Hybrid Exch 2019 Kerberos errors

Raymond Hellberg 6 Reputation points
2022-05-31T12:04:35.703+00:00

A few weeks ago my DC sec.logs started filling up with Event ID 4768, coming from our on-prem Exchange 2019 hybrid server. Both Exchange and DCs are fully patched. Typically:

TargetUserName host
TargetDomainName OurDomain.NO
TargetSid S-1-0-0
ServiceName krbtgt/OutDomain.NO
ServiceSid S-1-0-0
TicketOptions 0x40810010
Status 0x6
TicketEncryptionType 0xffffffff
PreAuthType -
IpAddress ::ffff:19X.XXX.XXX.XXX
IpPort 30544

We do not have any accounts named "host" in our domain so the error is correct, but what is that coming from? I ran a monitoring tool on the Exchange server and it happens when the Microsoft email-system tries to talk to our on-prem-server. This snippet shows typically that the account "host/mail.protection.outlook.com" is tried authenticated several times, but the DC's initially reject it because it does not exist. But after some tries, SMTP-traffic seems to flow anyhow. Exchange seems to function normally, no major errors elsewhere.
So what is going on here?

SMTP:Cmd STARTTLS, Server is currently able to negotiate the use of TLS {TCP:139, IPv4:138}
SMTP:Rsp 220 2.0.0 SMTP server ready, 29 bytes {TCP:139, IPv4:138}
SSL:SSLv2RecordLayer, Error (needs reassembly) {SSL:140, TCP:139, IPv4:138}
SSL:SSLv2RecordLayer, Encrypted Application Data (needs reassembly) {SSL:140, TCP:139, IPv4:138}
TCP:Flags=...A...., SrcPort=35552, DstPort=SMTP(25), PayloadLen=0, Seq=1157102882, Ack=1194422529, Win=16425 (scale factor 0x8) = 4204800 {TCP:139, IPv4:138}
SSL:SSLv2RecordLayer, Encrypted Application Data (needs reassembly) {SSL:140, TCP:139, IPv4:138}
TCP:[Continuation to #1036]Flags=...A...., SrcPort=35552, DstPort=SMTP(25), PayloadLen=1460, Seq=1157104342 - 1157105802, Ack=1194423482, Win=16421 (scale factor 0x8) = 4203776 {TCP:139, IPv4:138}
TCP:[Continuation to #1036]Flags=...AP..., SrcPort=35552, DstPort=SMTP(25), PayloadLen=612, Seq=1157105802 - 1157106414, Ack=1194423482, Win=16421 (scale factor 0x8) = 4203776 {TCP:139, IPv4:138}
TCP:Flags=...A...., SrcPort=SMTP(25), DstPort=35552, PayloadLen=0, Seq=1194423482, Ack=1157106414, Win=65534 (scale factor 0x8) = 16776704 {TCP:139, IPv4:138}
TCP:Flags=CE....S., SrcPort=7445, DstPort=Kerberos(88), PayloadLen=0, Seq=4044519019, Ack=0, Win=64240 ( Negotiating scale factor 0x8 ) = 64240 {TCP:141, IPv4:31}
TCP:Flags=.E.A..S., SrcPort=Kerberos(88), DstPort=7445, PayloadLen=0, Seq=1896283979, Ack=4044519020, Win=8192 ( Negotiated scale factor 0x8 ) = 2097152 {TCP:141, IPv4:31}
TCP:Flags=...A...., SrcPort=7445, DstPort=Kerberos(88), PayloadLen=0, Seq=4044519020, Ack=1896283980, Win=65534 (scale factor 0x8) = 16776704 {TCP:141, IPv4:31}
KerberosV5:AS Request Cname: host/mail.protection.outlook.com Realm: OURDOMAIN.NO Sname: krbtgt/OURDOMAIN.NO {TCP:141, IPv4:31}
KerberosV5:KRB_ERROR - KDC_ERR_C_PRINCIPAL_UNKNOWN (6) {TCP:141, IPv4:31}

TCP:Flags=...A...F, SrcPort=7445, DstPort=Kerberos(88), PayloadLen=0, Seq=4044519274, Ack=1896284076, Win=65534 (scale factor 0x8) = 16776704 {TCP:141, IPv4:31}
TCP:Flags=CE....S., SrcPort=7446, DstPort=Kerberos(88), PayloadLen=0, Seq=4015489666, Ack=0, Win=64240 ( Negotiating scale factor 0x8 ) = 64240 {TCP:142, IPv4:31}
TCP:Flags=...A...., SrcPort=Kerberos(88), DstPort=7445, PayloadLen=0, Seq=1896284076, Ack=4044519275, Win=8212 (scale factor 0x8) = 2102272 {TCP:141, IPv4:31}
TCP:Flags=...A.R.., SrcPort=Kerberos(88), DstPort=7445, PayloadLen=0, Seq=1896284076, Ack=4044519275, Win=0 (scale factor 0x8) = 0 {TCP:141, IPv4:31}
TCP:Flags=.E.A..S., SrcPort=Kerberos(88), DstPort=7446, PayloadLen=0, Seq=1613145770, Ack=4015489667, Win=8192 ( Negotiated scale factor 0x8 ) = 2097152 {TCP:142, IPv4:31}
TCP:Flags=...A...., SrcPort=7446, DstPort=Kerberos(88), PayloadLen=0, Seq=4015489667, Ack=1613145771, Win=65534 (scale factor 0x8) = 16776704 {TCP:142, IPv4:31}
KerberosV5:AS Request Cname: host/mail.protection.outlook.com Realm: OURDOMAIN.NO Sname: krbtgt/OURDOMAIN.NO {TCP:142, IPv4:31}
KerberosV5:KRB_ERROR - KDC_ERR_C_PRINCIPAL_UNKNOWN (6) {TCP:142, IPv4:31}

TCP:Flags=...A...F, SrcPort=7446, DstPort=Kerberos(88), PayloadLen=0, Seq=4015489921, Ack=1613145867, Win=65534 (scale factor 0x8) = 16776704 {TCP:142, IPv4:31}
9922, Win=8212 (scale factor 0x8) = 2102272 {TCP:142, IPv4:31}
TCP:Flags=...A.R.., SrcPort=Kerberos(88), DstPort=7446, PayloadLen=0, Seq=1613145867, Ack=4015489922, Win=0 (scale factor 0x8) = 0 {TCP:142, IPv4:31}
TCP:Flags=CE....S., SrcPort=7447, DstPort=49158, PayloadLen=0, Seq=1303772489, Ack=0, Win=64240 ( Negotiating scale factor 0x8 ) = 64240 {TCP:143, IPv4:4}
TCP:Flags=.E.A..S., SrcPort=49158, DstPort=7447, PayloadLen=0, Seq=3024248101, Ack=1303772490, Win=8192 ( Negotiated scale factor 0x8 ) = 2097152 {TCP:143, IPv4:4}
TCP:Flags=...A...., SrcPort=7447, DstPort=49158, PayloadLen=0, Seq=1303772490, Ack=3024248102, Win=65534 (scale factor 0x8) = 16776704 {TCP:143, IPv4:4}
MSRPC:c/o Bind: Netlogon(NRPC) UUID{12345678-1234-ABCD-EF00-01234567CFFB} Call=0x6F20 Assoc Grp=0x0 Xmit=0x16D0 Recv=0x16D0 {MSRPC:144, TCP:143, IPv4:4}
MSRPC:c/o Bind Ack: Call=0x6F20 Assoc Grp=0x4B313 Xmit=0x16D0 Recv=0x16D0 {MSRPC:144, TCP:143, IPv4:4}
NRPC:NetrLogonSamLogonEx Request, Encrypted {MSRPC:144, TCP:143, IPv4:4}
TCP:Flags=...A...., SrcPort=49158, DstPort=7447, PayloadLen=0, Seq=3024248230, Ack=1303775397, Win=4106 (scale factor 0x8) = 1051136 {TCP:143, IPv4:4}
NRPC:NetrLogonSamLogonEx Response, Encrypted {MSRPC:144, TCP:143, IPv4:4}
SSL:SSLv2RecordLayer, Error (needs reassembly) {SSL:140, TCP:139, IPv4:138}
SSL:SSLv2RecordLayer, Error (needs reassembly) {SSL:140, TCP:139, IPv4:138}

Exchange | Hybrid management
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4 answers

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  1. Raymond Hellberg 6 Reputation points
    2022-06-07T09:17:22.25+00:00

    Thank you for your suggestion, but that did not work.
    HCW is running just fine. (Also ran it very recently in conj. with cert renewal)


  2. Gabriel Cynowicz 0 Reputation points
    2023-02-08T12:31:54.8666667+00:00

    Did you ever get a resolution to this issue? The exact same thing is occurring on my hybrid Exchange 2019 servers.

    0 comments No comments

  3. Raymond Hellberg 1 Reputation point
    2023-02-08T14:47:15.2633333+00:00

    No solution. Seeing others also having this problem - quite annoying.. https://learn.microsoft.com/en-us/answers/questions/917013/event-id-4768?page=2#answers

    -Ray-

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  4. Rowan Swanepoel 0 Reputation points
    2023-06-19T12:11:42.4033333+00:00

    Hey there. Got the same issue with my environment. AD AuditPlus started freaking out over User: Null bad login creds, error 4625. Found out it was a health mailbox (after disabling them). This issue came up around October 2022's .net and monthly security updates.

    Logged a case with Microsoft

    Ended up being the cname mail.protection.outlook.com is not registered as an SPN (Service Principal Name) host for mail.protection.outlook.com. Recommend to verify the configuration of mail.protection.outlook.com for constrained delegation

    But don't know how to fix this

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