As for the source of randomness, it looks like the 0.9.8 release makes the appropriate set of WinCE calls to generate randomness. In crypto/rand/rand_win.c, there is a call to CryptAcquireContext and then CryptGenRandom. I assume these are working correctly.
There was a bug in source code, which was preventing the toolkit from making these calls on WinCE. There also is a number of improvements to WinCE support being *currently* added. I'd recommend to download latest 0.9.8 or HEAD snapshot at ftp://ftp.openssl.org/snapshot/, test it and report problem [as opposite to mentioning blanket "some tweaking was required"]. A.
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