Depends on the operating system. By default Microsoft will retransmit a TCP segment 5 times before it kills the connection. Each time it doubles the retransmission timer.
Here is the registry key information to change that if desired:
TcpMaxDataRetransmissions
Key: Tcpip\Parameters
Value Type: REG_DWORD - Number
Valid Range: 0 - 0xFFFFFFFF
Default: 5
Description: This parameter controls the number of times that TCP retransmits an individual data segment (non-connect segment) before it aborts the connection. The retransmission timeout is doubled with each successive retransmission on a connection. It is reset when responses resume. The base timeout value is dynamically determined by the measured round-trip time on the connection.
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