[Solution] - Error: LOGIN authentication failure [SMTP: STARTTLS failed (code: 220, response: ready for tls)]
I was remodeling my e-mail infrastructure and I ran into an issue about my PfSense TLS emailing.I had this error :
![](https://blog.lbdg.me/content/images/2021/01/firefox_31svkQYtd3-1.png)
My configuration looks nice
![](https://blog.lbdg.me/content/images/2021/01/firefox_Bp5nIerKjq.png)
PfSense isn't that good for providing email logs, so I decided to go deeper with a packet analysis. In Diagnotics => Packet Capture
![](https://blog.lbdg.me/content/images/2021/01/image.png)
Focusing on LAN interface and HOST 10.0.0.43 (my internal email server)
![](https://blog.lbdg.me/content/images/2021/01/firefox_K4KdlGQACU.png)
![](https://blog.lbdg.me/content/images/2021/01/image-1.png)
![](https://blog.lbdg.me/content/images/2021/01/firefox_RtrtHdwlOQ.png)
I pressed start, tested the email notification and stopped, then opened the downloaded .cap with wireshard.
![](https://blog.lbdg.me/content/images/2021/01/Wireshark_5oL4h8gWqM.png)
"Unknow CA", PfSense was rejecting my certificate because the CA is unknow, first I was like : how is it possible, I imported it in the Cert manager and then I remembered that it doesn't help for OS checking.
I added the CA this way :
https://blog.lbdg.me/freebsd-adding-self-signed-certificate-authority/
And :)
![](https://blog.lbdg.me/content/images/2021/01/image-2.png)