Hi, I am continuing to encounter errors in configuring the smtp server. I am sure the smtp server is not having problems because other applications on the same fleet server, are connecting correctly: Error encountered: { "message": "Validation Failed", "errors": [ { "name": "SMTP options", "reason": "mail error occurred: sending mail: unable to dial smtp host: SMTP connection error: read tcp 172.21.0.3:38764-\u003e35.XXX.XXX:126:465: timeout i/o" } ], "uuid": "2ae00f95-be98-4fc2-a04b-3390e313142b" } smtp_settings : {enable_smtp: true, sender_address: "support@company.it", server: "smtps.company.co.uk", port: 465,...} authentication_method : "authmethod_login" enable_smtp : true password : "cB1#i4YT^uWHlpW" port : 465 sender_address : "support@company.it" server : "smtps.company.it" user_name : "support@company.it" i tried to check availability via telnet and openssl from the container but i get this error: [root@itl-cslapp-67 ~]# docker exec Fleet openssl s_client -connect smtps.company.it:465 OCI runtime execution failed: exec failed: unable to start container process: exec: "openssl": executable file not found in $PATH: unknown

@Ibra you might want to screen logs for sensitive data before you send them along.

Also, welcome to use markdown

for inline code and triple

for code blocks. SMTP/S are both pretty "simple" in regards to getting working. Would double-check settings in the Fleet UI as these logs you are posting refer to several differing domains. Was awhile ago when setting one up myself, but believe 465 is deprecated, 587 is standard. Also do not think there are any "firewall" rules for the Fleet server that would be filtering or blocking. What do you have for infra? Baremetal? vps?

VPS, I tried now with office, to rule out problems with my mail server, but I get the same error