<![CDATA[javax.mail.MessagingException: Could not convert socket to TLS]]>Using mango 3.7.7, cannot send emails via our gmail account.
I've configured an application password and yet I receive this error:

{"cause":"MailSendException: Mail server connection failed; nested exception is javax.mail.MessagingException: Could not convert socket to TLS;\n  nested exception is:\n\tjavax.net.ssl.SSLHandshakeException: Invalid CertificateVerify signature. Failed messages: javax.mail.MessagingException: Could not convert socket to TLS;\n  nested exception is:\n\tjavax.net.ssl.SSLHandshakeException: Invalid CertificateVerify signature","smtpSessionLog":"DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Oracle]\nDEBUG SMTP: useEhlo true, useAuth true\nDEBUG SMTP: trying to connect to host \"smtp.gmail.com\", port 587, isSSL false\n220 smtp.gmail.com ESMTP x10sm15856991pff.214 - gsmtp\nDEBUG SMTP: connected to host \"smtp.gmail.com\", port: 587\nEHLO mangoGT5191\n250-smtp.gmail.com at your service, [122.56.205.5]\n250-SIZE 35882577\n250-8BITMIME\n250-STARTTLS\n250-ENHANCEDSTATUSCODES\n250-PIPELINING\n250-CHUNKING\n250 SMTPUTF8\nDEBUG SMTP: Found extension \"SIZE\", arg \"35882577\"\nDEBUG SMTP: Found extension \"8BITMIME\", arg \"\"\nDEBUG SMTP: Found extension \"STARTTLS\", arg \"\"\nDEBUG SMTP: Found extension \"ENHANCEDSTATUSCODES\", arg \"\"\nDEBUG SMTP: Found extension \"PIPELINING\", arg \"\"\nDEBUG SMTP: Found extension \"CHUNKING\", arg \"\"\nDEBUG SMTP: Found extension \"SMTPUTF8\", arg \"\"\nSTARTTLS\n220 2.0.0 Ready to start TLS\n","mangoStatusCode":5000,"mangoStatusName":"GENERIC_500","localizedMessage":"Email send failure"}

Any ideas on what to do to fix this?

Fox

]]>https://forum.mango-os.com/topic/5050/javax-mail-messagingexception-could-not-convert-socket-to-tlsRSS for NodeSat, 06 Jun 2026 19:16:56 GMTSun, 10 Jan 2021 22:12:03 GMT60<![CDATA[Reply to javax.mail.MessagingException: Could not convert socket to TLS on Mon, 11 Jan 2021 02:30:40 GMT]]>Ah good idea man,

mondays...

EDIT:

220 smtp.gmail.com ESMTP x15sm16801291pfa.80 - gsmtp

I get the feeling this is JDK related...

]]>https://forum.mango-os.com/post/26162https://forum.mango-os.com/post/26162Mon, 11 Jan 2021 02:30:40 GMT<![CDATA[Reply to javax.mail.MessagingException: Could not convert socket to TLS on Mon, 11 Jan 2021 02:26:21 GMT]]>Hey mate, can the underlying host machine connect to the mail server on that port?

Even try just...

telnet smtp.gmail.com 587

See if you get an answer similar to...

220 smtp.gmail.com ESMTP p9sm17466733pfq.136 - gsmtp

Although it does mention TLS so 587 should be correct? Certificate error is weird.

]]>https://forum.mango-os.com/post/26161https://forum.mango-os.com/post/26161Mon, 11 Jan 2021 02:26:21 GMT