Released quarantine emails not being delivered to exchange mailboxes

[nyquist340]

Hi guys,

I've managed to installed a new spam filter solution (ProxmoxMG) at the office (simple diagram below) and everything seemed to be working just fine, until I heard some people saying they were not receiving the mails they set to be delivered/released on the quarantine portal.

[Internet] --TCP 25--> [PMG] --TCP 25--> [Exchange Server 2013]

I've confirmed the emails were sent from the PMG host, but since I'm not a mail/exchange admin, I'm not totally sure where to start looking at on the exchange side... so I started with the MSGTRK logs and I found the following:

MSGTRK2020/04/17/18-1.LOG:2020-04-17T18:46:17.306Z,,,,exchangexxx,No suitable shadow servers,,SMTP,HAREDIRECTFAIL,170316928123011,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,2ac50629-a4d2-4bdb-3894-08d7e2ff9cd5,johndoe@domain.com,,555237,1,,,BHHS Florida Realxxxxxxx,donotreply@appfolio.com,bounces+600022-36d1-johndoe=domain.com@mailer.appfolio.com,,Incoming,,,,S:DeliveryPriority=Normal;S:OriginalFromAddress=bounces+600022-36d1-johndoe=domain.com@mailer.appfolio.com;S:AccountForest=domain.com
MSGTRK2020/04/17/18-1.LOG:2020-04-17T18:46:17.415Z,10.x.x.123,exchangexxx.domain.com,10.x.x.123,exchangexxx,08D7E1F008EE2138;2020-04-17T18:42:13.319Z;5,exchangexxx\Default exchangexxx,SMTP,RECEIVE,170316928123011,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,2ac50629-a4d2-4bdb-3894-08d7e2ff9cd5,,,555237,1,,,BHHS Florida Realxxxxxxx,donotreply@appfolio.com,bounces+600022-36d1-johndoe=domain.com@mailer.appfolio.com,0cA: ,Incoming,,10.x.x.111,10.x.x.123,S:FirstForestHop=exchangexxx.domain.com;S:ProxiedClientIPAddress=10.x.x.111;S:ProxiedClientHostname=pmg.domain.com;S:ProxyHop1=exchangexxx.domain.com(10.x.x.123);S:DeliveryPriority=Normal;S:OriginalFromAddress=bounces+600022-36d1-johndoe=domain.com@mailer.appfolio.com;S:AccountForest=domain.com
MSGTRK2020/04/17/18-1.LOG:2020-04-17T18:46:17.478Z,,,,exchangexxx,Quarantine,,DSN,DSN,170316928123012,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,0b12c93b-ff52-463e-c106-08d7e2ff9cfd,quarantine@domain.com,,558719,1,,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,No se puede entregar: BHHS Florida Realxxxxxxx,postmaster@domain.com,<>,,Originating,,,,S:DeliveryPriority=Normal;S:OriginalFromAddress=bounces+600022-36d1-johndoe=domain.com@mailer.appfolio.com;S:AccountForest=domain.com
MSGTRK2020/04/17/18-1.LOG:2020-04-17T18:46:17.478Z,,exchangexxx,,,,,AGENT,AGENTINFO,170316928123011,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,2ac50629-a4d2-4bdb-3894-08d7e2ff9cd5,johndoe@domain.com,,555478,1,,,BHHS Florida Realxxxxxxx,donotreply@appfolio.com,bounces+600022-36d1-johndoe=domain.com@mailer.appfolio.com,,Incoming,,10.x.x.111,10.x.x.123,S:AMA=SUM|v=0|action=|error=|atch=1;S:AMA=EV|engine=M|v=0|sig=1.313.1752.0|name=|file=;S:CompCost=|AMA=0;S:DeliveryPriority=Normal;S:OriginalFromAddress=bounces+600022-36d1-johndoe=domain.com@mailer.appfolio.com;S:AccountForest=domain.com
MSGTRK2020/04/17/18-1.LOG:2020-04-17T18:46:17.712Z,,exchangexxx,,,,,AGENT,AGENTINFO,170316928123012,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,0b12c93b-ff52-463e-c106-08d7e2ff9cfd,quarantine@domain.com,,558771,1,,,No se puede entregar: BHHS Florida Realxxxxxxx,postmaster@domain.com,<>,,Originating,,,,S:AMA=SUM|v=0|action=|error=|atch=2;S:AMA=EV|engine=M|v=0|sig=1.313.1752.0|name=|file=;S:CompCost=|AMA=0|ETR=0;S:DeliveryPriority=Normal;S:OriginalFromAddress=bounces+600022-36d1-johndoe=domain.com@mailer.appfolio.com;S:AccountForest=domain.com
MSGTRK2020/04/17/18-1.LOG:2020-04-17T18:46:17.853Z,10.x.x.123,exchangexxx,10.x.x.123,exchangexxx.domain.com,;250 2.0.0 OK;ClientSubmitTime:,internal SMTP send connector,SMTP,SEND,170316928123012,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,0b12c93b-ff52-463e-c106-08d7e2ff9cfd,quarantine@domain.com,250 2.1.5 Recipient OK,559518,1,,,No se puede entregar: BHHS Florida Realxxxxxxx,postmaster@domain.com,<>,2020-04-17T18:46:17.462Z;LSRV=exchangexxx.domain.com:TOTAL-HUB=0.390|DSN=0.014|CATSM-Malware Agent=0.156|CATSM=0.156|CRSL=0.034|CATRS-Index Routing Agent=0.033|CATRS=0.033|CAT=0.227|SMSC=0.007|SMSMBXD=0.111|SMS=0.124,Originating,,,,S:E2ELatency=0.391;S:Microsoft.Exchange.Transport.MailRecipient.RequiredTlsAuthLevel=Opportunistic;S:DeliveryPriority=Normal;S:OriginalFromAddress=bounces+600022-36d1-johndoe=domain.com@mailer.appfolio.com;S:AccountForest=domain.com
MSGTRK2020/04/19/05-1.LOG:2020-04-19T05:36:27.112Z,,,,exchangexxx,No suitable shadow servers,,SMTP,HAREDIRECTFAIL,170467251978306,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,cced5975-6d25-4346-7760-08d7e4239af0,johndoe@domain.com,,557995,1,,,SPAM: BHHS Florida Realxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx,donotreply@appfolio.com,postmaster@pmg.domain.com,,Incoming,,,,S:DeliveryPriority=Normal;S:OriginalFromAddress=postmaster@pmg.domain.com;S:AccountForest=domain.com
MSGTRK2020/04/19/05-1.LOG:2020-04-19T05:36:27.221Z,10.x.x.123,exchangexxx.domain.com,10.x.x.123,exchangexxx,08D7E1F008EE2C02;2020-04-19T05:35:27.471Z;1,exchangexxx\Default exchangexxx,SMTP,RECEIVE,170467251978306,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,cced5975-6d25-4346-7760-08d7e4239af0,,,557995,1,,,SPAM: BHHS Florida Realxxxxxxx,donotreply@appfolio.com,postmaster@pmg.domain.com,0cA: ,Incoming,,10.x.x.111,10.x.x.123,S:FirstForestHop=exchangexxx.domain.com;S:ProxiedClientIPAddress=10.x.x.111;S:ProxiedClientHostname=pmg.domain.com;S:ProxyHop1=MW2NAM12FT021.mail.protection.outlook.com(2a01:111:e400:fc65::88);S:ProxyHop2=exchangexxx.domain.com(10.x.x.123);S:DeliveryPriority=Normal;S:OriginalFromAddress=postmaster@pmg.domain.com;S:AccountForest=domain.com
MSGTRK2020/04/19/05-1.LOG:2020-04-19T05:36:27.440Z,,,,exchangexxx,Quarantine,,DSN,DSN,170467251978307,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,77dede5a-0c7e-4a49-aff1-08d7e4239b29,quarantine@domain.com,,561460,1,,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,Could not deliver: SPAM: BHHS Florida Realxxxxxxxx,postmaster@domain.com,<>,,Originating,,,,S:DeliveryPriority=Normal;S:OriginalFromAddress=postmaster@pmg.domain.com;S:AccountForest=domain.com
MSGTRK2020/04/19/05-1.LOG:2020-04-19T05:36:27.440Z,,exchangexxx,,,,,AGENT,AGENTINFO,170467251978306,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,cced5975-6d25-4346-7760-08d7e4239af0,johndoe@domain.com,,558236,1,,,SPAM: BHHS Florida Realxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx,donotreply@appfolio.com,postmaster@pmg.domain.com,,Incoming,,10.x.x.111,10.x.x.123,S:AMA=SUM|v=0|action=|error=|atch=1;S:AMA=EV|engine=M|v=0|sig=1.313.1852.0|name=|file=;S:CompCost=|AMA=0;S:DeliveryPriority=Normal;S:OriginalFromAddress=postmaster@pmg.domain.com;S:AccountForest=domain.com
MSGTRK2020/04/19/05-1.LOG:2020-04-19T05:36:27.612Z,,exchangexxx,,,,,AGENT,AGENTINFO,170467251978307,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,77dede5a-0c7e-4a49-aff1-08d7e4239b29,quarantine@domain.com,,561512,1,,,Could not deliver: SPAM: BHHS Florida Realxxxxxxxx,postmaster@domain.com,<>,,Originating,,,,S:AMA=SUM|v=0|action=|error=|atch=2;S:AMA=EV|engine=M|v=0|sig=1.313.1852.0|name=|file=;S:CompCost=|AMA=0|ETR=0;S:DeliveryPriority=Normal;S:OriginalFromAddress=postmaster@pmg.domain.com;S:AccountForest=domain.com
MSGTRK2020/04/19/10-1.LOG:2020-04-19T10:49:45.835Z,,,,exchangexxx,resubmitting in Delivery,,QUEUE,RESUBMIT,170467251978307,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,77dede5a-0c7e-4a49-aff1-08d7e4239b29,quarantine@domain.com,400 4.4.7 Message delayed,562259,1,,170467251978307,Could not deliver: SPAM: BHHS Florida Realxxxxxxxx,postmaster@domain.com,<>,,,,,,
MSGTRK2020/04/19/10-1.LOG:2020-04-19T10:49:45.850Z,,exchangexxx,,,,,AGENT,AGENTINFO,170467251978307,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,77dede5a-0c7e-4a49-aff1-08d7e4239b29,quarantine@domain.com,,562259,1,,,Could not deliver: SPAM: BHHS Florida Realxxxxxxxx,postmaster@domain.com,<>,,Originating,,,,S:AMA=SUM|action=p|error=|atch=0;S:CompCost=|ETR=0;S:DeliveryPriority=Low;'S:PrioritizationReason=AMS:1996429/1048576|ARC:412/500;2000';S:OriginalFromAddress=postmaster@pmg.domain.com;S:AccountForest=domain.com
MSGTRK2020/04/19/22-1.LOG:2020-04-19T22:49:49.567Z,,,,exchangexxx,resubmitting in Delivery,,QUEUE,RESUBMIT,170467251978307,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,77dede5a-0c7e-4a49-aff1-08d7e4239b29,quarantine@domain.com,,562371,1,,170467251978307,Could not deliver: SPAM: BHHS Florida Realxxxxxxxx,postmaster@domain.com,<>,,,,,,
MSGTRK2020/04/19/22-1.LOG:2020-04-19T22:49:49.583Z,,exchangexxx,,,,,AGENT,AGENTINFO,170467251978307,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,77dede5a-0c7e-4a49-aff1-08d7e4239b29,quarantine@domain.com,,562371,1,,,Could not deliver: SPAM: BHHS Florida Realxxxxxxxx,postmaster@domain.com,<>,,Originating,,,,S:AMA=SUM|action=p|error=|atch=0;S:CompCost=|ETR=0;S:DeliveryPriority=Low;'S:PrioritizationReason=AMS:1996429/1048576|ARC:412/500;2000';S:OriginalFromAddress=postmaster@pmg.domain.com;S:AccountForest=domain.com
MSGTRK2020/04/20/04-1.LOG:2020-04-20T04:36:52.837Z,,exchangexxx,,,,,AGENT,AGENTINFO,170467251978307,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,77dede5a-0c7e-4a49-aff1-08d7e4239b29,quarantine@domain.com,,562442,1,,,Could not deliver: SPAM: BHHS Florida Realxxxxxxxx,postmaster@domain.com,<>,,Originating,,,,S:AMA=SUM|action=p|error=|atch=0;S:CompCost=|ETR=0;S:DeliveryPriority=Normal;'S:PrioritizationReason=AMS:1996429/1048576|ARC:412/500;2000';S:OriginalFromAddress=postmaster@pmg.domain.com;S:AccountForest=domain.com
MSGTRK2020/04/20/04-1.LOG:2020-04-20T04:36:54.118Z,,,,exchangexxx,resubmitting in Delivery,,QUEUE,RESUBMIT,170467251978307,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,77dede5a-0c7e-4a49-aff1-08d7e4239b29,quarantine@domain.com,,562270,1,,170467251978307,Could not deliver: SPAM: BHHS Florida Realxxxxxxxx,postmaster@domain.com,<>,,,,,,
MSGTRK2020/04/20/04-1.LOG:2020-04-20T04:36:54.133Z,,exchangexxx,,,,,AGENT,AGENTINFO,170467251978307,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,77dede5a-0c7e-4a49-aff1-08d7e4239b29,quarantine@domain.com,,562270,1,,,Could not deliver: SPAM: BHHS Florida Realxxxxxxxx,postmaster@domain.com,<>,,Originating,,,,S:AMA=SUM|action=p|error=|atch=0;S:CompCost=|ETR=0;S:DeliveryPriority=Low;'S:PrioritizationReason=AMS:1996429/1048576|ARC:412/500;2000';S:OriginalFromAddress=postmaster@pmg.domain.com;S:AccountForest=domain.com
MSGTRK2020/04/20/16-1.LOG:2020-04-20T16:37:00.853Z,,,,exchangexxx,resubmitting in Delivery,,QUEUE,RESUBMIT,170467251978307,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,77dede5a-0c7e-4a49-aff1-08d7e4239b29,quarantine@domain.com,,562343,1,,170467251978307,Could not deliver: SPAM: BHHS Florida Realxxxxxxxx,postmaster@domain.com,<>,,,,,,
MSGTRK2020/04/20/16-1.LOG:2020-04-20T16:37:00.853Z,,exchangexxx,,,,,AGENT,AGENTINFO,170467251978307,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,77dede5a-0c7e-4a49-aff1-08d7e4239b29,quarantine@domain.com,,562343,1,,,Could not deliver: SPAM: BHHS Florida Realxxxxxxxx,postmaster@domain.com,<>,,Originating,,,,S:AMA=SUM|action=p|error=|atch=0;S:CompCost=|ETR=0;S:DeliveryPriority=Low;'S:PrioritizationReason=AMS:1996429/1048576|ARC:412/500;2000';S:OriginalFromAddress=postmaster@pmg.domain.com;S:AccountForest=domain.com
MSGTRK2020/04/20/19-1.LOG:2020-04-20T19:07:19.029Z,10.x.x.123,exchangexxx,10.x.x.123,exchangexxx.domain.com,;250 2.0.0 OK;ClientSubmitTime:,internal SMTP send connector,SMTP,SEND,170467251978307,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,77dede5a-0c7e-4a49-aff1-08d7e4239b29,quarantine@domain.com,250 2.1.5 Recipient OK,562416,1,,,Could not deliver: SPAM: BHHS Florida Realxxxxxxxx,postmaster@domain.com,<>,2020-04-19T05:36:27.424Z;LSRV=exchangexxx.domain.com:TOTAL-HUB=43200.000|RST=43200.000|QS=0.001|CRSL=0.001|CATCM-Outbound Trust Agent=0.147|CATCM=0.147|CAT=0.150|CRSL=0.001|CATCM-Outbound Trust Agent=0.003|CATCM=0.003|CAT=0.009|CRSL=0.002|CATCM-Outbound Trust Agent=0.035|CATCM=0.035|CAT=0.041|QDM=8444.583|SMSMBXD=0.142|SMS=0.270;QDM|QDM,Originating,,,,S:E2ELatency=135051.605;S:Microsoft.Exchange.Transport.MailRecipient.RequiredTlsAuthLevel=Opportunistic;S:DeliveryPriority=Low;'S:PrioritizationReason=AMS:1996429/1048576|ARC:412/500;2000';S:OriginalFromAddress=postmaster@pmg.domain.com;S:AccountForest=domain.com
MSGTRK2020/04/22/00-1.LOG:2020-04-22T00:22:48.852Z,,,,exchangexxx,No suitable shadow servers,,SMTP,HAREDIRECTFAIL,170755014787102,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,ef506d8c-b7c2-4ff4-78a7-08d7e653499a,johndoe@domain.com,,557946,1,,,SPAM: BHHS Florida Realxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx,donotreply@appfolio.com,postmaster@pmg.domain.com,,Incoming,,,,S:DeliveryPriority=Normal;S:OriginalFromAddress=postmaster@pmg.domain.com;S:AccountForest=domain.com
MSGTRK2020/04/22/00-1.LOG:2020-04-22T00:22:48.962Z,10.x.x.123,exchangexxx.domain.com,10.x.x.123,exchangexxx,08D7E4E4715544D7;2020-04-22T00:18:16.258Z;4,exchangexxx\Default exchangexxx,SMTP,RECEIVE,170755014787102,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,ef506d8c-b7c2-4ff4-78a7-08d7e653499a,,,557946,1,,,SPAM: BHHS Florida Realxxxxxxx,donotreply@appfolio.com,postmaster@pmg.domain.com,0cA: ,Incoming,,10.x.x.111,10.x.x.123,S:FirstForestHop=exchangexxx.domain.com;S:ProxiedClientIPAddress=10.x.x.111;S:ProxiedClientHostname=pmg.domain.com;S:ProxyHop1=MW2NAM12FT021.mail.protection.outlook.com(2a01:111:e400:fc65::88);S:ProxyHop2=exchangexxx.domain.com(10.x.x.123);S:DeliveryPriority=Normal;S:OriginalFromAddress=postmaster@pmg.domain.com;S:AccountForest=domain.com
MSGTRK2020/04/22/00-1.LOG:2020-04-22T00:22:49.009Z,,,,exchangexxx,Quarantine,,DSN,DSN,170755014787103,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,379a3999-c6cc-4e18-da1b-08d7e65349bb,quarantine@domain.com,,561364,1,,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,Could not deliver: SPAM: BHHS Florida Realxxxxxxxx,postmaster@domain.com,<>,,Originating,,,,S:DeliveryPriority=Normal;S:OriginalFromAddress=postmaster@pmg.domain.com;S:AccountForest=domain.com
MSGTRK2020/04/22/00-1.LOG:2020-04-22T00:22:49.009Z,,exchangexxx,,,,,AGENT,AGENTINFO,170755014787102,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,ef506d8c-b7c2-4ff4-78a7-08d7e653499a,johndoe@domain.com,,558140,1,,,SPAM: BHHS Florida Realxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx,donotreply@appfolio.com,postmaster@pmg.domain.com,,Incoming,,10.x.x.111,10.x.x.123,S:AMA=SUM|v=0|action=|error=|atch=1;S:AMA=EV|engine=M|v=0|sig=1.313.2035.0|name=|file=;S:CompCost=|AMA=0;S:DeliveryPriority=Normal;S:OriginalFromAddress=postmaster@pmg.domain.com;S:AccountForest=domain.com
MSGTRK2020/04/22/00-1.LOG:2020-04-22T00:22:49.321Z,,exchangexxx,,,,,AGENT,AGENTINFO,170755014787103,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,379a3999-c6cc-4e18-da1b-08d7e65349bb,quarantine@domain.com,,561416,1,,,Could not deliver: SPAM: BHHS Florida Realxxxxxxxx,postmaster@domain.com,<>,,Originating,,,,S:AMA=SUM|v=0|action=|error=|atch=2;S:AMA=EV|engine=M|v=0|sig=1.313.2035.0|name=|file=;S:CompCost=|AMA=0|ETR=0;S:DeliveryPriority=Normal;S:OriginalFromAddress=postmaster@pmg.domain.com;S:AccountForest=domain.com
MSGTRK2020/04/22/00-1.LOG:2020-04-22T00:22:49.587Z,10.x.x.123,exchangexxx,10.x.x.123,exchangexxx.domain.com,;250 2.0.0 OK;ClientSubmitTime:,internal SMTP send connector,SMTP,SEND,170755014787103,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,379a3999-c6cc-4e18-da1b-08d7e65349bb,quarantine@domain.com,250 2.1.5 Recipient OK,562163,1,,,Could not deliver: SPAM: BHHS Florida Realxxxxxxxx,postmaster@domain.com,<>,2020-04-22T00:22:48.993Z;LSRV=exchangexxx.domain.com:TOTAL-HUB=0.593|DSN=0.014|CATSM-Malware Agent=0.213|CATSM=0.214|CRSL=0.045|CATRS-Index Routing Agent=0.023|CATRS=0.023|CAT=0.285|QDM=0.038|SMSC=0.008|SMSMBXD=0.188|SMS=0.205,Originating,,,,S:E2ELatency=0.594;S:Microsoft.Exchange.Transport.MailRecipient.RequiredTlsAuthLevel=Opportunistic;S:DeliveryPriority=Normal;S:OriginalFromAddress=postmaster@pmg.domain.com;S:AccountForest=domain.com
MSGTRKMD2020/04/17/18-1.LOG:2020-04-17T18:46:17.853Z,,exchangexxx.domain.com,,exchangexxx,08D7E1F001E28ACC;2020-04-17T18:46:17.744Z;ClientSubmitTime:,,STOREDRIVER,DELIVER,170316928123012,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,0b12c93b-ff52-463e-c106-08d7e2ff9cfd,quarantine@domain.com,,559518,1,,,No se puede entregar: BHHS Florida Realxxxxxxx,postmaster@domain.com,<>,2020-04-17T18:46:17.462Z;SRV=exchangexxx.domain.com:TOTAL-DEL=0.125|UTH=0.003|SMRDI=0.012|SMR=0.012|SDDCC=0.012|SDDR=0.011|SDDPM-Conversations Processing Agent=0.005|SDDPM-Mailbox Rules Agent=0.013|SDDPM-Index Delivery Agent=0.037|SDDPM=0.057|SDDR=0.012|SDDAD=0.004|SDDS=0.017|SDD=0.110,Originating,,,,S:MailboxDatabaseName=Test;S:NDR=1;S:Mailboxes=472bd69a-c679-40a0-be0a-80eeb0844099;S:ToEntity=Hosted;S:E2ELatency=0.391;S:DeliveryPriority=Normal;S:OriginalFromAddress=bounces+600022-36d1-johndoe=domain.com@mailer.appfolio.com;S:AccountForest=domain.com
MSGTRKMD2020/04/20/19-1.LOG:2020-04-20T19:07:19.029Z,,exchangexxx.domain.com,,exchangexxx,08D7E4E4715D0776;2020-04-20T19:07:18.873Z;ClientSubmitTime:,,STOREDRIVER,DELIVER,170467251978307,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,77dede5a-0c7e-4a49-aff1-08d7e4239b29,quarantine@domain.com,,562414,1,,,Could not deliver: SPAM: BHHS Florida Realxxxxxxxx,postmaster@domain.com,<>,2020-04-19T05:36:27.424Z;SRV=exchangexxx.domain.com:TOTAL-DEL=0.281|UTH=0.004|SMRDI=0.127|SMR=0.127|SDDCC=0.012|SDDR=0.017|SDDPM-Conversations Processing Agent=0.014|SDDPM-Mailbox Rules Agent=0.028|SDDPM-Index Delivery Agent=0.003|SDDPM=0.046|SDDR=0.029|SDDS=0.086|SDD=0.141,Originating,,,,S:MailboxDatabaseName=Test;S:NDR=1;S:Mailboxes=472bd69a-c679-40a0-be0a-80eeb0844099;S:ToEntity=Hosted;S:E2ELatency=135051.605;S:DeliveryPriority=Low;'S:PrioritizationReason=AMS:1996429/1048576|ARC:412/500;2000';S:OriginalFromAddress=postmaster@pmg.domain.com;S:AccountForest=domain.com
MSGTRKMD2020/04/22/00-1.LOG:2020-04-22T00:22:49.587Z,,exchangexxx.domain.com,,exchangexxx,08D7E4E4715D31B5;2020-04-22T00:22:49.384Z;ClientSubmitTime:,,STOREDRIVER,DELIVER,170755014787103,<5e99f96b872c1_57793fcb4c18cb9c9776f@5f0a7effccf8.mail>,379a3999-c6cc-4e18-da1b-08d7e65349bb,quarantine@domain.com,,562161,1,,,Could not deliver: SPAM: BHHS Florida Realxxxxxxxx,postmaster@domain.com,<>,2020-04-22T00:22:48.993Z;SRV=exchangexxx.domain.com:TOTAL-DEL=0.218|UTH=0.003|SMRDI=0.016|SMR=0.016|SDDCC=0.013|SDDR=0.121|SDDPM-Conversations Processing Agent=0.012|SDDPM-Mailbox Rules Agent=0.003|SDDPM-Index Delivery Agent=0.003|SDDPM=0.020|SDDR=0.010|SDDAD=0.003|SDDS=0.020|SDD=0.187,Originating,,,,S:MailboxDatabaseName=Test;S:NDR=1;S:Mailboxes=472bd69a-c679-40a0-be0a-80eeb0844099;S:ToEntity=Hosted;S:E2ELatency=0.594;S:DeliveryPriority=Normal;S:OriginalFromAddress=postmaster@pmg.domain.com;S:AccountForest=domain.com

Did I miss something? Do I need to specifically whitelist the PMG IP Address?

By the way, the scoping settings for the receive connector are set like 0.0.0.0-255-255-255-255

Any help would be appreciated!

[#2]

Could you maybe do a message trace to see if it shows up in the logs?

You will need to use the Exchange Management Shell for this. 

get-messagetrackinglog -sender ADDRESS OF SENDER -recipients ADDRESS OF RECIPIENT | select MessageID,TimeStamp,Sender,Recipient,Status

[#3]

Hi @BemmelenPatrick 

It was due to a quarantine configuration which sent emails rated with a score higher than 4 to a quarantine@smooth.com address. Disabled the whole feature using PS as it was not necessary anymore with the edge mail filter appliance in place.

Regards!