WinGate 6 Can't Send eMail

[wrink]

Hi,

I'm trying to setup my Wingate email as a POP3/SMTP server. I am able to successfully send and receive email from Wingate to my Yahoo account, however my Comcast and Business email servers reject my email with the following message:

Your message did not reach some or all of the intended recipients.

Subject: Testing
Sent: 1/20/2008 9:06 PM

The following recipient(s) cannot be reached:

'williamrink@comcast.net' on 1/20/2008 9:06 PM
550 relaying denied


Object: Mail System
Time: 20-Jan-2008 21:05:50
Message ID: 0C01

Wingate System Message:
Incoming mail relay attempt blocked. Mail from
bill@rinkville.net [71.237.20.230] to williamrink@comcast.net denied

I have purchased a domain name 'rinkville.net' from GoDaddy and have setup a DNS redirector for my Cable Modem based server. I understood that this would prevent my domain from being considered being with a spammer.

Please let me know what I need to configure.

Thanks,
Bill
wrink101@yahoo.com

[adrien]

Hi

that IP address is a public address, is that on your internal LAN?

The denial looks to be coming from wingate itself, and it's because it thinks an external sender is trying to send a mail to a comcast address.

Since your WinGate install isn't the mail server for comcast, this would require a mail forward, this is the definition of relaying. Relaying from an external sender would make your WinGate server an open relay, so it's blocked by default.

So is this sender in this case really external? WinGate treats a sender as untrusted based on the trust policy in the email settings.

Regards

Adrien

[wrink]

Hi Adrian,

Here's what I have configured for my home network.

1. Cable Modem on Comcast network providing ISP services
2. Public Domain 'rinkville.net' purchased from GoDaddy pointing to 'public' IP address of my Cable Modem CPE IP, which is my D-Link router
3. D-Link wireless router protecting my network, using IP address 172.16.0.1 for LAN interface, public IP for WAN interface
4. Wingate Server with single Ethernet adapter interface using IP address 172.16.0.100 attached to Ethernet switch going to router
5. Created a Virtual Server on D-Link router pointing to Wingate Server
6. Wingate provides DHCP services (D-Link router DHCP server is disabled) to all LAN clients.
7. Wingate DHCP hands out leases with 172.16.0.100 for gateway and DNS addresses. All LAN clients send/recv packets through Wingate server allowing PureSight filtering and caching (this all works fine)
8. Created email domain on Wingate for 'rinkville.net'

I am able to send and receive email from my Outlook client to my Yahoo account using the 'rinkville.net' domain of my Wingate server.

I am able to receive email sent from my Yahoo, Comcast, and work email accounts to my 'rinkville.net' domain using my Outlook client.

Outlook is configured to use 'rinkville.net' for POP3 and SMTP, which means that it is sending packets to Wingate through the public IP address of the router (maybe my LAN Outlook clients should be using the 172.16.0.100 private IP address?)

I cannot send email to either Comcast or work email accounts when using my Wingate as the SMTP sever; i.e send email from my Outlook account using my 'rinkville.net' domain configured on my Wingate server. When I do I get the RELAY error messages.

[adrien]

Hi

I'd definitely recommend getting the LAN clients to connect directly to the WinGate server for SMTP.

Otherwise, if you turn on debug logging in the SMTP server you should be able to see what's going on. It sounds like the LAN clients may be connecting to the WinGate SMTP server from the outside (i.e. via your cable modem), in which case they will be deemed untrusted.

Regards

Adrien

[wrink]

Hi Adrian,

Unfortunately the Wingate SMTP server is still unable to deliver mail with the clients configured to use the local IP address of 172.16.0.100.

While the previous error message related to relaying has stopped, the mail still does not go through, so I think the IP change was necessary but wasn't the final fix.

Here is the error log for the SMTP service. You 'll notice that I stopped the service affter it failed several times so that it would stop pounding the destination server.

I'm sending a test email from 'rinkville.net' (wingate smtp server) to wrink101@charter.net in the following log.

01/24/08 21:57:52 Configuration changed
01/24/08 21:58:59 172.16.0.101 bill 0000044601 Requested: SMTP In: mail from bill@rinkville.net to bill@rinkville.net (606 Bytes)
01/24/08 21:58:59 172.16.0.101 bill 0000044601 Error: Client closed connection unexpectedly expecting RSET or QUIT - terminating
01/24/08 21:58:59 172.16.0.101 bill 0000044601 Traffic 275 487 0 0 1s
01/24/08 21:59:01 127.0.0.2 <system> 0000044602 Requested: SMTP Local: Message 0000000008 from bill@rinkville.net to bill delivered
01/24/08 21:59:04 127.0.0.2 <system> 0000044602 Traffic 0 0 0 0 3s
01/24/08 22:00:16 172.16.0.101 bill 0000044618 Requested: SMTP In: mail from bill@rinkville.net to wrink101@charter.net (67 KB)
01/24/08 22:00:18 172.16.0.101 bill 0000044618 Traffic 329 69067 0 0 3s
01/24/08 22:00:45 127.0.0.2 <system> 0000044625 Error: ==== Connection to ib1.charter.net failed
01/24/08 22:00:47 127.0.0.2 <system> 0000044625 Traffic 0 0 0 0 23s
01/24/08 22:01:04 Configuration changed
01/24/08 22:01:24 127.0.0.2 <system> 0000044637 Debug: Delivery for domain charter.net - MX lookup succeeded
01/24/08 22:01:24 127.0.0.2 <system> 0000044637 Debug: ==== Attempting connection to ib1.charter.net[216.33.127.20]
01/24/08 22:01:45 127.0.0.2 <system> 0000044637 Error: ==== Connection to ib1.charter.net failed
01/24/08 22:01:47 127.0.0.2 <system> 0000044637 Traffic 0 0 0 0 23s
01/24/08 22:03:24 127.0.0.2 <system> 0000044659 Debug: Delivery for domain charter.net - MX lookup succeeded
01/24/08 22:03:24 127.0.0.2 <system> 0000044659 Debug: ==== Attempting connection to ib1.charter.net[216.33.127.20]
01/24/08 22:03:45 127.0.0.2 <system> 0000044659 Error: ==== Connection to ib1.charter.net failed
01/24/08 22:03:47 127.0.0.2 <system> 0000044659 Traffic 0 0 0 0 23s
01/24/08 22:03:49 Service stopped
01/24/08 22:03:49 Configuration changed

[adrien]

Hi

that log just shows that WinGate is having trouble connecting to the mail server for charter.net.

That can be due to several reasons:

1. temporary issues with the charter.net server or their link (i.e. are you sure their server is available).

2. Some issue between the WinGate machine and their server. It's common for ISPs to block outbound connections on port 25. Standard fix for this is either

a) get your ISP to opt you out of port 25 blocking if they are
b) configure WinGate to deliver undeliverable mail to your ISPs SMTP server.

3. some local firewall issue blocking outbound connections on port 25.

Regards

Adrien

[kgoodknecht]

I see a couple of problems, read inlie please

The following recipient(s) cannot be reached:

'williamrink@comcast.net' on 1/20/2008 9:06 PM
550 relaying denied


Object: Mail System
Time: 20-Jan-2008 21:05:50
Message ID: 0C01

Wingate System Message:
Incoming mail relay attempt blocked. Mail from
bill@rinkville.net [71.237.20.230] to williamrink@comcast.net denied

When using Wingate for your incoming and outgoing mail gateway, the SMTP service needs bindings for both internal and external interfaces. Internal clients must use the the IP or name record that points to the internal IP of the Wingate SMTP server (this is your trusted interface). Mail coming from the internet must be routed to the external, Untrusted interface, and you have to set the appropriate relay permissions and domains in the email setup in Wingate.

It appears that 71.237.20.230 is your external IP, which gives you another serious issue, there is no PTR for the IP. This PTR must be setup by your ISP. Many SMTP servers, including all of aol.com, will not accept mail from an SMTP without a PTR.

All your MX records point to zoneedit.com SMTP servers, this can only be a valid setup if zoneedit then relays to you. If this is how it is being done, you need to setup zoneedit SMTP servers for your outgoing mail gateway, because many mail servers will consider mail coming from Wingate as spoofed because it isn't listed in your MX records. There is no SPF record telling SMTP servers that check SPF, that mail coining from your IP is is valid for your domain.

I have purchased a domain name 'rinkville.net' from GoDaddy and have setup a DNS redirector for my Cable Modem based server. I understood that this would prevent my domain from being considered being with a spammer.

I'm not sure what is in your thinking here, in order for other SMTP server to consider mail coming from Wingate as valid, you need to configure your public DNS with the proper records, or configure Wingate to use zoneedit for your mail gateway.