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StartTLS breaks between versions when upgrading

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  • Last reply by Matt

Jack
Jack
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StartTLS works fine in 102.13.0 but when I upgrade past that and up to 115.1.1 - StartTLS is broken and doesn't allow me to email out. Log with 102.13.0 version: Wed 2023-08-30 08:27:37.455: Accepting SMTP connection from 192.*:61492 to 192.*:587 Wed 2023-08-30 08:27:37.475: --> 220 mail ESMTP MSA Wed, 30 Aug 2023 08:27:37 -0600 Wed 2023-08-30 08:27:37.532: <-- EHLO [192.*] Wed 2023-08-30 08:27:37.532: --> 250-mail. Hello [192.*] [192.*], pleased to meet you Wed 2023-08-30 08:27:37.532: --> 250-AUTH LOGIN CRAM-MD5 PLAIN Wed 2023-08-30 08:27:37.532: --> 250-8BITMIME Wed 2023-08-30 08:27:37.532: --> 250-ENHANCEDSTATUSCODES Wed 2023-08-30 08:27:37.532: --> 250-PIPELINING Wed 2023-08-30 08:27:37.532: --> 250-CHUNKING Wed 2023-08-30 08:27:37.532: --> 250 SIZE Wed 2023-08-30 08:27:37.546: <-- AUTH CRAM-MD5 Wed 2023-08-30 08:27:37.546: --> 334 PE1E Wed 2023-08-30 08:27:37.594: <-- QnJhZ== Wed 2023-08-30 08:27:37.594: Authenticating Brad... Wed 2023-08-30 08:27:37.596: Authenticated as Brad Wed 2023-08-30 08:27:37.596: --> 235 2.7.0 Authentication successful Wed 2023-08-30 08:27:37.612: <-- MAIL FROM:<brad> BODY=8BITMIME SIZE=1429 Wed 2023-08-30 08:27:37.612: --> 250 2.1.0 Sender OK Wed 2023-08-30 08:27:37.624: <-- RCPT TO:<j*> Wed 2023-08-30 08:27:37.626: --> 250 2.1.5 Recipient OK Wed 2023-08-30 08:27:37.638: <-- DATA Wed 2023-08-30 08:27:37.640: --> 354 Enter mail, end with <CRLF>.<CRLF> Wed 2023-08-30 08:27:37.656: Message size: 1429 bytes Wed 2023-08-30 08:27:37.668: Outbreak Protection: Processing skipped. Authenticated connection. Wed 2023-08-30 08:27:37.685: Message creation successful: c:\*5048.msg Wed 2023-08-30 08:27:37.685: --> 250 2.6.0 Ok, message saved <Message-ID: <b85e7102-1635-3c42-c022-f6ca33c1e0c7@>> Wed 2023-08-30 08:27:37.690: <-- QUIT Wed 2023-08-30 08:27:37.690: --> 221 2.0.0 See ya in cyberspace Wed 2023-08-30 08:27:37.709: SMTP session successful (Bytes in/out: 1621/588)

Log with current version 115.1.1: ue 2023-08-29 10:32:50.363: Accepting SMTP connection from 192.:61026 to 192.:587 Tue 2023-08-29 10:32:50.378: --> 220 mail ESMTP MSA Tue, 29 Aug 2023 10:32:50 -0600 Tue 2023-08-29 10:32:50.399: <-- EHLO [192.] Tue 2023-08-29 10:32:50.399: --> 250-mail. Hello [192.*] [192.], pleased to meet you Tue 2023-08-29 10:32:50.399: --> 250-AUTH LOGIN CRAM-MD5 PLAIN Tue 2023-08-29 10:32:50.399: --> 250-8BITMIME Tue 2023-08-29 10:32:50.399: --> 250-ENHANCEDSTATUSCODES Tue 2023-08-29 10:32:50.399: --> 250-PIPELINING Tue 2023-08-29 10:32:50.399: --> 250-CHUNKING Tue 2023-08-29 10:32:50.399: --> 250 SIZE Tue 2023-08-29 10:32:55.600: Connection closed Tue 2023-08-29 10:32:55.600: SMTP session terminated (Bytes in/out: 22/257)

Error console: Sending failed; An error occurred while sending mail: Unable to establish a secure link with Outgoing server (SMTP) 192.* using STARTTLS since it doesn't advertise that feature. Switch off STARTTLS for that server or contact your service provider., exitCode=2153066790, originalMsgURI= 3 MessageSend.jsm:362:32 

   fail resource:///modules/MessageSend.jsm:362
   _deliveryExitProcessing resource:///modules/MessageSend.jsm:711
   sendDeliveryCallback resource:///modules/MessageSend.jsm:765
   OnStopRunningUrl resource:///modules/MessageSend.jsm:1424
   onerror resource:///modules/SmtpService.jsm:195
   _onNsError resource:///modules/SmtpClient.jsm:490
   _actionEHLO resource:///modules/SmtpClient.jsm:870
   _onCommand resource:///modules/SmtpClient.jsm:519
   _parse resource:///modules/SmtpClient.jsm:360
   _onData resource:///modules/SmtpClient.jsm:417


Any ideas?

StartTLS works fine in 102.13.0 but when I upgrade past that and up to 115.1.1 - StartTLS is broken and doesn't allow me to email out. Log with 102.13.0 version: Wed 2023-08-30 08:27:37.455: Accepting SMTP connection from 192.*:61492 to 192.*:587 Wed 2023-08-30 08:27:37.475: --> 220 mail ESMTP MSA Wed, 30 Aug 2023 08:27:37 -0600 Wed 2023-08-30 08:27:37.532: <-- EHLO [192.*] Wed 2023-08-30 08:27:37.532: --> 250-mail. Hello [192.*] [192.*], pleased to meet you Wed 2023-08-30 08:27:37.532: --> 250-AUTH LOGIN CRAM-MD5 PLAIN Wed 2023-08-30 08:27:37.532: --> 250-8BITMIME Wed 2023-08-30 08:27:37.532: --> 250-ENHANCEDSTATUSCODES Wed 2023-08-30 08:27:37.532: --> 250-PIPELINING Wed 2023-08-30 08:27:37.532: --> 250-CHUNKING Wed 2023-08-30 08:27:37.532: --> 250 SIZE Wed 2023-08-30 08:27:37.546: <-- AUTH CRAM-MD5 Wed 2023-08-30 08:27:37.546: --> 334 PE1E Wed 2023-08-30 08:27:37.594: <-- QnJhZ== Wed 2023-08-30 08:27:37.594: Authenticating Brad... Wed 2023-08-30 08:27:37.596: Authenticated as Brad Wed 2023-08-30 08:27:37.596: --> 235 2.7.0 Authentication successful Wed 2023-08-30 08:27:37.612: <-- MAIL FROM:<brad> BODY=8BITMIME SIZE=1429 Wed 2023-08-30 08:27:37.612: --> 250 2.1.0 Sender OK Wed 2023-08-30 08:27:37.624: <-- RCPT TO:<j*> Wed 2023-08-30 08:27:37.626: --> 250 2.1.5 Recipient OK Wed 2023-08-30 08:27:37.638: <-- DATA Wed 2023-08-30 08:27:37.640: --> 354 Enter mail, end with <CRLF>.<CRLF> Wed 2023-08-30 08:27:37.656: Message size: 1429 bytes Wed 2023-08-30 08:27:37.668: Outbreak Protection: Processing skipped. Authenticated connection. Wed 2023-08-30 08:27:37.685: Message creation successful: c:\*5048.msg Wed 2023-08-30 08:27:37.685: --> 250 2.6.0 Ok, message saved <Message-ID: <b85e7102-1635-3c42-c022-f6ca33c1e0c7@>> Wed 2023-08-30 08:27:37.690: <-- QUIT Wed 2023-08-30 08:27:37.690: --> 221 2.0.0 See ya in cyberspace Wed 2023-08-30 08:27:37.709: SMTP session successful (Bytes in/out: 1621/588) Log with current version 115.1.1: ue 2023-08-29 10:32:50.363: Accepting SMTP connection from 192.:61026 to 192.:587 Tue 2023-08-29 10:32:50.378: --> 220 mail ESMTP MSA Tue, 29 Aug 2023 10:32:50 -0600 Tue 2023-08-29 10:32:50.399: <-- EHLO [192.] Tue 2023-08-29 10:32:50.399: --> 250-mail. Hello [192.*] [192.], pleased to meet you Tue 2023-08-29 10:32:50.399: --> 250-AUTH LOGIN CRAM-MD5 PLAIN Tue 2023-08-29 10:32:50.399: --> 250-8BITMIME Tue 2023-08-29 10:32:50.399: --> 250-ENHANCEDSTATUSCODES Tue 2023-08-29 10:32:50.399: --> 250-PIPELINING Tue 2023-08-29 10:32:50.399: --> 250-CHUNKING Tue 2023-08-29 10:32:50.399: --> 250 SIZE Tue 2023-08-29 10:32:55.600: Connection closed Tue 2023-08-29 10:32:55.600: SMTP session terminated (Bytes in/out: 22/257) Error console: Sending failed; An error occurred while sending mail: Unable to establish a secure link with Outgoing server (SMTP) 192.* using STARTTLS since it doesn't advertise that feature. Switch off STARTTLS for that server or contact your service provider., exitCode=2153066790, originalMsgURI= 3 MessageSend.jsm:362:32 fail resource:///modules/MessageSend.jsm:362 _deliveryExitProcessing resource:///modules/MessageSend.jsm:711 sendDeliveryCallback resource:///modules/MessageSend.jsm:765 OnStopRunningUrl resource:///modules/MessageSend.jsm:1424 onerror resource:///modules/SmtpService.jsm:195 _onNsError resource:///modules/SmtpClient.jsm:490 _actionEHLO resource:///modules/SmtpClient.jsm:870 _onCommand resource:///modules/SmtpClient.jsm:519 _parse resource:///modules/SmtpClient.jsm:360 _onData resource:///modules/SmtpClient.jsm:417 Any ideas?

Modified by Matt

All Replies (1)

Matt
Matt
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I have edited your original question to make the actual error visible. The error says the server is not configured to offer starttls so Thunderbird does not try. This may have been a change in the most recent version, I have no idea. Previously it may have just tried and either failed or not in establishing a connection.

The log also confirms this as STARTTLS is not offered as a response to the EHLO command Wed 2023-08-30 08:27:37.532: <-- EHLO [192.*] Wed 2023-08-30 08:27:37.532: --> 250-mail. Hello [192.*] [192.*], pleased to meet you Wed 2023-08-30 08:27:37.532: --> 250-AUTH LOGIN CRAM-MD5 PLAIN Wed 2023-08-30 08:27:37.532: --> 250-8BITMIME Wed 2023-08-30 08:27:37.532: --> 250-ENHANCEDSTATUSCODES Wed 2023-08-30 08:27:37.532: --> 250-PIPELINING Wed 2023-08-30 08:27:37.532: --> 250-CHUNKING Wed 2023-08-30 08:27:37.532: --> 250 SIZE

The SMTP server needs to be configured to offer STARTTLS is the simple answer.