After some work I discovered that Windows Media Player (WMP) 9 through 11 on XP intermittently fail to play MP3 files hosted on S3
The 64 Bit Encoded S3 signature might contain an escaped plus which WMP does not handle correctly. So for example we expect this signature to go untouched.
Signature=pXucORkPxykKvQo%2B0Hv17jvSPVE%3D
Is improperly re-escaped (mangled) by WMP as the following. Notice the + and the equal sign.
Signature=pXucORkPxykKvQo+B0Hv17jvSPVE=
When decoded by Amazon's servers the plus is interpreted as a space and therefore neither the 64 bit encoding, nor the signature are valid causing the download to fail.
Wireshark was a huge help in watching the traffic flow and proving that WMP was mangling data.