This is what I did on QA site

1. edit "advanced uploading of files assignment" to restrict access until 2 other condition are met (as shown in pic 3)
2. Login as student and attempted both conditional activities and secured 100% on both (I have a good IQ ) (attached pic 1)
3. activity is still not available although the conditions are met(pic 2)

Well I am not sure if I missed out any settings, but looks like a bug to me.
PS: It worked fine when only one conditional activity was added.
Thanks