Avast 4 Home Email Scanner and SMTP with SSL

Hi.

I’ve an email account that sends out its emails through an SMTP server that requires authentication and SSL connection.

How should I go about configuring the scanner? Outlook Express keeps complaining about error with “authentication required” when sending messages. If not, I’ll have to stop and disable the email scanner.

Avast mail scanner doesn’t support SSL (Secure Socket Layer) connections.
But take a look here: http://forum.avast.com/index.php?topic=10428.0 to see how to set up secure email (Inbound POP3) with avast!.

Since SSL/TLS e-mail is encrypted and decrypted in the client, external virus scanners (including avast!) can’t read or scan it.
The solution is to pass e-mail in and out un-encrypted from your client (Outlook Express, Thunderbird, …) to a proxy program (Stunnel) that does the actual ssl or tls encryption/decryption of the pop3/smtp e-mail and communicates directly with the ISP server on the appropriate ports. Another drivers (OpenSSL) are need as a library of encryption/decryption routines.

avast doesn’t support SSL connections, it can scan encrypted emails (it doesn’t know the encryption key). This has been discussed in a number of threads, so a search of the forums could be useful. A search for Stunnel and Gmail would probably be best as this is a regular use of stunnel to connect to Gmail. The link provided by Technical is probably the best place to start.

How should I go about configuring the scanner? Outlook Express keeps complaining about error with "authentication required" when sending messages.

This is not a scanner issue but an OE issue, you need to tick the box in the accounts settings. Yes, you will have to find a way around the SSL issue, but “authentication required” has nothing to do with SSL. Many ISPs insist you logon to your smtp server to send email, especially if you aren’t connected to the Internet through their service.