Yes, the problem continues if I drop TLS.  This is what I did to test:

On the server I removed the certificate information, and I put
"DefaultEncryption Never"

Then on the client, just to be sure, I set the URI as such:
ipp://192.168.122.65:631/printers/TestPrinter?encryption=never

Thus, the server should not request TLS, and the client should not
request TLS.

The status on the client is this:

-------<start>------
processing since
Mon 31 Oct 2011 10:08:33 AM EDT 
"Unable to get printer status."
-------<end>-------

After "pending" for a few minutes.

No errors in the server error log.

If I remove the authentication requirement, the job goes through no
problem.

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https://bugs.launchpad.net/bugs/879625

Title:
  CUPS fails to request authentication when printing over IPP w/ TLS

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