Why do I get I/O errors when connecting via HTTPS to an Apache+mod_ssl server with Microsoft Internet Explorer (MSIE)?

The first reason is that the SSL implementation in some MSIE versions has some subtle bugs related to the HTTP keep-alive facility and the SSL close notify alerts on socket connection close. Additionally the interaction between SSL and HTTP/1.1 features are problematic in some MSIE versions. You can work around these problems by forcing Apache not to use HTTP/1.1, keep-alive connections or send the SSL close notify messages to MSIE clients. This can be done by using the following directive in your SSL-aware virtual host section:

Further, some MSIE versions have problems with particular ciphers. Unfortunately, it is not possible to implement a MSIE-specific workaround for this, because the ciphers are needed as early as the SSL handshake phase. So a MSIE-specific SetEnvIf won't solve these problems. Instead, you will have to make more drastic adjustments to the global parameters. Before you decide to do this, make sure your clients really have problems. If not, do not make these changes - they will affect all your clients, MSIE or otherwise.

The next problem is that 56bit export versions of MSIE 5.x browsers have a broken SSLv3 implementation, which interacts badly with OpenSSL versions greater than 0.9.4. You can accept this and require your clients to upgrade their browsers, you can downgrade to OpenSSL 0.9.4 (not advised), or you can work around this, accepting that your workaround will affect other browsers too:

will completely disables the SSLv3 protocol and allow those browsers to work. A better workaround is to disable only those ciphers which cause trouble.

This also allows the broken MSIE versions to work, but only removes the newer 56bit TLS ciphers.

Another problem with MSIE 5.x clients is that they refuse to connect to URLs of the form https://12.34.56.78/ (where IP-addresses are used instead of the hostname), if the server is using the Server Gated Cryptography (SGC) facility. This can only be avoided by using the fully qualified domain name (Fully Qualified Domain Name) of the website in hyperlinks instead, because MSIE 5.x has an error in the way it handles the SGC negotiation.

And finally there are versions of MSIE which seem to require that an SSL session can be reused (a totally non standard-conforming behaviour, of course). Connecting with those MSIE versions only work if a SSL session cache is used. So, as a work-around, make sure you are using a session cache (see the SSLSessionCache directive).