So, what about using stunnel to use as a relay point instead? Can i not pair stunnel to my mx record on port 25 to create a tls tunnel for the direct send option? I've seen articles for people doing this for option 1 and option 3 (O365 connector) but not option 2 (direct send). Double click on the icon and you can see Double click on the icon and you can see Step 3: Go back to your redis-cli The original file looks like this: Stunnel configuration file for Office 365 SMTP and POP3 Author: MessageOps, www ' Click Run as Administrator (Vista or W7), or click Open (XP) We are getting 'stunnel exited 5 time(s. However, since the sending device/software is not initiating TLS doesn't that mean they're going across the internet in plain text? I think so. I've been working with option 2 (direct send) and have had some success. servers, preparing for headless operation (continued) LILO, configuration with. Now, I'd like to retire the old relay service and use office 365 exclusively for email relay. So we've been using an old microsoft internal relay with tls on outgoing. stunnel-users Config to only listen when connect port is up roartysa. However for some old devices and insanely enough major products like vmware, zerto, and ilo/idrac authenticated email and start tls are not supported. stunnel-users Error -63 when connecting to Office 365 to retrieve emails sedick. #STUNNEL OFFICE 365 CONFIG WINDOWS#Our latest Windows installer includes the OpenSSL FIPS Provider. It can benefit from the FIPS 140-2 validation of the OpenSSL FIPS Provider, as long as the building process meets the OpenSSL FIPS 140-2 Security Policy. So we're using authenticated email with TLS. Stunnel uses the OpenSSL library for cryptography, so it supports whatever cryptographic algorithms are compiled into the library. We're sending emails with option 1 described here.
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