Getting message "Printing completed" but nothing is actually printed... randomly

I have a shared over the network printer connected via USB to a Windows box. I am printing from my Linux laptop with Pop_OS 19.10 but sometimes it will say that the print Job is complete but actually hasn't printed anything. I've already saw a loo of people with the same problem however, in my case it happens randomly. Today I've received an email with two pdfs. The first pdf I've tried to print didn't print, the second one printed without any problem. I've tried to print again the first pdf, just to check, but I had the same problem again. This has been happening to me for the couple of weeks or so. Up to that time I had no problem printing from my linux laptop. DISTRIB_ID=Ubuntu DISTRIB_RELEASE=19.10 DISTRIB_CODENAME=eoan DISTRIB_DESCRIPTION="Pop!_OS 19.10" NAME="Pop!_OS" VERSION="19.10" ID=ubuntu ID_LIKE=debian PRETTY_NAME="Pop!_OS 19.10" VERSION_ID="19.10" HOME_URL="https://system76.com/pop " SUPPORT_URL="http://support.system76.com " BUG_REPORT_URL="https://github.com/pop-os/pop/issues " PRIVACY_POLICY_URL="https://system76.com/privacy " VERSION_CODENAME=eoan UBUNTU_CODENAME=eoan LOGO=distributor-logo-pop-os cups: Installed: 2.2.12-2ubuntu1 Candidate: 2.2.12-2ubuntu1 Version table: *** 2.2.12-2ubuntu1 500 500 http://us.archive.ubuntu.com/ubuntu eoan/main amd64 Packages 100 /var/lib/dpkg/status smbclient: Installed: 2:4.10.7+dfsg-0ubuntu2.4 Candidate: 2:4.10.7+dfsg-0ubuntu2.4 Version table: *** 2:4.10.7+dfsg-0ubuntu2.4 500 500 http://us.archive.ubuntu.com/ubuntu eoan-security/main amd64 Packages 500 http://us.archive.ubuntu.com/ubuntu eoan-updates/main amd64 Packages 100 /var/lib/dpkg/status 2:4.10.7+dfsg-0ubuntu2 500 500 http://us.archive.ubuntu.com/ubuntu eoan/main amd64 Packages EDIT: I could print the file from CLI using lp file.pdf