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Which version of OpenSSL to use?

OpenSSL is a living tool and bugs are regularly fixed with the arrival of new versions. You should always use the more recent version available for trains 0.9.7 and 0.9.8 security reasons.

0.9.7: At least. The oldest version that can still be used, regarding standard support, is the 0.9.7h released on October 2005. The version 0.9.7k is known to be functional. Warning though: Those versions do not contain the latest security updates, you should, if possible, use the train 0.9.7's more recent version.

0.9.8: At least. The oldest version that can still be used, regarding standard support, is the 0.9.8k. Warning: This version does not contain the latest security updates, you should, if possible, use the train 0.9.8's more recent version.

The latest OpenSSL version is always available here. The newscenter is here.

To know which version of OpenSSL to use, enter openssl version

Note that it is sometimes necessary to use several versions of OpenSSL to prevent bugs from other products. For example: Outlook Express cannot check S/MIME signatures generated from version 0.9.7 and 0.9.8 (the issue still exists with versions 0.9.7k and 0.9.8c), even though everything's fine on version 0.9.6.

That issue most probably comes from Outlook Express, for the other S/MIME tools work perfectly fine with recent versions of OpenSSL.