Mail Server Error - 21055: auth: Error: od?

Hi,
Just upgraded to OSX 10.8 Mountain Lion, now my email services have gone AWOL.
The server logs are telling me [DateTime domain.com] log[21055]:auth: Error: od (username, ip address): authentication failed for user=me, method=DIGEST-MD5
From a client (MS offlook) point of view I'm getting :
Your message did not reach some or all of the intended recipients.
Subject:    test
      Sent: 06/08/2012 19:09
The following recipient(s) cannot be reached:
      '[email protected]' on 06/08/2012 19:10
            451 4.3.5 <unknown[ip address]>: Client host rejected: Server configuration error
This used to work quite well with Lion and the Server Admin Tools.
Is there anything I can try?
Thanks in advance,
Jeff.

Thanks for getting back to me red shift, everything is now up and working again.
I think it was somthing to do with some folder permissions and some mail settings. The mail server GUI supplied with Mountain Lion is all but useless and didn't help in any way in tracking down or resolving the problem. So, I've taken the plunge and set up MailServ for Mountain lion, its a much better mail server GUI client, and seemed to correct some of my postfix settings.
I've tinkered a bit with command line mail stuff, but not quite at a level where I can fully administer it.
Are there any good command line resources out there? This is somthing I need to improve on.
Cheers.

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Have you tried deleting the account and re-adding it on the phone?
What version of Exchange server are you running?

Outgoing/offline mail server errors (143 /and/ SSL checked?)

i am trying to do this zen and the art of motorcycle maintenance thing where i go through all my umpteen accounts on my desktop and laptop and check all the umpteen settings to try and troubleshoot an outgoing mail server / "offline" errors in mac mail. this seems like it is isolated to mac mail it would be REALLY NICE if there was some organization in here (or at least an explanation) so that all the possible settings (and all the various locations for them) didn't mean this effort is like 35 factorial with respect to possible mistakes that can be made.
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i am trying to do this zen and the art of motorcycle maintenance thing where i go through all my umpteen accounts on my desktop and laptop and check all the umpteen settings to try and troubleshoot an outgoing mail server / "offline" errors in mac mail. this seems like it is isolated to mac mail it would be REALLY NICE if there was some organization in here (or at least an explanation) so that all the possible settings (and all the various locations for them) didn't mean this effort is like 35 factorial with respect to possible mistakes that can be made.
/anyway/ i am reading various threads and my ISP service provider recommends port 143 for IMAP but i am seeing threads responses that highly suggest using SSL. however, if i change the checkbox next to the 143 port entry to have SSL checked this automatically changes the port to 993.
now i am not sure whether to replace the 993 with 143 as suggested or to leave off the setting for SSL.
any suggestions so i can isolate this setting from the thousands of variables that could be the cause of this (orther than it being basically embedded in the software and impossible to fix for one reason or another)?
it will be a real pain to change this setting (3 separate steps) on 15 different accounts (45 steps) on two different computers (90 steps for this one single variable) and then have to change it back again.
THANKS

Windows Mail server error 501

Every time I foreword an address or web page etc. using the "File" E-Mail Link the following happens. The e-mail is sent but there are five old error messages shown below. The e-mail goes trough but I have to hit the [close] box to clear the sent message. I can't figure out how to remove the old rejected e-mail addresses.
Here is a copy of the message.
The message could not be sent. The authentication setting might not be correct for your outgoing e-mail [SMTP] server. For help solving this problem, go to Help, search for "Troubleshoot Windows Mail", and read the "I'm having problems sending e-mail" section. If you need help determining the proper server settings, please contact your e-mail service provider.
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Mail Server Error

Hello,
I have checked to activate SMTP in Server Manager.
Ben when I want to add : enable inbound email, it takes a lot of time to save, the checkbox uncheckes itself, and in the system.log, I have this error :
May 27 20:45:13 tmachinix servermgrd[13357]: Exception in doCommand for module servermgr_mail: *** -[NSCFString appendString:]: nil argument
May 27 20:45:13 tmachinix servermgrd[13357]: --request was {\n command = writeSettings;\n configuration = {\n imap = {\n configdirectory = "";\n };\n postfix = {\n "enable_smtp_in" = 1;\n "virus_db_update_enabled" = 1;\n };\n };\n optionalArguments = {\n parameters = (\n "imap:configdirectory",\n "imap:enable_imap",\n "imap:enable_pop",\n "imap:enable_pop",\n "imap:enable_quota_warnings",\n "imap:enable_sieve",\n "imap:imap_auth_clear",\n "imap:imap_auth_cram_md5",\n "imap:imap_auth_gssapi",\n "imap:imap_auth_login",\n "imap:imap_auth_plain",\n "imap:log_level",\n "imap:lmtp_luser_relay",\n "imap:lmtp_luser_relay_enabled",\n "imap:lmtp_over_quota_perm_failure",\n "imap:max_imap_connections",\n "imap:notification_server_enabled",\n "imap:notification_server_address",\n "imap:notification_server_username",\n "imap:notification_server_password",\n "imap:notification_server_port",\n "imap:partitions",\n "imap:partition-default",\n "imap:pop_auth_apop",\n "imap:quotawarn",\n "imap:quota_custom_error",\n "imap:quota_custom_warning",\n "imap:quota_warn_frequency_days",\n "imap:servername",\n "imap:tls_server_options",\n "imap:tls_cert_file",\n "imap:tls_key_file",\n "imap:tls_ca_file",\n mailman,\n "postfix:always_bcc",\n "postfix:always_bcc_enabled",\n "postfix:auto_learn",\n "postfix:bayesian_enabled",\n "postfix:disable_vrfy_command",\n "postfix:enable_smtp",\n "postfix:enable_smtp_in",\n "postfix:enable_smtp_out",\n "postfix:enable_var_mail",\n "postfix:enable_virtual_domains",\n "postfix:full_reporting",\n "postfix:log_level",\n "postfix:log_rolling_days",\n "postfix:log_rolling_days_enabled",\n "postfix:luser_relay_enabled",\n "postfix:mailbox_transport",\n "postfix:black_hole_domains",\n "postfix:maps_rbl_domains_enabled",\n "postfix:message_size_limit",\n "postfix:message_size_limit_enabled",\n "postfix:msg_body_checks_enabled",\n "postfix:msg_header_checks_enabled",\n "postfix:mydestination",\n "postfix:mydomain",\n "postfix:myhostname",\n "postfix:mynetworks",\n "postfix:mynetworks_enabled",\n "postfix:mynetworks_style",\n "postfix:reject_invalid_host_enabled",\n "postfix:reject_unknown_host_enabled",\n "postfix:reject_non_FQDN_enabled",\n "postfix:reject_unknown_client_enabled",\n "postfix:reject_unauth_piplining_enabled",\n "postfix:relayhost",\n "postfix:relayhost_enabled",\n "postfix:smtp_sasl_auth_enable",\n "postfix:smtp_auth_relay_dict",\n "postfix:required_hits",\n "postfix:safe_reporting",\n "postfix:smtp_reject_list",\n "postfix:smtp_reject_list_enabled",\n "postfix:smtp_body_checks",\n "postfix:smtp_uce_controlls",\n "postfix:smtpd_pw_server_security_options",\n "postfix:spam_action",\n "postfix:spam_domain_name",\n "postfix:spam_log_level",\n "postfix:spam_notify_admin",\n "postfix:spam_notify_admin_email",\n "postfix:spam_ok_languages",\n "postfix:spam_ok_locales",\n "postfix:spam_quarantine",\n "postfix:spam_rewrite_subject",\n "postfix:spam_scan_enabled",\n "postfix:spam_subject_tag",\n "postfix:strict_rfc821_envelopes",\n "postfix:smtpd_helo_required",\n "postfix:text_only_attachments",\n "postfix:tls_server_options",\n "postfix:smtpd_tls_cert_file",\n "postfix:smtpd_tls_key_file",\n "postfix:smtpd_tls_CAfile",\n "postfix:virus_scan_enabled",\n "postfix:virus_action",\n "postfix:virus_scan_enabled",\n "postfix:virus_db_update_enabled",\n "postfix:virus_db_update_days",\n "postfix:virus_db_last_update",\n "postfix:virus_notify_admin",\n "postfix:virus_notify_admin_email",\n "postfix:virus_notify_recipients",\n "postfix:virus_notify_remote_recipients",\n "postfix:virus_quarantine",\n "postfix:virtual_domains",\n "postfix:group_expansion",\n nil\n );\n };\n}
(END)
And if I want to use the assistant to configure the email module, I get this error :
« NIL_RESPONSE_ERR (*** -[NSCFString appendString:]: nil argument) » during « writeSettings »
Please, help me.

Hello arnobeck, I would start with the basics, can you receive emails?
Everything bellow refers to settings under the mail service.
Are your Domain and Host names set to what you want? - General tab
Make sure Kerberos or CRAM-MD5 are checked. - Advanced tab
Check you have certificates selected for both SMTP SSL: and IMAP and POP SSL:. - Advanced tab
Check the certificates match the domain name set in the General tab. - Advanced tab
P.S. I'm not the most advanced with mail server service, but hopefully I can help.
Regards,
Graham

Mail Server Error: imtpunix[302]: DBERROR: critical database situation

This error shows up in the Mail Access log. Once the error occur mail services stop until the server is restarted. a reboot and a database rebuild takes care of thing, but the error keeps coming back. I haven't been able to find a pattern to when the error occurs although the last two nights it seems to have crapped out just about the time the nightly back ups (retrospect 6.1.126) run ... but that doesn't make sense because the volume containing the os and mail isn't part of the nightly backup.
In addition to serving as a mail server, this machine is hosting a small (extremely low volume website and shareing files for 7 users). Installation and file locations is all standard locations.
osx server 10.4.10 All latest server upgrades and security patches have been installed. disk permissions have been verified. disk space is >50% available.
any suggestions?

Sounds like OSX Server?
Consider posing your query in the apporpriate forum?
http://discussions.apple.com/category.jspa?categoryID=96

UTL_SMTP: can't connect to remote mail server (error: 421)

I'm trying to execute this command as SYS:
exec MYSCHEMA.send_mail_via_utl_smtp('[email protected]', '[email protected]', 'my subject', 'my message','mail.mydomain.com');
and I get this error:
Error starting at line 8 in command:
exec MYSCHEMA.send_mail_via_utl_smtp('[email protected]', '[email protected]', 'my subject', 'my message','mail.mydomain.com');
Error report:
ORA-29278: SMTP transient error: 421 Service not available
ORA-06512: at "SYS.UTL_SMTP", line 29
ORA-06512: at "SYS.UTL_SMTP", line 108
ORA-06512: at "SYS.UTL_SMTP", line 150
ORA-06512: at "MYSCHEMA.SEND_MAIL_VIA_UTL_SMTP", line 17
ORA-06512: at line 1
29278. 00000 - "SMTP transient error: %s"
*Cause:    A SMTP transient error occurred.
*Action:   Correct the error and retry the SMTP operation.
However, I can telnet successfully as root user to mail.mydomain.com. The stored procedure is:
create or replace
PROCEDURE send_mail_via_utl_smtp(
sender IN VARCHAR2,
recipient IN VARCHAR2,
subject IN VARCHAR2 DEFAULT NULL,
message IN VARCHAR2,
mailhost IN VARCHAR2 DEFAULT 'mailhost'
AS
mail_conn UTL_SMTP.connection;
crlf CONSTANT VARCHAR2(2) := CHR(13) || CHR(10);
smtp_tcpip_port CONSTANT PLS_INTEGER := 25;
BEGIN
mail_conn := UTL_SMTP.OPEN_CONNECTION(mailhost, smtp_tcpip_port);
UTL_SMTP.HELO(mail_conn, mailhost);
UTL_SMTP.MAIL(mail_conn, sender);
UTL_SMTP.RCPT(mail_conn, recipient);
UTL_SMTP.DATA(mail_conn, SUBSTR(
'Date: ' || TO_CHAR(SYSTIMESTAMP, 'Dy, dd Mon YYYY HH24:MI:SS TZHTZM') || crlf
|| 'From: ' || sender || crlf
|| 'Subject: ' || subject || crlf
|| 'To: ' || recipient || crlf
|| message,
1, 32767));
UTL_SMTP.QUIT(mail_conn);
END send_mail_via_utl_smtp;
Note that mail.mydomain.com is sitting on the application server, and not the database server (not sure if that is important here). Previously, I set things up doing the following as SYS user:
# cd $ORACLE_HOME/rdbms/admin
# sqlplus / as sysdba
SQL> @utlmail.sql;
Package created.
Synonym created.
SQL> @prvtmail.plb;
Package created.
Package body created.
Grant succeeded.
Package body created.
No errors.
SQL> ALTER SYSTEM SET smtp_out_server = "mail.mydomain.com" SCOPE=MEMORY;
System altered.
SQL> show parameter smtp_out_server
NAME TYPE VALUE
============
smtp_out_server string mail.mydomain.com
SQL> exec DBMS_NETWORK_ACL_ADMIN.CREATE_ACL('my_acl_email.xml','for my db acl to send email', 'MYSCHEMA', TRUE, 'connect');
PL/SQL procedure successfully completed.
SQL> exec DBMS_NETWORK_ACL_ADMIN.ASSIGN_ACL('my_acl_email.xml','mail.mydomain.com', 25, NULL);
PL/SQL procedure successfully completed.
It appears that the SYS user is permitted by the ACL, but is somehow blocked access to mail.mydomain.com on the application server. Are there any Linux configurations that need to occur in implementing this process? Or, am I missing something in configuring Oracle. I'm using 11.2.0.1.0. This is my first time setting this up. Does the database need to be cycled down then back up for any of these settings to take place?
Edited by: tem on Apr 20, 2012 2:45 PM

Thanks Justin, that helps a lot. Now, with the 'AUTH LOGIN' command, I'm getting the error:
ORA-29279: SMTP permanent error: 503 AUTH command used when not advertised
ORA-06512: at "SYS.UTL_SMTP", line 29
ORA-06512: at "SYS.UTL_SMTP", line 110
ORA-06512: at "SYS.UTL_SMTP", line 170
ORA-06512: at "JCLOCKGEN.SEND_MAIL_VIA_UTL_SMTP", line 22
ORA-06512: at line 1
29279. 00000 - "SMTP permanent error: %s"
*Cause:    A SMTP permanent error occurred.
*Action:   Correct the error and retry the SMTP operation.
UPDATE:
Actually, my procedure above uses this line:
UTL_SMTP.HELO(mail_conn, mailhost);
But I noticed Justin's code above uses:
UTL_SMTP.EHLO(mail_conn, mailhost);
When I change the HELO to EHLO, everything works fine. Here's the final code:
create or replace
PROCEDURE send_mail_via_utl_smtp(
sender IN VARCHAR2,
recipient IN VARCHAR2,
subject IN VARCHAR2 DEFAULT NULL,
message IN VARCHAR2,
mailhost IN VARCHAR2 DEFAULT 'mailhost',
auth_username IN VARCHAR2,
auth_password IN VARCHAR2
AS
mail_conn UTL_SMTP.connection;
crlf CONSTANT VARCHAR2(2) := CHR(13) || CHR(10);
smtp_tcpip_port CONSTANT PLS_INTEGER := 25;
BEGIN
mail_conn := UTL_SMTP.OPEN_CONNECTION(mailhost, smtp_tcpip_port);
UTL_SMTP.EHLO(mail_conn, mailhost);
--------------BEGIN AUTHENTICATION--------------
UTL_SMTP.command(mail_conn, 'AUTH LOGIN');
utl_smtp.command(mail_conn, utl_raw.cast_to_varchar2(utl_encode.base64_encode( utl_raw.cast_to_raw(auth_username))));
utl_smtp.command(mail_conn, utl_raw.cast_to_varchar2(utl_encode.base64_encode( utl_raw.cast_to_raw(auth_password))));
--------------END AUTHENTICATION--------------
UTL_SMTP.MAIL(mail_conn, sender);
UTL_SMTP.RCPT(mail_conn, recipient);
UTL_SMTP.DATA(mail_conn, SUBSTR(
'Date: ' || TO_CHAR(SYSTIMESTAMP, 'Dy, dd Mon YYYY HH24:MI:SS TZHTZM') || crlf
|| 'From: ' || sender || crlf
|| 'Subject: ' || subject || crlf
|| 'To: ' || recipient || crlf
|| message,
1, 32767));
UTL_SMTP.QUIT(mail_conn);
END send_mail_via_utl_smtp;
Edited by: tem on Apr 20, 2012 5:55 PM

Is this a Mail Server Error?

I'm trying to remove all errors, that are logged every five minutes.
Some I found in the discussions and removed them.
https://discussions.apple.com/thread/4207019?start=15&tstart=0
This was helpfull. But some errors left.
Jan 26 10:21:18 server com.apple.launchd[1] (com.apple.collabd.expire[1577]): Exited with code: 1
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Jan 26 10:21:18 server kernel[0]: Sandbox: sandboxd(1581) deny mach-lookup com.apple.coresymbolicationd
Jan 26 10:21:21 server.mydomain.com collabd[154]: [CSContentService:47 411c000 +11ms] Detected Magic Superuser Auth Token
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Just a suggestion, but wouldn't it be better to add this as continuation to the previous thread instead of starting a new thread.....? The previous solution poster may have more insight into this.

Mail Server Error: Fatal error: can't write proc file

I am a novice with OS X Server. It has been running fine for months but now I am having trouble. I get the following error log in SA:
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Dec 3 19:19:25 MasterControl imap[1763]: DBERROR: dbenv->open '/var/imap/db' failed: Permission denied
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Any help would be appreciated.

I rechecking the situation, the drive is showing that it is totally full. Its a 60 gig drive that yesterday had 10 gigs on it...now it is full. Not sure where the other 50 came from or where they are. I've just deleted some programs and the drive is still showing full.

Pop3 mail server error

For some reason whenever I launch the Mail App, on my MSN account it tells me "*Cannot Get Mail, the connection to the server "pop3.live.com" failed.* "
Do I need to change the settings or delete the account and then add it back again? Any help is greatly appreciated.

Go into the mail account settings and make sure the POP and SMTP server names and passwords are entered correctly. You shouldn't have to delete the accounts, but if all else fails, delete and re-enter them.

Exchange synchronises all folders but Inbox error Cannot Get Mail Server Error!

Initially I lost the inbox of my IPad running IOS 5 with my iPhone 4GS continuing to sync with my Exchange Server 2007 however changing mail setting on my phone has now stopped that working as well and I now have lost access to remote mail altogether.
I can still send mails from my Ipad and Iphone though if I send to myself they do not appear in the inbox but do appear in the Sent items.
If I delete mails they appear in deleted items
I have upgraded my IPad 3 to IOS 6 which has not changed anything. I have also tried an IPad 2 and that does not like my mailbox either. Tonight I created a new user on the server and sent mail to that mailbox. I set the settings on the IPad and the Inbox and other folders worked with no issues.
This problem started 2 weeks ago and before that I have never had problems with IOS devices syncing mail from my Exchange 2007 server.
My wife has a IPad 2 that links to the same Exchange Server and she has experienced none of these problems.
Any pointers on this would be most appreciated.
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OK, we fixed my boss' iPad issue. We are using Exchange 2010. Somehow, there was an issue with the device association in his Exchange account. We had to remove the device association from his Exchange account, delete the account from his iPad, then re-add the account.. He is now syncing again.
You may be able to remove the device association in OWA. Let us know if this works for you.
As to the cause of the issue, it is still unknown.

Since update, my iPhone 3 and iPad give me a mail server error for one of my email accounts. It says I have to correct mail settings, but I always use to get this email before.

I receive a "cannot get mail" message when my iPhone and iPad try to retrieve one of my email accounts. Since updating, it says to verify account information in mail settings. I haven't changed information.

Rarely data and settings are corrupted during an update. What happened when you verified the mail account settings as suggested? Even if they appear OK, I suggest deleting and reinstalling the account.

SAP PI Sender Mail Adapter error : Unexpected User response

Hello ,
I developed a scenario which requires Sender mail Adapter to connect a Third party system to PI, by going thro the links .
/people/michal.krawczyk2/blog/2005/12/18/xi-sender-mail-adapter--payloadswapbean--step-by-step
and PDFs in SDN.
When configured the sender mail adapter using POP Mail Server,faced the following error:gave the correct URL and Login credentials.
+" exception caught during processing mail message; java.io.IOException: unexpected user response; read -ERR Command is not valid in this state."+
Then used IMAP for the same mail server : error:
"exception caught during processing mail message; java.io.IOException: unexpected login response; read 001F BAD Command received in Invalid state."
Tried with another Mail server :
"exception caught during processing mail message; java.net.ConnectException: Connection timed out".
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Hi
There might be an connectivity issue from PI server to mail server. Please check with your BASIS to resolve the issue.,
Regards
Ramg

An error occurred sending mail: The mail server sent an incorrect greeting: * OK [CAPABILITY IMAP4rev1 LITERAL+ SASL-IR LOGIN-REFERRALS ID ENABLE STARTTLS AUTH

Hi, I am receiving emails but whenever I try and send I get the following message:
unable to send emails An error occurred sending mail: The mail server sent an incorrect greeting: * OK [CAPABILITY IMAP4rev1 LITERAL+ SASL-IR LOGIN-REFERRALS ID ENABLE STARTTLS AUTH=PLAIN AUTH=LOGIN] Dovecot ready..

What are your settings in Tools(or AppMenu/Options)/Account Settings/Outgoing Server (SMTP)? The error message suggests you must have STARTTLS connection security and normal password authentication:
https://getsatisfaction.com/mozilla_messaging/topics/mail_preferences-t1xeq

Cannot receive mail on Exchange 2013 CAS: 451 4.7.0 Temporary server error. Please try again later. PRX4

Hi all,
I have just deployed Exchange 2013 on two CAS boxes and two MBX boxes as follows:
10.10.20.11
CAS01
10.10.20.12
CAS02
10.10.10.11
MBX01
10.10.10.12
MBX02
If I telnet to the internet facing IP on CAS01 and attempt to send an email internally (to a mailbox on MBX01) I get the following:
220 smtp.myrealdomain.com Microsoft ESMTP MAIL Service ready at Wed, 26 Mar 2014 01:14:24 +1000
EHLO test.com
250-smtp.myrealdomain.com Hello [10.10.20.11]
250-SIZE 36700160
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-AUTH
250-8BITMIME
250-BINARYMIME
250 CHUNKING
MAIL FROM:[email protected]
250 2.1.0 Sender OK
RCPT TO:[email protected]
250 2.1.5 Recipient OK
DATA
354 Start mail input; end with <CRLF>.<CRLF>
Subject:Test email 452
This is test email 452
451 4.7.0 Temporary server error. Please try again later. PRX4
Connectivity Log on CAS01:
2014-03-25T15:27:15.353Z,08D11605A575FAE1,SMTP,internalproxy,+,Undefined 00000000-0000-0000-0000-000000000000;QueueLength=<no priority counts>
2014-03-25T15:27:15.353Z,08D11605A575FAE1,SMTP,internalproxy,>,"MBX02.myaddomain.com[10.10.10.12], MBX01.myaddomain.com[10.10.10.11]"
2014-03-25T15:27:15.353Z,08D11605A575FAE1,SMTP,internalproxy,>,Established connection to 10.10.10.12
2014-03-25T15:27:15.369Z,08D11605A575FAE1,SMTP,internalproxy,-,Messages: 0 Bytes: 0 (Attempting next target)
2014-03-25T15:27:15.369Z,08D11605A575FAE2,SMTP,internalproxy,+,Undefined 00000000-0000-0000-0000-000000000000;QueueLength=<no priority counts>
2014-03-25T15:27:15.369Z,08D11605A575FAE2,SMTP,internalproxy,>,Established connection to 10.10.10.11
2014-03-25T15:27:15.369Z,08D11605A575FAE2,SMTP,internalproxy,-,Messages: 0 Bytes: 0 (Retry : EHLO Options do not match for proxy)
2014-03-25T15:28:10.328Z,08D11605A575FAFA,SMTP,internalproxy,+,Undefined 00000000-0000-0000-0000-000000000000;QueueLength=<no priority counts>
2014-03-25T15:28:21.669Z,08D11605A575FAFA,SMTP,internalproxy,>,"MBX01.myaddomain.com[10.10.10.11], MBX02.myaddomain.com[10.10.10.12]"
2014-03-25T15:28:21.669Z,08D11605A575FAFA,SMTP,internalproxy,>,Established connection to 10.10.10.11
2014-03-25T15:28:21.669Z,08D11605A575FAFA,SMTP,internalproxy,-,Messages: 0 Bytes: 0 (Attempting next target)
2014-03-25T15:28:21.669Z,08D11605A575FAFF,SMTP,internalproxy,+,Undefined 00000000-0000-0000-0000-000000000000;QueueLength=<no priority counts>
2014-03-25T15:28:21.669Z,08D11605A575FAFF,SMTP,internalproxy,>,Established connection to 10.10.10.12
2014-03-25T15:28:21.669Z,08D11605A575FAFF,SMTP,internalproxy,-,Messages: 0 Bytes: 0 (Retry : EHLO Options do not match for proxy)
SmtpSend Log on CAS01:
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB5E,1,10.10.20.11:25495,10.10.10.12:25,+,,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB5E,2,10.10.20.11:25495,10.10.10.12:25,<,220 ********************************************************************************************************************,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB5E,3,10.10.20.11:25495,10.10.10.12:25,*,,Proxying inbound session with session id 08D11605A575FB5D
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB5E,4,10.10.20.11:25495,10.10.10.12:25,>,EHLO CAS01.myaddomain.com,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB5E,5,10.10.20.11:25495,10.10.10.12:25,<,250-MBX02.myaddomain.com Hello [10.10.20.11],
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB5E,6,10.10.20.11:25495,10.10.10.12:25,<,250-SIZE,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB5E,7,10.10.20.11:25495,10.10.10.12:25,<,250-PIPELINING,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB5E,8,10.10.20.11:25495,10.10.10.12:25,<,250-DSN,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB5E,9,10.10.20.11:25495,10.10.10.12:25,<,250-ENHANCEDSTATUSCODES,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB5E,10,10.10.20.11:25495,10.10.10.12:25,<,250-XXXXXXXA,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB5E,11,10.10.20.11:25495,10.10.10.12:25,<,250-XXXXXXXXXXXXXB,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB5E,12,10.10.20.11:25495,10.10.10.12:25,<,250-AUTH NTLM,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB5E,13,10.10.20.11:25495,10.10.10.12:25,<,250-XXXXXXXXXXXXXXXXXC,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB5E,14,10.10.20.11:25495,10.10.10.12:25,<,250-8BITMIME,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB5E,15,10.10.20.11:25495,10.10.10.12:25,<,250-BINARYMIME,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB5E,16,10.10.20.11:25495,10.10.10.12:25,<,250-XXXXXXXD,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB5E,17,10.10.20.11:25495,10.10.10.12:25,<,250-XXXXXXE,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB5E,18,10.10.20.11:25495,10.10.10.12:25,<,250-XXXXF,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB5E,19,10.10.20.11:25495,10.10.10.12:25,<,250 XXXXXXXXXXXXXG,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB5E,20,10.10.20.11:25495,10.10.10.12:25,*,,"EHLO options between current server and proxy target do not match : Chunking, Xrdst. Critical non
matching options : Chunking, Xrdst. Failing over."
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB67,0,,10.10.10.11:25,*,,attempting to connect
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB5E,21,10.10.20.11:25495,10.10.10.12:25,>,QUIT,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB67,1,10.10.20.11:25496,10.10.10.11:25,+,,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB5E,22,10.10.20.11:25495,10.10.10.12:25,<,221 2.0.0 Service closing transmission channel,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB5E,23,10.10.20.11:25495,10.10.10.12:25,-,,Local
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB67,2,10.10.20.11:25496,10.10.10.11:25,<,220 ********************************************************************************************************************,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB67,3,10.10.20.11:25496,10.10.10.11:25,*,,Proxying inbound session with session id 08D11605A575FB5D
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB67,4,10.10.20.11:25496,10.10.10.11:25,>,EHLO CAS01.myaddomain.com,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB67,5,10.10.20.11:25496,10.10.10.11:25,<,250-MBX01.myaddomain.com Hello [10.10.20.11],
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB67,6,10.10.20.11:25496,10.10.10.11:25,<,250-SIZE,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB67,7,10.10.20.11:25496,10.10.10.11:25,<,250-PIPELINING,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB67,8,10.10.20.11:25496,10.10.10.11:25,<,250-DSN,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB67,9,10.10.20.11:25496,10.10.10.11:25,<,250-ENHANCEDSTATUSCODES,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB67,10,10.10.20.11:25496,10.10.10.11:25,<,250-XXXXXXXA,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB67,11,10.10.20.11:25496,10.10.10.11:25,<,250-XXXXXXXXXXXXXB,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB67,12,10.10.20.11:25496,10.10.10.11:25,<,250-AUTH NTLM,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB67,13,10.10.20.11:25496,10.10.10.11:25,<,250-XXXXXXXXXXXXXXXXXC,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB67,14,10.10.20.11:25496,10.10.10.11:25,<,250-8BITMIME,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB67,15,10.10.20.11:25496,10.10.10.11:25,<,250-BINARYMIME,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB67,16,10.10.20.11:25496,10.10.10.11:25,<,250-XXXXXXXD,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB67,17,10.10.20.11:25496,10.10.10.11:25,<,250-XXXXXXE,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB67,18,10.10.20.11:25496,10.10.10.11:25,<,250-XXXXF,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB67,19,10.10.20.11:25496,10.10.10.11:25,<,250 XXXXXXXXXXXXXG,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB67,20,10.10.20.11:25496,10.10.10.11:25,*,,"EHLO options between current server and proxy target do not match : Chunking, Xrdst. Critical non
matching options : Chunking, Xrdst. Failing over."
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB67,21,10.10.20.11:25496,10.10.10.11:25,>,QUIT,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB67,22,10.10.20.11:25496,10.10.10.11:25,<,221 2.0.0 Service closing transmission channel,
2014-03-25T15:32:34.158Z,Inbound Proxy Internal Send Connector,08D11605A575FB67,23,10.10.20.11:25496,10.10.10.11:25,-,,Local
Can anyone help? I'm at the end of my Googling!

The answer has been found. In our case, we had to disable the Mailguard feature of the Cisco ASA between the CAS subnet and the MBX subnet. Essentially it was stripping AUTH commands from the SMTP handshake which meant the servers could not authenticate
to each other and establish a secured connection.
I guess for future reference, if you're getting a PRX4 error code you should look at any device that could be inspecting SMTP between your CAS and MBX servers.
This Microsoft KB article has more information: http://support.microsoft.com/kb/320027

Mail Server Error - 21055: auth: Error: od?

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