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https://answers.microsoft.com/en-us/msoffice/forum/msoffice_o365admin-mso_dep365-mso_o365b/smtp-server-doesnt-support-starttls/3bf73694-75f4-49e6-9bb8-baa8132677e5
May 04, 2017 · For more information, please refer to Option 1 (SMTP client submission) section of this article and check if all settings are correct. If all settings are correct and you can’t send out email using Office 365 account either, I recommend you test if the Office 365 server is working properly for this account for SMTP client submission.
https://community.spiceworks.com/topic/1477540-smtp-server-downsides-of-tls
Mar 15, 2016 · From a quick Google I don't think IIS SMTP supports opportunistic TLS, which is kind of surprising but then again maybe not. Tbh I wouldn't let the IIS SMTP service anywhere near the internet anyway, I would look at setting up some kind of perimeter relay based around Postfix or if you want to use Windows look at stuff like hmail or xwall or mailenable or basically anything other than IIS.4/5(37)
https://community.spiceworks.com/how_to/132978-smtp-relay-for-non-tls-enabled-devices-office-365
I just wanted add there is an even easier method to getting non-TLS devices talking to Office 365. In my situation we had an invoice processing system which did not support TLS. The vendor's recommendation was to do what this article describes, which is to stand up a …
https://support.microsoft.com/en-us/help/4014125/how-to-configure-iis-smtp-for-outgoing-tls-authentication
Mar 03, 2017 · For more information, see KB 3169958 Important notice for Office 365 email customers who have configured connectors. Because of this requirement, customers who use IIS SMTP Virtual Server to send data such as relay content, reports, and fax messages may have problems finding a channel through which to select the necessary certificate.
https://messageops.com/smtp-relay-with-office-365/
The one thing to keep in mind with sending via SMTP is you still have to authenticate if you want to use the Office 365 servers. It seems most applications and devices support SMTP authentication, the part they typically don’t support is TLS. Using this you can use devices that don’t support TLS with Office 365.
https://support.microsoft.com/en-us/help/2464556/failed-tls-connection-between-unified-communications-peers-generates-a
Nov 14, 2019 · Windows Server 2012 does not support the Schannel CTL functionality that was present in earlier versions of the Windows Server operating systems. For more information about how Windows Server 2012 manages trusted certificates, read the "Management of trusted issuers for client authentication" section of the following Microsoft TechNet article:
https://techcommunity.microsoft.com/t5/office-365/mail-relay-to-office-365-from-iis-smtp-relay/td-p/40862
Since about a month we cannot relay email from our IIS SMTP Relay to Office 365. This has worked for a long time, therefore I do not get why it is not working anymore. ... The remote SMTP service rejected AUTH negotiation. Hope you guys can help me out here. ... SMTP Server with TLS 1.2.
https://docs.microsoft.com/en-us/exchange/mail-flow-best-practices/how-to-set-up-a-multifunction-device-or-application-to-send-email-using-office-3
Determine what version of TLS your device supports by checking the device guide or with the vendor. If your device or application does not support TLS 1.2 or above: Use direct send (Option 2) or Office 365 SMTP relay (Option 3) for sending mail instead (depending on your requirements).
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