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I've been printing to our windows-connected printer for ages. And then I upgraded to High Sierra and now I can't print because of the "Hold for Authentication" message.

  1. I searched for a solution many times but nothing I've found has worked thus far.
  2. I went into keychain and searched for the printer but it wasn't there.
  3. In keychain I selected all items (logins, certificates) for that server and deleted them.
  4. After deleting items from keychain, I tried printing again and got to the Hold for Authentication again and so I opened the print job and it prompted me for authentication. Nothing I tried worked. I tried my normal windows password. I tried the server administrator password. I tried no password. None of this works.
  5. I deleted the printer and tried to set it up again. In the "Add" screen I browser the workgroup (called "workgroup") and selected the server (named "server") and it threw up a box "There was a problem connecting ... may not exist or it is unavailble at this time" type error.

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  1. I used RDP client and connected to the server using its name "server" and that worked fine (after accepting the certificate again - so I know the keychain thing was deleted properly)
  2. I used the Go > Connect to server and entered smb://server and this prompted me for my details (which worked) and connected me to a regular share (which worked). So my mac CAN talk to the server under regular smb, just not printing (I deleted my keychain passwords for this site before this step to ensure they authenticated again).

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  1. I tried installing support for Internet Printing Protocol on the server and tried connecting to that, but that also didn't work.
  2. Other Windows 7, 10 and Ubuntu clients on the same network can all print to the same printer.
  3. I waited till I went home, and printed to the printer there just fine. It's the same model printer, but it's connected off my home router rather than a windows server. So as usual there's some kink between Mac and Windows.

/edit

  1. I installed LPD on the server and tried connecting to it from the Mac and printing. This appears to connect to the printer (the dot turns green) and seems to print, but the page pauses and doesn't appear on the server queue at all.

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  • did you see this printmanager.com/cms.php?aid=75&fullpage=1&support=8 – Ruskes Oct 17 '18 at 4:02
  • Ok, thanks for the link. I installed Print and Document service, then LPD service (and set it up), and then connected to it from my Mac using LPD. The printer looks ready to go - but when I print, it goes immediate into "Pause" mode and then the resume button says "Copying print data" and immediately pauses again. The jobs don't appear on the printer management on the server. So I can at least see that a printer is available now, but no further. – frumbert Oct 17 '18 at 22:40
  • OK, lets work on that, tell me more (I do not have your set up so can not verify) – Ruskes Oct 17 '18 at 22:42
  • Server is Windows Home Server 2011 (old, but working) on a workgroup, pretty stock standard installation. The Printer is a Brother HL2142. What do you need to know? – frumbert Oct 17 '18 at 22:47
  • tell me more about this part, (The printer looks ready to go - but when I print, it goes immediate into "Pause" mode and then the resume button says "Copying print data" and immediately pauses again. The jobs don't appear on the printer management on the server. So I can at least see that a printer is available now) post screen shots if you have to - In your original post, remember I do not see what you see, so help a blind person. – Ruskes Oct 17 '18 at 23:24
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I'm not sure how helpful this will be but I offer it in the hopes it will generate an idea that might work.

On a Macbook Air with Mojave I usually map directly to the printer via IP Address which is the second icon from the left in the "Add" (printer) dialog box. I find this to be more reliable than printing via our print server which is one of our Active Directory domain controllers.

However, once you select the print server (in my case it is [DOMAIN NAME] > [Print Server]) it pops up an authentication dialog box "You are attempting to connect to the server "[SERVERNAME]" Click connect to continue"

Once you click connect you get a standard login dialog box with your username already filled in.

Don't use that username or your local password there

Instead you need to enter the name of the print server, sometimes referred to as the NETBIOS name, followed by a backslash " \ " and then a username of an account on that particular server. In my case it would be something like this:

domain\stevec [password]

In your case as you are not in an AD domain:

servername\username [password]

Windows expects authorization from outside the domain to be fully qualified. EG where the credentials are, a backslash and then the account/user name.

It could be that when you try and print there are cached credentials somewhere (possibly on the server?) that are messing you up.

I would delete the printer queue from the Mac and re-add it via the Printers & Scanners preference and choose the Windows printer option and logging in as a user on that PC.

Either that or select the "Default" or "IP" methods and completely bypass printing via your Windows server, if that is possible.

  • I've deleted the passwords in keychain and reauthenticated. When connecting to the printer in the past, it did NOT prompt for a password ; now it simply says there is a problem connecting. You can see from the gifs in my edit how I'm authenticating – frumbert Oct 17 '18 at 23:57
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I found this post via Google. I have an HP Officejet 4510 g510n-z and strangely enough, resetting (https://h30434.www3.hp.com/t5/Inkjet-Printing/OfficeJet-4500/m-p/585875/highlight/false#M548340) the printer solved the issue I had with continual 'Hold for Authentication' messages I was yielded when sharing a Windows printer (via built in Windows 10 x64 printer sharing) and attempting to print with OS X Mojave. 

The symptom was that even after authenticating with the local admin account (which is a Microsoft.com account, with my e-mail address/password) I would continually be prompted for the login/the local print status in Mojave would yield 'Hold for Authentication'. Attempting to use the 'Guest' login would yield the same outcome - continual 'Hold for Authentication' / no successful print.

Resetting the Printer solved the issue - I re-added the printer in Mojave, and clicked 'Guest' and can print successfully. 

Bizarre, I would have never thought that resetting the printer would solve a network/domain authentication problem.

Good luck!

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