more often. It was a total mess, and eventually proved irredeemable. I'd like to say I left the system in better shape than I found it but at the end of the day it didn't matter. Technically, this project is not dead so it doesn't meet this Ask HN's criteria, but I don't think they ever have or will make another major release of it. It will limp along until they start taking technical debt seriously.

The second one was a mobile app that was originally ported from some legacy J2ME app and "gotten to work" on the iPhone platform. It was pretty much a straight port, data structure by data structure, from Java to Objective C, and didn't really use the platform properly at all. For example, each and every control was hand-crafted to mimic the original J2ME app, rather than using the built in UIs that iPhone provided. It got to the point where nobody could touch it without it falling over, and no senior person was willing to work on it anymore. I was senior enough in my career at that point that I could insist that a complete re-write was the only way to go. We did that successfully and the previous pile of technical debt was killed.

Those examples aside, I'd say that almost every place I have worked suffered from technical debt to a large degree. The common theme was a huge legacy code base that suffered for years (decades) from repeated "just cram it in and get it to work" abuse. The metaphor I always like to use is: No home builder on earth would, when their requirements were to build a 5 story apartment building, take a single story single family home and just add 4 floors. But seemingly every company building software attempts to do this.

I am right now, but I can't take a step back and fix any of it because that wouldn't be "Agile". The project won't be declared a failure though, they will just keep adding more and more "resources" aka people to get the same amount of work done.

This is going to be vague for obvious reasons.

I worked on an EDA product for a short time. Its code base had a few components, some of which were written by the product team, and some of which were copied (without source history) from other teams. The team decided to make a cloud version of the product too, and to do that, the team split in half and each new team had their own copy of the code base.

No sharing code, because those other teams were our competition. There were teams working on components for our product, and another team working on a copy of our product, but nobody shared code. So bugfixes from one of the components would never make it into our code base. (The components were products in their own right.)

The code base was ~30 years old, and it had "survived" a port from Unix to Windows. The build system was a hellish nightmare of Cygwin, makefiles, Perl scripts, hard-coded paths, and unsupported internal tools, and after ~2 hours of manual fiddling it spat out a build. A few million lines of code, which according to my tests, would take ~10 minutes to build with a proper build system. I have a proper rant about the horrors I saw in the build system, I had never imagined that a build system could be so bad, and whenever I mentioned the name of the internal tool it was built on, company veterans on other teams would recoil.

Meanwhile, I witnessed how much damage the other developers were doing to the product. Some were trying to catch up with feature requests, some were adding hacks to the core algorithm to try and improve numerical stability, and some were doing real damage to the code base by adding buggy and poorly designed features--think major performance regressions, memory errors, and deadlocks fixed by adding calls to Sleep().

I tried to improve things as much as I could there. The company culture had some upsides (good work/life balance) but the internal competition strangled innovation, the wrong people made technical decisions, and the team didn't have a balanced set of skills.

The product hasn't been "killed" per se. It's still for sale. But it's the walking dead. Being EDA, licenses can run into five figures per seat, but the product's revenue was on a downward trend last time I checked. I have a couple friends that still work on the team but I'm encouraging them to apply for new jobs. I left when I got an offer from a major (big five) tech company.

I've been on one lack of loose coupling project. "All you're doing is importing from here and exporting to there, no problem, right?" and eighteen months later its somehow expanded into touching every part of the business except the vending machine firmware (no, was not a vending machine company). This leads to paralysis where touching anything makes anything and everything randomly crash. This was fundamentally a business process failure in that you can trivially specify a process too big for humans to implement, or even tool assisted humans. However the failure mode of technical debt could have hit a little less suddenly and catastrophically via some technical design decisions (should have jumped off the rails at 6 months and been redirected instead of patching around with the result of exploding at 18 months, etc).

I've been on two lack of refactoring/standardization projects. If you use rails, like back in the ver 1.0 era, you can't just stop updating and do something else, you have a tiger by the tail and if you don't keep up you'll never, ever, be able to catch up ever again. You can't go from 1.0 era to today where today is any time in the last five years. Scrap and complete rewrite. Of course management doesn't understand dependency trees and going back to OS and libraries from 2007 means rolling back 10 years of security patches or hand compiling everything and it would be a lot simpler to just rewrite.

I've been tangentially involved in a poor leadership situation where basically an entire department was forced out by a new leader, taking all their domain specific knowledge with them, and then the consultant friends brought in bled the company dry killing it in a race between expenses of consultants and smelly code being unusable. On paper the company died because of the financial load of switching completely over to outsourcing ("We're not a software company so we will not have developer employees anymore ... but we will have twice as many consultants working two thousand hours per year for five times the pay temporarily")

I've never experienced the parallel development trap, or lack of test suite, those must be interesting.

Killed - no. But I worked on several products that weren't able to move fast enough because of it, and lost money as result.

One of those products was released half a year late and turned out to be a poor market fit. The company closed several months later. It could've used this half a year to complete a pivot with another product, which could have been successful.

I have many times taken over projects that were so deep in technical debt that only extreme surgery would save it from being killed. It can take a long time to turn those projects around and make them healthy again but it is possible.

It's a good question, because all software has "technical debt". Which means "technical debt" is not a real thing, but a concept invented out of a limited understanding of the problem. Instead, there is always a tension between a simple solution and a more flexible one and there is always a way to make things simpler or more flexible or even more complex and less flexible. For many problems the key to keep both simplicity and flexibility is to decouple everything as much as possible, i.e. share nothing, functions, not object with methods, scalar arguments, not complex structures, libraries, not frameworks, etc., but there is still a lot of room to do it better, like DSLs, metaprogramming.

Have a small hardware one....

About 1986 I was tasked with moving a small block (a few KB) of data very quickly from cabinet A to B, with the racks full of custom electronics - no PCs, all original stuff on a flight sim with 386 Intel processors all over the place. The racks had Multibus backplanes.

I suggested a 'TAXI' fast optical link (oooh - optical..too radical) or a pair of Intel 589 (Ethernet) cards for an off-the-shelf solution. Nope, too expensive. Engineering Management suggested a twisted pair ribbon cable between the two adjacent racks - um, OK..

Long story short - me and the senior design engineer decided to use the Intel 8257 DMA controller chip to grab the bus and blast the data between the RAM on two cards.

After a short period of fails, we found that the engineers who designed our 386 cards did not bi-directional buffer the DMA request line onto the backplane as they never expected any other card except the master CPU ones to initiate a DMA, so the CPU cards could not see the line being toggled from elsewhere.

Engineers would not accept a change request for 'reasons'

Intel 589 cards is it then!

All because someone chose to omit one tristate buffer.

I owned the project and decided to kill it, I guess you can call it due to technical debt, but probably more accurately it was due to incompetence, both by the developers and by myself as their "manager".

my product was http://www.teamkpi.com/

I hired 3 mid-level PHP and jsp developers in Thailand and had them make the website + reporting page.

total nightmare. Don't hire developers and assume that they will rise to the occasion (learn new tricks). I gave them as much time as they needed to research and make sound engineering decisions, I ended up with a spaghetti nightmare Frankenstein mix of server side scripts mixed with client side script mixed with server side that generates client side script.

In Thailand at least, you always need a manager to force architecture and design decisions, and force devs to refactor poorly thought out solutions.

I was naive and thought that I could have a team of 3 figure out the web part while I write the desktop client and provide PM-level guidance.

I've seen projects die not because of the technical debt existing, but because of lack of addressing it. The developers got sick of working around the debt to do trivial things, they left. Customer support personnel left because of the constant manual "tweaking" they had to do due to the technical debt. Management focused on tacking on features instead of paying off any technical debt which was having rippling effects throughout the company.

Technical debt destroyed the team.

I've seen a whole company killed by technical debt. Because the software was written so badly far more developers had to be hired to firefight than the company could afford. The technical support team was similarly bloated to deal with the endless problems the customers had. Sales were low due to the bad reputation.

A rewrite was started, but never got anywhere. The company folded under the weight of its massive salary costs.

I've worked somewhere that died for a combination of reasons, one of which was an effect of technical debt and inappropriate outsourcing.

I don't think technical debt alone will kill you. But it may render you unable to cope with another problem, which will then kill you.

Back in '96 I was in a startup company in the Boston area. We had a B2B app that we customized per customer. It worked over dial-up. We didn't foresee affordable internet connections coming. When it did we couldn't rewrite critical subsystems quickly enough.

Because our product was customized per customer - not just look-and-feel, we coded their business rules into it - we had problems scaling. Further, our design didn't lend itself to rapid development.

First our sales team left. Then developers started to leave. Within a couple of years after I left, the company folded. Many good experiences had in that company. Many lessons learned.

Yes - Altavista

It took a year to build an index from a new crawl, and they were only doing incremental "freshness" updates in between where they updated certain pages. It was a fiasco.

I have never personally experienced a project failing because of technical debt. I have experienced "the opposite" of that where there was such a focus on doing things "the right way" it felt to me like development was slowed down by this. Our product iterations were slow and from my perspective it cost us valuable chances to test different product ideas.

I'm using this definition of technical debt.

  Technical debt is a concept in programming that reflects the extra development work that arises when code that is easy to implement in the short run is used instead of applying the best overall solution.[1]

[1] https://en.wikipedia.org/wiki/Technical_debt

##edit

The project I am referring to was a consumer web project. No mission critical type data.

In my experience (mostly consumer web, social media management for B2B) I have seen causes of failure to be heavily weighted towards product issues not engineering. The one big success I was a part of had the most technical debt. :) But that's probably because it lived the longest (and still lives today!). My experience is limited to being an employee at 4 different tech companies and several failed attempts of my own.

"Killed" as in "That was the reason it was ultimately replaced by a green field project, after ten years in the market" or "Killed" as in "It never shipped because it was so bogged down in technical debt we could not ship it"?

The former has happened to every project I know, which doesn't die for another reason (market disappearing, etc). The latter I have not experienced.

How about an entire company?

I worked for a dotcom back in the day. The underlying tech was appalling, to the extent they couldn't actually stay on the internet. We fixed this. They then proceeded to vastly expand the site, but every part of it was written as a special snowflake.

Five years later, they decided on a rebrand. This was literally a reskinning of the existing site. It took 50 odd people, ten months and more overtime than you care to think about. Many of those people were contractors.

Not only was this a huge expense, it prevented us from making the site any better. It was an extremely competitive market and the other sites ate our lunch. The next year was to be after round of redundancy, a financial statement that wrote the value of the business down to its cash reserves and finally a sell-off.

Ironically, the new owners turned it back into a viable business, but they had a very different attitude to technical debt.

I am dealing with a set of legacy apps that will eventually be phased out. There are 'generations' of code, trying to solve architectural problems that are never taken to completion. Making large moves like that is a form of technical debt; not taking every step through to completion (like, documenting the code ...) is another form of debt.

The original architect was, despite his outward appearance towards emphasizing correctness, was really not a great developer or a good technical lead. He insisted on writing "perfect" code, ignoring the rest of the development cycle or the people he worked with. Regardless, he left for reasons I am not really aware of last year. I knew he hated me, since I didn't share his obsession.

Fast forward to today ... the applications work. There is no more feature plans for it. But, it is frustrating to go back into it because the code is utter garbage. I am the only one who has any deep understanding of it in my company. Those who tried to understand it also struggled over it.

We are taking technical debt in the new application we are working on, but, we have been planning for it to happen. I have the chance with the devs I am working with to get this "right".

Throughout my career, the sense that I got was that people did not understand something critical: Owning code is a full-time job even after it is written. I never worked with technical leads that asserted that. They always made passing nods to the idea that we should comment more code or write more tests, as if it is just some tired dogma to follow, but no one has made a case to me for being clear on knowing what you are accomplishing, how one accomplishes it, planning to own the explanation of what the code does and what trade-offs were made and a plan to pay back the debt that was taken out. As tech lead now, I am continually communicating this; the progress is starting to show. I am just glad now my company is recognizing these needs too and is understanding the investment that comes with maintaining their major product.

Absolutely. Tangent but...

I've long thought that "premature optimization is the root of all evil" is sort of a waste of breath... not because it's wrong but because over-engineering is a far greater problem today than premature optimization.

Over-engineering is a plague in modern software. Most of the failures due to technical debt that I've seen involved cases where "smart" developers built swiss army chainsaws to do things that required a hammer. This also often results in products that require orders of magnitude more resources than they should, which makes cloud vendors like Amazon and Digital Ocean a lot of money I guess.

Do major design fails count as technical debt? Among other things I've run across an e-commerce site that required choosing a payment method before browsing products or putting things in the cart... (fortunately not my own job). (The reason for this odd choice was evidently that they wanted customers to have access to special offers/pricing/services/products depending depending on how they were going to pay. Cure worse than the disease type situation, IMO.)

I think I've worked for a company that did essentially mostly screw itself with technical debt, though.

They originally had overseas contractors write parts of their product without having a proper developer to assess and vet the results or requirements and it resulted in zero separation of concerns, business processes and display logic combined, and a terrible database structure. Eventually they wanted to move from their original layout and page design to a new one and it proved almost impossible without multiple developers spending around half a year. And even that was wasted effort because at the end of that they realized they wanted to actually have a mobile site and they still hadn't really created a good separation of concerns... Of course the whole time engineering and development wanted to refactor the business logic into separate code from the other layers, but management didn't want to expend resources on non-customer facing dev work.

I think the product still exists, but they've killed their momentum.

If the company has a government contract, the technical debt becomes a hidden feature.

Government customers rarely have the ability to independently assess what something should cost if done according to industry best practices. So what you do is bid low, with an extremely short time horizon to release. You get the contract, and now have license to run up a lot of technical debt, because it needs to be done fast and cheap.

Now you get to maintenance phase. That's where the money is. The typical government customer is never willing to spend even one penny on paying off the principal on technical debt, but will make the installment payments forever. They will spend $100k on one new feature, but not even $0.01 on reducing the price of new features. Many still use SLOC as a management metric. So you run your codebase up to a million lines of code, when the software itself is just another glorified CRUD app. For bonus points, you give yourself 100% test coverage on a bunch of functions that have boolean "isUnitTest" parameters.

I imagine this is similar to how VC firms loot companies by manipulating their financial structure. I find it to be extremely unethical, but there is literally nothing I can do individually to put a stop to it.

Yes.

I wrote a complicated and horrendously ugly scraping PHP script with hundreds of regexes to generate a PDF file from a CMS. It worked in about 90% of all articles, and for the rest only needing a few manual fixes in InDesign.

I always intended this as a stopgap measure till we implemented a clean document structure, of which both the web page and the PDF could be created. But that never happened. Then I left the company.

A few years later the company made a redesign of the website and totally scrapped the PDF feature.

However I still sometimes see these PDF pages out in the wild, mostly saved by the authors of the articles on their own web sites, because authors are allowed to link to their own content for free. It's a shame because I think these PDF versions of the articles were beautiful. But as you would say, technical debt killed the feature.

Another project for a NPO has been written in Python using an ancient back-end. When the shared hosting provider made an upgrade, the back-end died, and I was not able to repair it and I was not paid enough to invest too much time. I bluntly told the board that their project is as dead as a dodo, and they accepted that.

Yes, this is actually quite common. What I've seen happen, twice personally, is a large company asking teams of developers to work on a codebase they can't really understand, and have no chance ever to, because the code has basically got to the point of no return, in terms of messiness. What happens next IME is that progress mostly stops, and the company loses market share rapidly.

I have seen projects that were all but dead from technical debt, that management simply refused to believe were dead.

I once worked on a system that was so messed up that fixing any bug would create 2 more. At one point, the entire team was only working bug fixes for 6 months straight and in the end, we had more bugs than we started with.

We tried to refactor the code several times but it was just so fucked up.

This was the stuff of nightmares. Most of the module consisted of one class with 50,000+ lines of VB.NET code in a single file.

Global mutating state referenced in functions everywhere. Functions that were 500-1000 lines long (today I have ESLint limit functions to 10 lines).

After working on it for over a year, I recommended to my boss that they initiate a complete re-write and made it clear that in my estimation there was NO saving this code base.

I got moved to working on single page applications in JavaScript, but when I quit that job and moved on roughly a year and a half later, that code base was still in production, generating ever more bugs for that team.

When I was a consultant I saw it happen often, BUT, seldom does technical debt get called out explicitly as a reason for failure. More usually it goes like this:

feature requests with no mind to maintainability/cleanup -> tech debt -> slow dev. velocity -> failure to deliver features for the businesses -> failure to retain/grow/compete

Oh yeah, I've had a few projects killed by technical debt.

A lot of these are game mod related. Since hey, even the base game is a black box loaded with the technical dev of a team that could have been gone for decades. And the very tools and patches you're using on top of it were then also by people wanting theings done the 'quick' and 'easy' way over the 'right' way. Usually because said people constructed the tool in question for their project, and had designed it specifically for the environment they were working in rather than anyone else's. So you'll often see such a project completely fall apart because you don't understand all the code you used or how it interacts with the other stuff you used without understanding it.

But a few were actual work projects for clients. These fell apart because the following sequence of events occurred:

1. A coder was hired to work on the system and had a very different coding style to everyone else in the company. They thought they were being 'smart' but had overengineered the project by about a hundredfold.

2. They got sacked without telling anyone else how the project was constructed or why it was built that way. So developer B took over.

3. Developer B tried to 'rewrite' the system completely, but ended up merely creating a hodgepodge of his work and the other developer's work that ended up being rather unstable.

4. More features were requested from the client (which the system wasn't designed for), so three more developers each added them on independently. None of this work was commented, documented anywhere or stored in version control, so they bolted the features extras on, tested just that one part of the system and claimed it worked fine.

5. Project ran into large numbers of bugs, often ones which crashed the system or took down the database for a while. Multiple times a day, whatever developer was free would have to apply patches to whatever random thing stopped working in the last few hours.

6. Everyone ended up complaining that the system didn't work. Or that it should be rewritten. Or that it wasn't what the client 'wanted' at all despite the latter having changed their plans three times this week.

Either way, what should have been simple websites turned into giant unwieldy messes that no one developer understood the full design of. Which sat in endless limbo while developers ran around trying to patch up problems caused by no one having a coherent plan for the whole project.

Worked on a product that was written in a legacy technology and built over two decades. Company does not want to invest further in the product and just want to support existing clients that had done lot of customization on top of existing codebase. New players have come into the market and eaten away the market share of the category the product competes in. Its a slow death for the product now. Management feels that it is better to buy a new product built by another company rather than building the same product in-house with no guarantee of returns.

several start-ups folded on me, perhaps this was the most flagrant technical debt among them: Octek [then Octek-Foxboro, then shuttered ] was state of the art machine vision in 1980 but stuck with PDP-ll bus+boards in a box instead of investing in microprocessor single board systems and stuck with an odd-ball interpreted language "Magic-L". By 1986 they got run over by competitors with much lower price points and higher inspection rates. I could still make the boxes do the job but it was boutique stuff by then.

Not sure if it can be classified as technical debt but I worked at a place that had a very clever and profusely productive architect. As the company grew, some perks available to developers got cut to the point he decided to move on.

From that point on, the architecture froze. It still was possible to continue creating new features on top of it, but I am sure that architect would be able to provide both guidance and new solutions I feel may be needed. No one else picked up his tasks or views, nor was the architect position filled up.

Sort-of. I worked on a product that was a rewrite of an older product, and suffered second system syndrome.

The problem was that the original programmers didn't understand how to program with a database, and management was unwilling to address the core design flaws.

As a result, upper management told us we missed our market window and the project was killed. In reality, it was the technical debt from not understanding how to correctly write a data access layer that made us move too slowly to meet our market window.

I recently left a company with a software product that may die due to a misdiagnoses of tech debt. They are in the midst of an unnecessary rewrite with nothing to really show for it after almost a year.

The previous project has some issues but they were fixable with refactoring while continuing feature dev. The rewrite was done over my objections. New management had been hired and they were looking to make their mark. I left before it could all come crashing down.

Products are more often sidelined by technical debt than they are killed by it.

A typical scenario is:

1) Product becomes too hard to change but has many existing customers

2) Product is off-shored, and costs of maintenance are under-estimated because it depends on a vast technical ecosystem

3) Alternative products are developed to replace revenue of the original

The original product can live in this moribund state for decades.

Definitely have 10+ years ago. The non technical partners (majority) thought no refactoring was needed until it was almost too late. Company still exists but had to pivot quite a bit.

More recently another one which is being killed by tech debt but the tech is so old that only a rewrite can really save it and the income from it is just not high enough to warrant it.

(the former was written by me at first before the company really took off and the latter was an acquisition)

I've always felt that the damage done by technical debt was abysmal and frequently underestimated.

- opportunity cost for the product since you aren't fast enough to chase new revenue channels, this cost is almost invisible,

- the product can become plainly unable to run on newer platforms because of debt,

- unpleasantness of the codebase that will lead to loosing engineers.

It's a slow and excruciating process.

Yes. As a solopreneur, I had a moderately successful side project. When the app fell over, it took me two weeks to get it back online due to compounded tech debt. As a daily service, I lost most of my users when the app didn't work for 14 days. The app never recovered, and ultimately I sold it. One more vote against doing everything yourself.

My first company was consumed by technical debt. We all bickered about refactoring the database schema and improving the code, but investors wanted more "rooftops" (customers) now.

The company IP and employees were absorbed by the highest bidder and the company lost its funding after the CEO and CTO left.

In my experience tech debt doesn't kill codebases so much as make estimating impossible and therefore create tension between execs and engineers. It of course also makes working in the code suck.

Typically these projects are able to limp along until some other forces kill the company.

Sort of. I worked on a project that gradually lost customers due to instability and a lack of new features.

It's still around and still being maintained but it's a shadow of what it once was.

I've worked at multiple other companies which have gone through rounds of expensive rewrites.

I've worked on a product that would have looked like it. In truth it wasn't "technical debt" as such, it was bad decisions from the chief technical architect that he stood by the whole time.

I have worked on projects that are so old they called them legacy projects. Old Visual Basic, COBOL, Fortran, PreAnsi C, etc.

I've also upscaled databases and programs to modern technology.

Almost all of them. It becomes cheaper to buy someone else's product than to continue development. Because the NIH product has its costs spread over all the buyers.

Yes. My first job as an employee.

Shockingly enough, the “project” was a gigantic Excel spreadsheet. Accumulating debt on a thing like that is actually very easy.

I don't think they usually get killed. They just die slow and painful deaths.

People are reluctant to change them so they don't adapt.

Yes. It wasn't a mission critical project, so you could afford to kill it, post-mortem it, and build a new, better one.

Yes and no: the project had a lot of technical debt, but by the time I left the company, the project was still barely alive.

Any abandoned or maintained at a huge cost Java EE and related crapware would be a definitive example.

No, but I have worked on projects that were killed by a fear of technical debt.

I'm currently working on such a product.

So our answer is "yes"?

I guess you could say this is a form of technical debt, or technical stubbornness.

I used to work for a company that specialized in Solar Panel data. I was hired to help the company catch up on their client queue (those waiting for the product to be set up).. and when I first started they were behind by about 140 clients and I had gotten the client queue down to about 30 clients remaining.

So our company would sell solar panels to corporations, and then they would put kiosks in the lobbys of their buildings so their clients could come take a look at the energy savings and other information about the building. It was a very popular way of doing things, especially in cities like New York, Chicago, and Los Angeles. Well, my job was actually designing the graphics for what was displayed on those kiosks and then syncing the data with the graphics.

There was a platform that did the work, but I still had to design the graphics and type in all the serial and model numbers and all that to sync everything together and make it show it in chart form in a gorgeous view. Anyways, for years, it was being done in Flash. Unfortunately, as progressive and dominant as our company was -- at one time, their technology was the best, even having received several awards. Over the years, HTML5, JSON, and other technologies were better and faster -- and could read data from a database just like as our system could, but turnaround time for production was faster for others. It took about 1 week for us to develop, set up, and sync everything from system to database. Now these other companies were able to get everything done in days, rather than a week or more. I think a huge part of the problem was my company had these corporations interested but forgot to hire enough people to actually do the work.

We did have an in-house software developer working on improving this technology, upgrading the software, but they seemed very reluctant to adapt the new software quickly. I had worked in the new software for a few days, and then all of a sudden, they called me into an office, and laid me off. A few months later, everyone else followed, and today, I think the company only holds on to about 2 or 3 employees who just maintain all the kiosks and software because of the existing contracts. Or maybe they went under... their website doesn't even work anymore.

Why did they go under? We were warned that technology was changing fast and that we needed to do something about it... and it was just the reluctance of the CEO to adapt the technology and push it out faster. Our competition slaughtered us. Luckily, it was my second job, so I worked out a great deal with them on letting me go.. I got about a month of vacation time on the condition that I wouldn't go file for unemployment. Obviously, already having another job, it worked out in my favor.

I'm currently working on a project that hasn't died yet, but has gone through a lot of pain in the last couple years partly because of technical debt.

I ran the project for the first four years. It was my first large project and the first time I had run a team of any size. I made a few mistakes that might be worth learning from, but my mistakes weren't the only ones responsible for the debt.

The largest driver in the technical debt issue was the timelines. My boss was new to software development, and his expectations were not in line with reality. We frequently had to ship ad hoc features under tight deadlines to keep him happy. When I pushed back on the timelines he became unhappy. So we acquired debt in the form of 1) hastily designed sections of code that don't lend themselves to scalability or refactoring 2) a lot of small code smell issues that by themselves don't amount to much but in the aggregate form a kind of surface scum that makes future development and more importantly testing difficult and thus brittle.

The debt, and the accompanying bugs and delays it caused, eventually led to enough dissatisfaction that I was taken off the project (I am in a weird outside position now, sort of half on half off, supporting a tangent of the software but not working on the main branch or involved in architecture discussions, planning, or execution of the new replacement). A new manager was hired. We disagreed over strategy, so I was taken off the project.

He wanted to start over from scratch, which is what they are essentially doing now. The plan is to pattern the new solution off the old one by incorporating all the business rules (which they want me to document), but they have very different implementations in mind. They don't want to reuse existing libraries (some of which is driven by a lack of familiarity or understanding of those libraries, how they work, why they approached the problem the way they did).

They face some significant challenges:

1) their coding velocity is slow. more than 60% of the original team has left and been replaced, so a large part of the team hasn't been on the project for more than 2-3 months. this means that there is a significant dearth of institutional knowledge. i think a decent pace is good for development of software, but they aren't starting from scratch, and there's a lot of expectations to meet.

2) because of the dearth of institutional knowledge when they do start implementation, they are going to end up repeating many of the mistakes made by the old team. I have limited insight into what those are, but based on what exposure i do have, i can see planned missteps all ready.

3) my boss, the owner of the company, has learned some patience, but they've been at the rewrite for nearly 6 months and have little to show for it. in terms of feature parity with the old software, they are severely lacking. i don't expect he is going to be willing to wait another full year to get an app that does essentially what he already has only differently, even if that architecture is more flexible.

In all honesty, I hope they succeed. My boss is a good friend and this experience hasn't ruined that. I have and am dealing with some resentments, but I don't want him to fail. And because this project was my baby (so to speak) there is a part of me that wants it to live.

----------------------

In retrospect, I'm not entirely sure what I should have done differently. Had I ignored the requests for adhoc features, I likely wouldn't have made it as far as i did, because without those features he would have pulled the plug. The company grew at an exponential rate the first 2 to 3 years of that project, and part of what fueled that growth was the adhoc, fast turn around times of my dev team. We were incurring debt, but we were also making big gains.

If I was going to do this all over again here is what I would do:

1) I would push back more, in smaller increments, placing more emphasis on getting the details right before shipping. 2) I would push back more on requirement creep. My boss would frequently have these "great" ideas that he would insist we work on, which would get half done then discarded leaving the code base littered with dead ends that needed cleaning up later. Part of the debt we acquired stemmed from the fact that in order to keep a lot of those activities from impacting ongoing efforts, i built an architecture that was somewhat disjointed. the lots of little islands approach meant we had apps that were reinventing the wheel, taking different approaches, etc... 3) Place a greater emphasis on automated testing (fewer human testors, more test engineers).

The other aspect to this is the fact that when you are creating software to solve problems that don't currently have software solutions, you spend a fair amount of time going down trails that don't pan out. The R&D aspect left us with bit and pieces of code in the code base that were incomplete or incompatible, but that were relied upon by one app or another.

We lost time discovering that certain approaches didn't work.

I think thats it... I hope someone finds the story useful.

I did a Flex/AIR project a few years ago. At the time, it was a customer requirement. They had fired their previous provider, because their business model was to charge a subscription fee for the server-based product.

All their "media" was in flash format; so they made it a requirement, even though they could have saved themselves many tens of thousands of dollars in hardware costs by going to a mobile platform. (they did not have reliable access to networking in most of their deployments, and didn't want to bear the costs of rolling their own with cellular).

So I wrote the app in a "AIR isolated thick client" mode. There were many problems with garbage collection and application freezes, that could have been addressed had they funded migration to post-Adobe FLEX (Apache FLEX). But they ran out of funds for that.

Their platform was Win 7 laptops. The first hardware iteration was fine. The next year, when they started replacing the laptops, they hit a driver bug that caused the whole screen to freeze. With the next hardware iteration they were able to fix that, but they started having problems with AIR trying to download an update when they were not connected to a network (ie. deployed in the field). AIR behaved badly in this instance and refused to run.

When they moved to Windows 10, Adobe hadn't updated the AIR player yet, so they had another botched deployment.

It was in our contract to hand over the source code, so they tried to hire their own developer. I spent many hours very thoroughly documenting the code, and they had no hours budgeted for ongoing support. Judging by some of the desperate emails I was getting last year, before my Program Manager told them to fuck off, I think my documentation was not enough. Of course: the Dev Environment setup was Win 7, Eclipse 3.x with the Adobe plugin. I maintain a VM of the dev environment, but I doubt even I could follow my own directions to set it up anymore since the Adobe SDK of that version is so difficult to locate.

Had they listened to my original recommendation to write the entire application in Java, they would still be running fine.

That was my most recent experience with "death by technical debt".

Many years ago; a product died simply because a competitor bought our company, and tried to sell both products (because theirs was a "consumer market product", and ours was "enterprise market"). Over the next 18 months, they cut development to the enterprise product, and tried to tart-up the consumer product to meet the needs of our enterprise customers. I was a major account manager, so I watched one by one as our frustrated customers dumped everything our company sold, and went to the other competitor. So that product wasn't so much killed by technical debt as it was killed by moron MBA's.

In the end; all of those products are obsolete because nobody used dedicated backup tape library software anymore. It became a very small market because tape backup hardware never got commoditized, and prices just never came down from "insane". Even blank tapes were more expensive than a removable hard drive. Poor people just back up to the cloud, pay rent to someone else for their own data, and end up losing it.

I can probably think of about a dozen other examples from my long and miserable career in software.

Yes. I've been on projects that I believe would have succeeded if we'd approached them differently, with less debt. One was due to magpie syndrome - influential architects who enjoyed working with bleeding edge technology and convinced management not to listen to the more conservative recommendations of the developers who would be doing the majority of the work. The software was a wreck, and morale dropped (and the original architects left the team). I think the project would have worked with a better approach, but after a change in upper management, they decided to end the project completely.

Another was a rewrite of an application that had been very popular, but was written by someone who was actively learning on his own (a talented developer who later learned to write very clean and well organized code). It was, as I like to call it, "superglued" to the server. SQL statements that could have been handled with a join were instead handled by querying all the ids, running through them in a loop, building a new query, getting results, stashing them in an array, one by one. When those queries took too long, they were run in the background or just crashed the system. Changes were all made in place, on the prod system. There was no build, no archive, no nothing (this was in the early 2000s - even back then, this was a no-no, but it wasn't quite as shockingly unusual as it is now) I was part of a team that tried to rewrite it, but halfway through the organization was frustrated with the time and expense and terminated the project.

Interestingly, I think there's almost always a psychological or political factor in play when a project is killed purely by "Technical debt". In theory, debt itself shouldn't really play much of a role in whether a project is worth pursuing, because it's all sunk cost. If a project has a positive enough ROI that it would be worth pursuing as a greenfield project, then even the worst case scenario, trash everything and start over, is a net win.

However, I think what happens is that some people never wanted to see the project happen in the first place, or people get very frustrated with the expense, or people start to suspect that the failure was inevitable and that the technical problems are just a distraction. Think Jurassic Park (which in many ways is a story of a software project failure, a theme that is much stronger in the book). At the end, during the "post mortem", some of the characters think that the problem was in the approach. That with a bigger budget, less dependency on a few people, less corner cutting due to a lowball bid from a software developer, enforced through threats to reputation and lawsuits, that with a better approach it all would have worked. On the other hand, you have the chaotician, who insists from the start that a project like this will fail inevitably.

My guess is that if it was ever worth pursuing, it is always worth pursuing. The problem is, we can never really tell. Sometimes failure due to technical debt is taken as a sign that this failure was inevitable. Other times, it isn't.