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Exchange 2013 Outbound Email Send Connector via Smarthost configuration

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Last Modified: 2013-12-27
I need to configure Exchange 2013 to use my email providers settings as a smarthost to be used in a send connector. So far I have tried configuring the hostname with authentication and the right port but TLS / SSL doesn't seem to get enabled.

Here are the SMTP settings from the provider (Fastmail)


SMTP


Server: mail.messagingengine.com
Port: 465
SSL/TLS Encryption: Enabled (but not STARTTLS)
Authentication: PLAIN (Our SMTP ports are for authenticated SMTP only; you'll need to make sure your software supports authenticated SMTP and also set up a username and password)

Username: your FastMail username/login name/email address (must include @fastmail.fm part)

Password: your FastMail password

Alternatively, if you're client supports STARTTLS only, you can use port 587 with STARTTLS enabled.
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Commented:
Hi,

Exchange 2013 uses starttls, have you tried using port 587 instead of 465?

Regards,
Nav

Author

Commented:
I did try using port 587 as well.

I can ping the ips 66.111.4.73  and  82.145.212.145

Here are the protocol logs:



2013-12-26T09:00:40.652Z,Fastmail Outbound,08D0D02F6C4711F4,1,,66.111.4.73:587,*,,"Failed to connect. Error Code: 10060, Error Message: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond 66.111.4.73:587"
2013-12-26T09:00:40.653Z,Fastmail Outbound,08D0D02F6C4711F5,0,,66.111.4.72:587,*,,attempting to connect
2013-12-26T09:01:01.647Z,Fastmail Outbound,08D0D02F6C4711F5,1,,66.111.4.72:587,*,,"Failed to connect. Error Code: 10060, Error Message: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond 66.111.4.72:587"
2013-12-26T09:01:01.648Z,Fastmail Outbound,08D0D02F6C4711F6,0,,66.111.4.70:587,*,,attempting to connect
2013-12-26T09:01:22.652Z,Fastmail Outbound,08D0D02F6C4711F6,1,,66.111.4.70:587,*,,"Failed to connect. Error Code: 10060, Error Message: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond 66.111.4.70:587"
2013-12-26T09:01:22.653Z,Fastmail Outbound,08D0D02F6C4711F7,0,,66.111.4.71:587,*,,attempting to connect
2013-12-26T09:01:43.647Z,Fastmail Outbound,08D0D02F6C4711F7,1,,66.111.4.71:587,*,,"Failed to connect. Error Code: 10060, Error Message: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond 66.111.4.71:587"
2013-12-26T09:01:43.648Z,Fastmail Outbound,08D0D02F6C4711F9,0,,82.145.212.141:587,*,,attempting to connect
2013-12-26T09:02:04.646Z,Fastmail Outbound,08D0D02F6C4711F9,1,,82.145.212.141:587,*,,"Failed to connect. Error Code: 10060, Error Message: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond 82.145.212.141:587"
2013-12-26T09:02:04.646Z,Fastmail Outbound,08D0D02F6C4711FA,0,,82.145.212.145:587,*,,attempting to connect
2013-12-26T09:02:25.651Z,Fastmail Outbound,08D0D02F6C4711FA,1,,82.145.212.145:587,*,,"Failed to connect. Error Code: 10060, Error Message: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond 82.145.212.145:587"
2013-12-26T09:02:25.651Z,Fastmail Outbound,08D0D02F6C4711FB,0,,82.145.212.142:587,*,,attempting to connect
2013-12-26T09:02:46.692Z,Fastmail Outbound,08D0D02F6C4711FB,1,,82.145.212.142:587,*,,"Failed to connect. Error Code: 10060, Error Message: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond 82.145.212.142:587"
2013-12-26T09:02:46.692Z,Fastmail Outbound,08D0D02F6C4711FC,0,,82.145.212.143:587,*,,attempting to connect

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Commented:
based on this log, it seems that you are not able to connect to the remote server, if you use telnet / putty and try to connect to IP Port, do you get to see the banner of fastmail?
like this
telnet IP portNo

Author

Commented:
telnet mail.messagingengine.com 465:

Blank Screen - so connection is being established



telnet mail.messagingengine.com 587:

220 mail.messagingengine.com ESMTP ready
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Commented:
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Author

Commented:
I got it to work after using the IP address rather than the hostname. Thanks for your assistance!
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Commented:
Glad, it worked for you.

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