I am having some difficulty in understanding the relationships. Perhaps some type of diagram would be helpful. And some more config details would be helpful as well.
Based on your comment about a tunnel I will make a guess that the problem you face may be related to MTU. When you have tunnels they encapsulate the traffic and the result is a packet that is longer than what the originating host sent. If the host sends a frame that is already 1500 and the router adds some bytes for encapsulation then the result is a frame that is too big and requires fragmentation, which may be a problem. So I would suggest configuring ip tcp adjust-mss on routers on both ends of the tunnel.
If that does not help then please supply some additional detail.
I will also point out that if you configure this
permit ip any host 10.10.102.2
that it makes these lines that follow it redundant. They will never get a match
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