Please run the following command for some usefull printing related debugging 
info:
apport-collect -p cups 367429

Also provide a cups error_log after trying to print the second pdf file as 
described here:
https://wiki.ubuntu.com/DebuggingPrintingProblems#cupserrorlog

** Changed in: cups (Ubuntu)
       Status: New => Incomplete

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Document Viewer 2.26.0 times out (too many attempts) when printing quickly on a 
network printer
https://bugs.launchpad.net/bugs/367429
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