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Hi,
You can automate SQL Doc using the command line interface. So you can automate the generation of documentation as long as your agent or scheduler can use the command line. -
I know this is an old post, but I was able to successfully automate the documentation of databases using the command line interface. I wasn't able to get the username and password flags to work correctly (I think because of encryption), but if you create a project in sql doc, then save it you can open the project in notepad and modify the options to be what you want them to be then use the /project flag to generate the document more easily. The final command looks like this.
cd "C:Program Files (x86)Red GateSQL Doc 3" && sqldoc /project:"Path to sql doc projectsavedproject.sqldoc"
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Thanks!