Sorry if I'm posting this in the wrong place. I've wasted 2 full days and sporadic time throughout the last 3 weeks on this.
I recently migrated a site from Server 2003 to a new Windows Server 2008 server. Ever since the move, my emails to and from my email address bounce from the server. I've spent 3 weeks with tech support on both ends getting nowhere.
Here's a rundown of the problem and what I've done about it:
Problem 1: Email from my domain (call it mydomain .tld) sent to the new server (call it serverdomain .tld) always bounces
Emails sent from mydomain .tld to serverdomain .tld get bounced back INSTANTLY with the error "550-The mail server could not deliver mail to "user@ serverdomain .tld". The account or domain may not exist, they may be blacklisted, or missing the proper
dns entries."
Problem 2: Email from serverdomain .tld sent to mydomain .tld always bounces
Emails sent from serverdomain .tld directly to mydomain .tld always bounce back after a 5-10 second delay with the error "550 Sender verify failed."
All emails were sent directly from server to server using webmail interfaces.
Possible problems/solutions I've explored:
Spam Filtering:
The new server's mail server (SmarterMail 2010) has spam filter bouncing disabled. No blacklists or greylists are defined.
The server hosting my email account is a shared hosted server, so I don't have access to its spam settings, but I have been assured by their technical support that the server's IP address is not blacklisted or blocked in any way.
Blacklist tests at MXToolBox.org all come up clean.
SPF Records:
I have defined an SPF (TXT) record for the domain "v=spf1 ip4:xxx.xxx.xxx.xxx -all", which points to the IP address of the mail server / web server. I do not have a type (SPF) record as Windows Server doesn't have an option for this type of record.
SPF test passes without errors at www . kitterman.com/spf/validate.html. Test email through spf-test@ openspf.net returns no errors.
Reverse Lookup:
I have a working reverse IP set up and is confirmed by checking it at ipadmin.junkemailfilter.com/rdns.php that points back to serverdomain .tld.
Testing through Telnet actually works:
I followed the steps at technet.microsoft.com/en-us/library/bb123686.aspx to log into the SMTP server on the new server's end and was able to successfully send an email manually to the new server, even using the same email address that keeps failing to send
directly to the server.
Some observations from the logs:
When sending email from mydomain .tld to serverdomain .tld, NO LOG ENTRIES are created at serverdomain .tld. This leads me to believe something is blocking it before it ever connects to the server.
When sending email from serverdomain .tld to mydomain .tld, the following log entries are created:
13:02:50 [60055] Delivery started for user@ serverdomain .tld at 1:02:50 PM
13:02:53 [60055] Skipping spam checks: No local recipients
13:02:56 [60055] Sending remote mail for user@ serverdomain .tld
13:02:56 [60055] Initiating connection to xxx.xxx.xxx.xxx
13:02:56 [60055] Connecting to xxx.xxx.xxx.xxx:25 (Id: 1)
13:02:56 [60055] Connection to xxx.xxx.xxx.xxx:25 from xxx.xxx.xxx.xxx:65260 succeeded (Id: 1)
13:02:56 [60055] RSP: 220-mydomain-host.tld ESMTP Exim 4.77 #2 Wed, 24 Oct 2012 13:02:58 -0700
13:02:56 [60055] RSP: 220-We do not authorize the use of this system to transport unsolicited,
13:02:56 [60055] RSP: 220 and/or bulk e-mail.
13:02:56 [60055] CMD: EHLO serverdomain .tld
13:02:56 [60055] RSP: 250-mydomain-host.tld Hello serverdomain .tld [xxx.xxx.xxx.xxx]
13:02:56 [60055] RSP: 250-SIZE 52428800
13:02:56 [60055] RSP: 250-AUTH PLAIN LOGIN
13:02:56 [60055] RSP: 250-STARTTLS
13:02:56 [60055] RSP: 250 HELP
13:02:56 [60055] CMD: MAIL FROM:<user@ serverdomain .tld> SIZE=951
13:02:56 [60055] RSP: 250 OK
13:02:56 [60055] CMD: RCPT TO:<user@ mydomain .tld>
13:02:57 [60055] RSP: 550-Verification failed for <user@ serverdomain .tld>
13:02:57 [60055] RSP: 550-The mail server could not deliver mail to user@ serverdomain .tld. The account or domain may not exist, they may be blacklisted, or missing the proper dns entries.
13:02:57 [60055] RSP: 550 Sender verify failed
13:02:57 [60055] CMD: QUIT
13:02:57 [60055] RSP: 221 mydomain-host.tld closing connection
13:02:57 [60055] Bounce email written to 851023860056.eml
13:02:57 [60055] Delivery for user@ serverdomain .tld to user@ mydomain .tld has completed (Bounced)
13:02:59 [60056] Delivery started for at 1:02:59 PM
13:02:59 [60055] Delivery finished for user@ serverdomain .tld at 1:02:59 PM [id:851023860055]
13:03:02 [60056] Skipping spam checks: Internally Generated Message
13:03:05 [60056] Starting local delivery to user@ serverdomain .tld
13:03:05 [60056] Delivery for to user@ serverdomain .tld has completed (Delivered) Filter: None
13:03:05 [60056] End delivery to user@ serverdomain .tld
13:03:05 [60056] Delivery finished for at 1:03:05 PM [id:851023860056]
Configuration:
The new server uses Windows Server 2008 for DNS.
The mail server is also hosted at the same IP as the DNS server.
DNS Records for Serverdomain .tld:
[All xxx.xxx.xxx.xxx IP addresses point to the server's IP address]
----------------------------------
Forward Lookup Zone: Serverdomain .tld
(same as parent folder) (SOA) 57, servername., hostmaster.
(same as parent folder) (NS) servername
(same as parent folder) (MX) [10] xxx.xxx.xxx.xxx
(same as parent folder) (TXT) v=spf1 ip4:xxx.xxx.xxx.xxx -all
* (A) xxx.xxx.xxx.xxx
mail (A) xxx.xxx.xxx.xxx
mail (MX) [10] xxx.xxx.xxx.xxx
mail (TXT) v=spf1 ip4:xxx.xxx.xxx.xxx -all
ns1 (A) xxx.xxx.xxx.xxx
ns2 (A) xxx.xxx.xxx.xxx
www (A) xxx.xxx.xxx.xxx
Reverse Lookup Zone: xxx.xxx.xxx.in-addr.arpa (syntax of IP is backwards, does not include last 3 digits)
(same as parent folder) (SOA) 10, servername., hostmaster.
(same as parent folder) (NS) servername
xxx.xxx.xxx.xxx (PTR) Serverdomain .tld
I'm totally at a loss. This is not just blocking email to/from me, but it has blocked email to at least one other domain name as well. I can get no useful help from tech support on either end.
(I had to put spaces in all links in this post because it wouldn't let me post links. Also, this forum crashes every single time I try to post in IE9, but works fine in FireFox. How ironic is that...)