I've been receiving these errors for the past 24 hours when trying to send email via my Google Apps account using SMTP from Outlook:

<< Sending and Receiving' reported error (0x800CCC7D) : 'Your outgoing (SMTP) server does not support SSL-secured connections. If SSL-secured connections have worked in the past, contact your server administrator or Internet service provider (ISP).' >>

No settings have been changed on my machine. Has anyone else here been experiencing this when using Google Apps to send email from a desktop client?

Gmail is working fine and that uses the same settings, so I can't understand why it would be an ISP issue.

Just tested it in Thunderbird, Port 465 doesn't respond, but 587 works perfectly.

Well I'm using port 465, since that's what most of their documentation says. Thanks for the workaround though.

There is a continuity issue with the different pages on Gmail help.

The Outlook 2007 page POP setting page, which seems to be the most recent, suggests just 587 for SMTP, however the Outlook 2003 suggests 465 or 25.

Protocol on port 465 : Secure SMTP (with SSL)
Protocol on port 587: Message Submission (with TLS)

Google uses START TLS on 587 for message submission.

Relatively advanced than SMTP over SSL, hence expected to work most of the time.

BTW both 465 & 587 are working great for me :)

FYI – It looks like this is working for me again now.