Experiencing intermittent problems with outbound http Internet traffic that crosses an ASA (not in path of WAAS). Internal accelerated http has no problems. WAAS 4.1.5a with inline deployment at branch and data center (hosting Internet connection). Is there any specific config I need on the ASA? Everything I have seen posted regarding WAAS and ASA relates to ASA in the optimization path, which is not my case. Also having some problems with IPsec VPN client traffic terminated to ASA which would then be optimized by WAAS to access internal resources - http, CIFS and other applications.
I would try a couple of things. First on your ASA, try configuring the "inspect waas" setting to see if it is not liking the tcp options being passed through to it. That also might be the issue with the VPN traffic. Also on the VPN traffic, there might possibly be some fragmentation issues there? Take a look and adjust the MSS lower on the WAAS if you see fragmentation.
See if that helps,