Mac Mail / send from WorkMail Alias

Question

Hi there,

This could be an Apple problem, but it could also be an AWS problem. I have an alias set up on my WorkMail email address. If I use WorkMail's webmail, I can send from that alias by manually typing the alias address into the From field. Cumbersome, but it works.

In Mac Mail, I have added the alias as an additional email address on the relevant account. This previously also worked fine. "Previously", however, being a long a time ago. It hasn't worked for (possibly) years. I can select the alias when sending, and Mac Mail happily thinks it has sent from that alias. However, looking at the sent items in webmail, the sender address is my primary one, not the alias. And, of course, looking at the email received, it's from the primary address.

I've tried the only basic measure I could think of, to delete the additional email alias in Mac Mail and re-add it, to no avail.

Do you think this issue is WorkMail, or Mac Mail? Or a configuration issue somewhere? Does anyone else have the same issue?

Thanks,
Graham

robinkaws · Accepted Answer

HI Graham,

I'm sorry to inform you that in this case this is a limitation of AWS WorkMail. Sending from an alias is only supported in Windows Outlook and the WebMail. https://docs.aws.amazon.com/workmail/latest/userguide/email-messages.html#send_alias

Kind regards,
Robin

andreialecu · Answer

Hello Robin,

Is there any way to elevate this to the WorkMail team to be fixed?

We're using IMAP for what it's worth. What is Windows Outlook doing different for it to work, that Mac clients cannot do?

We're considering moving away from WorkMail due to the lack of this feature, but we'd really prefer not to.

Thanks!

ghp · Answer

It's possible to add and use outgoing WorkMail aliases in macOS Mail (tested on Mail v16 on macOS 15.4.1).

1. Open the Mail app and use the menu bar to navigate to **Mail** &rarr; **Settings** &rarr; **Accounts**
2. Select your WorkMail account and then click on the **Account Information** tab.
3. Under the **Email Addresses** dropdown, select **Edit email addresses...** and add all of the aliases you would like to use for outgoing mail.

The new entries will now show in the **From** dropdown when composing an email.

ghp · Answer

This is possible, but the solution is a bit convoluted.

In macOS Mail (tested with v16), you'll need to create both Email addresses and use a custom **Outgoing Mail Account** that uses [SES SMTP credentials](https://docs.aws.amazon.com/ses/latest/dg/smtp-credentials.html).

## Configure SES and generate SMTP credentials
1. First, you'll need to [configure an SES domain identity or a series of mail identities](https://docs.aws.amazon.com/ses/latest/dg/creating-identities.html). 
2. [Next, you'll create SMTP credentials](https://docs.aws.amazon.com/ses/latest/dg/smtp-credentials.html).  Deviating slightly from the docs, the IAM policy I used allows both`"ses:SendEmail"` and `"ses:SendRawEmail"` actions.

Take note of your region and submit a request to move out of the sandbox.

## Add alias email addresses to Mail client
1. Open the Mail app and use the menu bar to navigate to **Mail** → **Settings** → **Accounts**
2. Select your WorkMail account and then click on the **Account Information** tab.
3. Under the **Email Addresses** dropdown, select **Edit email addresses...** and add each alias you would like to use for outgoing mail.

## Configure a custom outgoing SMTP server for your Mail account
1. Open the Mail app and use the menu bar to navigate to **Mail** → **Settings** → **Accounts**
2. Select your WorkMail account and then click on the **Server Settings** tab.
3. For the **Outgoing Mail Account** field, select **Edit SMTP Server List...**
4. Create a new table entry.  In **Server Settings** form, uncheck the **Automatically manage connection settings** option.  
   - **User name** will be your SMTP username
   - **Password** will be your SMTPM password 
   - **Host Name** will take the form `email-smtp..amazonaws.com`
    - Enter `587` for **Port**
    - Check **Use TLS/SSL**
    - Select **Password** from the **Authentication** dropdown

With the outgoing mail server configured, you should now be able to send emails using any of the SES identities you created.  As a reminder, to receive mail at those addresses, you'll need to create account aliases or groups in Workmail for your user.

Using SES as your outgoing SMTP server also works on Thunderbird (tested with v147.0.1).

Mac Mail / send from WorkMail Alias

Configure SES and generate SMTP credentials

Add alias email addresses to Mail client

Configure a custom outgoing SMTP server for your Mail account

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