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Unable to connect to SMTP server requiring STARTTLS

Good afternoon,

I am installing a new implementation of WHD after a server crash. I am unable to connect to our smtp server to send mails. We are running a smtp server @ 192.168.91.7 on port 587 STARTTLS.

When saving the connection in Outgoing email accounts I get the following error:

Preferences were updated successfully. However, the following error occurred while attempting a connection with the SMTP server:

Permission denied: connect

Any idea why I am unable to send via this SMTP server. (we had no problems on the old box, but it was a slightly older version of WHD)

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Accepted answers

sum_giais

Do you have any security software that blocks smtp mail messaging? I've seen some antivirus software block that by default.

All comments

sum_giais

Try ruling out SolarWinds and use powershell to test mail.

Also might be worth looking into what versions of tls are enabled on each server (both smtp and orion).

https://docs.microsoft.com/en-us/dotnet/framework/network-programming/tls

https://docs.microsoft.com/en-us/powershell/module/microsoft.powershell.utility/send-mailmessage?view=powershell-7

johnmani

The Centos box (mail server) allows:

Accepted TLS12 128 bits AES128-SHA256

Accepted TLS12 128 bits AES128-SHA

Accepted TLS12 256 bits AES256-SHA256

Accepted TLS12 256 bits AES256-SHA

Accepted TLS12 128 bits AES128-SHA

Not sure how to check what versions of tls are on the WHD box, it is Windows server 2012.

When trying to send an email from an open ticket I receive the error:

Could not send e-mail to USER <USER@USERDOMAIN>
due to the following error:

Could not create transport for E-Mail messages: Permission denied: connect

johnmani

Also:

Encountered error while attempting to create transport for sending email: com.macsdesign.whd.util.EmailMessageController$CouldNotCreateTransportException: Could not create transport for E-Mail messages: Permission denied: connect

When checking the email history

sum_giais

Do you have any security software that blocks smtp mail messaging? I've seen some antivirus software block that by default.