ACTION REQUIRED: Set your SMTP password

[Ryan Schmidt]

On Nov 17, 2020, at 23:30, Clemens Lang wrote:

> Hi Ryan,
> 
> On Tue, Nov 17, 2020 at 10:17:29PM -0600, Ryan Schmidt wrote:
>> Could you provide more guidance on how to do this in Apple's Mail.app
>> on macOS, iOS, iPadOS?
> 
> I don't use Mail.app, so I had to check on this.
> 
>> Do we just edit our existing email account and add another SMTP server
>> to the list and hope that Mail.app knows how to select the right one
>> depending on the email address I select when I compose an email, or
>> that it will fall back to the second SMTP server if the first one
>> doesn't want to deliver the mail?
> 
> Unfortunately it seems Mail.app really isn't the most intelligent here.
> You can configure multiple SMTP servers, but it will only ever use the
> default one for your current account, regardless of what sender address
> you are using. If your current default server rejects the email,
> Mail.app offers you to choose a different SMTP server, but then makes
> that SMTP server the default. This will obviously cause problems the
> next time you switch sender addresses, because our SMTP only lets you
> send as your address.
> 
> See also this stackoverflow post, that discusses the issue:
> https://apple.stackexchange.com/questions/169062/use-only-smtp-server-without-a-mailbox
> 
> 
>> Or do we need to create an entirely new email account for the
>> macports.org address, set that account to use that new SMTP server,
>> and I don't know fill in garbage values for the incoming mail server
>> portion?
> 
> That seems to be the way to go, unfortunately. Mail.app won't let you
> fill in garbage as the incoming server, either, though.

I have for years already had my MacPorts address set up in a dummy Mail.app POP3 account that has garbage (a hostname that does not exist) for its incoming mail server. I don't remember why I set it up this way. I had it set to use the same SMTP server as my main IMAP account.

Now I've added the new MacPorts SMTP server to the list, but when I try to select it (or any of my other configured SMTP servers actually) for this dummy account, Mail.app changes it back to the previous selection after a few seconds. Maybe there is just something weird about this old Mail.app account and I will try making a new one.

A problem with having it set up this way is that your sent MacPorts mail is stored in a separate sent mail folder for this account on your Mac, rather than in the IMAP sent mail folder of your primary email account where you might want to have it.


> We may have to
> setup an IMAP server that accepts your login data, but does not actually
> give you any mail (since you don't have a mailbox on mail.macports.org).

Interesting idea. This might cause problems though if Mail.app insists on trying to store sent mail on the IMAP server which is what it would usually do.

Actually it looks like for IMAP Mail.app accounts you can specify where to store sent mail, so maybe that would work well after all.


>> The Settings screen of your web app says to use "encryption: STARTTLS
>> and "authentication method: AUTH PLAIN" but Mail.app doesn't refer to
>> such terms. There is an "Automatically manage connection settings"
>> checkbox. Should that be sufficient? If not, what should we select?
> 
> The automatic method should be sufficient. If you uncheck that box,
> you'll get the option to select these mechanisms, but that shouldn't be
> necessary.

Right, if you uncheck the box you get options, but none of the options mention "STARTTLS" or "AUTH PLAIN".