Moving printer to LAN, it's unable to send email.

darkcorner

In a small office there is an old network printer configured to send scans to an email address.
Up until last month, the network was immediately downstream from the router, 192.168.1.0.
I installed pfsense and now there is a LAN (192.168.121.0) where the printer has been moved together with all the PCs.
The printer gets its DHCP IP address from pfSense and Win10 PCs can both print and scan with its software. So everything is apparently working.
We want to continue sending the scans directly from the printer to the email address, but an error (not better identified in the documentation) is always returned.
I made all the suggestions that I read in some articles on the net.
On pfSense I also opened all LAN ports.
But the error remains.
I can't figure out what could possibly block the communication, assuming it's pfSense's fault.

Bob.Dig

@darkcorner Please make a network diagram.

SteveITS

@darkcorner What is the email/SMTP service being used?

michmoor

What does the firewall logs show?

darkcorner

As I said, I can't find any errors in the pfsense logs.
I find the error in the printer; or rather the error code because there is nothing more than explaining to me what the problem is, not even in the documentation in my possession.

The diagram

(( Internet by optic fiber 1000/1000 ))
           |
       [router]
           |
      [FritzBox] ====== Phones
           |
       [pfSense] --- [Switch DMZ] --- [NAS]
           |
     [Switch LAN] ---- [Printer]
         ||||
[PC1] [PC2] [PC3] [PC4]

We are using an SMTP server at an external ISP.
I was using port 465 and SSL/TLS for mailbox authentication.
These are the same settings and credentials that are used on Thunderbird, so they can't be wrong.

After several attempts, I set the authentication security to OFF and now I have no more error messages.
Tomorrow, Monday, attempts will be made directly from the printer. I, remotely, cannot run scans.

In my opinion, the problem may be that the printer (very old) uses a security level that is too old for the standard of the ISP.
I just want to be sure it's not pfSense blocking my connection.

Bob.Dig

@darkcorner said in Moving printer to LAN, it's unable to send email.:

In my opinion, the problem may be that the printer (very old) uses a security level that is too old for the standard of the ISP.

Doesn't make much sense because it has worked before, right?
A diagram with ip addresses would be preferred but also I don't see how an external email service could have problems with pfSense unless the prior router did more than we know.

darkcorner

@bob-dig said in Moving printer to LAN, it's unable to send email.:

Doesn't make much sense because it has worked before, right?

Right, but I started checking pfSense because I started from the usual user statement: "Since there is the new network, it doesn't work".
But in that period they also changed ISP. Credentials and settings remained the same, but (maybe) their previous ISP probably accepted an older SSL version.