Using Thunderbird 52.7.0 (32bit) and Davmail 4.8.5 (same problem with 4.8.2) connecting to Exchange 2003 with Java 1.8.0_171 and 1.8.0_172 not work, but work without problem with Java 1.8.0_161/1.8.0_162
davmail.log:
2018-05-04 13:52:21,026 DEBUG [main] davmail - OS Name: Windows 10 Java version: 1.8.0_172 64 System tray supported
2018-05-04 13:52:21,026 INFO [main] davmail - SWT not available, fallback to JDK 1.6 system tray support
2018-05-04 13:52:21,088 INFO [main] davmail - DavMail Gateway 4.8.5-2589 listening on SMTP port 1025 IMAP port 1143
2018-05-04 13:52:21,651 DEBUG [CheckRelease] davmail.DavGateway - DavMail released version: 4.8.5-2589
2018-05-04 13:52:37,219 DEBUG [davmail.imap.ImapServer] davmail - Connection from /127.0.0.1 on port 1143
2018-05-04 13:52:37,219 INFO [davmail.imap.ImapServer] davmail.connection - CONNECT - 127.0.0.1:1031
2018-05-04 13:52:37,835 ERROR [ImapConnection-1031] davmail.exchange.ExchangeSession - Connect exception: javax.net.ssl.SSLHandshakeException Remote host closed connection during handshake
2018-05-04 13:52:37,835 ERROR [ImapConnection-1031] davmail - DavMail configuration exception:
Connect exception: javax.net.ssl.SSLHandshakeException Remote host closed connection during handshake
davmail.exception.DavMailException: DavMail configuration exception:
Connect exception: javax.net.ssl.SSLHandshakeException Remote host closed connection during handshake
at davmail.exchange.ExchangeSessionFactory.handleNetworkDown(ExchangeSessionFactory.java:266)
at davmail.exchange.ExchangeSessionFactory.checkConfig(ExchangeSessionFactory.java:241)
at davmail.imap.ImapConnection.run(ImapConnection.java:81)
2018-05-04 13:52:37,835 DEBUG [ImapConnection-1031] davmail - > * BAD unable to handle request: DavMail configuration exception: Connect exception: javax.net.ssl.SSLHandshakeException Remote host closed connection during handshake
2018-05-04 13:52:37,835 INFO [ImapConnection-1031] davmail.connection - DISCONNECT - 127.0.0.1:1031
Maybe your Exchange server if configured with a certificate / algorithm that are no longer considered strong enough, you can launch DavMail with:
-Djavax.net.debug=ssl
to get more details.
More details on disabled cyphers at:
http://www.oracle.com/technetwork/java/javase/8u171-relnotes-4308888.html
Possible workaround:
https://www.java.com/en/configure_crypto.html
Can you please provide an update for this, did you check your server certificate ?