sending external email okay, but does not get delivered

[eboz]

We are using Exchange and Wingate. We are receiving external emails okay. when we send an external email out, it appears to go out okay but the recipient does not receive the email.

Not sure what is wrong.

[labull]

Are you using the SMTP services of WinGate. If so, turn on debug logging on the WinGate's SMTP server. If not, you can use Exchange's debug logging.

Either way, you'll be able to see the communication between SMTP servers to look for any error messages.

[eboz]

Yes using SMTP services and have debug logging on.

There is no error messages shown. For each email it shows terminated exit code 0.

[labull]

In that case we can only speculate.

Is the mail going to multiple locations or just one?

It could be anti-spam software at the receiving end deleting the mail.

[kgoodknecht]

Is Exchange delivering the mail to Wingate OK?
Exchange works better with Wingate, if you set up an SMTP connector with Wingate set up as the Smart host.

http://support.microsoft.com/default.as ... -us;265293

Or, is it Wingate that cannot deliver the mail?

If this is the case, there could be any one or more of serveral problems, depending on the SMTP server Wingate is trying to deliver to.
1. Your IP address could be on a black list.
2. Your ISP has blocked port 25 to SMTP servers outside of its relm from its client IPs, if this is the case see if your ISP will unblock port 25, or use your ISP's SMTP server as a relay.
3. You may not have a PTR record for your public IP Wingate delivers mail on. (Many if not most SMTP servers require PTRs for SMTP servers delivering to them.)

These are the major reasons most mail servers would not accept mail from yours. There are many other problems that are only supported by some SNTP servers, SPF, EHLO/HELO greeting, MX lookup or many other reasons. The only way to tell for sure is through testing you mail domain.

[eboz]

Exchange delivers the mail to Wingate and the email leaves Wingate.
I have checked and we have not been blacklisted, nor has our ISP blocked port 25.

Have checked the MX record, and tried using the EHLO,HELO commands with success.

I don't think that it has anything to do with anti spam software installed on the receiving email servers, as it is occurring with all emails that we have sent.

The mail simply goes from Outlook -> Exchange -> Wingate -> Recipient. There is no multi locations involved

[adrien]

Hi

Best way to check what is happening is to turn on debug logging in the SMTP server in WinGate.

That will give you the full log of delivery (as well as reception).

If the mail is being delivered by WinGate, but the receivers are not receiving it (is this all mail, or just some?), then you may need to forward to your ISPs mail server.

If you send an email directly to your ISPs server to these recipients, do they receive the mail?

Adrien