This issue started when my ISP (Comcast) started blocking port 25 for SMTP.
Using Outlook 2003 SP3
ISP is Comcast; but using Microsoft’s HotMail (Outlook.com) for my email.
My mail account settings are
Incoming mail server (POP3): pop3.live.mail
Outgoing mail server (SMTP): smtp.live.mail
My outgoing server (SMTP) requires authentication is checked
Use same settings as my incoming mail server is selected
Incoming server (POP3) port is set to 995
Outgoing server (SMTP) port is set to 587
This server requires an encrypted connected (SSL) is checked for both POP3 and SMTP
Test Account Settings works with no errors, but if I send an email out; Outlook attempts to send for a minute or two then issues the following error
Task ‘Hotmail – Sending’ 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).
Note: Hotmail requires a SSL connection.
At the same time the Event log shows
Event ID 36888 and the Source is Schannel
Now if I do nothing and just let Outlook sit there with the error message displayed, Outlook retries the send after a few minutes and the send is successful !
The only change in my mail settings for the Hotmail Account was the change of port 25 to 587. I never had a problem with Port 25 and SSL checked. I have tried ports 465 with SSL checked and unchecked with no success and port 587 with SSL of with no success.
Any ideas?