Welcome to the forum.
I would like to suggest a different workflow.
When you select Generate Primary Layout, RoboHelp does that based on the settings in whatever is set to be your primary layout. Better at least the first time to double click the layout so that you see the settings and can change things to how you want. After that, you can use Generate Primary Layout if you wish but I prefer to go via the layout itself and check the settings.
The XPJ file only changes when certain things need to be recorded in it and that is not every time you work on the project. In other words, don't worry about the date of the file.
Now to the PDF. Again not the best place to start and again better to go from the layout itself. You can try just generating a PDF but many users prefer to create a Word document and do some editing in that. It may just be tidying page breaks to improve appearance, it may be more, that's your call. Once the Word document is good, generate the PDF from there.
You will find the layouts I refer to in the Single Source Layouts pod. View > Pods.
See www.grainge.org for RoboHelp and Authoring tips
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Welcome to our community
Note that RoboHelp is capable of creating a variety of layouts. WebHelp, FlashHelp, AIR Help, Microsoft HTML Help, JavaHelp, Oracle Help, ePub and more.
Any of these layouts may be nominated as the Primary layout. So when you generate the Primary layout, you get whatever has been configured as the Primary layout.
Only certain actions will result in a change to the .XPJ file. The actions are indicative of major changes to the project. So I wouldn't fret the fact that the date time stamp wasn't updated.
Indeed the Printed Documentation Single Source Layout recipe is what you use to create PDF. Generally what happens is that RoboHelp creates a Microsoft Word document as an intermediate file type, then creates the PDF from that. As you might imagine, there are a host of things that can go wrong during the process. I might suggest that you first get a Word document to generate cleanly. Then once you do that, focus on PDF. I know that I typically gen a Word document and stop there. I just open Word and use Word to create the PDF.
If you look at the properties for the Printed Documentation Single Source Layout recipe (View > Pods > Single Source Layouts then right-click the Printed Documentation layout and choose Properties) you will see that PDF, Word or both are options at the top of the dialog.
Hopefully that gives you a nudge in the right direction.
My fellow Adobe Community Expert Peter Grainge has excellent info on Printed Documentation on his site at Grainge.org. Click the link below for that.
Helpful and Handy Links
LOL... Didn't see you pop in there, Peter!
Yeah! What he said!
Thank you, Peter! These instructions were very helpful. I went to your Web site and found excellent instructions for printing there.
Thank you, Rick! These instructions were very helpful.