How to send an email with a different “from” address in outlook

Choose the Outlook email address you want to send from

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What to Know

• Select From in the header of an Outlook new message, reply, or forward.
• Choose Other Email Address.
• Select an address or type one in and select OK.

This article explains how to send an email with any From address in Outlook for Office 365, Outlook 2019, 2016, 2013, and 2010.

How to Send an Email With Any From Address in Outlook

When you create a new message in Outlook, the email address you used to sign in to Outlook appears in the From field. If you have multiple email accounts and want to use an email address that is not associated with the account you opened in Outlook, edit the From field of the message and enter any email address you want.

To use any email address in the From field of a message you are composing in Outlook:

Start with a new message, reply, or forward in Outlook.

Go to the message header area and select From.

If the header area does not show the From field, go to Options and, in the Show Fields group, select From.

Select Other Email Address.

If the email address appears in the list, select the address and go to step 6.

In the From text box, type the email address that you want to appear in the From field.

Select OK.

Compose the message and select Send.

What May Happen When You Send With a Custom From Address in Outlook

Note that freely editing the From field is allowed in the email standards. Depending on the outgoing (SMTP) email server used for the default Outlook email account and the address you use in the From field, a number of things can happen:

• A server such as Gmail will let you send mail from a custom address to Gmail if the address is configured in their own settings for sending.
• If an address is not configured for sending in Gmail, Gmail changes the address in the From field to the one used with the account you set up in Outlook. The address used in the From field in Outlook is preserved in the X-Google-Original-From header line.
• The outgoing mail server may send the message, but the recipient’s email server may reject it because the server is not configured to send messages using the address in the From field. You will receive a delivery failure notification email.

What Can You Do When a Message Fails to Send Using a Custom From Address?

If you do run into message delivery problems with using a different From address in Outlook, you have two options:

Rob Woodgate is a writer and IT consultant with nearly 20 years of experience across the private and public sectors. He’s also worked as a trainer, technical support person, delivery manager, system administrator, and in other roles that involve getting people and technology to work together. Read more.

If you have multiple email accounts in Microsoft Outlook, you can change the “From” address in a new email. This is quicker than swapping to a different inbox, and lets you send emails from different addresses, even if they aren’t your own. Here’s how—with some caveats.

Outlook lets you send emails from any account you’ve set up in the email client, but also from any other email address, even if you haven’t set it up. That sounds worrying—and in some circumstances it is—but there are legitimate reasons to use this functionality as well as nefarious ones.

We’ll go through how this works, and how email providers prevent people from using it for harmful purposes.

Quickly Switch between Email Addresses

First, let’s go through the entirely legitimate process. To change the “From” address, you need to make the “From” field visible. Open a new email in Microsoft Outlook and then click Options > From. This will make the “From” field visible.

To change the “From” address, click the “From” button and select one of the email addresses you’ve added to Outlook.

The email address in the “From” field will change, and when you send an email, it will be sent from that address.

If all you want to do is quickly switch between your email accounts when you’re sending emails, that’s all there is to it.

But, what if you want to send an email from an account that you haven’t added to Outlook? Well, Outlook will let you do that, too, under certain circumstances.

Compose a new email and then click on the “From” button again. From there, select the “Other Email Address” option.

In the panel that opens, type in the address you want to send an email from and click “OK.”

Now send the message as normal. Will the email send, or will you get a delivery failure notification? And if it does send, will the recipient see it as coming from the email address you used, even if it’s not yours?

Both of those answers are dependent on who your email provider is.

How Email Providers Handle Messages Sent From a Different “From” Address

Microsoft Outlook itself, and other email clients like Thunderbird or Apple Mail, don’t do any checking on the email address from which you send. The client simply sends the email to your provider’s SMTP server (Simple Mail Transfer Protocol server, often called a mail server), and lets the SMTP server decide what to do with your email.

What will happen with your email is entirely dependent on how your email provider’s SMTP server is configured.

The big email providers, such as Google, Microsoft, Apple, and Yahoo, use something called SPF (Sender Policy Framework), DMARC (Domain-based Message Authentication, Reporting, and Conformance), and DKIM (Domain Keys Identified Mail) to prevent (among other things) people from sending emails from addresses (spoofing) that aren’t theirs. How each provider handles this situation is a bit different.

Google simply ignores the new email address you’ve used, and the recipient will see your Gmail address. In our example in the screenshots, Outlook sent the email to Gmail’s SMTP server, which worked out that the email address we were sending from—[email protected]—doesn’t belong to us, and so instead the recipient received an email from our original Gmail address.

Microsoft-hosted email accounts do things a bit differently. If you try to send an email from an address that you don’t have permission to access, a Microsoft email server (commonly referred to as an Exchange server) will not send the email. You’ll receive a Delivery Failure Notification instead.

However, if your company uses a Microsoft Exchange server to handle its email, it’s normally configured to allow you to send an email from any account you have access to, even if that account has not been added to your Outlook.

For example, if you have permission to send emails from “[email protected],” Outlook will send the email to the Exchange server and check that you have permission to send emails from the address. The server will then send the email to the recipient, regardless of whether you’ve added the “[email protected]” account to Outlook.

Other email providers will usually handle emails with the “wrong” address in a similar way to either Google or Microsoft. The easiest way to find out is to try it in Outlook and see what happens. Check your provider’s terms first though, as some might have a provision against doing this.

How Do Scammers Use Fake “From” Addresses?

Large email providers have all kinds of checks and protocols to try to find spam and phishing emails, including emails sent from a fake address. Scammers and phishers don’t use the big providers—they set up their own SMTP servers and send emails through those instead.

Scammers set up their SMTP servers to allow all of their emails though, forcing large providers like Google and Microsoft into a constant arms race to detect and stop scam and phishing emails from getting into your inbox.

Your email provider, be that Microsoft, Google, Apple, Yahoo, or any other provider, scans the email headers of every email you receive. One of the things these companies look for is that the “From” address matches the “Sender” address. If they don’t match, especially if they’re from completely different domains, that’s a red flag. It’s not the only thing that email providers use to determine if an email is suspicious, but it’s one of the more important checks they do.

In addition to your primary e-mail address (your “real” e-mail), you can also add a number of aliases to your e-mail account. When you send mail, your primary e-mail address is always listed as the sender. However, if you wish, you can also send e-mail with an alias or another name in the sender field. This guide describes how to set this up. This guide is written for Outlook 2016, but the information can also be applied to other e-mail servers.

Step 1: add the extra e-mail address to your account

• In Outlook 2016, click on File >Account settings >Account settings
• Then click on New (if you are not yet on the “E-mail” tab, go there first).
• Select Email Account and click Next
• In the next window, choose Manual setup or additional server types and click Next
• Select POP or IMAP, and then click Next.

• Fill in your name and the alias you wish to use to send e-mail.
• For Account type, fill in: POP3
• For Incoming mail server, fill in: none
• For Outgoing mail server (SMTP), fill in your server address: smtp-auth.ru.nl
• For Logon information, fill in your RU username and password. Tick the box: Remember password
• Press the button More settings
  
• In the Outgoing server tab, check My outgoing server (SMTP) requires authentication. Then select Use same settings as my incoming mail server.

• Go to the tab Advanced. For Outgoing server (SMTP), enter: 587 and for Use the following type of encrypted connection: TLS.
• Click OK.
• Click Next.
• Click Finish.

Step 2: Set up Outlook for multiple sender addresses

• First click Send/Receive, then on Send/Receive Groups andDefine Send/Receive Groups

• Click on the Edit button
• Select your new e-mail account
• Uncheck the Receive mail items box
• Click OK and then Close

How to send email from the different address in Outlook?

By default, the active email account is the sender address while creating a new email in Outlook. But in some times, you want to send email from different address, for example, in account [email protected], use [email protected] as sender address to send email. How can you deal with this job?

Actually, in Outlook, you can choose other email address as sender address in Message box.

In the Message box, click at From, a list with all email accounts’ addresses will be displayed, you can choose one as the sender address.

If there is no desired email address listed, you can click Other E-mail Address from the From drop down list, and type the email address you want in the From textbox in Send From Other E-mail Address dialog, click OK to change it as the sender address.

If you want to always use the default account as sender while replying emails, you can enable the Always reply with default account option in Kutools for Outlook.

Free install Kutools for Outlook, and then do as below steps:

1. Click Kutools > Options in Options group.

2. In the Options dialog, under Reply tab, check Always reply with default account option. Click OK to close the dialog.

From now on, whichever account you are in, the default account will be used as the sender while replying emails.

Always reply with default account

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How to Send an Email From a Delegated Account in Outlook

If you have been delegated access to someone else’s email account, you can send an email as that person from Microsoft Outlook. You can only send emails as people who have delegated their email account to you through Google Apps.

When you email a message as someone else in Outlook, no reference to you or your account will appear in the email. However, the email message you send will appear in your personal Sent Items folder and will not appear in the Sent Items folder of the person from whose account you sent the email. Information Technology recommends that you always blind copy the owner of the email account so that they can have a copy of email messages sent in their name.

Send an email from a delegated account

1. Open a new email message.
2. Click the Options tab.
3. In the “Show Fields” group, select “From.” The “From” field will appear above the “To” and “Cc” fields at the top of your email message.
4. Click the [From] button and select “Other Email Address.”
5. Enter the full email address in the blank or search for the email address by clicking [From…]. You will only be able to send emails from an email account that you have been given delegate access to.
6. Click [OK].
7. Enter the rest of your email information and click [Send].

Keywords: send an email as someone else, send email as my boss, send an email as an org, send email from proxy account, proxy email, proxy access, delegate access, delegee

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Instructions for how to send an email from a different email address you have access to within Outlook for Windows.

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Outlook.com can now properly send e-mails from other e-mail addresses without saying “on behalf of.” We’ll show you how to set it up.

Related stories:

• How to use two-step verification with your Microsoft account
• How to use Outlook.com e-mail with keyboard shortcuts
• How to add and use Outlook.com e-mail aliases

Microsoft recently announced that Outlook.com had 400 million active accounts . In the announcement, they also revealed a welcome new feature for users who send e-mails from other accounts in Outlook.com. In the past, e-mails sent from Outlook.com would say, “on behalf of,” so there was no way to hide the originating Outlook.com account. Now you can send e-mails from other accounts that look exactly as if they were sent from the originating e-mail service provider (Gmail, Yahoo Mail, Comcast, etc.). Here’s how to set it up:

Step 1: Go to Settings > More mail settings. Under the “Managing your account” section, click on “Your email accounts.” Scroll to “Add an email account, then click on the “Add a send-and-receive account” button.

Screenshot by Ed Rhee/CNET

Step 2: Enter your e-mail account information, including e-mail address and password, then click Next. If you’re having trouble getting Outlook.com to log in to your other e-mail account, click on the link to “Advanced options.” From here, you can set specific POP3 and SMTP server settings. Keep in mind that in order to add a Gmail account, you’ll first need to enable POP download from your Gmail account first. Also, if you’re using two-step verification, you’ll need to create an application password to use with Outlook.com.

Step 3: Once you’ve successfully logged in to your other e-mail account with Outlook.com, you’ll be asked to choose where you want the e-mails to be saved. Choose a new folder or an existing one, then click “Save.”

Step 4: After your e-mail account has been added, click on the “Go to your Inbox” button.

Screenshot by Ed Rhee/CNET

Now when you begin composing a new message, you can click on your name to open a drop-down list of e-mail addresses you can use.

Screenshot by Ed Rhee/CNET

That’s it. If you want the default “From” address to be the account you just added, go back to settings where you added the new account and scroll all the way to the bottom. You’ll find a drop-down menu of accounts than you can choose as your default “From” address.

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Small businesses often use multiple email addresses to route correspondence to the appropriate areas in the company, such as sales or general information. Responding to these queries from one umbrella email address can come across as unprofessional. However, Microsoft Outlook provides a way to handle multiple email accounts and addresses all on one machine.

Add Email Account

Click the “File” tab and select “Info.”

Click the “Add Account” button under Account Information.

Follow the on-screen prompts to configure and add the new email address.

Change Display Address

Compose the message you want to send from a different email address.

Click the “From” button and select the account name you want to display when sending this message.

Click the “Send” button to transmit the message with the different display name.

Many people have figured out how to send an email to many email addresses with a ; (semi-colon) or use the To button to add lots of addresses in the To or Cc fields.

However if you think about it, any one of those recipients can click Reply to All and instantly send an email to a ready made mailing list. The giving away of everyone’s email address to all and sundry could be considered as bad manners and if any one of those recipients was a little unscrupulous might even harvest those email addresses for other purposes such as SPAM.

It would only take one of the recipients to have a computer infected with Malware or a Trojan virus and hey presto all email addresses could be harvested for lots of annoying SPAM or online threats.

So how can I send one email to many people without giving away everyone’s email address?

The answer is to use the Bcc (Blind Carbon Copy) field. Any address placed in this field will be hidden from view to recipients. So if you put all your email addresses in the Bcc field no-one receiving the email will see anyone’s email address and it will be marked To ‘Undisclosed Recipient’

I can see the To and Cc field – but I cannot see a Bcc field.

Create a new email and then click on View in the menu bar at the top. Select Bcc Field and hey presto there it is.

Some people do not seem to get Emails sent as Bcc

Unfortunately there are some particularly crude and aggressive SPAM filters out there that may view an email sent without any address in the To field as dubious and therefore SPAM. If this is the case you could try including your own email address in the To field (after all you are giving everyone your address by sending the email). Also some ISPs (notably BT Broadband) sometimes put limits on how many people you can send one email to. If this is the case you might try sending in batches of less than 20 recipients per email.

I get a message “Too Many Recpients”

Most email providers restrict how many recipients you can send one email to

Shared mailboxes allow a group of users to view and send email, and share a calendar from a common mailbox.

If your mailbox has been set up and opened then this guide will explain how to add it to the ‘From’ field so that you can send an email from your shared mailbox

Before you start.

• You will need to have gone through the process of setting up your shared mailbox before you can open it.
• You will need to have opened your new shared mailbox

Instructions

Setting the ‘From’ field to send messages from the shared mailbox

1. Compose a new email. If the From field is not already visible (above the To. field) select Options > From within the new email window.

Fig 1. Select ‘Other E-mail Address’ in the ‘From’ field
View a larger version

2. Select the From field > Other Email Address. When prompted enter the Display Name or email address of the shared mailbox and select OK. When the From field is selected this should now display the email address of the shared mailbox as an available option.

Fig 2. Send from Other E-mail Address window
View a larger version

The new message window can now be closed. If prompted to save the message as a draft select No, as the ‘From’ setting has already been applied.

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FAQ: How to send mail on behalf of another user?

Microsoft Outlook allows one user to send mail on behalf of another user. You can set up delegate permissions so that someone can send messages on your behalf.

Delegate user for send mail on behalf

Procedures: (For Outlook Web App)

The current version of Outlook Web App will not let you delegate permissions for other colleagues to view your Mailbox. You can grant permissions for mailbox or calendar. For additional permissions to the calendar and Mailbox are administered from the full Outlook client and cannot be controlled through OWA.

Procedures: (For Office 2016/2013/2010)

• Start Outlook.
• From the ribbon menu, click “File“.
• Click “Account Settings” -> “Delegate Access”
  

  For Office 2016/2013	For Office 2010

• Click the “Add” button.
  

Select a user from the global address list, click “Add“, and click “OK“.

Choose “Editor” from the list of Permissions for the Inbox. You are recommended to tick the option “Automatically send a message to delegate summarizing these permissions” as well. Then click “OK“.

Send messages using on behalf

On user given Delegate permission to send messages on your behalf, do the following procedures: (For Outlook Web App)

• Log in to your mailbox using Outlook Web App.
• Click new New mail above the folder list. A new message form will appear in the reading pane.
• Click the more options menu , and then click Show From.
  

Right click the email address and choose Remove.

On user given Delegate permission to send messages on your behalf, do the following procedures: (For Outlook 2016/2013)

• Open a new email message.
• From the ribbon menu, choose “Options“, in the “Show Fields” session, click the “From” button. Then the “From” selection button will be shown. Click on it and select “Other Email Address. “.
  

Select the owner from the global address list or type the account name. Then fill in other fields and the message body as needed, and click Send.

When the message is received, the From Field looks similar to ” Delegate on Behalf of Owner ” where Delegate is equal to the name of the user with Delegate permissions and Owner is equal to the name of the mailbox owner.

You can send email as a person or group if you have been granted Send As permissions to that specific user’s mailbox or group. You can send email on behalf of a person or group if you have been granted Send on Behalf permissions to that specific user’s mailbox or group.

Permission to act on behalf of another user or group is commonly referred to as delegate access. The Send As permission is an example of a delegate access permission that can be granted to a user by an administrator. The Send on Behalf permission is another example of a delegate access permission that can be granted to a user by another user. With Send on Behalf permissions, a user may send emails that are marked as, “on behalf of” another user. This is not the same as Send As permissions, which allow emails to be sent as if they actually came from another user. Other delegate access permissions that can be granted to a user include the permission to open and manage another user’s calendar and email.

Note:
This feature is only available if you’re using Office 365 email or other Microsoft Exchange-based email.

This article describes how to send email as, or on behalf of, a person or group using Outlook. For information about how to send email as, or on behalf of, a person or group using Outlook on the web (previously known as Outlook Web App, or OWA) see, KB0011019, Sending email as, or on behalf of, a person or group (for Outlook on the web users).

This article describes how an Outlook user may:

Prerequisites

The steps in this article assume that you have Outlook open on your desktop and have been granted Send on Behalf permissions, or Send As permissions, to the other person’s mailbox or group.

Sending a message as, or on behalf of, a person

To send a message as, or on behalf of, a person, proceed as follows.

1. From within Outlook, click New Email.

A new Message window opens, with your email address in the From field.

1. In the new Message window, click, From, and select the required sender email address from the list of sender email addresses shown.

1. If the required address is not shown, then:
   1. Click, Other E-Mail Address.

The Send From Other E-Mail Address dialogue box appears.

1. In the text box, start typing the required email address.

A list of email addresses appears beneath the text box.

1. Click on the required email address.
2. Click, OK.

The new email address now replaces your email address in the From field.

1. In the To field, add recipients then, in remaining fields, add a subject and the contents of the message as required.
2. Click, Send.

The recipient receives the email message sent on behalf of the user. For example, the From field on the received email is marked as:

From: Billy On Behalf Of David.

Sending a message as, or on behalf of, a group

To send a message as, or on behalf of, a group, proceed as follows.

1. From within Outlook, click New Email.

A new Message window opens, with your email address in the From field.

1. In the new Message window, click, From, and select the group email address from the list of sender email addresses shown.
2. If the required address is not shown, then:
   1. Click, Other E-Mail Address.

The Send From Other E-Mail Address dialogue box appears.

1. In the text box, start typing the required email address of the group.

A list of email addresses appears beneath the text box.

1. Click on the required email address.
2. Click, OK.

The new group email address now replaces your email address in the From field.

1. In the To field, add recipients then, in remaining fields, add a subject and the contents of the message as required.
2. Click, Send.

The recipient receives the email message sent on behalf of the group. For example, the From field on the received email is marked as:

From: Billy On Behalf Of Technical Support Group.

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A long-requested feature to send emails from an alias in Office 365 seems to be finally released. The feature has not been announced yet, but it’s already documented in the service description and seems to work fine.

This new feature should become available for Outlook on Windows this month and for Outlook Online later this year according to the roadmap. But I have tested both and it seems to work in Outlook Online as well.

When you use an alias to send an email from it will be preserved in the From and Reply to field for the recipient. The recipient will see only your alias and not your primary email address.

Enable Send Email from Alias Office 365

The send from alias option is turned off by default, so if you want to use this feature you will need to enable it in the Exchange Online Admin center or with PowerShell.

1. Open the Exchange Admin Center
2. Click Settings >Mail flow
3. Enable Turn on sending from aliases

office 365 send as alias

You can also enable plus addressing if you want to use that as well. Read more about it here.

Using PowerShell

Make sure you have the latest Exchange Online PowerShell module installed when using the PowerShell option. We can enable the feature by setting the SendFromAliasEnabled to True in the organization config:

It can take a couple of minutes until the feature is fully working in your tenant. During my first test, I could send the mail from the alias, but the reply-to field wasn’t set. The recipient just saw my primary email address.

After waiting another 5 minutes and testing it again everything worked as expected.

How to Send as Alias in Outlook

Your Microsoft Office 365 administrator will need to add an alias to your account first before you can use this feature. Users can’t create aliases themself.

To send mail from your alias address in Outlook is pretty simple. Make sure that the From field is displayed (otherwise enable it under options).

• Select From
• Choose Other email address..
• Type your alias and click Ok

The next time you can just select the alias from the dropdown menu in the From field.

I have tested it by sending email from the alias to Gmail and other Exchange Online tenants and everything seems to work. The recipient only sees the alias address and the reply goes back to the alias as well.

How To Send as Alias in Office 365

You can also send emails from your alias address in Office 365 with Outlook Online. The initial setup is the same, you will need to enable the feature with PowerShell as described above.

Step 1 – Add the From field

1. Click on New Message in Outlook Online.
2. Click on the 3 dots
3. Choose Show From in the dropdown menu

Step 2 – Add your Alias Address

Now we will need to add your alias address. The first time we will need to type the address, the next time you can easily select it.

1. Click on From
2. Choose Other email address…

Step 3 – Send as Alias

You can now type in your alias address in the From Field. And when done click on Send.

Wrapping Up

Because the feature to send email as alias in Office 365 has not been official released yet by Microsoft you should be careful with using this for important emails. Just keep an eye on the roadmap or the message in the Admin Center to known when this option is fully supported.

If you have any questions just drop a comment below.

If you’re going on vacation or will be out of reach for a while, changing the reply address for an email can be a useful way to keep in touch. The process is simple once you know how but this being Microsoft, it isn’t as straightforward as it could be.

For example, if you’re sending an email from work but won’t have access to work email but you will be able to access your personal email, you can send an email from work and have the recipient reply to your home. It is one of the many reasons you may need to change a reply to address for email messages in Outlook 2016.

If you need to change the ‘Reply To’ address for email messages in Outlook, this tutorial is for you.

Change the Reply to Address in Outlook 2016

If you or your organization uses Microsoft Exchange servers, users cannot permanently change their reply to address in Outlook. You can modify reply to addresses for individual mails, but not set it permanently. You will have to contact your IT team if you use Exchange.

Typically you would change the reply to address for an individual email or a couple of emails and that would be it. However, if you want to permanently add or change the reply to address you can do that too, except if you use Exchange as already mentioned.

Change the Reply to Address for Each Email

If you only need to change the address for one or two emails, you can make the change in each individual mail.

1. Open a new email in Outlook.
2. Select Options >Direct Replies To in the ribbon.
3. Check the box next to Have replies sent to if it isn’t already checked and hit Select Names.
4. Select an email address from the list or use a ; and type the email address into the box. If using multiple email addresses, separate with a ‘;’.
5. Make sure all addresses are listed in the box next to Reply To at the bottom of the window. Hit Reply To if they don’t to add them.
6. Select OK and Close to go back to the email.
7. The Direct Replies To box should remain gray if it is set up correctly.
8. Complete and send the email as normal.

You can use this method as many times as you like and add as many reply to addresses as you like. Normal usability rules apply though, try not to include every person you know and create endless email chains. Nobody likes those.

Change the Reply to Address Permanently in Outlook 2016

If you want to permanently have all email replies delivered to a different inbox, you can do that too. The upside is that once set, you don’t need to specify addresses every time you send a mail. The downside is that you can only include a single email address rather than multiple addresses.

To permanently change the reply address, you need to delve into Outlook account settings.

1. Open Outlook and select File.
2. Select Account Settings and Account Settings.
3. Select the Email tab and the email address you want to modify.
4. Select Change from the options and the More Settings button on the right.
5. Add the email address in the box next to Reply Email and select OK.
6. Select Next and close the Test window.
7. Select Finish and close the Email Account screen.

Now when you send emails, any replies will be permanently directed to the address you specified in step 5.

Set an Out of Office Reply in Outlook 2016

If you would rather go on vacation without worrying about email or work, it might just be easier to set up an out of office reply. This is a canned response to anyone who emails you telling them you’re not there and will be back on a certain date. In work or at school, this is a courtesy that should be used anytime you’re not around to answer emails.

1. Open Outlook and select File.
2. Select Automatic Replies underneath Account Settings.
3. Now, select Send automatic replies , set the start/end date and time, create an email or use an organizational template, and then select OK.

Now all you have to do is remember to turn it off once you’re back. It might be useful to create a calendar entry reminding you to do that on your return. If you’re anything like me, you will forget and it will be a colleague reminding you, or worse, your boss yelling at you to turn it off!

Using Outlook

It’s fairly easy to change your Reply to address in Outlook. Whether you’re going out of town or you just want to setup a generic email response, you now know how to adjust those settings.

Were you successful in changing you Reply to address? Share your experiences below.

• Context
• Answer
  • Configuring Outlook 2013 / 2016
  • Sending emails from the mailing list

Context

• You have an MIT exchange account .
• You have installed Microsoft Outlook 2013 / 2016 for Windows, which is provided by IST for MIT students, faculty and staff .
• You have set up Outlook 2013 / 2016 for Windows to connect to MIT Exchange (see How do I setup Outlook 2013 for Windows to connect to MIT Exchange for the first time? or How do I setup Outlook 2016 for Windows to connect to MIT Exchange for the first time?)
• You wish to send email using a mailing list or email alias as the listed FROM address.

Answer

MIT’s Exchange environment does not allow outgoing mail with a “fake” FROM address. This prevents sending mail with a FROM address other than the individual sender’s and also prevents the re-directing or “re-disting” of mail. However, there are easy work-around for every mail client program except the web-based Outlook Web Access.

The general solution is to set up a separate email account in your mail program specifically for sending mail with this “fake” FROM address via MIT’s SMTP server, rather than via the Exchange environment. This second account can be configured alongside the personal Exchange account. As an added benefit, this will still allow you to use authenticated SMTP to send these messages, preventing them from being flagged as spam and maintaining the ability to verify the sender of the message.

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You want to benefit from the many advantages of Google Docs and Gmail but need emails to be sent from your Microsoft account? You can do this if you add another email address to Gmail. Once set up properly, you’ll be able to send emails from your Outlook account, Hotmail account, Windows Mail account, or even an alias email you’ve created.

Once configured, Gmail will allow you to choose the email you want your messages sent from whenever you’re composing an email. 👉 ✉️

In this article I’ll demonstrate the process step by step by connecting an Outlook.com email in Gmail. I’ll also show you how this feature can be used in an add-on like Yet Another Mail Merge, which can send mass emails through your newly connected email account.

Add your Microsoft email account to Gmail in 7 simple steps

1. In Gmail, open settings and head to the ‘Accounts and Import’ tab.
2. Under the ‘Send mail as:’ heading, select ‘Add another email address.’

1. Follow the prompts and log in to your Microsoft account.

If you’re not sure whether or not to check ‘Treat as an alias,’ consult this article from Google which spells the decision out very clearly.

1. After you’ve specified your Microsoft account, Gmail will automatically configure the necessary SMTP server, secure connection, and port info. If you run into issues with this step, confirm the specific steps and inputs with your email provider.

1. If it didn’t start automatically, click the button in the settings pane to start the verification process.

1. You should have received a confirmation email from Gmail, either click the link or use the confirmation code provided

1. Confirm desired behavior for the email (optional final step). Choose how you want Gmail to operate when replying to a message and make the newly added account default if desired.

Send an email from your Microsoft account in Gmail

Now that you’ve added access to your Microsoft email or hotmail account, Gmail will give you the option to select the email address you want your message to be sent from when composing a new message.

Configure Yet Another Mail Merge to send a mail merge from your Microsoft account

Using a Microsoft email does not limit you to Microsoft Office. One of the many great reasons to use Google Docs is the ability to access its hundreds of great add-ons. Users of the Yet Another Mail Merge add-on can configure their newly connected Microsoft account to be used for emails they send.

If you don’t know what a mail merge is, or are interested in how you could use YAMM, click here to learn more.

Configure YAMM to send email from your Microsoft account in two simple steps

1. From the ‘Start Mail Merge’ screen, open the ‘Alias, filters, personalized attachments…’ menu.

1. Select the account you wish to use from the ‘Send from:’ dropdown.

Once you’ve configured YAMM to send email from the correct account, we suggest that you immediately run a test mail merge from your account to confirm everything is working. If this is the first time you’ve used your Microsoft account with YAMM, there will be a security check required from Microsoft. They do this to confirm that the emails sent from the YAMM add-on are in fact coming from you.

That’s all you need to add another email address to Gmail, and allow a connected add on to send email from your Microsoft account.

“I have multiple email addresses attached to Outlook 2016, but when I send emails they’re always sent from one address mailbox, which isn’t necessarily the one I’m using at the time.”

Sound familiar? We sometimes find that users have multiple mailboxes set up on their Outlook installations, but no matter which mailbox they are viewing, any emails sent automatically go from a single, “default account” within Outlook. It can be very irritating to manually change the “Send From” address every time you attempt to send an email.

How do I fix this?

Step 1) Open up your outlook and select “File” in the top left-hand corner of your screen.

Step 2) Then select the “Options” button, this will present you with the following screen.

Step 3) Click on the “Mail” Tab and scroll down to the section called “Send Messages”. This will lead you to the following screen.

Step 4) All you now need to do is un-tick the box labelled “Always use default account when composing new messages”, as soon as this is done, click OK on the bottom of the screen and the setting will be applied.

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Not quite what you were looking for?

A number of problems with Outlook can generally be fixed by creating a new mail profile.

How to send email from a different email address than your own in Exchange Online.: the ‘Send as’ and ‘Send on behalf of’ features.

Send as

In most cases, ‘Send as’ is the appropriate choice for delegating mailbox access or sending from a role-based address:

• Enables a person or group (i.e. distribution lists) to send email from their own mailbox that appers to come from a different email adress.
• Replies go to the ‘Send as’ email address.
• If you are sending as a shared mailbox, a copy of the sent message goes to the Sent folder in the shared mailbox. If you added the shared mailbox it as an additional mailbox in your own Outlook, the sent item will appear in your own mailbox’s Sent folder. If necessary, you can move the message to the ‘correct’ Sent folder.
• Works when sending both internal and external email, displayuing the ‘Send as’ email address in the ‘From’ field.

How to ‘Send as’ another email address

Assuming you have ‘Send as’ privileges the email address, select the ‘Send as’ address when compsing an email. The replies go to ‘Send as’ address.

Outlook Windows

1. Click the Options tab, click From > More options to display the From field in your new email.
2. Click the From button and select Other Email Address:

NB – If you can’t see the address in the GAL you may need to manually update your offline address list. Click on the Send/Receive tab in Outlook then Send/Receive Groups. Select Download Address Book.. then OK and allow the sync to complete before trying to add the address again.

Outlook for Mac

Select an email address in the pull-down menu beside the From button:

Outlook Web App

Click the From button to open the drop-down menu showing the email addresses from which you can choose to Send As:

Outlook mobile app (iOS)

Open a new email message and tap the arrow beside your email address at the top of the screen to open the drop-down menu to choose a Send As address:

Send on behalf of

We don’t recommend using this option. It gives someone full rights to manage your mailbox. It lets them to send email as you, directly from your mailbox – this can be set up as purely Send On Behalf by an Admin, but users can use Outlook to Delegate Access to one or more users. Delegate Access gives Send On Behalf rights, access to folders in that user’s mailbox and will change how meeting requests are received by the user.

• Only works on email that is internally routed inside the Exchange Online environment (Exchange to Exchange email) – it does not take effect on email that gets externally routed via the internet. External recipients will not see the Sent on behalf of address in the From field – they will see the actual sender’s email address.
• Replies go to the Send on behalf of address (although recipients inside the Exchange Online environment will also see the actual sender’s address displayed).
• Send On Behalf emails will end up in the sender’s mailbox’s Sent Items folder.
• The mailbox owner needs to assign permissions to other people before they can Send on behalf of them.

NOTE: Delegated Access and Send As permissions can cause conflict if used together: if you grant both Delegated Access and Send As permissions to someone, the Send As feature stops working.

If you Delegate Access rights to your mailbox, the nominee is automatically given Send on behalf of rights.

How many times have you clicked send on an email only to realize a few seconds later that you’ve accidently emailed the wrong person, sent a snarky comment to an entire list of people, or left an embarrassing typo in the first line?

I don’t mind confessing to a couple of email howlers in my past that illustrate exactly how the settings below can be life savers!

• A few years ago, when applying for jobs, I sent a resume to the wrong potential employer. Now, incorrectly addressing a job application is poor form. Unsurprisingly, I didn’t hear back.

• Another time, I typed the “to” address on an important note too quickly and failed to check that the correct address had auto-filled. A day or two later I was left trying to explain to the actual intended recipient why they had never received my important message.

Fortunately, there are a few settings in Microsoft Outlook that can help you avoid these embarrassing moments. Here’s what you need to do.

Disable Auto-Complete for the address line

When you add recipients to a new email in Outlook by typing the address, you’ll notice that Outlook provides suggestions as you type based on your contact list and previously emailed addresses.

Sometimes that’s a useful, time-saving feature. Other times, it creates a high risk that you’ll accidently send an email to the wrong contact. I’ve lost count of the times I’ve received a strange email in my inbox, only to receive a follow up a few minutes later along the lines of: “Sorry! I meant to send that to my colleague Richard in Accounting.”

You might find it easier to simply disable Auto-Complete entirely. Here’s what to do:

STEP ONE

On the File tab choose Options > Mail.

STEP TWO

Under Send messages, uncheck the option Use Auto-Complete List to suggest names when typing in the To, Cc, and Bcc lines.

Turn on MailTips

Every version of Outlook since 2010 has included the MailTips alerts feature, which can help to avoid common email mistakes.

For example, MailTips can be set so that you receive an alert if you’re about to click Reply All to a large recipient list or if you’ve selected a group email address rather than an individual.

Usually, MailTips is automatically enabled. To check that it’s turned on, or to amend the instances in which MailTips will display a warning, follow these steps:

STEP ONE

Open Outlook and select File > Options > Mail. Under MailTips, click MailTips Options. (Note that MailTips will only show if your account uses an Exchange. If you don’t see this option then, sorry, it’s not available to you).

STEP TWO

Check to see that the option Display automatically when MailTips apply is checked and that all of the MailTips to be displayed are selected. Click OK.

Enable deferred sending

Most email clients, Outlook included, are set up to send email as soon as you click Send. That’s where we often get into trouble. Have you ever wished you’d had an opportunity, a few minutes later, to edit a message or stop it from being sent?

That’s where Outlook’s deferred sending rules come into play. By setting up this simple rule, anyone can delay delivery of mail for up to 120 minutes. Here’s how to set it up:

STEP ONE

On the File tab choose Manage Rules & Alert > New Rule.

STEP TWO

In the dialog box that appears, under Start from a Blank Rule, click Apply rule on messages I send, and then click Next.

STEP THREE

Select any conditions you wish this rule to apply to. If you’d like all messages to be deferred, do not select any boxes. Outlook will ask you to confirm that you wish to apply the rule to all messages that you send.

STEP FOUR

Now, in the Select action(s) list, select defer delivery by a number of minutes. You’ll be prompted to edit the rule description. Click on the underlined phrase a number of and enter the number of minutes you’d like your outbound messages to be held before they’re sent. Click OK, then Next, select any exceptions you’d like to the rule (if any), and you’re set!

To send your first message, you need to set up an email account in Snov.io . You can add multiple accounts to your email accounts list. Here’s the instruction on how to set up an Outlook account.

Settings while adding an Outlook account

In your account settings, go to the Email Accounts tab and click the Add button. You will see email account type options – Gmail, SMTP, Outlook, and Exchange.

Select the Outlook option in the pop-up window.

Then, fill in the SMTP Settings:

From name – a name the recipient will see in incoming messages from you.
From email – email address from which emails will be sent.
Username – your Outlook email address.
Password – your password from the email account that you indicated in the Username field.

Fill in the rest of the settings:

SMTP Host – the name of the email server smtp.office365.com SMTP Port – port 587 for email sending and settings for using TLS .
Messages per day – the maximum number of messages that can be sent from this account per day. This parameter shouldn’t exceed the limit set by your provider (if applicable).
Fixed delay or Random delay (in seconds) – the time interval between sending emails. The delay between messages cannot be less than the default one (5 sec).

Next, fill in the IMAP Settings so that we can track replies to campaigns sent from this email account:

IMAP Host – outlook.office365.com IMAP Port – port 993 and settings for using SSL .

If you want to receive a reply to another email address, check the Set a different reply-to address option in SMTP settings and enter the email address you want to get a reply to.

Next, in IMAP settings, check the Use different email accounts for receiving emails option and fill in the following:

Username – the email address you want to receive replies to.
Password – your password from the email account that you indicated in the Username field.

Now check the validity of the entered data by clicking the Send a test email to check connection button.

A connection to the test server will be established. If it is successful, you will see a Success icon.

You may also add a signature to your email account or set up your own custom tracking domain.

Click the Save Settings button and build your first drip email campaign .

Additional settings if the connection failed

Please note that the connection to Snov.io can fail to succeed. You will need to enable two-step verification and create an app password:

1. Set up 2-Step Authentication in Outlook

Setting up two-step verification is a reasonable way to keep your account secure. Besides, it will help avoid difficulties with the connection.

To set up 2-Step Authentication, follow the instructions:

Step 1. Go to Security settings and sign in with your Microsoft account.

Step 2. In the Two-step verification section, choose Set up two-step verification to turn it on.

Step 3. Follow the instructions. You may optionally set up your smartphone with an app password if you sync your Outlook email on the phone.

2. Setting up an app password

An app password is a password generated in a random way that you provide only once instead of your regular password while signing in to an app or device that doesn’t support two-step verification.

To create an app password, take the following steps:

Step 1. Navigate to Security settings and sign in with your Microsoft account.

Step 2. In the App passwords section, choose Create a new app password .

Step 3. Copy the generated app password.

Step 4. Enter the generated app password instead of your regular password to the Outlook email account while setting up a Snov.io account.

That’s all. Watch this in action:

Now you are ready to launch an email drip campaign .

Unannounced but Welcome Update

Exchange Online mailboxes can have multiple SMTP proxy addresses (also known as aliases). One of the addresses, called the primary SMTP address, is stamped on outbound messages. Exchange Online can accept and deliver email addressed to any proxy address for a mailbox, but up to now users have been unable to use their non-primary SMTP addresses when sending messages.

This week, Microsoft rolled out an update to allow clients to send messages using any SMTP proxy address assigned to a user’s mailbox. This is Microsoft 365 roadmap item 59437, which the roadmap says is due for release in June 2021. The early release of a useful new feature is always appreciated, even if I suspect that the feature is only released on the Exchange Online side at present with some client-side work still to come to make the task easier to perform.

Update April 27: Message center notification MC252942 says that OWA will get support for the send from proxy address feature in early May.

Mergers and Acquisitions and Other Uses

Being able to send email using a selected proxy address is useful in several scenarios. For instance, if your company is involved in a merger, your mailbox might have addresses for both the old and new company. This happens to allow users to continue to receive email using their old and new addresses, and while people usually send new messages using the new company email address, it might be that they need to use the old address until the merger is fully closed. More prosaically, people might have addresses accumulated over the years generated using different address schemes.

Figure 1 shows the email addresses available to an account as seen through user settings in the Microsoft 365 admin center. One is the primary address, used by default whenever the user sends email. The others are the proxy addresses. As you can see, a proxy address can use any of the domains registered for the tenant (the accepted domains).

The proxy addresses for a mailbox can be examined using the Get-ExoMailbox cmdlet. Although most of the addresses are SMTP (the uppercased SMTP address is the default), we also see a SIP address for IM communications and an SPO address for use when SharePoint Online generates email on behalf of the user (like a sharing invitation). Some mailboxes have many proxy addresses while others have just a few.

I’m trying to determine if it’s possible in Outlook(2010 specifically) to select the from address on a per-message basis if the user has multiple valid SMTP addresses on their Exchange mailbox. This is one of those things that is apparently un-googleable. For bonus points, it would be awesome if you could set the default from address per-contact.

4 Answers 4

In the message window, switch to the Options tab, then enable “From”. This will add a “From” input above the “To” line. You can put any mailbox for which you have Send As permission.

In the web interface.

• Start a new email
• Click three dots menu and select ‘Show From’
• Right-click your name, select ‘remove’
• Type in the distribution group address you have rights to send as

It will then be a selection in the From drop down going forward.

It looks to me like the OP is asking to choose between multiple SMTP addresses assigned to an individual user’s Exchange mailbox.

You cannot choose from the various SMTP (or other proxy types) set on the user’s mailbox object in the Active Directory in Outlook. @Stephen Jennings describes how to choose a different recipient object to send “From”, but the default SMTP address for the object you select will be stamped on the outgoing message.

The only way to do what you want would be to create multiple recipient objects in the Directory, assign each the appropriate default “From” address, and grant the appropriate user “Send As” permission to them. Then the user can send “From” the appropriate recipient and the address stamped on the outgoing message will be as-expected.

I’d recommend creating Distribution Group objects for the alternate “From” addresses and making the user a member of the groups (as well as granting Send As permission on the groups to the user) so that they’ll receive any replies sent to those addresses.

In general I try to never hand-specify alternate addresses (that is, add addresses not managed by policy) on Exchange recipients and to always use groups to facilitate “alternate” addresses for users. I do this for the reason above, amongst others.

1. Open the File menu

Click File at the top left of your screen.

2. Open the Rules and Alerts window

Click the Manage Rules & Alerts button towards the bottom of the Account Information menu.

3. Create a new rule

Click the New Rule. button

4. Apply the rule to all messages

Select ‘Apply rule on messages I receive’ then click Next. Do not select any options on the next screen and click Next.

When asked if you wish to apply the rule to every message you receive, click Yes.

5. Set who to forward your mail to

Tick the box for ‘redirect it to people or public group ‘. This will forward a copy of the message to another user while keeping a copy in your own Inbox.

Under Step 2 click the ‘ people or public group ‘ link and select the user you wish to forward to from the address list. Click Next.

If you do not wish to add any exceptions to the rule (i.e. all mail will be forwarded) click Next.

6. Enable the forwarding rule

Give your rule a name and click Finish. The rule will now be enabled. Click OK.

7. Turning off forwarding

Click the Manage Rules & Alerts button from the File menu. From the list of rules, untick the box next to the forwarding rule and click OK.

Use the instructions below to forward email from Outlook 2016/2013 for Windows.

How to forward your email from Outlook

1. Open Outlook.
2. Click the Home tab and then select Rules (located toward the center of ribbon).
   
3. Select Manage Rules & Alerts from the drop down.
   
4. Select New Rule.
   
5. Select Apply rule on message I receive located near bottom of list, then click Next.
   
6. Click Next (don’t select anything).
   
7. Click Yes when asked This rule will be applied to every message you receive. Is this correct?.
   
8. On the next list select the following actions (see image below):

The rule should be listed, with the box checked, in the Rules and Alerts window. Click OK and you’re done.

Nowadays, it is quite likely that you have multiple email accounts configured in Outlook.

Especially when working from home, you don’t want to end up sending your business emails via your private account or vice versa.

Also, when you have access to a Shared Mailbox or are a delegate for the mailbox of a colleague, you could find yourself inadvertently send from these mailboxes or forget to select it when needed.

By adding this simple VBA macro to Outlook, you can prevent sending emails from the wrong email address.

Check Sending Account VBA macro

The CheckSendingAccount macro shows you a dialog with your selected sending account or also even the address, for each emails that you send.

There is nothing else that you need to configure or change about your sending routine; You press the Send button and Outlook shows you the following dialog box;

When you send from an address which is different from the primary address of your account, you’ll be notified in the following way;

This can for instance occur when you have a second address (alias) assigned to your account or when sending on behalf of a Shared Mailbox or a colleague or manager as a Delegate.

Press the OK button to send the message or press Cancel to prevent sending the message. When cancelling, you’ll return to your message Draft so you can adjust the sending account and/or From address of the message.

Quick Install

Use the following instructions to configure the macro in Outlook;

1. Download this code-file ( checksendingaccount.zip ) and copy the code from the CheckSendingAccount.txt file or copy the code below.
2. Open the VBA Editor (keyboard shortcut ALT+F11)
3. Paste the copied code in the ThisOutlookSession module.
4. Sign your code so you won’t get any security prompts and the macro won’t get disabled.

ThisOutlookSession module in the VBA Editor.

Macro Code

The following code is contained in the zip-file referenced in the Quick Install. You can use the code below for review or manual installation.

Check Sending Account with an add-in

Instead of using a macro, you can also use an add-in to control or assist you with selecting the right account and/or address when sending an email.

They can give you a prompt similar to the macro or you can define rules so the right account and address is selected automatically.

Some popular add-ins which can do this are;

Safeguard Send by Sperry Software

• Contains many configurable warnings like whenever you …
• …send an email outside your company’s domains.
• …send an email where the From address does not match the signature line.
• …send an email where the From address contains specific words.
• …many more
• Discount code: BH93RF24

MAPILab Toolbox (Message AutoFill module) by MAPILab

• Contains 20 (small) handy modules like Message AutoFill to automatically set the sending account and/or From address based on the folder that you are in.
• Other modules like…
• …vCard Converter
• …Find and Replace
• …Reminders Assistant
• …”Reply All” Forget
• Discount code: 4PM76A8

• Set your desired sending account for every e-mail.
• Sent items are stored in a folder of your choice or deleted immediately if you so choose.
• Public Exchange folders are supported.
• Save your rules on a file server and share them with other users.
• Supported are rules based on the recipient’s address, email categories, contact categories, and folders/mailboxes.