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I am having the same issue. If I exclude a machine from filtering adobe updates just fine. Otherwise the flash installer displays the message "cannot contact a reliable source" after about 46%. I ran testlogserver and could not find any "blocked" sites or categories. If needed I can post the log. I'm open to any suggestions.
I had the same problem took me 3weeks with websense to solve this.
What you have to do is log into your appliance then log into Content Gateway Manger
Next click on the configure tab and expanded protocols and select HTTP
Then select Cacheability scroll all the way down and edit the Caching Policy.
I added a lot of entries but it works just follow this below and it should work. (you have to wait 24 hours so that cache release from the appliance or you can call websense and they can log in as root and do it ASAP)