Mail.app: Select outgoing (SMTP) server per message?

Dear community members,
I'm looking for a solution to the following problem:
I do have multiple e-mail accounts which are configured in the following way: One of them is the master account (let's say [email protected]) added to Mail.app as a POP account. The other ones (let's call them [email protected] and [email protected]) are on different servers and are configured to forward all incoming mail to [email protected] They are, however, not added to Mail.app as additional accounts. That is because it's not necessary for receiving mail with these addresses, since all incoming mail is forwarded to [email protected], anyway, and therefore immediately available in Mail.app.
The problem arises when sending e-mails within Mail.app. I can easily add all three addresses in the "Mail" > "Settings" > "Accounts" settings window by entering them in the e-mail-address-field separated by comma (e.g. "[email protected], [email protected], [email protected]“). This allows me to select the desired outgoing address on a per-message basis in the compose window.
There is, however, a problem with this: This setting means that mail from all three addresses is being sent using the same SMTP server. This can cause problems for domains that do have SPF-records, for example. Therefore, I'd very much prefer to not only select the outgoing mail address on a per-message-basis, but also the SMTP-server I'd like to use. Since Mail.app allows me to add multiple SMTP servers in the account's settings window, I believe there has to be a way to select which one to use on a per-message-basis? Whenever there's a problem with an SMTP-server, a window opens up asking me which of the alternative SMTP servers I'd like to use, instead. This indicates that this function exists – it's just far from obvious for me where to find it in a normal usage scenario.
Does anyone have an idea? Any hint is welcome!
Thanks
Nick

That has nothing to do with it. I ended up working around the problem by changing the account name.
But I still think this is a bug, so I won't mark the topic as answered (a workaround is not the solution).

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I had this problem too but I fixed it today.
Go to the mail menu preferences.
Click on account in question.
Select the outgoing SMTP mail server (the one offline), this has a drop down list, click on the edit server list.
Click on the advanced button.
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Make sure SSL is unchecked (unless your provider requires it, mine does not work with it checked).
Have authentication set to password.
User name should be your email address for that account.
Make sure correct password is entered (for some strange reason my password box was blank on this account).
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Hello Jeba1969
Use Connection Doctor to see what is causing it to be offline, like a incorrect password or a different setting for authentication. Check out the article below to get a start on troubleshooting your issues with sending mail.
OS X Mail: Troubleshooting sending and receiving email messages
http://support.apple.com/kb/ts3276
Mail Setup Assistant
http://www.apple.com/support/macosx/mailassistant/
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haavee:
Thanks for your reply on this thread.
And thanks for the confirmation: Yes, often difficult, and completely unworkable in some cases.
To my surprise, I've been able to find very few people reporting similiar observations. Very little about this issue at all on the web.
I looked for command-key variations on Format --> Make Plain Text, hoping for a block action, but none I tried was any different.
Here is my current view of the issue:
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• The "can't insert" issue, as well as those mysterious rectangle-surrounded blocks, seems very correlated with the presence of html <div> sections in the message. It is awkward to experiment, so I've only done a limited amount. My observations so far:
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Looking at the upper right of the window in which I'm composing this message, there's a button "HTML" that lets me see --and edit-- the underlying HTML. On first glance, there's not enough functionality to, say, efficiently clean up all insert-resistant blocks in a message, but it looks practical to clean up individual blocks, and maybe that's all it would take.    Though I imagine that the user base for these forums is not very different from that of mail.app, I'm guessing adding this function to mail.app isn't even a dim possibity. Oh, well...
I note you are happy with your solution, so I'll try see if a variation of it might help me.
Thanks,
h.2

Is there a way to bypass having to use an outgoing SMTP server?

Hi all,
I'm always mailing from different places with my MacBook, and it's a drag that I have to figure out the outgoing SMTP server the whole time.
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Mail.app: Select outgoing (SMTP) server per message?

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