Spooling multiple files into one from other programs
Hello, I am trying to print multiple files from an estimation/engineering program into one file and Adobe doesn't spool them. The file name prompt with folder location comes up, I type the name I want and then this happens: 
Nothing happens after that. A file is not saved. Also the 2 or more selected/tagged files to combine while printing to pdf don't spool and print to pdf.
I used to be able to select Adobe PDF after tagging a handful of files and then I get the file name prompt, name it and it spooled and printed all the selected files into the one PDF.
Any suggestions would help me. It's super frustrating because in order to combine all these I have to first print them with Microsoft Print to PDF and have to save each individual file as it spools. I then have to select all those files and go through the combining process with Adobe. It's very inefficient and annoys me.
Please help if you can. Thank you!