Hi all,

Running the latest code, Apache James 3.8.2 Server JPA Guice.

I'm seeing this error below when attempting to deliver to some recipients'
mail servers:

2025-07-22 12:17:49.917 [DEBUG] o.a.j.t.m.r.d.MailDelivrer - Exception
delivering message
(Mail1753186668620-a77a76bb-d3f4-4170-9f5e-8ca8159a2276-to-zzzzzzz.com) - Could
not convert socket to TLS
2025-07-22 12:17:49.918 [INFO ] o.a.j.t.m.r.d.MailDelivrer - Could not
convert socket to TLS

My mailetcontainer.xml contains the following, it seems to work on most
occasions but (sod's law) not when the customer is testing it.

<processor state="relay" enabledJmx="true">
   <mailet match="ALL" class="RemoteDelivery">
       ....
       <startTLS>true</startTLS>
   </mailet>
</processor>

I enabled -Djavax.net.debug=ssl:handshake:verbose, -Dmail.debug=true and
after inspecting stderr I believe what's causing it is not trusting the
remote server's SSL certificate which causes Javamail to abandon the
connection.

Testing with openssl, it seems that the SSL certificate CN doesn't match
the server hostname.

This must be a common problem in the wild.

Does anyone have any workarounds? I've tried setting
-Dmail.smtp.ssl.trust=* but it doesn't seem to make any difference.

Many thanks in advance.

Kind regards
Matt Pryor
Research and Development Manager

The International Presence Group of Companies
EMAIL: pr...@presencebpm.com
URL: www.International-presence.com

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