asked on 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)
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.
ExchangeEmail ServersEmail Protocols
Last Comment
Navdeep
ASKER
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:
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,* ,,attempti ng 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,* ,,attempti ng 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,* ,,attempti ng 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. 212.141:58 7,*,,attem pting to connect
2013-12-26T09:02:04.646Z,Fastmail Outbound,08D0D02F6C4711F9, 1,,82.145. 212.141:58 7,*,,"Fail ed 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. 212.145:58 7,*,,attem pting to connect
2013-12-26T09:02:25.651Z,Fastmail Outbound,08D0D02F6C4711FA, 1,,82.145. 212.145:58 7,*,,"Fail ed 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. 212.142:58 7,*,,attem pting to connect
2013-12-26T09:02:46.692Z,Fastmail Outbound,08D0D02F6C4711FB, 1,,82.145. 212.142:58 7,*,,"Fail ed 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. 212.143:58 7,*,,attem pting to connect
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
like this
telnet IP portNo
ASKER
telnet mail.messagingengine.com 465:
Blank Screen - so connection is being established
telnet mail.messagingengine.com 587:
220 mail.messagingengine.com ESMTP ready
Blank Screen - so connection is being established
telnet mail.messagingengine.com 587:
220 mail.messagingengine.com ESMTP ready
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ASKER
I got it to work after using the IP address rather than the hostname. Thanks for your assistance!
Glad, it worked for you.
Exchange 2013 uses starttls, have you tried using port 587 instead of 465?
Regards,
Nav