CUPS printing to IPP w/ SSL on port 443 to a Windows 2008 Server

[Chris Poupart]

I am having the hardest time getting CUPS to print to a Windows 2008 R2 hosted print queue using IPP with SSL on port 443.

I have successfully done this from CUPS on an OS X machine (with CUPS version 1.4.4), however using the same URL on an Ubuntu machine (with cups 1.4.3 or on Ubuntu Mavrik with CUPS 1.4.4) things do not work.

To add confusion to the issue, CUPS on Ubuntu thinks that the job was sent successfully.  However, it never shows up in the queue on the Windows 2008 server.

Just for fun, it works to the same server over http (port 80 with no encryption).

The URL that is being used is (roughly):

http://windows2008r2.example.com:443/printers/WindowsPrintQueue$/.printer?encryption=always

At this point, I am at a complete loss.  I will be working with the Windows admin sometime this afternoon to see if we can identify anything on the Windows side, but at this point there is nothing obviously wrong.

If anyone has any ideas/suggestions, I would love to hear them!