Skip to content

Certificate Validation Failure

Jump to bottom
Malcolm Stewart edited this page Mar 9, 2022 · 10 revisions

This topic shows the usual pattern of packets when the client fails to validate the server certificate.

In the client application, the error is similar to this:

System.Data.SqlClient.SqlException:
A connection was successfully established with the server, but then an error occurred during the login process.
(provider: SSL Provider, error: 0 - The certificate chain was issued by an authority that is not trusted.)
---> System.ComponentModel.Win32Exception: The certificate chain was issued by an authority that is not trusted

Frame  Date and Time        Source IP    Dest IP      Description
-----  -------------------  -----------  -----------  -----------------------------------------------------------------------------------
TCP 3-way handshake establishes a basic TCP connection.

590    8:34:51 AM 3/9/2022  10.10.10.10  10.10.10.20  TCP:Flags=CE....S., SrcPort=56277, DstPort=1433, PayloadLen=0, 
593    8:34:51 AM 3/9/2022  10.10.10.20  10.10.10.10  TCP:Flags=.E.A..S., SrcPort=1433, DstPort=56277, PayloadLen=0, 
596    8:34:51 AM 3/9/2022  10.10.10.10  10.10.10.20  TCP:Flags=...A...., SrcPort=56277, DstPort=1433, PayloadLen=0, 

The PreLogin packet from the client inidcates data encryption is required. This also implies the client will try to validate the certificate.

599    8:34:51 AM 3/9/2022  7.2773307  10.10.10.10  10.10.10.20  TDS:Prelogin, Flags=...AP..., SrcPort=56277, DstPort=1433, PayloadLen=104,

- Tds: Prelogin
  + PacketHeader: SPID = 0, Size = 104, PacketID = 1, Window = 0
  - PreLoginPacketData: 
   - PreloginOptions: 
    + PreloginOptionTokens: 
    - PreloginOptionData: 
     + VersionData: 
     - EncryptionData: 
        Encryption: ENCRYPT_ON 1 (0x1)
     + InstOptData: 
     + ThreadIDData: 
     + MARSData: 
     + TRACEIDLengthData: 
     + FederatedLengthData:

602    8:34:51 AM 3/9/2022  10.10.10.20  10.10.10.10  TDS:Response

The SSL/TLS handshake results in the server sending a certificate to the client. For data encryption, the client tries to validate the certificate.

605    8:34:51 AM 3/9/2022  10.10.10.10  10.10.10.20  TLS:TLS Rec Layer-1 HandShake: Client Hello.
614    8:34:51 AM 3/9/2022  10.10.10.20  10.10.10.10  TCP:Flags=...A...., SrcPort=1433, DstPort=56277, PayloadLen=0,
617    8:34:51 AM 3/9/2022  10.10.10.20  10.10.10.10  TLS:TLS Rec Layer-1 HandShake: Server Hello. Certificate. Server Key Exchange. Server Hello Done.

- TLS: TLS Rec Layer-1 HandShake: Server Hello. Certificate. Server Key Exchange. Server Hello Done.
  - TlsRecordLayer: TLS Rec Layer-1 HandShake:
     ContentType: HandShake:
   + Version: TLS 1.2
     Length: 847 (0x34F)
   - SSLHandshake: SSL HandShake Server Hello Done(0x0E)
      HandShakeType: ServerHello(0x02)
      Length: 81 (0x51)
    + ServerHello: 0x1
      HandShakeType: Certificate(0x0B)
      Length: 517 (0x205)
    - Cert: 0x1
       CertLength: 514 (0x202)
     - Certificates: 
        CertificateLength: 511 (0x1FF)
      + X509Cert: Issuer: SSL_Self_Signed_Fallback, Subject: SSL_Self_Signed_Fallback
      HandShakeType: Server Key Exchange(0x0C)
      Length: 233 (0xE9)
      ServerKeyExchange: Binary Large Object (233 Bytes)
      HandShakeType: Server Hello Done(0x0E)
      Length: 0 (0x0)

The certificate is a SSL_Self_Signed_Fallback certificate, which means that it cannot be validated, so the client terminates the connection.

686    8:34:51 AM 3/9/2022  10.10.10.10  10.10.10.20  TCP:Flags=...A...F, SrcPort=56277, DstPort=1433, PayloadLen=0,
710    8:34:51 AM 3/9/2022  10.10.10.20  10.10.10.10  TCP:Flags=...A...., SrcPort=1433, DstPort=56277, PayloadLen=0,
713    8:34:51 AM 3/9/2022  10.10.10.20  10.10.10.10  TCP:Flags=...A...F, SrcPort=1433, DstPort=56277, PayloadLen=0,
719    8:34:51 AM 3/9/2022  10.10.10.10  10.10.10.20  TCP:Flags=...A...., SrcPort=56277, DstPort=1433, PayloadLen=0,

Clone this wiki locally