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Inbound Email Delivery Issue – TLS Mode Mismatch (Implicit TLS vs STARTTLS)
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- Inbound Email Delivery Issue – TLS Mode Mismatch (Implicit TLS vs STARTTLS)
Topic: Inbound Email Delivery Issue – TLS Mode Mismatch (Implicit TLS vs STARTTLS)

by cre8tress on Thursday, September 18, 2025
Hello Dynu Support,I am troubleshooting inbound email with your Store/Forward service. My server is correctly accepting implicit TLS connections, but your relays appear to attempt STARTTLS. This causes TLS handshakes to fail, which is unrelated to authentication.Evidence:My server accepts implicit TLS on port 2525 (working test):openssl s_client -connect server.petadorn.com:2525 -servername server.petadorn.com </dev/nullCONNECTED(00000003)depth=2 C=US, O=Internet Security Research Group, CN=ISRG Root X1verify return:1depth=1 C=US, O=Let's Encrypt, CN=R13verify return:1depth=0 CN=server.petadorn.comverify return:1---Certificate chain 0 s:CN=server.petadorn.com i:C=US, O=Let's Encrypt, CN=R13...SSL-Session: Protocol : TLSv1.3 Cipher : TLS_AES_256_GCM_SHA384Verify return code: 0 (ok)This shows the certificate (CN=server.petadorn.com) is valid and TLS negotiation succeeds.Exim log shows STARTTLS attempts failing (not authentication):2025-09-18 23:10:29 TLS error on connection from www.dynu.com [162.216.242.29]:59728 (SSL_accept): error:0A000126:SSL routines::unexpected eof while reading2025-09-18 23:19:48 TLS error on connection from www.dynu.com [162.216.242.29]:59750 (SSL_accept): error:0A000126:SSL routines::unexpected eof while reading2025-09-18 23:27:34 TLS error on connection from [192.168.0.112]:60170 (SSL_accept): timed outThese errors happen when your relay connects using STARTTLS against a port configured for implicit TLS. That is a mode mismatch, not a username/password issue.Request:Please confirm that your MX servers (mx1.dynu.com and mx2.dynu.com) can deliver to my server (server.petadorn.com) on port 2525 (or 26) using SSL/TLS (implicit) instead of STARTTLS.If you test delivery with implicit TLS, the handshake will succeed, and mail should flow correctly.Thank you,Pamela
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Author | Topic: Inbound Email Delivery Issue – TLS Mode Mismatch (Implicit TLS vs STARTTLS) |
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cre8tress Joined: 4/23/2025 |
![]() Thursday, September 18, 2025 11:35 PM
Hello Dynu Support,I am troubleshooting inbound email with your Store/Forward service. My server is correctly accepting implicit TLS connections, but your relays appear to attempt STARTTLS. This causes TLS handshakes to fail, which is unrelated to authentication.Evidence:My server accepts implicit TLS on port 2525 (working test):openssl s_client -connect server.petadorn.com:2525 -servername server.petadorn.com </dev/nullCONNECTED(00000003)depth=2 C=US, O=Internet Security Research Group, CN=ISRG Root X1verify return:1depth=1 C=US, O=Let's Encrypt, CN=R13verify return:1depth=0 CN=server.petadorn.comverify return:1---Certificate chain 0 s:CN=server.petadorn.com i:C=US, O=Let's Encrypt, CN=R13...SSL-Session: Protocol : TLSv1.3 Cipher : TLS_AES_256_GCM_SHA384Verify return code: 0 (ok)This shows the certificate (CN=server.petadorn.com) is valid and TLS negotiation succeeds.Exim log shows STARTTLS attempts failing (not authentication):2025-09-18 23:10:29 TLS error on connection from www.dynu.com [162.216.242.29]:59728 (SSL_accept): error:0A000126:SSL routines::unexpected eof while reading2025-09-18 23:19:48 TLS error on connection from www.dynu.com [162.216.242.29]:59750 (SSL_accept): error:0A000126:SSL routines::unexpected eof while reading2025-09-18 23:27:34 TLS error on connection from [192.168.0.112]:60170 (SSL_accept): timed outThese errors happen when your relay connects using STARTTLS against a port configured for implicit TLS. That is a mode mismatch, not a username/password issue.Request:Please confirm that your MX servers (mx1.dynu.com and mx2.dynu.com) can deliver to my server (server.petadorn.com) on port 2525 (or 26) using SSL/TLS (implicit) instead of STARTTLS.If you test delivery with implicit TLS, the handshake will succeed, and mail should flow correctly.Thank you,Pamela
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Friday, September 19, 2025 4:18 AM