Recently, awareness has been raised about a number of “blind” attacks that can be performed against the Transmission Control Protocol (TCP) and similar protocols. The consequences of these attacks range from throughput-reduction to broken connections or data corruption. These attacks rely on the attacker's ability to guess or know the four-tuple (Source Address, Destination Address, Source port, Destination Port) that identifies the transport protocol instance to be attacked. While there have been a number of proposals to mitigate these Vulnerabilities, the most obvious mitigation -- TCP port randomization -- has been the one least engineered. In this paper we analyze a number of approaches for the random selection of client port numbers, such that the possibility of an attacker guessing the exact value is reduced. We discuss the potential interoperability problems that may arise from some port randomization algorithms that have been implemented in a number of popular operating systems, and propose a novel port randomization algorithm that provides the obfuscation while avoiding the interoperability problems that may be caused by other approaches. While port randomization is not a replacement for cryptographic methods, the described port number randomization algorithms provide improved security/obfuscation with very little effort and without any key management overhead.