Office 365 to On Premise Connector Validation Test Email Received but Status: Failed

[spajce]

Hi everyone, please kindly help us from this issue

When we send an email from Office 365 to On Premise Email, we encountered this issues:

1. Your message to person@companyname.com.ph couldn't be delivered. company.com.ph suspects your message is spam and rejected it. 
2. Your message to person@companyname.com.ph couldn't be delivered. The recipients weren't found at company.com.ph

We have cloudflare dns setup with 2 MX Records

;; MX Records
companyname.com.ph.	1	IN	MX	1 xxxxx.prod.sin2.secureserver.net.
companyname.com.ph.	1	IN	MX	0 companyname-com-ph.mail.protection.outlook.com.

We have connector setup: Office 365 to On Premise Connector

upon validation with send test email the email was actually received but the connector validator says "Send test email - FAILED"

but actually the test email was successfully received

Detailed Log

 

Timestamp:8/4/2020 2:20:33 AM
EventId:RECEIVE
Source:SMTP
MessageSubject:Test email for connector validation
MessageId:<8ca2b598-16a6-4db6-acc5-c23dadf4f421@HK0PR03MB3858.apcprd03.prod.outlook.com>
Recipients:webmaster@company.com.ph
RecipientCount:1
RecipientStatus:
SourceContext:08D836FAB88AC3C1;2020-08-04T02:20:32.877Z;0
Sender:O365ConnectorValidation@company.com.ph
EventData:InboundTlsDetails:TLS=SP_PROT_TLS1_2_SERVER TLSCipher=CALG_AES_256 TLSKeyLength=256 TLSKeyExAlg=CALG_ECDH_EPHEM, MimeParts:Att/Emb/MPt:0/0/1, MessageValue:MediumHigh, Replication:SG2PR03MB3865, FirstForestHop:HK0PR03MB3858.apcprd03.prod.outlook.com, DeliveryPriority:Normal, OriginalFromAddress:<>, AccountForest:APCPR03A004.PROD.OUTLOOK.COM


Timestamp:8/4/2020 2:20:33 AM
EventId:RECIPIENTINFO
Source:RESOLVER
MessageSubject:Test email for connector validation
MessageId:<8ca2b598-16a6-4db6-acc5-c23dadf4f421@HK0PR03MB3858.apcprd03.prod.outlook.com>
Recipients:webmaster@companyname.com.ph
RecipientCount:1
RecipientStatus:MailUser.Contact.Resolver.CreateRecipientItems.30
SourceContext:
Sender:O365ConnectorValidation@companyname.com.ph
EventData:SenderVerdict:NotFound.OneOff.Sender.10, DeliveryPriority:Normal, OriginalFromAddress:<>, AccountForest:APCPR03A004.PROD.OUTLOOK.COM


Timestamp:8/4/2020 2:20:33 AM
EventId:SETROUTE
Source:AGENT
MessageSubject:Test email for connector validation
MessageId:<8ca2b598-16a6-4db6-acc5-c23dadf4f421@HK0PR03MB3858.apcprd03.prod.outlook.com>
Recipients:webmaster@companyname.com.ph
RecipientCount:1
RecipientStatus:
SourceContext:Advanced Routing - Connector Based Router
Sender:O365ConnectorValidation@companyname.com.ph
EventData:ConnectorRedirect:smtp:DefaultTlsOpportunistic(companyname.com.ph), DeliveryPriority:Normal, OriginalFromAddress:<>, AccountForest:APCPR03A004.PROD.OUTLOOK.COM


Timestamp:8/4/2020 2:20:34 AM
EventId:AGENTINFO
Source:AGENT
MessageSubject:Test email for connector validation
MessageId:<8ca2b598-16a6-4db6-acc5-c23dadf4f421@HK0PR03MB3858.apcprd03.prod.outlook.com>
Recipients:webmaster@companyname.com.ph
RecipientCount:1
RecipientStatus:
SourceContext:CatContentConversion
Sender:O365ConnectorValidation@companyname.com.ph
EventData:AMA:EV|engine=S|v=0|sig=20200803.024|name=|file=|hash=|phash=, AMA:EV|engine=A|v=0|sig=202008032321|name=|file=|hash=|phash=, AMA:EV|engine=M|v=0|sig=1.321.551.0|name=|file=|hash=|phash=, SDA:SDG|MID=4754528798168|MN=HK0PR03MB3858, TRA:ETRP|ruleId=3a8df934-1fac-423d-ae5b-4518fb084f7a|st=2020-06-25T01:18:47.0000000Z|ExecW=0|ExecC=0|Conditions=ISUP,M.F,0, TRA:ETRP|ruleId=4aa54303-df42-4eca-8e47-67709d1d017f|st=2020-06-25T01:19:29.0000000Z|ExecW=0|ExecC=0|Conditions=IP,F,0, TRA:ETRP|ruleId=b824a79a-7455-4757-b60f-af0430256962|st=2020-06-24T03:20:30.0000000Z|ExecW=0|ExecC=0|Conditions=IP,F,0, TRA:ETRP|ruleId=f89c6a0b-0849-46cb-876c-5968abdc3cf8|st=2020-06-25T01:20:36.0000000Z|ExecW=0|ExecC=0|Conditions=ISUP,M.F,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=(3230221)(823300339)(823320095)(20180801173)(4000002)(3233001)(3231646)(944501678)(15041020)(15015020)(15022040)(2019022201238)(7699060)(76000230)(930200077)(76010050)|sfp=0|fprx=|mlc=|mlv=|list=1|di=|rd=|h=HK0PR03MB3858.apcprd03.prod.outlook.com|ctry=|cltctry=|lang=|cip=|dir=Originating|alat=0|mlat=3|rlat=3|asf=, CFA:LTC|RPLHCFR=34|RPLSLR=0|RPLAPR=34|RPLMR=0|RPL=68|RSP=74, PCFA:SUM|dkim=0|hctfp=ce80adcf-b625-4473-b8bf-f27d8e3f67ab, SFA:SUM|SFV=SKI|IPV=NLI|SRV=|SCL=-1|SCORE=0|LIST=0|DI=|RD=|H=HK0PR03MB3858.apcprd03.prod.outlook.com|CIP=|SFP=0|ASF=0|CTRY=|CLTCTRY=IPV6|LANG=en|LAT=0|LAT=0|LAT=0|FPR=A8C2707E.E93100B.89F093CD.D44EEEC9.20067|DIR=OUT, PCFA:SUM|dkim=0|URLRW=0, CompCost:C|SFA=0, DeliveryPriority:Normal, OriginalFromAddress:<>, AccountForest:APCPR03A004.PROD.OUTLOOK.COM


Timestamp:8/4/2020 2:20:34 AM
EventId:AGENTINFO
Source:AGENT
MessageSubject:Test email for connector validation
MessageId:<8ca2b598-16a6-4db6-acc5-c23dadf4f421@HK0PR03MB3858.apcprd03.prod.outlook.com>
Recipients:webmaster@companyname.com.ph
RecipientCount:1
RecipientStatus:
SourceContext:AgentFork
Sender:O365ConnectorValidation@companyname.com.ph
EventData:PCFA:OCAT|dkim=0, DeliveryPriority:Normal, OriginalFromAddress:<>, AccountForest:APCPR03A004.PROD.OUTLOOK.COM


Timestamp:8/4/2020 2:20:35 AM
EventId:SENDEXTERNAL
Source:SMTP
MessageSubject:Test email for connector validation
MessageId:<8ca2b598-16a6-4db6-acc5-c23dadf4f421@HK0PR03MB3858.apcprd03.prod.outlook.com>
Recipients:webmaster@companyname.com.ph
RecipientCount:1
RecipientStatus:250 2.1.5 Recipient OK
SourceContext:
Sender:O365ConnectorValidation@companyname.com.ph
EventData:E2ELatency:2.775, ExternalSendLatency:1.090, ToEntity:HybridOnPrem, FromEntity:Unknown, MsgRecipCount:1, IncludeInSla:True, SendingOrg:companynamedevt.onmicrosoft.com, ExpirationTimeV2:8/5/2020 2:20:32 AM, ExpirationStartTimeReason:OriginalSubmit, ExpirationIntervalReason:OriginalSubmit, OutboundProxyTargetIPAddress:104.47.125.36, OutboundProxyTargetHostName:companyname-com-ph.mail.protection.outlook.com, OutboundProxyFrontEndIPAddress:[2a01:111:e400:7ebd::27]:25, OutboundProxyFrontEndName:SG2APC01FT133, OutboundTlsDetails:TLS=SP_PROT_TLS1_2_CLIENT TLSCipher=CALG_AES_256 TLSKeyLength=256 TLSKeyExAlg=CALG_ECDH_EPHEM, IsSmtpResponseFromExternalServer:True, DeliveryPriority:Normal, Oorg:companyname.com.ph, OriginalFromAddress:<>, AccountForest:APCPR03A004.PROD.OUTLOOK.COM

[#2]

Did you set up a receive connector on on-premises to accept emails from O365 ?

[#3]

Yes, we had, that validation above that was our connector setup(office 365 to on premise) and then sometimes we can received an email from office 365 to on premise then we keep trying "send again" until the recipient received the email from office 365

PS. We already coordinate with office 365 engineering support team about this issue, initially we have no issues with the connector setup. we already send the message trace report to them. will post the updates and feedbacks from this issue soon.

[#4 · Accepted solution]

Update:

We had changed the values from cloudflare setup in MX Record

from xxxx.prod.sin2.secureserver.net to  mail.xxxx.com.ph

We just follow the instructions from godaddy on how to  properly setup the MX Record in our premise server https://uk.godaddy.com/help/configuring-dns-for-your-cpanel-domain-8852

the two issues has been resolved, 

1. Your message to person@companyname.com.ph couldn't be delivered. company.com.ph suspects your message is spam and rejected it. 
2. Your message to person@companyname.com.ph couldn't be delivered. The recipients weren't found at company.com.ph

and the validation status result is failed in connector validation, but anyway as I mention above even the the validation status result is failed we still received an email that the connector is setup can delivered an email to our onprem server.