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Thread: Win7 64bit, Outlook 2010 Outlook cannot connect to your outgoing (SMTP) e-mail server

  1. #1
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    Exclamation Win7 64bit, Outlook 2010 Outlook cannot connect to your outgoing (SMTP) e-mail server

    This is the message:
    Send test e-mail message: Outlook cannot connect to your outgoing (SMTP) e-mail server. If you continue to receive this message, contact your server administrator or Internet service provider (ISP).

    Here are some logs:
    With defaults:
    2011.03.27 13:57:40 SMTP (smtp.theonlinebusiness.com): Port: 25, Secure: no, SPA: no
    2011.03.27 13:57:40 SMTP (smtp.theonlinebusiness.com): Finding host
    2011.03.27 13:58:01 SMTP (smtp.theonlinebusiness.com): Disconnected from host

    Using SSL on incoming gives this error:
    Log onto incoming mail server (POP3): Outlook cannot connect to your incoming (POP3) e-mail server. If you continue to receive this message, contact your server administrator or Internet service provider (ISP).
    2011.03.27 14:02:30 POP3 (pop.theonlinebusiness.com): Port: 995, Secure: SSL, SPA: no
    2011.03.27 14:02:30 POP3 (pop.theonlinebusiness.com): Finding host
    2011.03.27 14:02:30 POP3 (pop.theonlinebusiness.com): Connecting to host
    2011.03.27 14:02:31 POP3 (pop.theonlinebusiness.com): Disconnected from host

    2011.03.27 14:02:17 SMTP (smtp.theonlinebusiness.com): Port: 465, Secure: SSL, SPA: no
    2011.03.27 14:02:17 SMTP (smtp.theonlinebusiness.com): Finding host
    2011.03.27 14:02:17 SMTP (smtp.theonlinebusiness.com): Connecting to host
    2011.03.27 14:02:19 SMTP (smtp.theonlinebusiness.com): Disconnecting from host
    2011.03.27 14:02:19 SMTP (smtp.theonlinebusiness.com): Disconnected from host

    Using only on outgoing on 465, SSL
    2011.03.27 14:01:03 SMTP (smtp.theonlinebusiness.com): Port: 465, Secure: SSL, SPA: no
    2011.03.27 14:01:03 SMTP (smtp.theonlinebusiness.com): Finding host
    2011.03.27 14:01:03 SMTP (smtp.theonlinebusiness.com): Connecting to host
    2011.03.27 14:01:24 SMTP (smtp.theonlinebusiness.com): Disconnected from host

    Using only on outgoing on 465, TLS
    2011.03.27 13:51:23 SMTP (smtp.theonlinebusiness.com): Port: 465, Secure: TLS, SPA: no
    2011.03.27 13:51:23 SMTP (smtp.theonlinebusiness.com): Finding host
    2011.03.27 13:51:23 SMTP (smtp.theonlinebusiness.com): Connecting to host
    2011.03.27 13:51:44 SMTP (smtp.theonlinebusiness.com): Disconnected from host

    Earthlink needs smtpauth rather than just smpt
    2011.03.27 13:38:43 SMTP (smtpauth.theonlinebusiness.com): Port: 465, Secure: TLS, SPA: yes
    2011.03.27 13:38:43 SMTP (smtpauth.theonlinebusiness.com): Finding host
    2011.03.27 13:38:43 SMTP (smtpauth.theonlinebusiness.com): Connecting to host
    2011.03.27 13:39:04 SMTP (smtpauth.theonlinebusiness.com): Disconnected from host

    Help or a direction would be appreciated!

  2. #2
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    Try turn off secure login. Use only plain text login.

  3. #3
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    If you mean, "my outgoing SMTP server requires authentication" there is no difference. If I enter an incorrect email or password, I get the same message. I would say it is failing before it gets to authentication.

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