outgoing mail connector fails

[eaglex01]

i cannot seem to validate my connector to send mail through PMG using o365, here is the log from my test

Detailed log
Timestamp:09/02/2026 15:07:09
EventId:RECEIVE
Source:SMTP
MessageSubject:Test email for connector validation
MessageId:<5620fd8c-cc96-40e7-8bb9-3c74c06751d2@substrate-int.office.com>
Recipients:****@gmail.com
RecipientCount:1
RecipientStatus:
SourceContext:08DF062090A7BB7F;2026-09-02T15:07:08.038Z;0
Sender:O365ConnectorValidation@connectitnet.com
EventDataroxyHop1:SN7PR04CA0055.outlook.office365.com(2603:10b6:806:120::30), MimeParts:text:us-ascii|html:N/A|att:0|embed:0|parts:1|type:Normal|compliance:Compliant|from:Compliant, MessageValue:MediumHigh, ReplicationS2PR01MB994133, InboundTlsDetails:TLS=SP_PROT_TLS1_2_SERVER TLSCipher=CALG_AES_256 TLSKeyLength=256 TLSKeyExAlg=CALG_ECDH_EPHEM, CorrelationId:d4820dcd-4144-42a7-1d27-08df0903db64, FirstForestHop:SA5PR01MB994140.prod.exchangelabs.com, FromEntity:Internet, ProxiedClientIPAddress:2603:10b6:806:120:cafe::7d, ProxiedClientHostname:SA1PR01MB6527.prod.exchangelabs.com, DeliveryPriority:Normal, OriginalFromAddress:<>, AccountForest:NAMPR01A009.PROD.OUTLOOK.COM


Timestamp:09/02/2026 15:07:09
EventId:RECIPIENTINFO
Source:RESOLVER
MessageSubject:Test email for connector validation
MessageId:<5620fd8c-cc96-40e7-8bb9-3c74c06751d2@substrate-int.office.com>
Recipients:****@gmail.com
RecipientCount:1
RecipientStatus:NotFound.OneOff.Resolver.CreateRecipientItems.10
SourceContext:
Sender:O365ConnectorValidation@connectitnet.com
EventData:SenderVerdict:NotFound.OneOff.Sender.10, AllowAliases:Y, ExtRecipCount:1, MsgRecipCount:1, DeliveryPriority:Normal, OriginalFromAddress:<>, AccountForest:NAMPR01A009.PROD.OUTLOOK.COM


Timestamp:09/02/2026 15:07:10
EventId:SETROUTE
Source:AGENT
MessageSubject:Test email for connector validation
MessageId:<5620fd8c-cc96-40e7-8bb9-3c74c06751d2@substrate-int.office.com>
Recipients:****@gmail.com
RecipientCount:1
RecipientStatus:
SourceContext:Advanced Routing - Connector Based Router
Sender:O365ConnectorValidation@connectitnet.com
EventData:Microsoft.Exchange.Hygiene.TenantOutboundConnectorCustomData:Name=Outbound via PMG_Test_2026-09-02T15:06:43.409Z;ConnectorType=Partner;UseMxRecord=False, DeliveryPriority:Normal, OriginalFromAddress:<>, AccountForest:NAMPR01A009.PROD.OUTLOOK.COM


Timestamp:09/02/2026 15:07:10
EventId:AGENTINFO
Source:AGENT
MessageSubject:Test email for connector validation
MessageId:<5620fd8c-cc96-40e7-8bb9-3c74c06751d2@substrate-int.office.com>
Recipients:****@gmail.com
RecipientCount:1
RecipientStatus:
SourceContext:CatContentConversion
Sender:O365ConnectorValidation@connectitnet.com
EventData:TRA:ETR|ruleId=89114773-0bf1-4d37-93e7-d0f5421df18b|st=10/2/2025 5:42:11 PM|action=SetHeader|sev=1|mode=Enforce, TRA:ETRP|ruleId=89114773-0bf1-4d37-93e7-d0f5421df18b|st=2025-10-02T17:42:11.0000000Z|ExecW=0|ExecC=0|Actions=SH,0|Conditions=IP,M.A,0;IIP,M.F,0, TRA:ETRP|ruleId=7fbb2fb4-e42d-4310-96cf-15e111ff4221|st=2025-06-03T14:00:35.0000000Z|ExecW=0|ExecC=0|Conditions=IP,M.A,0;IIP,M.F,1;IMTP,,0;CP,R-P,0, TRA:ETRP|ruleId=2525f801-9a37-42fe-bdfb-9708d19b3c43|st=2025-01-22T19:47:16.0000000Z|ExecW=0|ExecC=0|Conditions=IMP,M.SI,0, TRA:ETRP|ruleId=3f24ffbb-7453-4480-bae1-7361212c8ebc|st=2024-06-24T23:18:32.0000000Z|ExecW=0|ExecC=0|Conditions=IP,F,0, TRA:ETRP|ruleId=42cf7458-1f4c-4a4d-af3e-a5072832a16e|st=2024-06-25T19:21:29.0000000Z|ExecW=0|ExecC=0|Conditions=IP,F,0, TRA:ETRP|ruleId=6d5b2b44-797b-422c-bcb7-6491a0713d09|st=2024-06-25T18:21:03.0000000Z|ExecW=0|ExecC=0|Conditions=IP,F,0, TRA:ETRP|ruleId=9dca3646-f79a-4130-900c-5fde6d8a87ab|st=2024-06-26T06:38:25.0000000Z|ExecW=0|ExecC=0|Conditions=IP,F,0, TRA:ETRP|ruleId=f833fb07-ff3f-4517-b596-88548e838482|st=2026-07-22T17:35:13.0000000Z|ExecW=0|ExecC=0|Conditions=MRP,X-D-I,0, TRA:ETRI|MsgType=Normal|Ex=|IsKnown=|FipsStatus=NoFips|AttchUns=|ceErr=|Synth=False-Na-ON, CFA:AS|sfv=NotSpam|rsk=Low|scl=0|bcl=0|score=|sfs=(4505004)(77100063)(771110134)(771130229)(771210324)(771230059)(4550008)(823303075)(4100075)(445011)(5000001)(2016111802454)(6043475)(201702281528297)(446008)(201703131430171)(201703061421076)(201703061750409)(4560004)(421057)(944501754)(52106096)(14220107086)(99994043)(52107095)(78114045)(888945051)(88880062)(88902107)(88910131)(88905372)(88908190)(52450103)(8888601105)(888860108)(202501151400033)(888946042)(15041020)(15015020)(15022040)(5500365)(5510169)(5410006)(54410012)(54510246)(54710214)(5420034)(76000349)(8020094)(202411133463)(930200206)(9307002143)(6201001)(2024102216202)|sfp=0|fprx=|mlc=|mlv=|list=1|di=|rd=|h=SA1PR01MB6527.prod.exchangelabs.com|ctry=|cltctry=|lang=|cip=|dir=Originating|alat=0|mlat=22|rlat=22|asf=, CFA:LTC|RPLEPPR=0|RPLHCFR=4|RPLSLR=2|RPLAPR=1|RPLMR=4|RPL=13|RSP=38, SFA:SFA|sfv=NotSpam|rsk=High|scl=0|bcl=0|score=|sfs=(13230040)(366016)(61400799027)(10070799003)(376014)(10067099003)(56012099006)(18002099003)(16102099003)(16130700020)|sfp=0|fprx=|mlc=|mlv=|list=1|di=|rd=|h=SA1PR01MB6527.prod.exchangelabs.com|ctry=|cltctry=|lang=|cip=|dir=Originating|alat=0|mlat=61|rlat=61|asf=, PCFA:SUM|hctfp=00000000-0000-0000-0000-000000000000, SFA:SUM|SFV=NSPM|IPV=NLI|SRV=|SFS=13230040|SFS=366016|SFS=61400799027|SFS=10070799003|SFS=376014|SFS=10067099003|SFS=56012099006|SFS=18002099003|SFS=16102099003|SFS=16130700020|SCL=1|SCORE=0|LIST=0|DI=|RD=|H=SA1PR01MB6527.prod.exchangelabs.com|CIP=|SFP=1501|ASF=0|CTRY=|CLTCTRY=IPV6|LANG=en|LAT=1|LAT=0|LAT=1|FPR=A88274D4.C9FD20A.47F8B0FE.D451CEE9.20072|DIR=OUT, CompCost:C|ETR=54, DeliveryPriority:Normal, OriginalFromAddress:<>, AccountForest:NAMPR01A009.PROD.OUTLOOK.COM


Timestamp:09/02/2026 15:07:11
EventId:AGENTINFO
Source:AGENT
MessageSubject:Test email for connector validation
MessageId:<5620fd8c-cc96-40e7-8bb9-3c74c06751d2@substrate-int.office.com>
Recipients:****@gmail.com
RecipientCount:1
RecipientStatus:
SourceContext:CatFinalCleanup
Sender:O365ConnectorValidation@connectitnet.com
EventDataCFA:OCAT|dkim=1, DeliveryPriority:Normal, OriginalFromAddress:<>, AccountForest:NAMPR01A009.PROD.OUTLOOK.COM


Timestamp:09/02/2026 15:07:12
EventId:BADMAIL
SourceSN
MessageSubject:Test email for connector validation
MessageId:<5620fd8c-cc96-40e7-8bb9-3c74c06751d2@substrate-int.office.com>
Recipients:****@gmail.com
RecipientCount:1
RecipientStatus:
SourceContext:
Sender:O365ConnectorValidation@connectitnet.com
EventDataeliveryPriority:Normal, OriginalFromAddress:<>, AccountForest:NAMPR01A009.PROD.OUTLOOK.COM, BadmailReason:Suppress NDR of a rejected or expired DSN


Timestamp:09/02/2026 15:07:12
EventId:FAIL
Source:SMTP
MessageSubject:Test email for connector validation
MessageId:<5620fd8c-cc96-40e7-8bb9-3c74c06751d2@substrate-int.office.com>
Recipients:****@gmail.com
RecipientCount:1
RecipientStatus:[{LED=554 5.7.1 <****@gmail.com>: Relay access denied};{MSG=};{FQDN=pmg2.connectitnet.com};{IP=x.x.x.x};{LRT=9/2/2026 3:07:11 PM}]
SourceContext:
Sender:O365ConnectorValidation@connectitnet.com
EventData:OutboundProxyTargetIPAddress:x.x.x.x, OutboundProxyTargetHostNamemg2.connectitnet.com, OutboundProxyTargetEhloDomainmg2.connectitnet.com, OutboundProxyFrontEndIPAddress:[2603:10b6:80f:fc04::114]:25, OutboundProxyFrontEndName:SN1PEPF00030A0F.mail.protection.outlook.com, OutboundTlsDetails:TLS=SP_PROT_TLS1_3_CLIENT TLSCipher=CALG_AES_256 TLSKeyLength=256 TLSKeyExAlg=None, IsSmtpResponseFromExternalServer:True, Microsoft.Exchange.Transport.MailRecipient.RequiredTlsAuthLevel:CertificateValidation, IsDsn:False, Microsoft.Exchange.Hygiene.TenantOutboundConnectorCustomData:Name=Outbound via PMG_Test_2026-09-02T15:06:43.409Z;ConnectorType=Partner;UseMxRecord=False, E2ELatency:4.384, ExternalSendLatency:3.411, ToEntity:Internet, FromEntity:Internet, MsgRecipCount:1, IncludeInSla:True, SendingOrg:connectitnet.onmicrosoft.com, ProcessedRC:1, ExpirationTimeV2:9/3/2026 3:07:07 PM, ExpirationStartTimeReason:OriginalSubmit, ExpirationIntervalReason:OriginalSubmit, SmtpSecData:-1;-1, MimeParts:text:us-ascii|html:N/A|att:0|embed:0|parts:1|type:Normal|compliance:Compliant|from:Compliant, OutboundIpPool:1501, OutboundIpPoolName:HighRiskOutboundPool, DeliveryPriority:Normal, OriginalFromAddress:<>, AccountForest:NAMPR01A009.PROD.OUTLOOK.COM




am i missing something?

 

[AlexHK]

I am not very familiar with o365, but it seems the problem is just that your PMG is refusing to accept the mail:

554 5.7.1 <...@gmail.com>: Relay access denied from pmg2.connectitnet.com

Try sending an email to your own domain instead of gmail (for this quick test only).

Having said that, see here:
https://pmg.proxmox.com/pmg-docs/chapter-pmgconfig.html#pmgconfig_mailproxy_networks

You can add additional internal (trusted) IP networks or hosts. All hosts in this list are allowed to relay.

You normally need to tell PMG from which network to accept mail.

Not sure how that works with o365, since you don't have a dedicated IP I guess (and hence everyone from said network would be allowed to send email via your PMG install).

As said, I am not familiar with o365, so it could be that am am on the wrong track here.

PS: is this o365 connector trying to deliver the mail to PMG port 25 or 26? PMG wants it on port 26. see here:

Thread 'Documentation on how to outbound relay from Office 365?'

Oct 20, 2020

I have found several threads none with an answer on how to properly allow a domain to relay outbound email from their O365 to PMG to then deliver.
Any direction appreciated.

• MiamiJack
• Replies: 8
• Forum: Mail Gateway: Installation and configuration