Good question and informative, helpful answer. I've two follow up questions: Will using Apple Script inside the app create any challenges related to selling the app via the AppStore? Is it better to use Scripting Bridge (SB) framework? I reckon SB would enable communicating with the scriptable app in a more robust manner? a) What are the deployment / entitlement related considerations to consider when using SB instead of the Apple Script?

This is great, thank you very much for the comprehensive answer.

Would you be able to post the full structure of your Xcode project? Following the documentation, I would think that you would need to put your localised help within folders with specific names corresponding to the available localisations, as below

Thanks for taking the time to comment on my question. Yes, I can see that the whole help mechanism looks very delicate. Although there are some elements that appeal to me, like ability to nicely integrate contextual help. Sorry for the vague, question let me clarify. When you try to access help, which functions correctly, let's say in Safari following menu options Help -> Safari Help will open a page with Safari help welcome page. The title you see says Safari User Guide. I'm not able to achieve that outcome in my app. When I follow menu options MyApp -> MyApp Help, the help viewer does not open on the landing page for MyApp but on the generic welcome page. The title says Need help? Find answers here. Concerning your point: Help books are very delicate. The best course of action is to find one of those rare 3rd party apps that has one that works and copy what they've done. You can't copy Apple apps because they do really wild things with help that you can't replicate. I reckon this may be a very good suggestion, I'll definitely have a look also happy to consider any pointers of good projects with nicely implemented help. https://github.com/scris/skim-pdf has decently implemented multilingual help so I will start there.