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Exchange 2013 Outbound Email Send Connector via Smarthost configuration

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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elchermans
Asked:
elchermans
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1 Solution
 
NavdeepCommented:
Hi,

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

Regards,
Nav
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elchermansAuthor 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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NavdeepCommented:
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
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elchermansAuthor 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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NavdeepCommented:
So now 587 works well. Did fastmail provided any specific settings for setting up TLS? in exchange 2013, it will try to submit the msg using tls and if tls is not available it will switch to non tls mode. Also know as opportunistic TLS.

btw does your provider require you to use trusted certificate? TLS can fail if certificate requirements are strict.

Check this article on mutual tls. This for 2010 but the concept is almost the same.
http://technet.microsoft.com/en-us/library/bb123543%28v=exchg.141%29.aspx

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