Email healthcheck notification: "Relay error: Connect to smtp.live.com timed out"

[RoundHouse1924]

@girish
https://port25check.cloudron.io/ produces an error, as the cert is only for api.cloudron.io

[girish]

@roundhouse1924 that's expected. it's not a website and not meant to be connected via http/https. It's only on port 25. you can try telnet port25check.cloudron.io 25 .

[JOduMonT]

Is anybody try one of these delisting process ??

https://sender.office.com

This one seams to be specifically for live.com and ...

https://support.microsoft.com/en-us/supportrequestform/8ad563e3-288e-2a61-8122-3ba03d6b8d75

https://sendersupport.olc.protection.outlook.com/snds/index.aspx

I did the 2 first one, the first is pretty quick you receive an email and validate if the IP of your server is in their internal block list,
the second is a form is a little bit more elaborate they ask for error message and if you have a website related to that domain.

[jayonrails]

Hi,

I have the same problem on my Cloudron right now:

Relay error: Connect to port25check.cloudron.io timed out. Check if port 25 (outbound) is blocked

Port 25 is not blocked.

[nebulon]

Can you run telnet port25check.cloudron.io 25 via SSH on your server to see if it works?

[jayonrails]

Hi,

it does work on my server:

telnet port25check.cloudron.io 25
Trying 165.227.67.76...
Connected to api.cloudron.io.
Escape character is '^]'.
works
Connection closed by foreign host.

Is it important? I am using Postmark as a mail relay on all my outgoing mails, so I think it is not neccesary to have port 25 open in general, because it is never used?

[nebulon]

If you use a mail relay for all your domains, then this should not be relevant. I do wonder why it tests for it then and also why the check fails, since the code also just checks like that. Can you open the mail status tabs on all domains to see if this was just a temporary issue?

[jayonrails]

@nebulon said in Email healthcheck notification: "Relay error: Connect to smtp.live.com timed out":

If you use a mail relay for all your domains, then this should not be relevant.

Thanks for clarification!

@nebulon said in Email healthcheck notification: "Relay error: Connect to smtp.live.com timed out":

an you open the mail status tabs on all domains to see if this was just a temporary issue?

I will check and let you know if I found something.

[RoundHouse1924]

I had one domain using an external relay and having port 25 closed on the VPS. The above error was present, but disappeared when port 25 was opened.

So, the port 25 check seems to be unnecessary and confusing for domains that use external relays.

[girish]

@RoundHouse1924 said in Email healthcheck notification: "Relay error: Connect to smtp.live.com timed out":

So, the port 25 check seems to be unnecessary and confusing for domains that use external relays.

The port 25 check is skipped for domains with a relay. If you find otherwise, please let us know, cause it's a bug. I just tested it with a relay and it is skipped.

[RoundHouse1924]

@girish
The situation I described was with v7.3.6 when I had only one outgoing domain and it used an external relay.

Now with v7.4.1, I have 3 outgoing domains. One via the same external relay; the other 2 using the internal SMTP. Port 25 is open on the VPS and all 3 status lights are green.

So, in order to test your answer, I blocked outgoing Port 25 on the VPS firewall.

As expected, the 2 direct domains go red.

However, the external relay domain's Cloudron status page shows:-
MX record = Current value: [not set]
DMARC record = Current value: [not set]
SMTP Status Outbound SMTP (Relay) = Connection timeout

Looks to me that, with Port 25 closed, the SMTP check is made, but times out.

The puzzler is to know what could be causing the MX and DMARC record checks to fail --- just because Port 25 is closed.

EDIT:
With Port 25 closed, Uptime Kuma and Tiny Tiny RSS cannot do their stuff, so I've now reopened it.

[girish]

Strange, why would Uptime Kuma and TTRSS fail with port 25 closed ?

Here's what I did:

• Block the outbound port 25 - iptables -A OUTPUT -p tcp --destination-port 25 -j DROP

• Check status:
  

• Unblock - iptables -D OUTPUT 1

• Check status again:
  

[girish]

And when a relay is configured:

[RoundHouse1924]

Strange indeed, but I blocked the VPS Port 25. Whilst blocked, I restarted Kuma and Tiny but to no avail.

All up and running now with 25 unblocked.