Email stopped working

About months back my email sending went from working fine to a blase of red errors across the screen. I did start looking into it and to be honest I can’t remember my original setup. So I quickly opted for the PDF and manual send. Unfortunately I have just realised I must have missed one. I was wondering why the bank account was so low until I did a deep dive. I downloaded the latest version. Slightly better the test function works.
I have a set up a private stmp server and it tests fine. I get a test message at my account.
When I try to use email for a customer it just hangs.

I had the very same thing happen yesterday, version 19.7.60.
I had not changed anything except regular updates installed.
All email settings looked good, but I re-entered username and password, hit test and, as before successfully sent email to me.
Then went back to try and send an invoice to one of my other email addresses and it was working again.
It was the first time this month I had tried emailing an invoice so I’m not sure which version it started in.
But I was getting a big red error message, customer did not receive the email but I received my copy of it.

@Andrew_Armstrong, what actual version number are you using? I just tested the process end-to-end on v19.7.64 and everything works fine. (I refer to emailing a transaction to an email address not connected to Manager in any way, not just to sending the test email from the Email Settings page.)

Just updated to latest before I tested. 19.7.64

I have several email accounts and will use them for testing. I have a y7 account so it’s not connected to my hosting account.

As I said when I realised I was nearly broke because no one had paid me I started just sending pdfs.

I did spend quite a few hours trying different accounts and settings on multiple occasions.

After the update tonight I had the test emails. But not from the invoice.

I just tried again. It just sits scrolling the send bars

I did just get a time out error

System.Net.Mail.SmtpException: System.Net.Mail.SmtpException: The operation has timed out.
at System.Net.Mail.SmtpClient.Send(MailMessage message)
at ManagerServer.HttpHandlers.Businesses.Business.Email.Post()