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VizAlerts respects the Page Setup settings for each view so you’ll need to set the landscape or portrait for each of your views in and then republish.
Regarding the last 2 containing multiple pages: Are each (or both) set up as:
1) a dashboard that effectively has multiple pages from a scrollbar
2) a worksheet or dashboard using the Pages Shelf
3) a worksheet or dashboard with “pages” created by a filter or parameter with multiple values
4) a worksheet that extends across multiple pages (i.e. has a scrollbar). (This would be really unusual behavior since Tableau’s default is to show all the pages).
5) something else?
I was able to update my PDF settings by setting my fit to "Entire View", adjusting the fixed height so that the data was readable, and then adjusting the page scaling (within the page setup) to be equal to the length of the report. I added an extra page to the length to ensure that any longer reports would be captured in my Viz.
Thank you so much for pointing me in the right direction!