@Matt,
IF you look in the Delivery log for the 602 error are you seeing a stack trace? I have seen this on some older servers that do not support some of the newer ciphers as well. Here is an example I found from an older server that was resolved by Moving (or upgrading ) the server to a newer OS.
[2024.07.23] 17:02:46.995 [46988399] RSP: 250-8BITMIME
[2024.07.23] 17:02:46.995 [46988399] RSP: 250-DSN
[2024.07.23] 17:02:46.995 [46988399] RSP: 250 CHUNKING
[2024.07.23] 17:02:46.995 [46988399] CMD: STARTTLS
[2024.07.23] 17:02:47.026 [46988399] RSP: 220 2.0.0 Ready to start TLS
[2024.07.23] 17:02:47.034 [46988399] Exception: One or more errors occurred. (Authentication failed because the remote party sent a TLS alert: 'HandshakeFailure'.)
[2024.07.23] Stack: at System.Threading.Tasks.Task.ThrowIfExceptional(Boolean includeTaskCanceledExceptions)
[2024.07.23] at System.Threading.Tasks.Task.Wait(Int32 millisecondsTimeout, CancellationToken cancellationToken)
[2024.07.23] at MailService.RelayServer.Clients.SMTP.ClientConnectionSync.InitiateSsl(Boolean validateAllCerts)
[2024.07.23] at MailService.RelayServer.Clients.SMTP.SmtpClientSession.GiveStartTls(String sessionId)
[2024.07.23] Inner Exception: Authentication failed because the remote party sent a TLS alert: 'HandshakeFailure'.
[2024.07.23] Inner Stack: at System.Net.Security.SslStream.ForceAuthenticationAsync[TIOAdapter](Boolean receiveFirst, Byte[] reAuthenticationData, CancellationToken cancellationToken)
[2024.07.23] 17:02:47.035 [46988399] Attempt to ip, '94.46.175.142' success: 'False'
Hope this helps.
~Tony
Tony Scholz
System/Network Administrator
SmarterTools Inc.
www.smartertools.com