Post 03- 10 Migration multiple Relay not Permitted errors from recipient

Hello all - I recently just started a new job in an organization that just recently upgraded from an Exchange 2003 environment, to Exchange 2010. Just within the past week, we finally took down our last 2003 system. Since then, we have received
a good number of bounce back messages from recipient servers with various specific error messages, but with a common theme "smtp relay not permitted". What's strange is at my last employer, we migrated from 2003 to 2007 and I recall having a similar
situation, but I can't for the life of me recall what the solution was.
So far, through a few hours of Google searching, all I have found are sources suggesting that this issue is a recipient server config problem, but I have a very hard time believing that it isn't a problem on my end, with this many of essentially the same
errors popping up. Also - I have noticed that if a user attempts to re-send an email to the recipient that previously bounced back, it will work.
I'm not sure what sort of config info from my server / local network I should share here, but i'll gladly share whatever may be necessary.
Here are a few of the bounce message that we have received (names/email addresses removed)
From: Microsoft Outlook
Sent: Monday, May 02, 2011 8:28 AM
To: name_removed
Subject: Undeliverable: FW: Dodson upkeep
pop-borzoi.atl.sa.earthlink.net rejected your message to the following e-mail addresses:
(recipient removed)
pop-borzoi.atl.sa.earthlink.net gave this error:
Authentication required. Help at http://www.earthlink.net/go/emailsettings
A problem occurred during the delivery of this message to this e-mail address. Try sending this message again. If the problem continues, please contact your helpdesk.
Diagnostic information for administrators:
Generating server: my_server
(recipient removed)
pop-borzoi.atl.sa.earthlink.net #550 Authentication required. Help at http://www.earthlink.net/go/emailsettings ##
From: Microsoft Outlook
Sent: Monday, May 02, 2011 9:47 AM
To: name removed
Subject: Undeliverable: RE: open invoice
mustang.ws9100.net rejected your message to the following e-mail addresses:
recipient removed
mustang.ws9100.net gave this error:
webmail.twgi.net (myserver.twgi.net) [65.242.24.100]:40159 is currently not permitted to relay through this server. Perhaps you have not logged into the pop/imap server in the last 30 minutes or do not have SMTP Authentication turned on in your email client.
A problem occurred during the delivery of this message to this e-mail address. Try sending this message again. If the problem continues, please contact your helpdesk.
Diagnostic information for administrators:
Generating server: myserver.twgi.net
recipient_removed
mustang.ws9100.net #550-webmail.twgi.net (myserver.twgi.net) [65.242.24.100]:40159 is currently not 550-permitted to relay through this server. Perhaps you have not logged into 550-the pop/imap server in the last 30 minutes or do not have SMTP 550 Authentication
turned on in your email client. ##
From: Microsoft Outlook
Sent: Monday, May 02, 2011 5:10 PM
To: name removed
Subject: Undeliverable: message subject removed
UNUSED-216-37-170-254.UNUSED.epix.net rejected your message to the following e-mail addresses:
recipient removed @cargas.com
UNUSED-216-37-170-254.UNUSED.epix.net gave this error:
Unable to relay for [email protected]
Your message wasn't delivered due to a permission or security issue. It may have been rejected by a moderator, the address may only accept e-mail from certain senders, or another restriction may be preventing delivery.
Diagnostic information for administrators:
Generating server: myserver.twgi.net
[email protected]
UNUSED-216-37-170-254.UNUSED.epix.net #550 5.7.1 Unable to relay for [email protected] ##
From: Microsoft Outlook
Sent: Tuesday, May 03, 2011 12:31 PM
To: name removed
Subject: Undeliverable: RE: SMO Destwin Implementation
cpanel-2.host.chi1.int-i.net rejected your message to the following e-mail addresses:
recipient [email protected]
cpanel-2.host.chi1.int-i.net gave this error:
webmail.twgi.net (myserver.twgi.net) [65.242.24.100]:27609 is currently not permitted to relay through this server. Perhaps you have not logged into the pop/imap server in the last 30 minutes or do not have SMTP Authentication turned on in your email client.
A problem occurred during the delivery of this message to this e-mail address. Try sending this message again. If the problem continues, please contact your helpdesk.
Diagnostic information for administrators:
Generating server: twgiex.twgi.net
[email protected]
cpanel-2.host.chi1.int-i.net #550-webmail.twgi.net (myserver.twgi.net) [65.242.24.100]:27609 is currently not 550-permitted to relay through this server. Perhaps you have not logged into 550-the pop/imap server in the last 30 minutes or do not have SMTP
550 Authentication turned on in your email client. ##
From: Microsoft Outlook
Sent: Tuesday, May 03, 2011 5:29 PM
To: name removed
Subject: Undeliverable: FW: Landscaping
host.clearimaging4.com rejected your message to the following e-mail addresses:
[email protected]
host.clearimaging4.com gave this error:
sorry, that domain isn't in my list of allowed rcpthosts; no valid cert for gatewaying (#5.7.1)
A problem occurred during the delivery of this message to this e-mail address. Try sending this message again. If the problem continues, please contact your helpdesk.
Diagnostic information for administrators:
Generating server: myserver.twgi.net
[email protected]
host.clearimaging4.com #553 sorry, that domain isn't in my list of allowed rcpthosts; no valid cert for gatewaying (#5.7.1) ##
From: Microsoft Outlook
Sent: Wednesday, May 04, 2011 8:39 AM
To: name removed
Subject: Undeliverable: FW: Proof of Insurance request
n22.c07.mtsvc.net rejected your message to the following e-mail addresses:
[email protected]
n22.c07.mtsvc.net gave this error:
relay not permitted
A problem occurred during the delivery of this message to this e-mail address. Try sending this message again. If the problem continues, please contact your helpdesk.
Diagnostic information for administrators:
Generating server: myserver.twgi.net
[email protected]
n22.c07.mtsvc.net #550 relay not permitted ##

Also, i FINALLY have an excerpt from our send logfile that matches up to an email bounce:
Bounce message:
From: Microsoft Outlook
Sent: Sunday, May 08, 2011 9:43 AM
To: sender removed
Subject: Undeliverable: RE: Load of gas
server1.cbayhosting.com rejected your message to the following e-mail addresses:
recipient removed ([email protected])
server1.cbayhosting.com gave this error:
<[email protected]>... Relaying denied. Proper authentication required.
Your message wasn't delivered due to a permission or security issue. It may have been rejected by a moderator, the address may only accept e-mail from certain senders, or another restriction may be preventing delivery.
Diagnostic information for administrators:
Generating server: myserver.twgi.net
[email protected]
server1.cbayhosting.com #550 5.7.1 <[email protected]>... Relaying denied. Proper authentication required. ##
Send connector log file:
2011-05-08T13:43:01.761Z,Send mail to Internet,08CDAB5926F2B37D,2,15.32.0.46:9323,69.94.111.23:25,<,"220 server1.cbayhosting.com ESMTP Sendmail 8.13.7/8.13.7; Sun, 8 May 2011 09:43:02 -0400",
2011-05-08T13:43:01.761Z,Send mail to Internet,08CDAB5926F2B37D,3,15.32.0.46:9323,69.94.111.23:25,>,EHLO myserver.twgi.net,
2011-05-08T13:43:01.761Z,Send mail to Internet,08CDAB5926F2B37F,0,,64.18.4.10:25,*,,attempting to connect
2011-05-08T13:43:01.793Z,Send mail to Internet,08CDAB5926F2B37D,4,15.32.0.46:9323,69.94.111.23:25,<,"250-server1.cbayhosting.com Hello webmail.twgi.net [65.242.24.100], pleased to meet you",
2011-05-08T13:43:01.793Z,Send mail to Internet,08CDAB5926F2B37D,5,15.32.0.46:9323,69.94.111.23:25,<,250-ENHANCEDSTATUSCODES,
2011-05-08T13:43:01.793Z,Send mail to Internet,08CDAB5926F2B37D,6,15.32.0.46:9323,69.94.111.23:25,<,250-PIPELINING,
2011-05-08T13:43:01.793Z,Send mail to Internet,08CDAB5926F2B37D,7,15.32.0.46:9323,69.94.111.23:25,<,250-8BITMIME,
2011-05-08T13:43:01.793Z,Send mail to Internet,08CDAB5926F2B37D,8,15.32.0.46:9323,69.94.111.23:25,<,250-SIZE,
2011-05-08T13:43:01.793Z,Send mail to Internet,08CDAB5926F2B37D,9,15.32.0.46:9323,69.94.111.23:25,<,250-DSN,
2011-05-08T13:43:01.793Z,Send mail to Internet,08CDAB5926F2B37D,10,15.32.0.46:9323,69.94.111.23:25,<,250-ETRN,
2011-05-08T13:43:01.793Z,Send mail to Internet,08CDAB5926F2B37D,11,15.32.0.46:9323,69.94.111.23:25,<,250-AUTH LOGIN PLAIN,
2011-05-08T13:43:01.793Z,Send mail to Internet,08CDAB5926F2B37D,12,15.32.0.46:9323,69.94.111.23:25,<,250-DELIVERBY,
2011-05-08T13:43:01.793Z,Send mail to Internet,08CDAB5926F2B37D,13,15.32.0.46:9323,69.94.111.23:25,<,250 HELP,
2011-05-08T13:43:01.793Z,Send mail to Internet,08CDAB5926F2B37D,14,15.32.0.46:9323,69.94.111.23:25,*,2722844,sending message
2011-05-08T13:43:01.793Z,Send mail to Internet,08CDAB5926F2B37D,15,15.32.0.46:9323,69.94.111.23:25,>,MAIL FROM:[email protected] SIZE=8054,
2011-05-08T13:43:01.793Z,Send mail to Internet,08CDAB5926F2B37D,16,15.32.0.46:9323,69.94.111.23:25,>,RCPT TO:<[email protected]>,
2011-05-08T13:43:01.855Z,Send mail to Internet,08CDAB5926F2B37F,1,15.32.0.46:9324,64.18.4.10:25,+,,
2011-05-08T13:43:01.886Z,Send mail to Internet,08CDAB5926F2B37D,17,15.32.0.46:9323,69.94.111.23:25,<,250 2.1.0 <[email protected]>... Sender ok,
2011-05-08T13:43:01.886Z,Send mail to Internet,08CDAB5926F2B37D,18,15.32.0.46:9323,69.94.111.23:25,<,550 5.7.1 <[email protected]>... Relaying denied. Proper authentication required.,
2011-05-08T13:43:01.902Z,Send mail to Internet,08CDAB5926F2B37D,19,15.32.0.46:9323,69.94.111.23:25,>,QUIT,
2011-05-08T13:43:01.918Z,Send mail to Internet,08CDAB5926F2B37D,20,15.32.0.46:9323,69.94.111.23:25,<,221 2.0.0 server1.cbayhosting.com closing connection,
It looks like the address that exchange is attempting to connect to, to send to chesapeake.net is at IP: 69.94.111.23. However, MX lookup for chesapeaeke.net returns mx: mxsrv.chesapeake.net 216.240.101.22

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Post 03- 10 Migration multiple Relay not Permitted errors from recipient

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