As far as I know, this is either a bug in TCL, Eggdrop's implementation of TCL or a bug introduced by compiling Eggdrop in cygwin (Windrop).
In any case, there's not a whole lot one can do, unless you can find a concrete way to reproduce it and/or are able to provide the developers with a backtrace. The cygwin version of eggdrop (from windrop.cjb.net) is stripped of any debug information, which makes the back traces unreliable and useless for the most part. You'll have to compile or obtain a version yourself with extended debugging (configured without --enable-strip).
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