Consider the following scenario:
1) an ancient openssl-0.9* ebuild is installed
2) openssl-1.0* is emerged (which is in the same slot as the old openssl-0.9* ebuild)
3) openssl-0.9* is emerged (this time, with new ebuild which is installed in a different slot than the old 0.9* and the new 1.0 ebuild)
In step (2), libssl.0.9.8 is preserved ("equery f openssl" lists it as part of the openssl-1.0* package).
In step (3), libssl.0.9.8 is installed again, but it is not removed from preservation and "equery f openssl" actually lists libssl.0.9.8 two times: as a preserved lib it is part of openssl-1.0* and as part of openssl-0.9* package.
Portage should handle (3) more gracefully.
This should be fixed in 2.2.0_alpha34 (among many other preserve-libs fixes, including bug 286527). Please re-open if you can still reproduce it.
(In reply to comment #1)
> This should be fixed in 2.2.0_alpha34 (among many other preserve-libs fixes,
> including bug 286527).
I meant bug 286714.
I confirm, it's fixed in alpha34.