SMTP just won't work

Posted on 2008-11-17
Last Modified: 2013-11-30
I have an off-site user, with Outlook 2007 who is unable to send via SMTP.  She is attempting to use the account from her ISP (no port 25 blocking issue).  The ISP (clearwire) uses Gmail for both PO3 and SMTP service.  There is one very odd aspect to this issue, if we run a test in the account settings dialog, it completes just fine (although the test message never seems makes it through). No issues with incoming (POP).  We've attempted to use no encryption (port 25), SSL (port 465) and TSL (587) to no avail.  We've contacted the ISP and they say it's our issue.  When we change the encryption, we have seen errors that say that the method is not allowed - although both clearwire and gmail say to use SSL.  On a side note, this happened after the user was away for about a week, she did set up a rule to be used as an auto-reply, but we have since removed the rule.
Any suggestions would be highly appreciated.
Question by:JamesonJendreas
    LVL 97

    Accepted Solution

    Hello JamesonJendreas,

    1. Check these important settings:
    a. My outgoing server requires authentication (or Password or Challenge/Response for iMac)
    b. Change the server timeout time from 1 min to 5 min
    c. Uncheck leave a copy of email on server.
    d. Try alternate SMTP port number: 25, 465, or 587. To send try using SSL and 587.
    e. Change the outgoing server to

    2. Do you have a firewall blocking the connection?  Email virus checking?  Popup Blocker? Temporarily disable them.

    3. Update Outlook to latest configuration. Outlook 2000 should have SP3. Outlook 2002 should have SP3.  Outlook 2003 should have SP2.

    4. Use the Captcha verification to unlock your account

    5. See if the solutions here will help

    6. You ISP may be blocking Gmail server. Use your ISP SMTP server.

    Hope this helps!
    LVL 1

    Author Comment

    I'll Check items 4 and 5 and e.  All others are covered (as noted above the ISP uses google mail as their mail service, so the ISP defiant isn't blocking the mail, using updated Outlook 2007, tried all SSL TLS ports, and have turned off firewall and removed all AV programs).
    LVL 57

    Assisted Solution

    I have assumed you have followed:

    Could you install a packet capture program (I recommend Wireshark, on her PC and have her catpure traffic attempting to send e-mail?  Then you can see what is going on.
    LVL 1

    Author Comment

    Yeah, those were the original instructions we were using.  I'll check into running a packet capture program.
    LVL 1

    Author Comment

    User took her unit into her ISP, and they said it was a "faulty power supply for the modem", and was not retaining a constant connection. Oddly SMTP was the ONLY service that was timing out

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