Mail from exchange clients getting lost

More than likely the mail is queued in Exchange and you just aren't searching for it correctly.

If this is a new deployment, your problem is probably related to incorrect or incomplete configuration of Exchange to relay mail.

If I had to guess, I'd say you have yet to configure a default send connector.

This is a good guide, pay close attention to step 6, as the * is important:

http://www.ithacks.com/2013/04/26/configure-exchange-2013-to-send-external-email/

ok. i left one part out in my initial post. the server was setup and already working for about 2 days. then suddenly mails to the internet started to bounce. so i checked online and changed a few setting. turnes out the firewall was causing the problem. so the firewall has been replaced and i am trying to undo those changes . i already checkd the settimngs for he different receive connectors and the send connector. i already fixed that part(i think). so i think there must be something else i have overlooked.

The issue only happened for internal to external mail. I believe you already Send Connector does exist. Could you verify what smarthost that you pointing to?

Could you send a test mail and do message tracking:

http://exchangeserverpro.com/exchange-2013-front-end-proxy/

For mail send and receive purposes, port 25 is the only port necessary in the firewall pointing to exchange. Port 443 should also be open if you plan on allowing mobile and web access. Other than that, I don't see the firewall being the problem.


Are you familiar with how to grab a packet capture with wireshark? I recommend running a capture on the server while you attempt to send an email. You should be able to see (or not see) if the server is making an outbound connection attempt, and if there is an error. Filter by SMTP once you stop the capture. 3 minutes should be sufficient time to see some activity.

It could also be your PTR record. Did you set up a PTR with your ISP? This would likely affect a portion of domains that you attempt to relay to, but probably not all.

Are you getting any bounce or delayed messages from the mail server daemons?

Are you using a smarthost, or are you relaying directly to/from the internet?

Jkockler i would sure like to look into wireshark. but i want to clear something. i am ble to connect to the mailserver. i sent out a mail. it gets out of my outbox and into my sent items. problem is that the recipient never gets it. not internal not external. so even if i sent a mail to myself i don't receive it.
so i think someweher i messed up the mail handling from the exchange server.

I understand that. An email in your sent items simply means the email was released to your exchange server, out of Outlook. A packet capture will show you what happens after Exchange accepts that email, (or not show you, in a scenario where the Exchange server does not have the necessary information configured to route mail, which I believe is ultimately your issue, a send connector configuration problem.) and from there we can decipher the problem.

If you see smtp traffic in the capture, it will be traffic of your mail server attempting outbound connections to other mail servers, in order to relay your test messages.

If Exchange is getting that far, the errors shown in the smtp exchange (in wireshark), will tell us your problem.

However, if there is no smtp traffic in your packet capture, then the problem is Exchange has no idea how to get that email out of itself, because of an incorrect or incomplete configuration.

You can also check your event logs on the exchange server for errors during the time Exchange is trying to do something with your test message.

ok jkockler. i tried wireshark. nothing about smtp showing up. tried a view times to sent mail. nothing poppin up. it is tracking communication with the exchange server. but that's it. but i found an error on the exchange server saying: "Anti-spam agents are enabled, but the list of internal SMTP servers is empty. If there are any MTAs between this server and the Internet, populate this list by using the Set-TransportConfig cmdlet in the Exchange Management Shell."
how and where do i correct this?

From the Exchange 2013 administrative GUI - >Go to Mail flow > Send connectors. On the Send connectors page, what do you have listed?

i attached a screenshot of the send connector
send-connector.jpg

i forgot to mention that i created that connector for sending internet mail

Okay I need to see what's under the edit option, so probably a few screen shots there, also might need to see the accepted domains tab, and email addresses policy tab.

Ok. Here you go. Hope this info is enough.
send-connector.zip

Okay I see a few possible issues.

First, are you really using a smarthost? A Smarthost is a service from a vendor, where they spool your mail before it gets to your Exchange server.

The smarthost address "smtp.sr.net" looks fishy to me.

Next, you should have "use external dns lookup settings on servers with transport roles" checked, in the scoping tab of your send connector properties.

ok. the smarthost adress is from our local isp here in suriname. i checked the use external dns lookup option as you suggested. nothing has changed. still unable to sent internal or external mail.