What could be blocking me from signing into iTunes on my network?

I have a Server 2003 R2 environment with two Server 2003 R2 DCs running AD.  I have an eSafe security device acting as my firewall/spam filter.  We have always blocked iTunes and Apple products but are embracing iPhones and iPads so I need to be able to connect and update them.  I believe this to be an eSafe issue but nothing is being logged when I try and fail.  It is, however, still collecting its normal log data as other things are blocked.

I can open iTunes but get the following messages when trying to login:

XP OS=We could not complete your iTunes Store request.  The network connection was reset.

Mac OSX=We could not complete your iTunes Store request.  The secure network connection was refused.

In eSafe, I have whitelisted:

*.apple.com*
*.itunes.com*
*.itunes.apple.com*
*.ax.itunes.apple.com*
*.gs.apple.com*
17.151.36.30
17.171.27.65
17.149.156.10
63.235.36.115

When I run the iTunes diagnostic tool it tells me that the "Secure link to the iTunes Store failed."

Any advice or suggestions you can offer would be much appreciated.

Thanks