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I have a client who uses Acrobat Pro DC through Creative Cloud. She frequently has to print multiple PDFs simultaneously. She does this by highlighting a large chunk of them in Windows Explorer, right clicking, and selecting Print. All the documents are sent to the default printer as print jobs. The problem is that, slowly and one-by-one, all the jobs will cause a generic "the document <filename> could not be printed." The job will attempt to restart itself and sometimes this will succeed in causing the document to be printed, but most of the time the user has to open it up in Acrobat and print it again. This will go on for all the rest of the print jobs.
Through testing, I verified that this error does not appear if she does the same method for a Word document. I also verified this does not happen if she opens a PDF in Acrobat first, and then prints it through the Print dialog box.
I spent an hour and a half on this, doing online research and testing, and the best workaround I could figure out was to have her select a chunk of PDFs, right click to open them in Acrobat, and then right click again to print them all. I have read a bit about printing them as a batch, but I do not think this solution will be acceptable for her since it is too "involved" and she isn't very tech savvy.
The printer is a Ricoh device running from the client's server. Our network engineer suggested it may have something to do with the printer driver on the server not getting along with Adobe Acrobat. Anyway, the user never had this problem occur when she used eCopy, but for outside reasons the company forced everyone to switch to Adobe Acrobat.
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It might be worth trying to make a custon Action using the Action Wizard. If you follow the prompts, it's pretty straight-forward. You could build it to include files in a specific folder, or have the action prompt for the files to be printed.
I hope this helps.
My best,
Dave