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Windows Server 2008 R2 Thread, IIS & SMTP Server in Technical; Hi Guys, Not really sure if this is in the correct area or not but I am trying to setup ...
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    staningrimsby's Avatar
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    IIS & SMTP Server

    Hi Guys,

    Not really sure if this is in the correct area or not but I am trying to setup an SMTP Server in IIS on Server 2008 R2 to connect to gmail I have followed various instructions like the site below;

    Setting up SMTP server in Windows .. to use Gmail

    All seemed to go well but when I try to send a test email it just goes straight to the Ďbadmailí folder, I presume this means it canít connect to the SMTP at Gmail, can anyone please tell me if I have to set something up in the actual Gmail account, or is there a port on the Server \ External firewall I need to open ???

    Been doing this for 2 days now and donít feel like Iím getting anywhere.

    Cheers in advance
    Stan.

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    In the Gmail account POP needs to be enabled (Settings > Forwarding and POP/IMAP)

    Then in IIS SMTP settings :

    Delivery Tab

    Outbound security

    Basic authentication
    Username : yourgmailaddress@gmail.com (replace gmail.com with google apps domain if applicable)
    Password : yourgmailpassword

    Tick TLS encryption

    Click OK

    Outbound Connections

    TCP port 587

    Click OK

    Advanced

    Smart host smtp.gmail.com

    Click OK

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    staningrimsby's Avatar
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    Yep that's exactly what I did but the test messages just keep going straight into the badmail folder.

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    Paste the following in a notepad

    From: myname@mydomain.com
    To: someone@somedomain.com
    Subject: testing

    This is the test message body.
    (From address should be the one you've set up in IIS and the To address should be valid)

    Then save the notepad in c:\inetpub\mailroot\pickup as "test" (include the quotation marks as this makes sure no file extension is put on the end) and it should work.

    I only set this up myself yesterday afternoon!

  5. Thanks to googlemad from:

    staningrimsby (21st March 2013)

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    staningrimsby's Avatar
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    Thank you for that just re-installing IIS then will give it a go.

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    Thank you so much you are a star , it would appear that all my configuration was correct it was the format the test email was going out on was not correct. The initial test emails have worked fine I just need PSF to connect and test it with the software now.

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    One quick question Googlemad,

    I managed to send 2 successful test messages but when I went to try again the messages are just sat in the queue folder and won’t go anywhere, do you no why ???

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    Sadly not!

    Maybe give it a couple of restarts...

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    Its ok all sorted, tried re-starting the service and nothing, logeed into gmail and re-set the password and its back up and running again.

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