![]() Now - guess what … Exchange does support plaintext-logins when configured correctly, but only using the method "LOGIN". If a self-signed certificate does not exist, create the certificate with the command openssl req -new -x509 -days 365 -nodes -config stunnel.cnf -out. TorGuard offers OpenVPN obfuscation, Stunnel, OpenConnect, and Shadowsocks. If the E-Mail-Server does not support "PLAIN", E-Mail-Notifications will fail - typically with "Authentication mechanism not supported". Fast 24/7/365 support No logs, no leaks, 100 private Supports Windows. PfSense (our version is 2.1.5-RELEASE, but I guess other versions are also affected) seems to support several Authentication mechanisms for SMTP (at least that's what I gathered from the various files), but it ALWAYS uses "PLAIN". This creates a private key, and self-signed certificate. The mail server logs do not reveal anything more. ![]() ![]() We are using Stunnel 5.13 and below are the config file content and the the client PC logs. make cert This will run the following commands: openssl req -new -x509 -days 365 -nodes -config stunnel.cnf -out stunnel.pem -keyout stunnel.pem. We cannot get stunnel SMTP to work with Office 365 mail server. While researching the issue that pfSense won't send using our Exchange 2010 Server I found the underlying cause for it. Generating the stunnel certificate and private key (pem) In rder to generate certificate and corresponding private key, simply do a. The problem is not exactly with Office 365 Mail servers - rather with Exchange (and potentially other mailservers as well):
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