The D&D Insider service went unsupported and devoid of new content around 2014 and eventually shut down on the end of 2019
As Quadratic Wizard elaborated in their very well researched answer to my question about when the site existed, the service ran from June 6, 2008 till the night of December 31, 2019 to January 1st, 2020.
However, the website started to wind down about 5 years before finally being terminated:
- The last issue of Dungeon/Dungeon magazine was issued in December 2013.
- Technical support for the tools ended in August 2014, as Glen Nelson remembers. At that time it was also announced, that the magazine would no longer be updated.
- In 2015 the Insider moved to a different URL, as Glen Nelson and V2Blast told us.
- By 2017, only very few browsers actually supported much of the Microsoft Silverlight framework that supported the site and it took outdated browsers to access the service (see below).
Result for D&D 5e
Due to the shutdown of content updates in 2014 and the many problems with 5e technical content described by Tobold and Wax Eagle, it is highly unlikely that any 5e content was released via D&D Insider.
With the mounting problems to access the site with an up-to-date browser starting in 2014 and topping in 2017 due to the framework no longer being supported by modern browsers, there was likely no incentive to work on the site at all - including any 5e content.
Fate of TDT's 5E tool / dnddungeonscape.com
Wax Eagle told us about Trap Door Technologies, and GMNoob told us about the (then running) product beta on dnddungeonscape.com. The Beta page saw the internet before July 10th 2014 and was live since the week before September 29th, which is the date of the Week 1 Recap. But that was shortlived. The last working capture of the Beta-Site was October 27th.
On October 30th 2014 the project was announced to have failed, and the site was shut down on the night of 31st October to 1st November:
Today, we have news that is both sobering and hopeful. Wizards of the Coast and Trapdoor Technologies will no longer be working together to develop DungeonScape for Fifth Edition D&D, and we will not be releasing the product in its current form. The beta program on all platforms will be shutting down at noon (MST) on Friday, October 31.
On or before December 14th, dnddungeonscape.com became redirected to the Morningstar project on the Trapdoortechnologies page. In early 2015, the Kickstarter Campaign codenamed Morningstar had failed too. Starting March 2015 the company offered a product called StoryBook. The Domain lapsed around November 2017 and was soon to be bought by a crypto-site.
DND Insider only got an official successor in 2022
The death of those projects and sites didn't deter others to step into the breach. D&D Beyond started Beta in March 2017 as a project by Curse (then a Twitch subsidiary) and went live on August 15. In 2018, the site was bought up by Fandom Inc., best known as a wiki provider. Finally, this one site was acquired by Hasbro and given to Wizards of the Coast, making it the official tool since May 18, 2022.
In its way, DNDbeyond has become the successor to Insider, and in many parts achieved functionality and usability that Insider never had.
Technical background on Silverlight's death
The shutdown is arguably very related to the announced end of Microsoft Silverlight, on which a lot of the page's architecture was dependent. The first version of the framework was made in 2007 and in total it was comparatively short-lived, starting to be replaced by alternatives around 2011. Silverlight's active development was stopped in or around 2012 but Microsoft kept up maintenance and support. In 2015, the upcoming death bell for the framework was announced to come in 2021, giving ample forewarning. As a result, major browsers removed their plugins from at earliest 2014 1 until about 2017. The last plugin for a very outdated Windows Browser was finally made unavailable on October 12, 2021.
In some way, the death of Insider matches to the death of many Flash-game sites from the early internet: Both Insider relying on Silverlight and Flash-executibles lingered far beyond their framework was actively developed and carried on their duty.
Flash eventually died the death of having the plug pulled, very akin to Silverlight, though the latter had faded into obscurity far before then. Adobe finally put down Flash Player between January 1 and 12, 2021. It was in some way an act of mercy, as Flash Player had become a festering hulk of security flaws and shoddy programming over 26 years of maintenance - and was related to at least two windows updates breaking. As a result of the shutdown, a large chunk of Internet history have become hard to execute and research everywhere but China, but the death was announced long enough to allow the preservation of some parts.
1 - it is system-dependent when MS pulled Silverlight from Internet Explorer 7-8. The first systems that most likely could not support it properly in the first place lost access in 2014.