I am having issues relaying SMTP emails to remote domains in MailEnable, and need some assistance identifying what exactly I am missing in the server setup.
My setup was actually working fine until yesterday when I added an SPF record to the DNS setup of the server. Then starting last night (the next time the system tried to send automated emails), the emails to remote addresses began failing. From what I can tell, I am authenticating on the inbound portion of the SMTP call, but when it tries to connect outbound to send the message to the other server it acts like I have not authenticated.
Background: This is my own server, leased from a hosting company. I have access to all settings for the site in IIS/Plesk/MailEnable. Every time my custom-written VB.NET application tries to send an email to another address on my own domain, it works fine. Every time my app tries to send the same email to an address on a remote domain, I receive an email back from [email protected] with the following:
MailEnable: Message could not be delivered to some recipients.
The following recipient(s) could not be reached:
Recipient: [SMTP:[email protected]]
Reason: 551 This mail server requires authentication before sending mail from a locally hosted domain. Please reconfigure your mail client to authenticate before sending mail.
I have a simple VB.NET test program I have written to try to debug this:
Dim replyTo As New System.Net.Mail.MailAddress("[email protected]", "MyUser")
Dim subject As String = "Test subject"
Dim SendTo As String = "[email protected]"
Dim body As String = "This is the email."
Dim message As New System.Net.Mail.MailMessage
message.From = New System.Net.Mail.MailAddress("[email protected]", "MyUser")
message.ReplyToList.Add(replyTo)
message.BodyEncoding = System.Text.Encoding.ASCII
message.IsBodyHtml = True
message.Subject = subject
message.Bcc.Add("[email protected]")
message.Body = body
Dim smtp As New System.Net.Mail.SmtpClient("mydomain.com")
Dim smtpCredential As System.Net.NetworkCredential = New System.Net.NetworkCredential("[email protected]", "password")
smtp.UseDefaultCredentials = False
smtp.Credentials = smtpCredential
smtp.Port = 587
smtp.Send(message)
In MailEnable, I have:
For completeness, here is the SPF record that was set up in the DNS yesterday:
v=spf1 a mx ipv4:75.XX.XX.XX include:_spf.google.com -all
MailEnable also created a file on the root drive of the server called SMTP-IN-TOP.TXT that logs the top count of authentications that come in, and I see all of my attempted counted in this file:
Recent Top Users Authentications During Previous Hour
[email protected] 4
And finally, here are the activity and debug logs from MailEnable showing one of the transaction attempts:
Activity:
09/01/13 15:07:26 SMTP-IN 5300BA9154CC413AAD202DE4FBA6CB71.MAI 596 75.XX.XX.XX 220 mydomain.com ESMTP MailEnable Service, Version: 7.0-- ready at 09/01/13 15:07:26 0 0
09/01/13 15:07:26 SMTP-IN 5300BA9154CC413AAD202DE4FBA6CB71.MAI 596 75.XX.XX.XX EHLO EHLO mydomain-web-01 250-mydomain.com [75.XX.XX.XX], this server offers 4 extensions 127 21
09/01/13 15:07:26 SMTP-IN 5300BA9154CC413AAD202DE4FBA6CB71.MAI 596 75.XX.XX.XX AUTH {blank} 334 UGFzc3dvcmQ6 18 41 [email protected]
09/01/13 15:07:26 SMTP-IN 5300BA9154CC413AAD202DE4FBA6CB71.MAI 596 75.XX.XX.XX AUTH d29iVFY= 235 Authenticated 19 10 [email protected]
09/01/13 15:07:26 SMTP-IN 5300BA9154CC413AAD202DE4FBA6CB71.MAI 596 75.XX.XX.XX MAIL MAIL FROM:<[email protected]> 250 Requested mail action okay, completed 43 34 [email protected]
09/01/13 15:07:26 SMTP-IN 5300BA9154CC413AAD202DE4FBA6CB71.MAI 596 75.XX.XX.XX RCPT RCPT TO:<[email protected]> 250 Requested mail action okay, completed 43 36 [email protected]
09/01/13 15:07:26 SMTP-IN 5300BA9154CC413AAD202DE4FBA6CB71.MAI 596 75.XX.XX.XX RCPT RCPT TO:<[email protected]> 250 Requested mail action okay, completed 43 34 [email protected]
09/01/13 15:07:26 SMTP-IN 5300BA9154CC413AAD202DE4FBA6CB71.MAI 596 75.XX.XX.XX DATA DATA 354 Start mail input; end with <CRLF>.<CRLF> 46 6 [email protected]
09/01/13 15:07:27 SMTP-OU D65C7059FE274FBCBA296953ABA4221F.MAI 780 50.XX.XX.XX CONN 220 recipientserver.com ESMTP MailEnable Service, Version: 6.53-- ready at 09/01/13 15:07:26 0 86
09/01/13 15:07:27 SMTP-OU D65C7059FE274FBCBA296953ABA4221F.MAI 780 50.XX.XX.XX EHLO EHLO mydomain.com 250-recipientserver.com [75.XX.XX.XX], this server offers 4 extensions 18 127
09/01/13 15:07:27 SMTP-OU D65C7059FE274FBCBA296953ABA4221F.MAI 780 50.XX.XX.XX MAIL MAIL FROM:<[email protected]> SIZE=423 551 This mail server requires authentication before sending mail from a locally hosted domain. Please reconfigure your mail client to authenticate before sending mail. 43 169
09/01/13 15:07:27 SMTP-OU D65C7059FE274FBCBA296953ABA4221F.MAI 780 50.XX.XX.XX QUIT QUIT 221 Service closing transmission channel 6 42
09/01/13 15:07:28 SMTP-IN 8E182A43292745538949A1160E407982.MAI 780 127.0.0.1 220 mydomain.com ESMTP MailEnable Service, Version: 7.0-- ready at 09/01/13 15:07:28 0 0
09/01/13 15:07:28 SMTP-OU D65C7059FE274FBCBA296953ABA4221F.MAI 576 127.0.0.1 CONN 220 mydomain.com ESMTP MailEnable Service, Version: 7.0-- ready at 09/01/13 15:07:28 0 85
09/01/13 15:07:28 SMTP-IN 8E182A43292745538949A1160E407982.MAI 780 127.0.0.1 EHLO EHLO mydomain.com 250-mydomain.com [127.0.0.1], this server offers 4 extensions 123 18
09/01/13 15:07:28 SMTP-OU D65C7059FE274FBCBA296953ABA4221F.MAI 576 127.0.0.1 EHLO EHLO mydomain.com 250-mydomain.com [127.0.0.1], this server offers 4 extensions 18 123
09/01/13 15:07:28 SMTP-IN 8E182A43292745538949A1160E407982.MAI 780 127.0.0.1 MAIL MAIL FROM:<> SIZE=1052 250 Requested mail action okay, completed 43 24
09/01/13 15:07:28 SMTP-OU D65C7059FE274FBCBA296953ABA4221F.MAI 576 127.0.0.1 MAIL MAIL FROM:<> SIZE=1052 250 Requested mail action okay, completed 24 43
09/01/13 15:07:28 SMTP-IN 8E182A43292745538949A1160E407982.MAI 780 127.0.0.1 RCPT RCPT TO:<[email protected]> 250 Requested mail action okay, completed 43 32
09/01/13 15:07:28 SMTP-OU D65C7059FE274FBCBA296953ABA4221F.MAI 576 127.0.0.1 RCPT RCPT TO:<[email protected]> 250 Requested mail action okay, completed 32 43
09/01/13 15:07:28 SMTP-IN 8E182A43292745538949A1160E407982.MAI 780 127.0.0.1 DATA DATA 354 Start mail input; end with <CRLF>.<CRLF> 46 6
09/01/13 15:07:28 SMTP-OU D65C7059FE274FBCBA296953ABA4221F.MAI 576 127.0.0.1 DATA DATA 354 Start mail input; end with <CRLF>.<CRLF> 6 46
09/01/13 15:07:28 SMTP-OU D65C7059FE274FBCBA296953ABA4221F.MAI 576 127.0.0.1 DATE 250 Requested mail action okay, completed 1063 43
09/01/13 15:07:28 SMTP-IN 05D1026706304C7F941CD6348057CC71.MAI 780 127.0.0.1 QUIT QUIT 221 Service closing transmission channel 42 6
09/01/13 15:07:28 SMTP-OU D65C7059FE274FBCBA296953ABA4221F.MAI 576 127.0.0.1 QUIT QUIT 221 Service closing transmission channel 6 42
Debug:
09/01/13 15:07:26 ME-I0135: Authenticating User:[email protected] using Authentication Provider Credentials
09/01/13 15:07:26 ME-I0107: [596] Relay Granted: Sender IP (75.xx.xx.xx) is within an authorized IP range.
09/01/13 15:07:26 ME-I0101: [596] Local Delivery: Address ([SMTP:[email protected]]) is local.
09/01/13 15:07:26 ME-I0149: [596] 5300BA9154CC413AAD202DE4FBA6CB71.MAI was received successfully and delivery thread was initiated
09/01/13 15:07:26 ME-E0070: (recv) socket [596] error during [DATA] command from host 75.xx.xx.xx. Socket was disconnected - Error: (10054)
09/01/13 15:07:26 ME-I0074: [596] (Debug) End of conversation
09/01/13 15:07:27 ME-I0018: [2B8847ABCC1242EDBF3417D32DA6DB59.MAI] Outbound message from ([SMTP:[email protected]]) requeued as [D65C7059FE274FBCBA296953ABA4221F.MAI] to the target domain [otherdomain.com]
09/01/13 15:07:27 ME-I0123: Domain [otherdomain.com] has MX list [mail.otherdomain.com]
09/01/13 15:07:27 ME-I0026: [D65C7059FE274FBCBA296953ABA4221F.MAI] Sending message
09/01/13 15:07:27 ME-IXXXX: [D65C7059FE274FBCBA296953ABA4221F.MAI] DNS resolved to the following record: IP Address=50.XX.XX.XX, Family=2, Type=1, Protocol=6
09/01/13 15:07:27 ME-IXXXX: [D65C7059FE274FBCBA296953ABA4221F.MAI] Remote server returned a response indicating a permanent error. Server Response: (551 This mail server requires authentication before sending mail from a locally hosted domain. Please reconfigure your mail client to authenticate before sending mail.**)
09/01/13 15:07:27 ME-E0036: [D65C7059FE274FBCBA296953ABA4221F.MAI] MAIL FROM command Failed.
09/01/13 15:07:27 ME-E0008: [D65C7059FE274FBCBA296953ABA4221F.MAI] Outbound, could not send the command to the server (error 10038).
09/01/13 15:07:27 ME-E0060: [D65C7059FE274FBCBA296953ABA4221F.MAI] - Message could not be delivered to target domain (otherdomain.com). Message returned to Sender.
09/01/13 15:07:28 ME-I0119: Domain [mydomain.com] has used local loopback address [127.0.0.1] because it is hosted locally.
09/01/13 15:07:28 ME-I0026: [D65C7059FE274FBCBA296953ABA4221F.MAI] Sending message
09/01/13 15:07:28 ME-IXXXX: [D65C7059FE274FBCBA296953ABA4221F.MAI] DNS resolved to the following record: IP Address=127.0.0.1, Family=2, Type=1, Protocol=0
09/01/13 15:07:28 ME-I0101: [780] Local Delivery: Address ([SMTP:[email protected]]) is local.
09/01/13 15:07:28 ME-I0149: [780] 8E182A43292745538949A1160E407982.MAI was received successfully and delivery thread was initiated
09/01/13 15:07:28 ME-I0049: [D65C7059FE274FBCBA296953ABA4221F.MAI] Send Completed Successfully
09/01/13 15:07:28 ME-I0074: [780] (Debug) End of conversation
OK, found the problem. The "external" address I was using to test the problem is actually on the old server that our website was on prior to moving to this dedicated server. Apparently the site/mail setup on that server for our site was never removed once we moved off of it. So when sending and from our new server to an address still hosted on that old server, the old server interpreted the email as coming from an internal address that was not authenticated.