Email Questions

I am looking into automating a lot of my accounting work now and one of the things that I am looking into is Emailing Invoices.

  1. If I have understood the documentation correctly, one cannot schedule emailing invoices? Is this correct?

Enter your own Email address. Entering an address here will not change the address from which the email is sent. But the new address will be shown as a “reply-to” address.

  1. Is this correct? Where do you put the email address where the email is sent from or does manager use the username as the email address sent from and this field above is just the reply email address? If so, I would recommend that this field be called Reply or NO-reply Email Address

For security reasons, Manager does not support port 465. Begin by trying port 587. Most SMTP servers will support both ports, so this should generally not be an issue.

  1. @lubos what security reasons would this be? My own investigation of using Port 465 versus 587 lead me to conclude that Port 465 SSL is actually more secure than Starttls on the grounds that Port 465 starts and ends encrypted, but Starttls actually starts unencrypted and upgrades the connection to encrypted. I think a lot of the confusion comes from the assumption that people think that Port 465 only uses SSL, but it can be secured using TLS.


it is a reply mail address. you can configure custom smtp mail to suit your needs.

port 587 is the one recommended for message submissions by mail clients to mail servers. all submission servers or MSAs are mandated to implement SMTP authentication, a process wherein an SMTP client is required to log-in and authenticate with the mail server it is connecting to before it can be granted access. because port 587 is associated with these submission servers, then the use of port 587 typically implies the use of authentication. this authentication mechanism prevents the propagation of spam and malware.

port 465 was first introduced as an idea to encrypt messages using SSL. but it will need using separate ports, one for plaintext messages and another for encrypted messages. in SMTP, the port chosen for encrypted connections was 465 which was never recognized by the body responsible to develop internet standards as an official port for SMTP. a plaintext SMTP connection can be upgraded to a secure connection encrypted by either TLS or SSL by simply executing the STARTTLS command only if the server supports it.

I understand the history behind Port 465 and Port 587 and I understand why the body responsible for Internet Standards wants to change to Port 587. However, my point still stands. Port 465 is still more secure than Port 587 on the basis that Port 587 upgrades the connection to a secure one. It starts off unencrypted.

Actually this is for technical reasons. Manager is written in .NET and standard library doesn’t support 465. To support 465 I’d need to include 3rd-party library which I was reluctant to do as 465 has been depreciated and 587 is new standard anyway.

I appreciate that. Technically 465 has been deprecated, but I think in reality its actually more secure. I was just wondering if you had seen something that I had missed. Thank you for clarifying that.