SMTP connection has abruptly stopped working

Did you recently install an SSL on your BlueHost account? Did that somehow interfere with your DNS settings for your email? Or perhaps your BlueHost account is “protecting” you from FastMail if it is not detecting that you are securely connecting to your FastMail account. It might be as easy as changing your port settings, and FastMail can tell you what those should be. I’m sure they offer a secure port setting.

I’ve been on Bluehost since June and SSL has been active since then too. And I’m using the port settings that FastMail gave for connecting via SSL.

As far as I know, nothing has changed from a few days ago when Newsletter was working fine so I’m very frustrated.

Perhaps you can explain how Newsletter is supposed to work. Correct me if I’m wrong but I’m assuming it goes something like this when I click on “send a test mail message”:
1. The Newsletter program running on the Bluehost server where my instance of WordPress is running calls some mail service (PHP?)
2. Newsletter provides the name of the SMTP server, the port number, and the login credentials that I specified in the Newsletter Settings tab.
3. Bluehost’s mail service attempts to connect but can’t.

Is the “did not match” error message something that Bluehost’s mail service is generating or is it something that Fastmail’s server is saying in response to the connection attempt?

Also, does the “CN” mentioned in the error message refer to a CNAME? Is there something I need to specify for my domain like an A record or a CNAME record or something?

Thanks for the suggestions – I need more!

Did some more poking around and found this article:
https://www.thenewsletterplugin.com/test-newsletter-delivery-mailtrap

So I tried to follow the instructions and here’s what happened:
1. I opened a Mailtrap account and copied the host, port (25), username, and password into the SMTP section of Newsletter. The instructions say “without enabling SMTP”, so I changed the “Enable the SMTP” setting to “No” and hit “Save”. It responded with “SMTP configured but NOT enabled.”

2. I gave it a test email address and hit “Send a test mail to this address”. It kind of hung. The page’s tab in my browser got the spinning circle and it times out.

3. I tried port 465 too. Same thing. I tried turning TLS on. Same thing.

4. I tried port 2525 and it immediately failed: “connection refused”.

So now I’m confused. I had the “Enable the SMTP” setting set to “No” so why did it attempt to connect to mailtrap? I clearly don’t understand what “Enable the SMTP” means – can someone explain?

Also, what can I conclude from the Mailtrap test not working?

Thanks!

I am only just starting with Newsletter myself, but had had some experience with BlueHost, so if your SSL is not recent, I think my best suggestion now is to just call FastMail and/or BlueHost support. Email should be email, so somebody ought to be able to tell you where the two services are not shaking hands properly. They might ping-pong you back and forth between the two services a couple of times, but if you take careful notes (or screenshots) of what they tell you, hopefully you’ll be able to reconcile them.

Hi, that kind of error can be explained this way: you try to connect to the SMTP server (with SSL). Bluehost is blocking the connection returned responding in place of fastmail with his own SSL certificate. So the certificate does not match.

Report to blueost that problem, asing if they’re blocking outgoing SSL connections to that SMTP server.

Stefano.

In case anyone else hits this problem in the future, I thought I’d write up how it all turned out.

I reached out to Bluehost’s tech support and they found that their security package, Mod_Security, was blocking the connection. Evidently they were able to whitelist the rule that Mod_Security had been applying and now everything seems to work.

Thanks, Stefano, for pointing me in the right direction. Thanks, Bluehost, for being responsive and helpful.