I was involved with the deployment of Plone in a large UK bank (hint: now publicly owned). This was for about 35,000 commercial banking traders, so was definitely a large system, especially considering most of those users authenticated each day.
This was deployed on a cluster of about a dozen machines, including both Linux and Solaris servers, with a big EMC storage array (live sync with DR centre via SRDF). A complete replica of this at the DR site too.
The odd thing I noticed was whilst this particular division was quite progressive and willing to adopt an Open Source solution, the rest of the business was not so willing... yet very happy to develop software internally for use.
If anyone here has worked in a large (non-software) corporation they will know that pretty much every piece of software that has been developed by someone in-house goes on to become a support headache over the years. Especially once the person who wrote it leaves the organisation. Just go read The Daily WTF... these things are real.
At the start of this project, the bank did not officially support Linux, so we had to develop all our own procedures and support infrastructure. By the end of the project, the bank was asking our team to help form the bank's global Linux support policy.
So one way of explaining OSS to bosses at these organisation is by telling them that it is like in-house developed software, but has he advantage that there is a whole community of people out there to help support it. In the case of Plone (and other well established OSS projects) there are commercial support companies out there that will give you paid-for support and SLAs. Not only that, but you have a choice of companies, rather than just one software vendor in a typical commercial software scenario.
As Paul Everitt (of Zope fame) once said many years ago: 'Software is not an asset, it is a liability'. Some very true words to try and get over to some organisations.
-Matt