Crazy Issue with Cisco ASA 5505

So I'll do my best to explain this issue and I was hoping maybe someone else has seen this before.

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I have a Cisco ASA 5505 with 2 VLANS 192.168.1.0 and 192.168.2.0. Both VLANS have DHCP running on their respective interfaces on the ASA. On the 192.168.2.0 there are 4 POS machines (windows 10). On one of the POS machines there is a software client to run credit cards in which the other 3 machines talk to the one with the client. The device with the client is 192.168.2.104.

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Here's where things get weird....

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None of the other 3 machines can run cards through that client UNLESS there is a continuous ping running in the background to the 192.168.2.102 device. If you stop the ping the machines cannot talk through the CC Client (NETePay)

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Has anyone seen anything like this before? It's worth mentioning that this didn't happen until the ASA was installed. Cisco TAC has logged into the device and verified the configuration and claim they see no issues.