Does RH 2019 new include the ability to generate output via command line, with the output target a cloud location - such as Azure or Amazon Web Services? I'm guessing this would require a special target location/URL/service, along with corresponding user login credentials for the cloud/hosting service/site in the command line. I believe this functionality existed in prior RH versions, but never personally tested it.
The overarching goal here is to automate a nightly help build + upload/update/posting to a cloud service. It may be that there are better tools to automate the uploading/posting part of this process - in which case, I would be interested in hearing what tools/services (batch file + Windows scheduler, etc.) others are using for handling that, and their experience with those tools.
Note: I have successfully generated output via command line on/to my local PC/machine in RH 2019, so I do have that "part of the puzzle" figured out. I have some experience with batch files and scheduling services, so finding a solution to automate the build portion should be a problem - it's really a matter of automating the upload process, and whether that can be handled by specifying a cloud location/service with user credentials into the RH command line output.
What you want is the publish command.
So you'd generate locally as you're doing, then publish the generated output to the server. Whether it works specifically for Azure I couldn't say, but it does provide password options.
While this link is for an old version of RH, I assume the new one should be similar. The specific heading you want is "Publish layouts from the command prompt"
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The syntax for command line generation is in the RoboHelp Reimagined sample project and at https://tinyurl.com/tbbmloo
Create your preset to publish. Then use command line generation for that preset.