Cannot send mail to certain recipients. SMTP STARTTLS failure (8922)

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Symptoms

Cannot mail certain recipients. The sender sees this in the GW Client:

 

 

 

The reason given for the delay: 420 TCP write error

 

 

 

The following is shown in the GWIA log:

 

 

 

07:11:54 2323 DMN: MSG 2815270 Attempting to connect to mail12.surftown.se 07:11:54 2323 DMN: MSG 2815270 Connected to [212.97.132.52] (mail12.surftown.se) 07:11:54 2323 DMN: MSG 2815270 SMTP STARTTLS failure (8922) 07:11:55 2323 DMN: MSG 2815270 SMTP session ended: [212.97.132.52] (mail12.surftown.se)

 

 

 

 

Diagnosis

The best way to troubleshoot this would be to get a packet trace. On the GWIA server:

 

 

 

tcpdump -i any -s 0 -w /root/surftown.cap host 212.97.132.52

 

 

 

This will capture data just for that ip. Note that you cannot filter on a single IP if the recipient has multiple ones.

Open the packet trace in Wireshark. Look at the client and server hellos:

Client Hello. That is you:

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You are indicating that you support TLS up to 1.2. Ideally the receiving mailserver should use that version, but instead:
 
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Here the receiving mailserver uses TLS 1.0 and that protocol is regarded as unsecure and was deprecated in June 2018. GW 18.2 will not talk to him.

Solution

Ask the admin of the receiving mailserver to upgrade to a supported version of SSL

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Anonymous
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  • When I first upgraded to 18.2 I added --ssloption "ssl_op_allow_tls_v1_1,ssl_op_allow_tlsv1" to my POA configs to support Macs. It was working and didn't think anything more of it.  Tuesday I upgraded my last remaining domain and PO to 2018.2 and much of my environment stopped working. The POAs would fail to connect to the MTAs. Finally I added the switch to my MTAs and the POAs began to work again. I had to update every POA, MTA and GWIA to allow tls1 before mail was working again.

     

    This whole thing would have been avoided if either there was a new Mac client or if the new Web client that's still in development was featured completely enough to replace the 10 year Mac client. 

     

Comment
  • When I first upgraded to 18.2 I added --ssloption "ssl_op_allow_tls_v1_1,ssl_op_allow_tlsv1" to my POA configs to support Macs. It was working and didn't think anything more of it.  Tuesday I upgraded my last remaining domain and PO to 2018.2 and much of my environment stopped working. The POAs would fail to connect to the MTAs. Finally I added the switch to my MTAs and the POAs began to work again. I had to update every POA, MTA and GWIA to allow tls1 before mail was working again.

     

    This whole thing would have been avoided if either there was a new Mac client or if the new Web client that's still in development was featured completely enough to replace the 10 year Mac client. 

     

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