CODEWITHSUNDEEP
iissslsmtp
mjohnjoseph
mjohnjoseph

Reputation: 1

IIS SMTP TLS encryption

I enabled TLS in IIS SMTP Virtual Server with a self-signed server certificate. Made sure that the certificate has the FQDN of the server. Checked the TLS encryption checkbox in Virtual SMTP > Properties > Delivery tab > Outbound Security.

When I try to send mail using Pickup folder in c:\inetpub\mailroot the email does not get delivered with TLS. Also, the TLS encryption checkbox becomes unchecked automatically.

Do you know what might be causing this problem?

Regards John

Upvotes: 0

Views: 4365

Answers (2)

foxontherock
foxontherock

Reputation: 1841

I think you did the same error as me... all I wanted is my outgoing emails to be tls encrypted and remove the "gmail security warning" on my messages.
If you're using the integrated IIS SMTP service from windows server, you don't need to install any certificates to do that.
The solution IS NOT to hit the "require tls encryption" in the "Access" tab.
Instead, go to the "Delivery" tab, hit "Outbound Security", then check "TLS encryption".

Upvotes: 3

Fred
Fred

Reputation: 9

Self-signed certs does not work for SMTP, that's why it's unchecked.

Worth noting that IIS SMTP can only use implicit TLS where the connection is encrypted from start and not the wide used explicit TLS where a secure connection starts after the STARTTLS command is sent.

Upvotes: 0

Related Questions