Email weirdness

I just noticed something. I have two email accounts, a primary account and a secondary account. I use the secondary for Web sites, etc., that require a contact address but I may or may not visit again. I receive email from both accounts, of course. However, when sending mail, I noticed that if I try to send a message from my secondary account, I get a bounce message from the Time-Warner server telling me that the message cannot be sent as configured and to check the SMTP server settings. I then have to change the message sender in the email to my to send the message. Or, if I switch the user name to in the Outgoing server settings for the secondary email account, the message is sent without a problem. I noticed that the email address (user name) on the Outgoing server for the secondary account ( is different than the Incoming Mail Server user name ( for that account. However, if I change the Outgoing server user name to on that secondary account, I can send email from that address but then cannot send email from my primary address! Because Mail will change the user name for the Outgoing server on both accounts so that they are identical for each account. That is, it will change the Outgoing server user name on my primary account to Of course, then I am unable to send mail from my primary account, so I have to change it back, and the initial problem returns. I have JPGs showing the preferences panels if this isn’t clear. Is this fixable?

In Mail (on the Mac at least) are you using a different set of (named) Outgoing server settings for each email address, or using the same settings for both (while and just changing the username/password combination)?

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In Mail settings, there is a list of SMTP servers, each of which has a User Name. You also have a set of Accounts, each of which has a list of Email Addresses (of which one is selected).

Time Warner is enforcing a rule that the From: email address matches the SMTP server userid. That is, you can’t send mail “from” TWC that is for a different email.

Make sure that:

  • You have two SMTP servers defined in Mail > Settings > Accounts > (any non iCloud account) > Server Settings > Outgoing Mail Server (SMTP) > Account > Edit SMTP Server List. One server should use the primary User Name (email address) and the other should use the Secondary
  • The Server settings for the primary account has the primary SMTP selected in Server Settings
  • The secondary account has the secondary SMTP selected

I can’t tell from your problem description if you’re already set up this way, or if you just have one SMTP server defined and you’re editing it.

The setup looks like this for the secondary account. The Outgoing settings are the same except for the username. As follows:

I think you only have one server defined, so when you change the User Name it is updating that one server – which therefore affects both the accounts that are using it.

Click on “Time-Warner SMTP server” and select Edit SMTP Server List. You need two SMTP servers set up, with different names (e.g. Time-Warner Primary and Time-Warner Secondary). Setup the same settings except for the User Name on teach.

Then go back and select the right server for each account, and then edit the list again. It should show that each one is “in Use By Account” to the right account.

I think there’s a setting in Mail somewhere that effects whether it will only use the SMTP server you select or will consider them to be a list of alternate servers, from which it can pick one. But I don’t see that setting now.

As it stands (I’m using Catalina, by the way), under Mail>Account, I see the list of accounts. Each of the Time-Warner accounts (under the Preferences menu) has the same “description,” and both use my primary email address for the username (email address). Is it merely a question of giving each a different name?

OK. I did that, set up two server names with separate usernames but now the primary server refuses to send mail. I can only send from the secondary for some reason!

OK. Fixed them both. I had to update the Outgoing port address and authentication method, both of which were incorrect for some reason. Port should be 587 and auth. should be password. Now both email address seem to be sending correctly.

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