Do you get sun.security.provider.certpath. SunCertPathBuilderException: unable to find valid certification path to requested target when you try to send a mail from java via smtp(TLS and SSL)? There are 2 possible problems:

One option could be from the antivirus/firewall which prevent the communication for a specific port(default 465 for SSL and 587 for TSL) or for the java.exe. In the case you have a recent JDK/JRE and you use a well-known service this is probably the problem. Just try to disable the antivirus and to send again the mail from java. If it doesn’t work check the next point

You have an invalid/expired certificate for the email server so the SSL/TLS authentication doesn’t work properly. In order to overcome this you have to install the valid certificate.

Exception in thread “main” java.lang.RuntimeException: javax.mail.MessagingException: Could not convert socket to TLS;
nested exception is:
javax.net.ssl.SSLHandshakeException: sun.security.validator.ValidatorException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target
at util.SendMail.mainTLS(SendMail.java:58)
at util.SendMail.main(SendMail.java:22)
Caused by: javax.mail.MessagingException: Could not convert socket to TLS;
nested exception is:
javax.net.ssl.SSLHandshakeException: sun.security.validator.ValidatorException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target
at com.sun.mail.smtp.SMTPTransport.startTLS(SMTPTransport.java:1907)
at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:666)
at javax.mail.Service.connect(Service.java:317)
at javax.mail.Service.connect(Service.java:176)
at javax.mail.Service.connect(Service.java:125)
at javax.mail.Transport.send0(Transport.java:194)
at javax.mail.Transport.send(Transport.java:124)
at util.SendMail.mainTLS(SendMail.java:53)
… 1 more
Caused by: javax.net.ssl.SSLHandshakeException: sun.security.validator.ValidatorException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target
at sun.security.ssl.Alerts.getSSLException(Unknown Source)
at sun.security.ssl.SSLSocketImpl.fatal(Unknown Source)
at sun.security.ssl.Handshaker.fatalSE(Unknown Source)
at sun.security.ssl.Handshaker.fatalSE(Unknown Source)
at sun.security.ssl.ClientHandshaker.serverCertificate(Unknown Source)
at sun.security.ssl.ClientHandshaker.processMessage(Unknown Source)
at sun.security.ssl.Handshaker.processLoop(Unknown Source)
at sun.security.ssl.Handshaker.process_record(Unknown Source)
at sun.security.ssl.SSLSocketImpl.readRecord(Unknown Source)
at sun.security.ssl.SSLSocketImpl.performInitialHandshake(Unknown Source)
at sun.security.ssl.SSLSocketImpl.startHandshake(Unknown Source)
at sun.security.ssl.SSLSocketImpl.startHandshake(Unknown Source)
at com.sun.mail.util.SocketFetcher.configureSSLSocket(SocketFetcher.java:549)
at com.sun.mail.util.SocketFetcher.startTLS(SocketFetcher.java:486)
at com.sun.mail.smtp.SMTPTransport.startTLS(SMTPTransport.java:1902)
… 8 more
Caused by: sun.security.validator.ValidatorException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target
at sun.security.validator.PKIXValidator.doBuild(Unknown Source)
at sun.security.validator.PKIXValidator.engineValidate(Unknown Source)
at sun.security.validator.Validator.validate(Unknown Source)
at sun.security.ssl.X509TrustManagerImpl.validate(Unknown Source)
at sun.security.ssl.X509TrustManagerImpl.checkTrusted(Unknown Source)
at sun.security.ssl.X509TrustManagerImpl.checkServerTrusted(Unknown Source)
… 19 more
Caused by: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target
at sun.security.provider.certpath.SunCertPathBuilder.engineBuild(Unknown Source)
at java.security.cert.CertPathBuilder.build(Unknown Source)
… 25 more