I have a problem with 0365 Exchange (non hybrid) email inbound through PMG
Email coming in from non - 0365 domains, or o365 sending through proofpoint are delivered with no issue.
When i try to send from a normal 0365 exchange account I see the message below coming in to PMG
The log looks like its being delivered, PMG will loop the message 7 times before its discarded.
I have a valid receive connector set up in exchange allowing mail from the PMG IP.
Not sure if anyone else has delt with this?
2025-03-16T08:45:37.301488-04:00 pmg postfix/smtpd[24596]: connect from mailgw.visn.net[207.170.142.45]
2025-03-16T08:45:37.378105-04:00 pmg postfix/smtpd[24596]: Anonymous TLS connection established from mailgw.visn.net[207.170.142.45]: TLSv1.3 with cipher TLS_AES_256_GCM_SHA384 (256/256 bits) key-exchange ECDHE (secp384r1) server-signature RSA-PSS (4096 bits) server-digest SHA256
2025-03-16T08:45:37.917263-04:00 pmg postfix/smtpd[24596]: DFD3BB0035A: client=mailgw.visn.net[207.170.142.45]
2025-03-16T08:45:37.966046-04:00 pmg postfix/cleanup[24604]: DFD3BB0035A: message-id=<CH2PR14MB4120262B775F5296FD13186CAFDC2@CH2PR14MB4120.namprd14.prod.outlook.com>
2025-03-16T08:45:37.967951-04:00 pmg postfix/qmgr[22443]: DFD3BB0035A: from=<awoldman@microadv.com>, size=10093, nrcpt=1 (queue active)
2025-03-16T08:45:38.021472-04:00 pmg pmg-smtp-filter[24447]: B0152867D6C7F202AB2: new mail message-id=<CH2PR14MB4120262B775F5296FD13186CAFDC2@CH2PR14MB4120.namprd14.prod.outlook.com>#012
2025-03-16T08:45:38.024686-04:00 pmg postfix/smtpd[24596]: disconnect from mailgw.visn.net[207.170.142.45] ehlo=2 starttls=1 mail=1 rcpt=1 bdat=1 quit=1 commands=7
2025-03-16T08:45:38.641612-04:00 pmg pmg-smtp-filter[24447]: B0152867D6C7F202AB2: SA score=2/5 time=0.583 bayes=undefined autolearn=disabled hits=ARC_SIGNED(0.001),ARC_VALID(-0.1),DKIM_SIGNED(0.1),DKIM_VALID(-0.1),DMARC_PASS(-0.1),EMPTY_MESSAGE(2.344),HTML_MESSAGE(0.001),MIME_HTML_MOSTLY(0.1),RCVD_IN_DNSWL_BLOCKED(0.001),RCVD_IN_VALIDITY_CERTIFIED_BLOCKED(0.001),RCVD_IN_VALIDITY_RPBL_BLOCKED(0.001),RCVD_IN_VALIDITY_SAFE_BLOCKED(0.001),SPF_HELO_FAIL(0.001),SPF_PASS(-0.001),TVD_SPACE_RATIO(0.001),URIBL_BLOCKED(0.001)
2025-03-16T08:45:38.646874-04:00 pmg postfix/smtpd[24611]: connect from localhost.localdomain[127.0.0.1]
2025-03-16T08:45:38.649074-04:00 pmg postfix/smtpd[24611]: 9E611B01531: client=localhost.localdomain[127.0.0.1], orig_client=mailgw.visn.net[207.170.142.45]
2025-03-16T08:45:38.651666-04:00 pmg postfix/cleanup[24604]: 9E611B01531: message-id=<CH2PR14MB4120262B775F5296FD13186CAFDC2@CH2PR14MB4120.namprd14.prod.outlook.com>
2025-03-16T08:45:38.692785-04:00 pmg postfix/qmgr[22443]: 9E611B01531: from=<awoldman@microadv.com>, size=12018, nrcpt=1 (queue active)
2025-03-16T08:45:38.693195-04:00 pmg postfix/smtpd[24611]: disconnect from localhost.localdomain[127.0.0.1] ehlo=1 xforward=1 mail=1 rcpt=1 data=1 commands=5
2025-03-16T08:45:38.693591-04:00 pmg pmg-smtp-filter[24447]: B0152867D6C7F202AB2: accept mail to <admin@groovable.net> (9E611B01531) (rule: default-accept)
2025-03-16T08:45:38.696551-04:00 pmg pmg-smtp-filter[24447]: B0152867D6C7F202AB2: processing time: 0.682 seconds (0.583, 0.033, 0)
2025-03-16T08:45:38.696937-04:00 pmg postfix/lmtp[24605]: DFD3BB0035A: to=<admin@groovable.net>, relay=127.0.0.1[127.0.0.1]:10024, delay=0.83, delays=0.1/0/0.04/0.69, dsn=2.5.0, status=sent (250 2.5.0 OK (B0152867D6C7F202AB2))
2025-03-16T08:45:38.697755-04:00 pmg postfix/qmgr[22443]: DFD3BB0035A: removed
2025-03-16T08:45:41.198117-04:00 pmg postfix/smtp[24612]: Trusted TLS connection established to groovable-net.mail.protection.outlook.com[52.101.40.4]:25: TLSv1.3 with cipher TLS_AES_256_GCM_SHA384 (256/256 bits) key-exchange ECDHE (secp384r1) server-signature RSA-PSS (2048 bits) server-digest SHA256
2025-03-16T08:45:42.995890-04:00 pmg postfix/smtp[24612]: 9E611B01531: to=<admin@groovable.net>, relay=groovable-net.mail.protection.outlook.com[52.101.40.4]:25, delay=4.3, delays=0.04/0/2.6/1.7, dsn=2.6.0, status=sent (250 2.6.0 <CH2PR14MB4120262B775F5296FD13186CAFDC2@CH2PR14MB4120.namprd14.prod.outlook.com> [InternalId=213223651422772, Hostname=BY5PR14MB4146.namprd14.prod.outlook.com] 24291 bytes in 0.288, 82.364 KB/sec Queued mail for delivery)
2025-03-16T08:45:42.996446-04:00 pmg postfix/qmgr[22443]: 9E611B01531: removed
GUI logs
Bounce email:
This is the mail system at host pmg.visn.net.
I'm sorry to have to inform you that your message could not be delivered to one or more recipients. It's attached below.
For further assistance, please send mail to postmaster.
If you do so, please include this problem report. You can delete your own text from the attached returned message.
The mail system
<admin@groovable.net>: host
groovable-net.mail.protection.outlook.com[52.101.42.16] said: 554 5.4.14
Hop count exceeded - possible mail loop ATTR1
[CO1PEPF000066EB.namprd05.prod.outlook.com 2025-03-17T13:11:17.228Z
08DD64D7F222A3E8] (in reply to end of DATA command)
Email coming in from non - 0365 domains, or o365 sending through proofpoint are delivered with no issue.
When i try to send from a normal 0365 exchange account I see the message below coming in to PMG
The log looks like its being delivered, PMG will loop the message 7 times before its discarded.
I have a valid receive connector set up in exchange allowing mail from the PMG IP.
Not sure if anyone else has delt with this?
2025-03-16T08:45:37.301488-04:00 pmg postfix/smtpd[24596]: connect from mailgw.visn.net[207.170.142.45]
2025-03-16T08:45:37.378105-04:00 pmg postfix/smtpd[24596]: Anonymous TLS connection established from mailgw.visn.net[207.170.142.45]: TLSv1.3 with cipher TLS_AES_256_GCM_SHA384 (256/256 bits) key-exchange ECDHE (secp384r1) server-signature RSA-PSS (4096 bits) server-digest SHA256
2025-03-16T08:45:37.917263-04:00 pmg postfix/smtpd[24596]: DFD3BB0035A: client=mailgw.visn.net[207.170.142.45]
2025-03-16T08:45:37.966046-04:00 pmg postfix/cleanup[24604]: DFD3BB0035A: message-id=<CH2PR14MB4120262B775F5296FD13186CAFDC2@CH2PR14MB4120.namprd14.prod.outlook.com>
2025-03-16T08:45:37.967951-04:00 pmg postfix/qmgr[22443]: DFD3BB0035A: from=<awoldman@microadv.com>, size=10093, nrcpt=1 (queue active)
2025-03-16T08:45:38.021472-04:00 pmg pmg-smtp-filter[24447]: B0152867D6C7F202AB2: new mail message-id=<CH2PR14MB4120262B775F5296FD13186CAFDC2@CH2PR14MB4120.namprd14.prod.outlook.com>#012
2025-03-16T08:45:38.024686-04:00 pmg postfix/smtpd[24596]: disconnect from mailgw.visn.net[207.170.142.45] ehlo=2 starttls=1 mail=1 rcpt=1 bdat=1 quit=1 commands=7
2025-03-16T08:45:38.641612-04:00 pmg pmg-smtp-filter[24447]: B0152867D6C7F202AB2: SA score=2/5 time=0.583 bayes=undefined autolearn=disabled hits=ARC_SIGNED(0.001),ARC_VALID(-0.1),DKIM_SIGNED(0.1),DKIM_VALID(-0.1),DMARC_PASS(-0.1),EMPTY_MESSAGE(2.344),HTML_MESSAGE(0.001),MIME_HTML_MOSTLY(0.1),RCVD_IN_DNSWL_BLOCKED(0.001),RCVD_IN_VALIDITY_CERTIFIED_BLOCKED(0.001),RCVD_IN_VALIDITY_RPBL_BLOCKED(0.001),RCVD_IN_VALIDITY_SAFE_BLOCKED(0.001),SPF_HELO_FAIL(0.001),SPF_PASS(-0.001),TVD_SPACE_RATIO(0.001),URIBL_BLOCKED(0.001)
2025-03-16T08:45:38.646874-04:00 pmg postfix/smtpd[24611]: connect from localhost.localdomain[127.0.0.1]
2025-03-16T08:45:38.649074-04:00 pmg postfix/smtpd[24611]: 9E611B01531: client=localhost.localdomain[127.0.0.1], orig_client=mailgw.visn.net[207.170.142.45]
2025-03-16T08:45:38.651666-04:00 pmg postfix/cleanup[24604]: 9E611B01531: message-id=<CH2PR14MB4120262B775F5296FD13186CAFDC2@CH2PR14MB4120.namprd14.prod.outlook.com>
2025-03-16T08:45:38.692785-04:00 pmg postfix/qmgr[22443]: 9E611B01531: from=<awoldman@microadv.com>, size=12018, nrcpt=1 (queue active)
2025-03-16T08:45:38.693195-04:00 pmg postfix/smtpd[24611]: disconnect from localhost.localdomain[127.0.0.1] ehlo=1 xforward=1 mail=1 rcpt=1 data=1 commands=5
2025-03-16T08:45:38.693591-04:00 pmg pmg-smtp-filter[24447]: B0152867D6C7F202AB2: accept mail to <admin@groovable.net> (9E611B01531) (rule: default-accept)
2025-03-16T08:45:38.696551-04:00 pmg pmg-smtp-filter[24447]: B0152867D6C7F202AB2: processing time: 0.682 seconds (0.583, 0.033, 0)
2025-03-16T08:45:38.696937-04:00 pmg postfix/lmtp[24605]: DFD3BB0035A: to=<admin@groovable.net>, relay=127.0.0.1[127.0.0.1]:10024, delay=0.83, delays=0.1/0/0.04/0.69, dsn=2.5.0, status=sent (250 2.5.0 OK (B0152867D6C7F202AB2))
2025-03-16T08:45:38.697755-04:00 pmg postfix/qmgr[22443]: DFD3BB0035A: removed
2025-03-16T08:45:41.198117-04:00 pmg postfix/smtp[24612]: Trusted TLS connection established to groovable-net.mail.protection.outlook.com[52.101.40.4]:25: TLSv1.3 with cipher TLS_AES_256_GCM_SHA384 (256/256 bits) key-exchange ECDHE (secp384r1) server-signature RSA-PSS (2048 bits) server-digest SHA256
2025-03-16T08:45:42.995890-04:00 pmg postfix/smtp[24612]: 9E611B01531: to=<admin@groovable.net>, relay=groovable-net.mail.protection.outlook.com[52.101.40.4]:25, delay=4.3, delays=0.04/0/2.6/1.7, dsn=2.6.0, status=sent (250 2.6.0 <CH2PR14MB4120262B775F5296FD13186CAFDC2@CH2PR14MB4120.namprd14.prod.outlook.com> [InternalId=213223651422772, Hostname=BY5PR14MB4146.namprd14.prod.outlook.com] 24291 bytes in 0.288, 82.364 KB/sec Queued mail for delivery)
2025-03-16T08:45:42.996446-04:00 pmg postfix/qmgr[22443]: 9E611B01531: removed
GUI logs
Bounce email:
This is the mail system at host pmg.visn.net.
I'm sorry to have to inform you that your message could not be delivered to one or more recipients. It's attached below.
For further assistance, please send mail to postmaster.
If you do so, please include this problem report. You can delete your own text from the attached returned message.
The mail system
<admin@groovable.net>: host
groovable-net.mail.protection.outlook.com[52.101.42.16] said: 554 5.4.14
Hop count exceeded - possible mail loop ATTR1
[CO1PEPF000066EB.namprd05.prod.outlook.com 2025-03-17T13:11:17.228Z
08DD64D7F222A3E8] (in reply to end of DATA command)