Exchange 2013 Emails stuck in Queue

Dear Team,

Can you please help me in solving the issue.

I have a single exchnage server 2013.
I am using DuoCircle Outbound SMTP to send my emails (also uses 1and1 in case any issue).

From yesterday evening all the emails are going to Queue and the Smart Host Connector Delivery is showing Active.

I am also using FortiDDNS for IP.

I ahve rebooted DC and Exchange server. Removed Kaspersky Security also.

Please help me sort out the issue.
Raneesh AIT EngineerAsked:
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David SankovskySenior SysAdminCommented:
Have you tried skipping your Smart Host send connector? Try and see if your server can send directly to the internet - if it ca, the problem is with the server providing the smart host, otherwise something is wrong with the exchange itself - you can also try and perform a full telnet test mail from your exchange server to the smart host to see if it responds correctly.
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Raneesh AIT EngineerAuthor Commented:
Dear David,

Now i am getting an error (still through Smart host only).

441 4.4.1 Error encountered while communicating with primary target IP Address.
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Raneesh AIT EngineerAuthor Commented:
Hi David,

I have skipped smarthost but still the error is
441 4.4.1 Error encountered while communicating with primary target IP Address.
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Raneesh AIT EngineerAuthor Commented:
HI
I changed back to Smarthost.

Now its showing SmartHostconnectordelivery as retry and the error as 441 4.4.1
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Shreedhar EtteCommented:
Hi Raneesh,

Please make sure you have proper rules configured outbound firewall rule and also check it not an issue from ISP.

Have look at this questions as well:
https://www.experts-exchange.com/questions/28220238/Exchange-2013-mail-flow-issues.html
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Raneesh AIT EngineerAuthor Commented:
Hi Shreedhar,

My Firewall is disabled on the server.
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Shreedhar EtteCommented:
Please share the complete error. I am talking about physical firewall and not Windows Firewall.
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Raneesh AIT EngineerAuthor Commented:
Hi Sreedhar ,

It was working till yesterday and it suddenly stopped working. We havent done any chnages on Firewall.
I am receiving all the email send to my domain. But outgoing is the problem.
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Shreedhar EtteCommented:
Can you check the outbound connector and share the full error description?
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Raneesh AIT EngineerAuthor Commented:
Hi Shreedhar,

I have attached the screenshot of the Mail Queue viewer. The status of delivery type  showing acive and but all emails are in queue.
I have delected th send connector and create new also.
mail.jpg
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Raneesh AIT EngineerAuthor Commented:
also Front end transport showing unhealthy
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Shreedhar EtteCommented:
To Check if Smarhost is expecting connections:
- Open a CMD prompt
- TELNET outbound.mailhop.org <port>

Replace <port> with port number your smart host is accepting connection.

- After executing above command to should get some response  like below:
220 outbound.mailhop.org ESMTP

- Then Exeute below commands (Replace user@mydomain.com with your internal user email address):
mail from:<user@mydomain.com> ENTRE

rcpt to:<your@gmail.com> ENTRE

data
This is test mail
.
ENTRE

Refer:
https://community.spiceworks.com/how_to/11-test-email-flow-using-smtp-commands

Did you check with smarthost provider for any issue at there end?
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Raneesh AIT EngineerAuthor Commented:
Hi Shreeshar
this what i have done

220 atomex1.atomoptions.ae Microsoft ESMTP MAIL Service ready at Tue, 26 Dec 2017 19:11:03 +0400
mail from:<raneesh@atomoptions.ae>
503 5.5.2 Send hello first
rcpt to:<raneeshkalam@gmail.com>
503 5.5.2 Send hello first
data
503 5.5.2 Send hello first

l
quit
500 5.3.3 Unrecognized command
221 2.0.0 Service closing transmission channel


Connection to host lost.
PS C:\WINDOWS\system32>
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Raneesh AIT EngineerAuthor Commented:
Hi Shreedhar,


220 atomex1.atomoptions.ae Microsoft ESMTP MAIL Service ready at Tue, 26 Dec 2017 19:16:34 +0400
helo mail.atomoptions.ae
250 atomex1.atomoptions.ae Hello [192.168.1.5]
mail from:<raneesh@atomoptions.ae>
250 2.1.0 Sender OK
rcpt to:<raneeshkalam@gmail.com>
550 5.7.1 Unable to relay

please find the updated error.
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Shreedhar EtteCommented:
Please change the atomex1.atomoptions.ae to your smarthost name and then execute commands.
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Raneesh AIT EngineerAuthor Commented:
when i change to smarthost name the telnet is not working.
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Shreedhar EtteCommented:
Hi Ranessh,

Looks like an issue with smart host end or you outbound SMTP connection might be blocked.

Did you get any error while connecting using Telnet? If yes, Please post here.

Also check application vent logs and see if you find error related to Exchange Transport.
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Raneesh AIT EngineerAuthor Commented:
Only Transport warning i am getting is
Transport service is disconnecting performance counters with process lifetime from their old process.
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Raneesh AIT EngineerAuthor Commented:
Hi Shreedhar,

I sorted out the issue. The issue was port 25 was blocked by our ISP so i used alternate port for send connector.
Now the emails are going fine.
Thanks for your advice and help.
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Raneesh AIT EngineerAuthor Commented:
I tried to telnet to Smart host and then found out the issue. So i tried the alternate and it is working and subsiquently changed on Exchange also.
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