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not a laptop, a VM that I've built with a similar environment but:

http://i.imgur.com/YyawOxc.png http://i.imgur.com/V33bYuv.png

I think that is because you're using IE 8...

It says it's "Probably Okay", even when I have Superfish's certificate enabled. (I have the program installed, but the cert sticks around.)

The site cannot detect that you have an extra root certificate lying around on your computer. If you visit the website without the Superfish program installed, you just evaluate the SSL settings of your browser.

First thing I did when I saw that URL was to run it through Qualys' SSL Labs test. Multiple issues, no forward secrecy, weak ciphers, grade set to 'C'. Oh, the irony.

https://www.ssllabs.com/ssltest/analyze.html?d=howsmyssl.com

Uh, because it needs to allow weak clients to connect in order to report on them?

Turns out you are right. Asked & answered on the project page today: https://github.com/jmhodges/howsmyssl/issues/44