In my lab, I setup Exchange 2010 SP1: EX2 - CAS/HT; EX3 & EX4 - MB in a DAG. Test sendingt/receiving internally OK. Also the internal mailboxes can receive email sent from Internet. When I sent messages to Internet, they were gone from Outbox but not reached the mailboxes on Internet. I did create a Send Connector to Internet (Address *). How to troubleshoot this? I suspect that my ISP may block my outgoing messages to Internet. Is there a way to find out? Thanks.

Are you getting any NDR's? If so what are they. If you just want to test SMTP to the internet, try the SMTPDiag tool: http://www.microsoft.com/downloads/details.aspx?familyid=bc1881c7-925d-4a29-bd42-71e8563c80a9&displaylang=en Tim Harrington - Catapult Systems - http://HowDoUC.blogspot.com

Does it support Exchange 2010 on Windows 2008 R2?

It is a stand-alone, command line tool to test outbound SMTP traffic. If you are worried about your ISP, then this is the first start. If that works, then you can troubleshoot Exchange. Tim Harrington - Catapult Systems - http://HowDoUC.blogspot.com

Hi Check with your ISP, they will help you with this Maybe you have to use them as a smarthostJonas Andersson MCTS: Microsoft Exchange Server 2007/2010 | MCITP: EMA 2007/2010 | MCSE/MCSA Blog: http://www.testlabs.se/blog

We know most ISP's block outbound SMTP port 25, please first contact the ISP to confirm whether this is the case. Does the exchange server use your own DNS server? Please check if the messages are stuck in the remote domain queue: 1. Open Exchange Management Console, expand to Toolbox. 2. Under mail flow tools, open "Queue Viewer", do you see the messages in the remote domain queue? This happens if exchange server cannot connect to this remote domain. Most of this issues are caused by the DNS record. Please verify the DNS record in your DNS server make sure that you have correct DNS record for that remote domain. If you do not see the messages in the Queue Viewer, I suspect that the messages has been deliver to the remote domain, but they are blocked by the mail server of the remote domain.

did not get clear answer from ISP about if outgoing SMTP blockied. I am not sure if I need to do DNS forwarding on my internal DNS server to ISP DNS server. BTW. I use the same domain name internally as on Internet, e.g. mydomain.com Using smtpdiag.exe with following result on my EX2 server (CAS/TH): C:\SmtpDiag>smtpdiag sender@mydomain.com receiver@remotedomain.com Searching for Exchange external DNS settings. Computer name is EX2. VSI 1 has the following external DNS servers: There are no external DNS servers configured. Checking SOA for remotedomain.com. Checking external DNS servers. Checking internal DNS servers. SOA serial number match: Passed. Checking local domain records. Checking MX records using TCP: mydomain.com. Warning: The TCP DNS query returned no results. Checking MX records using UDP: mydomain.com. Warning: No MX or A records were found for the local domain. If the records are not configured, incoming mail can fail to be delivered to this server. Checking remote domain records. Checking MX records using TCP: remotedomain.com. Warning: The TCP DNS query returned no results. Checking MX records using UDP: remotedomain.com. Error: No MX or A records were found for the remote domain. Verify that the remote domain is valid. Your firewall allows outbound DNS queries (Windows NT/2000 Server requires TCP), and your DNS server can resolve external domains.

Looks like you are having a DNS issue. Can you browse the internet from this server or do an nslookup to an external domain?Tim Harrington - Catapult Systems - http://HowDoUC.blogspot.com

I am talking about DNS issue in DNS forum. will come back when the issue resolved. Thanks.

Hello Ian3, On E2010 server :-- For outbound :-- I) Create a Send Connector with proper properties Type: SMTP, Address: *, Cost 1. Network: Use MX DNS Records to route email automatically & Source server E2010 server II) Checked the Last Error on the Queue viewer for all the Email stuck on the queue and Troubleshoot according to that. III) Try to Telnet MX 25 of any Domain affected domain & checked whether u are able to drop mail to remote domain. If it was delivered then it was perfect & if not then Checked Port 25 is blocked on your firewall & your ISP. It will help you.EXCHANGE2010, MCSE, MCTS, MCSA MESSAGING, CCNA & GNIIT

My DNS issue should be resolved since I can get any mx records from Internet using nslookup. I sent a test message to 3 mailboxes: one is my mailbox of my ISP and the other 2 are hotmail.com and Acompany.com. The message reached my mailbox of my ISP but not the other 2 on Internet. Is my ISP blocking them? The following is smtpdiag result: D:\>smtpdiag sender@mydomain.com receiver@hotmail.com Searching for Exchange external DNS settings. Computer name is EX2. VSI 1 has the following external DNS servers: There are no external DNS servers configured. Checking SOA for hotmail.com. Checking external DNS servers. Checking internal DNS servers. SOA serial number match: Passed. Checking local domain records. Checking MX records using TCP: mydomain.com. Checking MX records using UDP: mydomain.com. Both TCP and UDP queries succeeded. Local DNS test passed. Checking remote domain records. Checking MX records using TCP: hotmail.com. Checking MX records using UDP: hotmail.com. Both TCP and UDP queries succeeded. Remote DNS test passed. Checking MX servers listed for receiver@hotmail.com. Connecting to mx4.hotmail.com [65.55.92.184] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx4.hotmail.com. Connecting to mx4.hotmail.com [65.55.92.168] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx4.hotmail.com. Connecting to mx4.hotmail.com [65.54.188.126] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx4.hotmail.com. Connecting to mx4.hotmail.com [65.54.188.110] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx4.hotmail.com. Connecting to mx4.hotmail.com [65.54.188.94] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx4.hotmail.com. Connecting to mx4.hotmail.com [65.54.188.72] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx4.hotmail.com. Connecting to mx4.hotmail.com [65.55.92.152] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx4.hotmail.com. Connecting to mx4.hotmail.com [65.55.92.136] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx4.hotmail.com. Connecting to mx4.hotmail.com [65.55.37.72] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx4.hotmail.com. Connecting to mx4.hotmail.com [65.55.37.120] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx4.hotmail.com. Connecting to mx4.hotmail.com [65.55.37.104] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx4.hotmail.com. Connecting to mx3.hotmail.com [65.55.92.152] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx3.hotmail.com. Connecting to mx3.hotmail.com [65.55.37.120] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx3.hotmail.com. Connecting to mx3.hotmail.com [65.55.37.104] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx3.hotmail.com. Connecting to mx3.hotmail.com [65.55.37.72] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx3.hotmail.com. Connecting to mx3.hotmail.com [65.55.92.168] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx3.hotmail.com. Connecting to mx3.hotmail.com [65.54.188.126] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx3.hotmail.com. Connecting to mx3.hotmail.com [65.54.188.110] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx3.hotmail.com. Connecting to mx3.hotmail.com [65.54.188.94] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx3.hotmail.com. Connecting to mx3.hotmail.com [65.54.188.72] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx3.hotmail.com. Connecting to mx3.hotmail.com [65.55.92.184] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx3.hotmail.com. Connecting to mx3.hotmail.com [65.55.92.136] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx3.hotmail.com. Connecting to mx2.hotmail.com [65.55.37.72] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx2.hotmail.com. Connecting to mx2.hotmail.com [65.55.37.120] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx2.hotmail.com. Connecting to mx2.hotmail.com [65.55.37.88] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx2.hotmail.com. Connecting to mx2.hotmail.com [65.55.92.152] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx2.hotmail.com. Connecting to mx2.hotmail.com [65.54.188.72] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx2.hotmail.com. Connecting to mx2.hotmail.com [65.54.188.126] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx2.hotmail.com. Connecting to mx2.hotmail.com [65.54.188.110] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx2.hotmail.com. Connecting to mx2.hotmail.com [65.54.188.94] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx2.hotmail.com. Connecting to mx2.hotmail.com [65.55.92.184] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx2.hotmail.com. Connecting to mx2.hotmail.com [65.55.92.168] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx2.hotmail.com. Connecting to mx2.hotmail.com [65.55.92.136] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx2.hotmail.com. Connecting to mx1.hotmail.com [65.55.37.104] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx1.hotmail.com. Connecting to mx1.hotmail.com [65.54.188.72] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx1.hotmail.com. Connecting to mx1.hotmail.com [65.54.188.126] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx1.hotmail.com. Connecting to mx1.hotmail.com [65.54.188.110] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx1.hotmail.com. Connecting to mx1.hotmail.com [65.54.188.94] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx1.hotmail.com. Connecting to mx1.hotmail.com [65.55.92.168] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx1.hotmail.com. Connecting to mx1.hotmail.com [65.55.92.152] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx1.hotmail.com. Connecting to mx1.hotmail.com [65.55.92.136] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx1.hotmail.com. Connecting to mx1.hotmail.com [65.55.37.120] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx1.hotmail.com. Connecting to mx1.hotmail.com [65.55.92.184] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx1.hotmail.com. Connecting to mx1.hotmail.com [65.55.37.72] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx1.hotmail.com. Connecting to mx4.hotmail.com [65.55.37.88] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx4.hotmail.com. Connecting to mx3.hotmail.com [65.55.37.88] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx3.hotmail.com. Connecting to mx2.hotmail.com [65.55.37.104] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx2.hotmail.com. Connecting to mx1.hotmail.com [65.55.37.88] on port 25. Connecting to the server failed. Error: 10060 Failed to submit mail to mx1.hotmail.com. D:\>

Does your ISP require authentication? What are their instructions to connect to them, do you need to use them as a smarthost? If they requre you to use them as a smarthost, then the SMTP diag tool might fail since it is trying to send directly to the internet. Tim Harrington - Catapult Systems - http://HowDoUC.blogspot.com

My ISP told me no smarthost is provided but no clear answer about whether ISP blocks outgoing traffic or not. My question is that can we find out the answer by using smtpdiag or some other methods? Thanks.

Hi Ian3, You can run Telnet to check whether the 25 port is opening or not: On another computer which is connect to your ISP (has a public IP address), Open CMD, type: telnet 10.172.11.20 25 10.172.11.10 is the public IP address of your exchange server. If the 25 port is blocked, you will be unable to connect to the exchange server. If there's no problem on port 25, please check SMTP queue: 1. Send a message to a Internet recipient such as xxx@hotmail.com. 2. Open Exchange Management Console, expand to Toolbox. 3. Under mail flow tools, open "Queue Viewer", do you see the messages in the "hotmail.com" queue? If no, we can consider that the mail has been delivered to hotmail.com. But it is blocked by the mail server of hotmail. Please verify the reverse-DNS for your exchange server. Most of the mail severs will not accept e-mail from senders who fail a reverse-DNS lookup. Please remember to click “Mark as Answer” on the post that helps you, and to click “Unmark as Answer” if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread. Thanks