In v10.0 of DNN the platform will be removing all instances of Telerik controls including the Telerik.Web.UI.dll from the bin directory. The HTML Editor takes a hard dependency on these controls through the deprecated web project which leverages the Telerik Controls. The entire Inline Editing toolbar for the HTML Editor module uses telerik controls. Those are not part of the CKEditor but Telerik.
The view code for inline editing
https://github.com/dnnsoftware/Dnn.Platform/blob/8e172097c733654512be334d10a936f75e0ed27b/DNN%20Platform/Modules/HTML/HtmlModule.ascx#L8-L21
The class definition for `DnnToolBarButton
https://github.com/dnnsoftware/Dnn.Platform/blob/8e172097c733654512be334d10a936f75e0ed27b/DNN%20Platform/DotNetNuke.Web.Deprecated/UI/WebControls/DnnToolBarButton.cs#L13
If these controls are not refactored prior to the v10 release inline editing will not function on any HTML Editor. Even if you use a custom HTML Editor Provider, the telerik controls are built right in to the view.
Remove all instances of telerik controls that are used in the HTML Editor Module
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One option to solve this would be using CKEditor 4 in inline mode
Would this potentially fix the issue I have with #3999?
I don't think it would fix that. Your error message in #3999 cites a 404 error loading a js page. That appears to be an issue isolated to the Client Dependency Framework which minimizes the files and combines it into 1 js/css file
So interestingly InlineEditorEnabled is set to true by default on a clean install but inline editing does not show up, soooo what would be the plan here ? Do we simply kill the inline editing all together or what ?
I'm not seeing this on my test site. I looked at this in #4142, and wasn't able to reproduce an issue. I just removed Telerik DLLs from my local and I still get working inline editing.

Am I missing something?
Those controls in the HTML module are from DotNetNuke.WebControls, not DotNetNuke.Web.Deprecated
https://github.com/dnnsoftware/Dnn.Platform/blob/ed13b3579cc0e7310f7a40ae9c4d241d7fe32cf4/DNN%20Platform/Modules/HTML/HtmlModule.ascx#L2
Which is apparently just a binary without source. 🤷🏻♂️
I really don't remember much about my research on this, it was quite some time ago. Looks like it is something we can close as it appears what I thought was being used is not being used.
@bdukes I am curious, how do you get inline editing working on current version ?
Nothing special, I just go into edit mode, and then when I mouse over the module content there's a pencil floating on the top left.

Oh, I kinda feel dumb now, I never used that lol. I thought it was only for the module title lol...
😃
There is also one for the module title (if your container uses the title). It's a lot more useful for editing the title. Since editing the content uses contenteditable, there's a lot you can't control markup-wise. It's once of those nice features that can also cause you a lot of trouble.