Did you create IronPython yourself? Signing is a kind of PITA, and you will need to provide your full key to get a real signature. We have included the MS public key in the distribution, but this can only be used for delayed signatures. We have a delay fix included in the assembly, which can lead to the creation of a delayed subscription, even if you use the full key (I'm not sure what the compilers do here).
Perhaps you can fully sign the assembly using sn or the mono equivalent. You can also disable validation before installing in the GAC using sn (this is what we are developing IronPython).
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