How to Print to a Windows Connected Printer from Mac. Sometimes you may notice that you print jobs are stuck in the queue with the message On hold (authentication. Mac printing in detail. This section of the manual is split into different sections for ease of use, one section covering Mac OS 10.8+ installations, and another covering Windows hosted print queue A print queue displays information about documents that are waiting to be printed, such as the printing status, document owner, and number of pages to print.
Having a problem with my image where the first time a user goes to print the job is held in the local queue for authentication. This happens even though the correct information is already stored in the keychain access.
The CUPS popup for authentication never appears. If I go to the print queue and click the refresh button the CUPS authentication window appears with the correct information already filled in and works. It also works normally for all subsequent print jobs beyond the first one. Normally this would not be a problem after the first print except my labs use Deep Freeze so the setting is reset each night and the process begins again.
Does anyone have an idea of a way I can fix this on my entire site without printing a job from each computer? I'm running into exactly the same issue, only in my case I am attempting to deploy printers to individual machines via policy and/or Self Service. The printers are served up via a Windows print server. I have installed them on my Mac and then used Casper Admin to load them into our distribution point. Under normal circumstances, sending a print job to the printer should give me an authentication window, at which point I enter my AD credentials and away we go. Deploying the printers to both Mavericks and Yosemite machines creates exactly the same result as the described above.
The first time I attempt to print, the printer job halts with a 'Hold for Authentication' message, but the login prompt never comes up. Looking at that print job I can cancel the job, or I can hit the refresh button, which will then bring up the login prompt. If I cancel, I can start the job again, and it will prompt me for my credentials as expected. From then on, I don't run into the issue again, printing behaves as expected. This behavior only happens when the printers are deployed from Casper. Installing these printers manually does not cause the 'Hold for Authentication' message.
Rebooting the machine immediately after deployment did not seem to have an effect on the issue. The first print job still hangs. I also attempted to add the printer in Casper Admin without ever doing a test print to it, just on the off chance that the first add of the printer had somehow managed to associate itself to my credentials (I realize it's extremely unlikely, but I have to hit every angle). Obviously, this isn't the end of the world. The workarounds described above are easy, and the whole thing is a minor annoyance for me personally.
That being said, I want deployment to be transparent to my customers, not something where I have to immediately present a required workaround. If you are printing to SMB print queues in OS X and want the process to be seamless, kerberos authentication should really be used. 