Cannot connect with TSL/SSL

[jimcavoli]

Yeah, I think I misinterpreted your question a little - glad you're all set though!

[TestDesk]

Good day @all

I hope you are well. I am happy to be with you and to work with you on solutions and feedbacks.

Currently, I have the following problem, short summary:

• FreeScout installed and mailbox set up - works.
• Checked email settings (system) with a test email - works
• Mailbox set up for incoming email - works

Now the problem:
Sending an e-mail via the mailbox (SMTP) does not work.

The following error message appears:

Expected response code 220 but got code "500", with message "500 Unrecognised command"

I have checked the settings for SMTP several times. With the same settings I was able to set up Thunderbrid without any problems.

I took my settings from the official description, see screenshot.

What I noticed:
As soon as I set the encryption from TLS to NONE, the sending works.

Is it a BUG or have I overlooked something?

Thanks in advance for your help.

[nebulon]

@testdesk your settings do seem to be ok, we use the same settings on our FreeScout instance just fine.

Do you have any additional plugins installed in FreeScout? Generally if encryption set to None, it should still perform StartTLS upon connection so you should still be fine there. However I do wonder what the difference might be here.

Are there any further hints in the FreeScout log view? (the one built into FreeScout itself)

[TestDesk]

Hello @nebulon
Wow! That's a reaction time

I don't have any plugins installed.

The log from FreeScout shows the following (The last 4 entries):

Can I look somewhere to see if StartTLS was really used?

THX

[imc67]

@testdesk on two FreeScout instances I use this:

SMTP: mail
Port: 2525
Encryption: no

[TestDesk]

Hello @imc67

Unfortunately, this does not work for the mailboxes, but only for the system settings, at least not for me.

I just tried it, error. I know the settings, they also work with Wordpress and Nextcloud very fine.

THX

[nebulon]

@testdesk hm so also not really more information from FreeScout on the error.
Freescout does not have the Cloudron mail addon enabled, since a common use-case is to use external mailboxes as well. This is why it is correct to use the regular mailserver domain in this case my.example.com

@girish can correct me if I am wrong here, but I don't think the mail server even allows non secure transfer anyways, so if encyption set to "no" it is fine as well.

Still I have to see if I can reproduce this with a new FreeScout instance against the Cloudron mail server later today.

[girish]

@testdesk Setting encryption to NONE is correct setting when FreeScout is installed on the same server as Cloudron mail. When FreeScout is installed in another server, then you have to use TLS.

The reason is a bit esoteric. Internally, Cloudron uses containers and the mail container is called 'mail'. Many apps don't work properly if you try to connect with the hostname as 'mail' but the TLS certificate says 'my.domain.com' (because of hostname mismatch). So, for historic reasons, we do not enable TLS for connection within the server itself. In this case, FreeScout is in same server as mail server and thus TLS option is not available. This is totally safe because the full connection is within the server. If you move your freescout to another server, then remember to put it to TLS.

[girish]

I have put a doc note here - https://docs.cloudron.io/apps/freescout/#cloudron-mailbox

[ianhyzy]

@girish I've copied the info from the screenshot here (Freescout and cloudron are on the same machine; mailgun is configured as the outbound SMTP provider in Cloudron settings; there are two mail-enabled domains) but I'm getting an error about the port being closed:

Could this be my firewall/ISP or did I misconfigure something?

[micmc]

@ianhyzy Try PORT 2525 with TLS/SSL encryption

Andy

[ianhyzy]

@micmc Got the same port blocked error with that:

[micmc]

@ianhyzy Try NO encryption?

[ianhyzy]

@micmc same error

[micmc]

@ianhyzy I'm guessing your 'mail' mx is the cloudron one and that ALL email settings are enabled and GREEN for the domain you use for your FreshScout?

[ianhyzy]

@micmc Yup, green light and works with other apps

[micmc]

@ianhyzy I meant the status like this for the specific domain

[ianhyzy]

@micmc yup, all good:

[girish]

@ianhyzy said in Cannot connect with TSL/SSL:

Could this be my firewall/ISP or did I misconfigure something?

Yes, most likely. Is port 587 open in your firewall ? Also, if this server is at home, do you have loopback NAT working on your router?

[micmc]

@ianhyzy Your SMTP outbound is set as RELAY not as DIRECT this is something I was wondering because normally Cloudron should sety this automatically at installation time if your SMTP status is set. It seems to me that it might means you've set an outbound SMTP service on this domain and you now try to use the direct settings.