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Email Delivery Failure

I have tried all of the various SMTP options for mail delivery, however, the server fails to properly send mail regardless of the method I use. It recognizes the method it is attempting to send with, but always fails with an error stating that there is no appropriate protocol.
org.simplejavamail.mailer.internal.MailerException: Third party error
	at org.simplejavamail.mailer.internal.SendMailClosure.executeClosure(SendMailClosure.java:91)
	at org.simplejavamail.mailer.internal.AbstractProxyServerSyncingClosure.run(AbstractProxyServerSyncingClosure.java:56)
	at org.simplejavamail.internal.util.concurrent.AsyncOperationHelper$1.run(AsyncOperationHelper.java:75)
	at java.base/java.util.concurrent.Executors$RunnableAdapter.call(Executors.java:515)
	at java.base/java.util.concurrent.FutureTask.run(FutureTask.java:264)
	at java.base/java.util.concurrent.ThreadPoolExecutor.runWorker(ThreadPoolExecutor.java:1128)
	at java.base/java.util.concurrent.ThreadPoolExecutor$Worker.run(ThreadPoolExecutor.java:628)
	at java.base/java.lang.Thread.run(Thread.java:829)
Caused by: javax.mail.MessagingException: Could not convert socket to TLS
	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 org.simplejavamail.mailer.internal.util.TransportRunner.runOnSessionTransport(TransportRunner.java:75)
	at org.simplejavamail.mailer.internal.util.TransportRunner.sendMessage(TransportRunner.java:48)
	at org.simplejavamail.mailer.internal.SendMailClosure.executeClosure(SendMailClosure.java:82)
	... 7 common frames omitted
Caused by: javax.net.ssl.SSLHandshakeException: No appropriate protocol (protocol is disabled or cipher suites are inappropriate)
	at java.base/sun.security.ssl.HandshakeContext.<init>(HandshakeContext.java:170)
	at java.base/sun.security.ssl.ClientHandshakeContext.<init>(ClientHandshakeContext.java:98)
	at java.base/sun.security.ssl.TransportContext.kickstart(TransportContext.java:221)
	at java.base/sun.security.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:443)
	at java.base/sun.security.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:421)
	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)
	... 14 common frames omitted
05:17:06.349 [pool-24-thread-1] WARN  c.s.c.c.p.provider.EmailServiceImpl - Email cannot be delivered
It, however, properly reflects the options as I change them in the config.
DEBUG o.s.m.internal.util.SessionLogger - starting async mail with session (host: smtp.<REDACTED>.com, port: 587, username: <REDACTED>, authenticate: true, transport: SMTP)
DEBUG o.s.m.internal.util.SessionLogger - starting async mail with session (host: smtp.<REDACTED>.com, port: 587, username: <REDACTED>, authenticate: true, transport: SMTPS)
DEBUG o.s.m.internal.util.SessionLogger - starting async mail with session (host: smtp.<REDACTED>.com, port: 587, username: <REDACTED>, authenticate: true, transport: SMTP_TLS)