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Back in 2010, 4th Edition D&D was the main deal in D&D-land, and Wizards of the Coast did offer the Dungeons and Dragons Insider service, which was (on the stack) described as:

[...] the Dungeons & Dragons Insider subscription is a good purchase. You get access to an online database containing every rules option from every source; you get a character builder, which also has all the options (Windows and Mac only); and you get daily articles. - Bryant, 2010

However, as of 2021, this purchase or subscription is no longer existent, its tools vanished in the winds and it appears to me, that it might have gone away together with the Damnatio Memoriae of 4th Edition by WotC. However, that is just a hunch.

From when till when did the D&D Insider exist as a subscription service?

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June 6, 2008 to December 31, 2019

This ENWorld thread declares that D&D Insider was live as of Jun 6, 2008. An archived copy of the D&DI News page, also dated June 6, 2008, announces the launch of the new Dragon and Dungeon. That issue's Ampersand column names that date "D&D Day", and signifies the the official launch of the D&D 4e core rulebooks.

However, as that article states, most of the D&D Insider features were not available at launch. D&D Insider at this point consisted of Dragon and Dungeon magazines. According to this Gleemax forum post by D&D Insider executive producer Ken Troop, dated June 7, 2008, the Compendium and other tools were not available at launch.

The service was meant to launch fully complete as a paid service, but was initially free due to its incomplete status. As late as this Ampersand article dated May 7, 2008, WotC were still hoping to have at least the Compendium ready at launch, with the service charging a price of $14.95/month following an initial period of beta testing and introductory pricing.

The last Dragon/Dungeon issues were December 2013, but the service was still available. By July 29, 2014, for example, you could still subscribe to D&D Insider, at $9.95/month or $5.95/month with annual subscription. It consisted mainly the Compendium, character builder, monster builder, and the Dragon and Dungeon magazines. You could still subscribe to D&D Insider after the release of D&D 5th edition.

According to this article, D&D Insider was scheduled to finally shut down on December 31, 2019. This Reddit thread shares an email notice that the service would be free of charge during December 2019 and anyone who already paid for that month would be offered refunds. You can see in the web archive that the Compendium search page was still online as of December 22, 2019, but unavailable by May 24, 2020.

The reason given for the shutdown was that Microsoft was ending support for the Silverlight platform, which the D&D Character Builder relied on after moving from a Windows-only desktop program to a web-based Silverlight version. The advantage of the Silverlight version was that it opened up Mac support, but a major reason for the change was probably to prevent people from simply paying for a single month and downloading all the character data, or just pirating a copy.

Several major features were ultimately never completed, including a character visualizer, dungeon builder, 3D virtual gametable, and 2D virtual gametable.

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  • \$\begingroup\$ Cudos for coming back and finding a very precise window with all the backup. \$\endgroup\$
    – Trish
    Nov 10, 2022 at 8:48
  • \$\begingroup\$ Insider was predated by roughly one year of "Gleemax" \$\endgroup\$
    – Trish
    Sep 9, 2023 at 21:48
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Started around June 2008; stopped being actively supported in August 2014; fully shut down on January 1, 2020

Start Date

I believe June 2008 was when D&D Insider started. At least, that's when Dragon 364, the first Dragon magazine in D&D Insider, launched, so if it isn't exact, it's probably pretty close.

I unfortunately no longer have my receipt for when I started paying for it.

End Date

I don't have the exact end date, but official support ended in August 2014; that is when WotC sent an email that no new Dragon / Dungeon articles would be published, and tools would no longer be updated. I stopped paying for it shortly after.

However, the existing resources on D&D Insider remained accessible to subscribers even after that point. In December 2015, D&D Insider moved to a new URL (dndinsider.com). However, DDI was finally shut down on January 1, 2020 because Microsoft Silverlight would stop being supported at that time, and without that, the tools used by DDI could not function. (Active subscribers were informed of this in December 2019, apparently.)

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    \$\begingroup\$ Here's a relevant update from 2015 about D&D Insider moving to a new URL. Also, according to this article, DDI was shut down on January 1, 2020 because Microsoft Silverlight would stop being supported at that time, and without that, the tools used by DDI could not function. (Active subscribers were informed of this in December 2019, apparently.) \$\endgroup\$
    – V2Blast
    Dec 9, 2021 at 0:06
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    \$\begingroup\$ @V2Blast I remember this. It was increasingly hard to access, unfortunately, especially if you were on a Mac. But it was pretty great while it lasted. \$\endgroup\$ Dec 9, 2021 at 21:11
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    \$\begingroup\$ Sorry for un-hooking, but Quadratic Wizard could offer the more precise numbers and back them up better. Such is the rule of best answer for this kind of history-of-gaming researches. \$\endgroup\$
    – Trish
    Nov 10, 2022 at 8:48
  • \$\begingroup\$ No need to be sorry, that's how this is supposed to work. Its a bit embarrassing, checking my work, that I misread Dragon 364 as 2009 when it was 2008 (and June instead of July), so I was just full of off by one errors. Going to correct that just to prevent any accidental misinformation \$\endgroup\$ Nov 13, 2022 at 22:02

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