http://www.squeaksource.com/WebClient/ says

To install SqueakSSL you need to download and install the binary
version of the plugin and then install SqueakSSL via:

(Installer ss)
	project: 'SqueakSSL';
		install: 'SqueakSSL-Core';
		install: 'SqueakSSL-Tests'.

But how do I install the plugin? Is it possible to do so
programmatically/in an automated fashion?

Otherwise these will stay sad and yellow:
http://build.squeak.org/job/ExternalPackage-WebClient/1/#showFailuresLink

frank