We build HTMLhelp (CHM) help files for our application, currently use Robohelp 8 and are evaluating Robohelp 2020.
In Robohelp 8 we have a Main window with TOC etc for the application help and a Popup window for dialogue level help (slimmed down, no left hand pane etc.). The application calls the help with the window name and it all works fine.
After upgrading one of the help files to Robohelp 2020 the dialogue level help still works but it opens in the Main window (not Popup). The master page styling is also for the main window and not dialogues. Since the application is not changed and is calling Popup something else has changed.
I can see the popup window settings and they look to be imported correctly. Am stuck. Any ideas / suggestions ? Is this a bug or do I need to do something different ?
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I do know that not everything is the same in 2020 but I don't have the details of what is different. You may have to go to Support on this one. See https://helpx.adobe.com/contact/enterprise-support.other.html#robohelp for your Adobe Support options. The email link firstname.lastname@example.org is recommended as it reaches a team dedicated to Technical Communication Suite products including RoboHelp.
If you are only generating CHMs, I wouldn't have thought there is much point in upgrading. The exception to that is that RoboHelp 8 is not supposed to be compatible with current versions of Windows. If it's working and that is all you need, there's little point.
The more modern responsive and frameless outputs can work locally but are not single file installations. If you go that route, go frameless as that is where future development will be focussed.
My site www.grainge.org includes many free Authoring and RoboHelp resources that may be of help.