Send Emails Seamlessly from Alias Addresses in Outlook - Mystrika

Tired of juggling multiple email accounts? Unlock the power to send from alternate aliases directly within Outlook and manage all your communications in one place.

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What is an Email Alias and How Does it Work?

An email alias is an additional email address that is linked to your primary email account. Aliases allow you to receive emails addressed to alternate addresses without needing to create entirely separate inboxes.

Defining an Email Alias

An email alias, also known as an alternate or proxy email address, is simply a secondary address tied to your primary email account. For example, if your main email is [email protected], you could create an alias like [email protected].

Any email sent to [email protected] would automatically be routed to your [email protected] inbox. The sender would have no indication that it’s an alias, the email would look just as if it was sent directly to your regular email.

Aliases are often used to:

Segment incoming emails by purpose or project using different addresses.
Obfuscate your main email address for privacy reasons.
Change employee email addresses without disrupting correspondence.

So in short, an alias gives you an additional email without needing a separate mailbox or account. It’s a handy way to organize and manage incoming communication.

How Email Aliases Function

Behind the scenes, aliases work through the use of proxy addresses within email protocols and servers. When an alias is created, it is mapped to the primary SMTP email address on the mailbox server.

When an external email server delivers a message to an alias address, the receiving mail server checks its configuration and redirects the message to the proper inbox.

There it will sit alongside emails sent to the main email address. Replies get sent back to the original sender’s address, so the redirect remains invisible.

Some key points on how aliases operate:

Aliases only work for incoming emails, they cannot be used to send messages by default. More on this later.
Aliases appear in the user’s contacts and display the same name as the primary email.
Any emails sent to an alias will show up in the Sent Items folder properly addressed to the alias.
Aliases function at the server level, so all email clients will display the same aliased emails.

The process is handled seamlessly via SMTP servers and protocols. And since aliases sit on the same mailbox, there are no syncing issues across multiple accounts.

Key Benefits of Using an Email Alias

Leveraging email aliases provides some useful advantages:

Maintain Privacy and Control Sharing

By using an alias when signing up for services or mailing lists, you can obscure your real email address and maintain privacy. This also allows you to segment senders into aliases and turn them off if they start sending spam.

Filter and Organize Incoming Emails

Different aliases can represent different areas to route messages – work projects, clients, newsletters, etc. You can automate filtering by sender address using aliases.

Simplify Changing Employee Addresses

Instead of needing to update all contacts when an employee leaves, you can assign projects or roles a generic alias that remains constant.

Identify Sources of Spam

By using unique aliases when signing up for sites and services, you can identify sources of spam if a certain alias starts receiving unwanted email.

Consolidate Multiple Inboxes

Aliases allow consolidating communication into one inbox instead of checking multiple accounts. This provides a unified view of all incoming emails.

Transition to New Domains

When transitioning to a new domain, aliases on the old domain can route messages to new inboxes to prevent disruptions.

Avoid Overuse of Shared Mailboxes

Aliases help allocate emails without assigning full-on shared mailboxes that count against licensing.

The flexibility of adding additional addresses on the fly makes aliases a powerful tool for managing all types of email correspondence. And unlike forwarding to external accounts, aliases keep everything within the same mailbox interface.

Enabling the Send As Alias Feature in Outlook

Outlook doesn’t allow sending from alias addresses by default – you can only receive emails to aliases. To unlock this capability, you need to enable the “Send As Alias” feature. Here’s how to check for existing aliases, turn on the setting, and understand its limitations.

Checking for Existing Aliases in Your Outlook Account

Before enabling Send As alias, it’s a good idea to review existing aliases already configured for your account. Here’s how to check:

Outlook Desktop

Open Outlook and go to the Home tab
Click on Account Settings and select Account Settings again
Go to the Email tab and click on Edit under your account
Under Send mail as, any aliases will be listed

Outlook Web/Mobile

Go to Outlook.office.com and sign in
Click your profile icon and go to View account
Select Your app settings
Go to Mail and your aliases will display under Send as

You can also check in the Exchange admin center or via PowerShell if you have admin access. This will show all aliases across your organization.

If you don’t see the alias you want, you may need to create a new alias before sending from it.

Turning on Send As Alias in Outlook Online and Desktop App

The Send As alias capability must be enabled by the tenant admin in Office 365 or Exchange Online. Here are the steps to activate it:

Via Exchange Admin Center

Sign in to https://admin.exchange.microsoft.com
Go to Mail flow > Send as alias and toggle to enable
Click save – may take up to an hour fully activate

Via PowerShell

Run these commands in Exchange Online PowerShell:

Set-OrganizationConfig -SendFromAliasEnabled $true

This will immediately enable the feature for the entire tenant.

Once enabled by the admin, users can start sending from aliases in Outlook desktop and web clients.

Understanding the Limitations of the Send As Alias Feature

There are some limitations to understand with the send as alias capability:

It only works for Exchange Online, not on-premises Exchange servers.
Shared mailboxes don’t fully support sending from aliases yet.
Outlook for Mac cannot send from aliases at this time.
There are some reported issues replying from aliases in Outlook desktop.
Aliases don’t always sync properly with mobile devices.
Some Exchange Online rules may not process aliased emails properly.
The sent address reverts to

Sending Emails from an Alias Address in Outlook

Outlook does not allow sending from alias addresses by default – only receiving emails. However, Microsoft has added functionality to enable this feature across Outlook desktop, web, and mobile apps. Here’s how to configure and use it.

Sending from an Alias in the Outlook Desktop App

To send an email from an alias in Outlook desktop, follow these steps:

Open a new email window in Outlook.
Click on Options > From to open up the From field.
Click on From and select Other Email Address…
In the popup box, type the alias email address you want to use.
Click OK after entering the alias. This will populate the From field.
Compose your email body and recipient as usual. The alias will now be displayed as the sender.
Click Send to send the email from your alias address.

The recipient will see the email as coming from your designated alias, with no indication it is rerouted.

Here are some tips for sending Outlook emails from aliases:

The alias email popup may not appear if the Send As Alias feature is not enabled, more details on configuration coming up.
You can choose aliases from a drop-down selector once used previously in the From field.
Any emails sent from an alias will show that address in your Sent Items folder.
Replies to alias emails will continue back to the alias by default.

So with just a few clicks, you can easily change the sending alias in Outlook desktop.

Sending from an Alias in the Outlook Mobile App

The Outlook mobile app for iOS and Android also supports sending emails from alias addresses using these steps:

Tap the Compose button to start a new email in the Outlook mobile app.
Tap the From field, which will open a dropdown menu.
Tap Add Another Email at the bottom of the From dropdown menu.
Type the alias email address you want to use.
Tap Add to add the alias.
The From field will now show the selected alias email.
Compose your email and tap Send when ready.

The mobile Outlook app will now save any aliases you use for quick selection next time.

A few things to note about Outlook mobile app aliases:

Syncing the aliases from desktop may require reloading the mobile app profile.
Custom name mappings for aliases is not yet supported.
Some reported issues with aliases on shared or delegate mailboxes.

But for most basic alias needs, the Outlook mobile apps now provide this functionality.

Sending from an Alias in Outlook on the Web

The Outlook on the web interface allows sending from aliases as well. Use these steps:

Open Outlook on the web and login.
Click New message to start a new email.
Click the From field, but it may not be shown by default.
If not visible, click the three dots icon in the top toolbar and select Show From.
This will open the From dropdown – click on Other Email Address…
Type the alias email you want to use and click Use this address.
The alias email will now show in the From field.
Compose and send the email as normal.

Like the other Outlook versions, any aliases used in the From field will be saved for future selection in Outlook on the web.

Some pointers for managing aliases in Outlook on the web:

Aliases can be added to the From dropdown manually or synced from desktop.
Default name for aliases is the primary mailbox name.
Replies will go back to the original alias email by default.

-Aliases work when accessing via OWA on mobile browsers too.

So across all major Outlook platforms – desktop, web, and mobile – you can now send emails from your alternate alias addresses.

Replying from an Alias Address in Outlook

When someone responds back to an email you sent from an alias in Outlook, the reply will maintain the original alias address by default.

For example, if you send an email from [email protected], the reply will go back to that address, not your primary email.

This allows an ongoing email conversation thread to consistently use the alias address rather than revealing your true email.

Some tips for replying to alias emails:

Both parties must have aliases enabled to preserve threading.
Forwarding emails to external addresses will break alias replies.
Aliases work for replies between Office 365/Outlook.com users.
If sync issues, replies may default back to primary email intermittently.
Name mismatches can also disrupt the alias threading experience.

As long as both sender and recipient maintain aliases throughout the conversation, Outlook preserves this for back-and-forth communication.

So not only can you send from an alias, but replies to your aliased emails will stay within that alias by default in Outlook.

Using Aliases for Shared Mailboxes and Delegate Access

Aliases can provide additional benefits when utilized with shared mailboxes and delegate access in Outlook. Here are some ways aliases can help organize and streamline these types of configurations.

Configuring Send As Permission for Aliases

To use an alias from a shared mailbox or as a delegate sender, you need to configure the “Send As” permission for the alias. Here are the steps:

In the Exchange Admin Center (EAC), open the shared mailbox properties.
Go to mailbox delegation and open the delegate’s permissions.
Check the box for “Send As” and select the alias to allow sending from.
Click save to apply the permission.

This allows assigning send as rights for specific aliases to mailbox delegates.

Instead of blanket wide-open send as access, you can restrict delegates to only use designated aliases when sending emails from the shared mailbox.

Sending as an Alias from a Shared Mailbox

Once aliases are permissioned properly, users can send from a shared mailbox alias using:

Open the shared mailbox in Outlook desktop using the “Open Shared Folder” option.
Click the From field and select Other Email Address.
Choose the alias you have access to send from.
Compose and send the message.

The recipient will see the aliased address as the sender from the shared mailbox.

No indication it is from a delegate or shared mailbox using an alias.

Some tips for aliases with shared mailboxes:

Requires Exchange Online, not supported for on-prem mailboxes.
Aliases not showing? May take up to an hour to apply delegated permissions.
Apps like Outlook mobile do not support aliases for shared mailboxes currently.

So granting send as permissions to aliases provides more control over shared mailboxes.

Sending as a Delegate from an Alias Address

A similar approach allows delegates to send from an alias when opening someone else’s mailbox:

Use the “Open Another Mailbox” option in desktop Outlook.
Access the mailbox you have delegated permissions for.
Change the From address to use one of the mailbox owner’s aliases.
Compose and send the email from the alias.

This allows delegates to keep correspondence organized in a mailbox owner’s alias without creating new emails or folders.

Some pointers on using delegates with aliases:

Need to grant delegates SendAs permission to the alias.
Helps obscure what mailbox a delegate is actually accessing.
Shared naming across delegates and mailboxes.

So with proper permissions configured on the aliases, delegates can utilize a mailbox owner’s aliases to simplify sending emails on their behalf.

Overall, enabling aliases for shared mailboxes and delegates streamlines communications

Best Practices When Using Aliases for Emails

Aliases provide a great way to organize and manage your incoming emails. But some best practices will help ensure aliases are used properly and avoid potential issues.

Limiting the Number of Aliases Per User

While you can create up to 400 aliases per Office 365 mailbox, it is wise not to go overboard when assigning multiple addresses.

Too many aliases makes organization more complex, increases storage usage, and complicates configuration. Follow these tips:

Audit currently enabled aliases and disable unused ones.
Start with 1-3 aliases per employee for essential purposes.
Avoid creating individual aliases for each sender – use rules and filters instead.
Consider department or function aliases over personal ones.
Develop a consistent alias naming convention.
Get manager approval for adding additional aliases.
Document approved alias requests and business justification.
Review alias usage quarterly and prune unnecessary ones.

Keeping aliases under control will maximize the benefits while minimizing administrative headaches. The flexibility can work against you if aliases proliferate unmonitored across your organization.

A good rule of thumb is to stick to five or less aliases per mailbox. Monitor growth through audits and Office 365 usage reports.

Monitoring Which Aliases are Enabled

To control alias sprawl, you need visibility into which aliases each user has configured. Some ways to monitor active aliases:

Review in Office 365 Admin Portal

Navigate to Users > Active Users in the admin portal.
Select a user and view email addresses under Aliases.
Check for unused, old, or duplicate aliases to remove.

Use Exchange Online PowerShell

Retrieve all aliases for a mailbox with Get-Mailbox cmdlet:

Get-Mailbox jsmith | Select EmailAddresses

Or fetch all mailboxes and aliases:

Get-Mailbox -ResultSize Unlimited | Select PrimarySMTPAddress,EmailAddresses | Export-CSV aliases.csv

Query in Azure AD Using Graph API

Programmatically extract alias data from Azure AD using the Microsoft Graph API.

Use Third-Party Audit Tools

Office 365 management tools like Vyapin’s Mailbox Audit provide alias oversight.

Actively monitoring aliases is vital to ensure alignment with business needs and prevent unnecessary sprawl.

Keeping Track of Sent Emails from Aliases

To maintain accountability when using aliases for sending, you need visibility into which emails are sent from each address.

Journaling can capture copies of all outbound alias emails. Enable journaling in Office 365 to store sent item records.
Exchange transport rules can tag external emails from aliases for easier filtering.
Run Message Trace to search alias sender history.
Enable audit logging to record Send As actions.
Use third-party tracking tools for visibility into all alias email traffic.

Proper oversight is necessary when users can send from addresses besides their primary email. This provides accountability and avoids potential misuse of aliases.

Backing Up Aliases

Like all Office 365 data, it is critical to backup your mailbox aliases in case of errors, accidental deletions, or loss of access rights.

Use account provisioning tools that can re-sync aliases and proxy addresses from backups.
Backup the entire Office 365 mailbox using tools like Kernel Office 365 Backup & Restore.
Extract aliases using PowerShell scripts for backups:

$aliases = Get-Mailbox -ResultSize Unlimited | Select PrimarySMTPAddress,EmailAddresses  

Export-CSV $aliases aliases.csv

Multi-factor authentication should be required for adding or modifying aliases.
Monitor Office 365 audit logs for suspicious alias changes.

Proper controls and change management around aliases will prevent unwanted data loss or compliance issues.

Following Microsoft best practices for Office 365 backups ensures alias continuity and recovery capability. Don’t take aliases for granted – make sure critical address data gets backed up.

Troubleshooting Issues with Send As Alias

Like any new email feature, you may encounter some technical hiccups when first configuring Outlook to send emails using aliases. Here are some troubleshooting tips for common challenges.

Alias Not Showing Up in From Field

If your alias does not appear as an option in the From dropdown menu in Outlook, try these troubleshooting steps:

Confirm the Send As Alias feature is enabled for your Office 365 tenant. Run the following PowerShell command to check:

Get-OrganizationConfig | ft SendFromAliasEnabled

If recently enabled, wait up to an hour for tenant changes to fully propagate.
Ensure the alias is assigned to the mailbox as a proxy address and synced.
Reboot Outlook to refresh settings and reload address book.
Clear Outlook cache and reload profile or re-add account.
Try using another client like OWA to test if issue is isolated.
On mobile, check if alias needs reloading in account profile.
If using shared or delegated mailbox, ensure proper permissions configured.
Verify alias domain matches the primary email domain.

From field syncing can take time if aliases were recently changed. Follow these steps to troubleshoot aliases missing in action.

Replies Show Primary Email, Not Alias

When replying to an aliased email you sent, responses may incorrectly revert to your primary email address. Try these troubleshooting tips:

Ensure both sender and recipient have send as alias enabled.
If forwarding emails outside Office 365/Outlook.com, replies will use your main email address instead of alias.
Verify the reply-to field does not override your alias somehow.
Check for display name mismatches between accounts causing sync issues.
If recently changed aliases, give a day or two for caching and DNS changes.
Temporarily disable any forwarding rules on aliases during testing.
Trace email headers end-to-end to check for routing issues.

With some trial and error, you can troubleshoot reply-to alias problems. It mainly comes down to proper configuration on both ends.

Errors When Trying to Enable Send As Alias

If encountering issues when enabling the send as alias feature for your Office 365 tenant, try these tips:

Run PowerShell as administrator and connect to Exchange Online to avoid permission issues.
No dashes are allowed in the domain names when enabling the feature.
There may be conflicts with previous scripts or tools that managed aliases – check for leftover settings.
Enable aliases at the tenant level, not just for specific users.
After running enable command, give it an hour or two to take effect across your organization before troubleshooting errors.
Check Office 365 admin portal to validate changes were applied.
Monitor health dashboards for potential service issues during feature enablement.
Contact Office 365 support if errors persist without explanation.

Patience and layered troubleshooting is key when rolling out new mailbox capabilities like send as alias. Persevering through initial glitches can pay off with this powerful email management feature.

Alternative Options to Send Emails from Other Addresses

While Office 365’s send as alias capability provides one approach, there are a few other ways to send emails from additional addresses besides your primary email.

Forwarding Emails from an Alias Address

Automatically forwarding emails from an alias to your main inbox is a simple alternative to send as alias.

To configure forwarding for an alias in Office 365:

In the admin portal, go to Users > Active Users and select the mailbox.
Click Mail on the top menu.
Select Forwarding and enter the alias address you want to forward.
Choose to keep a copy in the alias inbox or redirect everything.
Click save after entering the forwarding details.

Now emails sent to that address will automatically route based on your forwarding rules into your primary mailbox or another specified account.

Some benefits of forwarding compared to send as alias:

More straightforward to configure forwarding rules.
Works across email providers – forwards to Gmail etc.
Messages arrive from the original alias address.

Drawbacks include:

Cannot reply from the alias, exposes true email address.
Requires checking multiple inboxes.
Original emails not stored directly in main inbox.

Overall, forwarding provides a simpler but less integrated way to leverage aliases compared to send as functionality.

Using Distribution Groups or Shared Mailboxes

Distribution groups and shared mailboxes can also serve as a makeshift way to send from alternate email addresses.

To use groups for sending emails:

Create a new distribution group or shared mailbox with an alias address.
Add your primary mailbox as a member of that distribution group.
Send emails on behalf of the group name, which uses the alias address.

Benefits of this approach:

Allows responding as the group alias because it has a mailbox.
Shared permissions model fits some use cases better.

Downsides:

Cannot customize the name, uses group display name.
Shared mailboxes count against license limits.
No individual tracking and management.

Distribution groups should be selectively leveraged as a simple team alias alternative, when permitted by your email policies.

Registering a New Email Account

If forwarding and groups do not meet your needs, creating entirely separate email accounts for each address is an option.

This provides full customization and independence for sending emails from any address. But lacks convenience and unified management.

Drawbacks include:

Multiple mailboxes and accounts to manage.
No central inbox for all incoming messages.
Per user email licensing costs.
Manual forwarding or CCing between accounts.

Due to the administrative overhead, separate email accounts only make sense for specific use cases like board members, certain shared resources, or external recipients.

For most alias needs, Office 365’s integrated send as alias capabilities can prevent juggling multiple email accounts. But alternatives provide flexibility in special scenarios when configured selectively and strategically.

Key Takeaways for Sending Emails from an Alias in Outlook

Sending emails from alias addresses is a valuable capability – when used properly. Here are some key lessons:

Enable thoughtfully – Only turn on for groups that need it to avoid misuse. Follow change management processes.
Monitor usage – Audit which users have aliases enabled and track volume sent. Keep under control.
Limit aliases – More than 5 per user is risky without business justification. Set org-wide alias policies.
Use rules wisely – Be selective with forwarding or groups. Maintain compliance and security.
Mind the details – Display names, hybrid routing, and replies take finesse. Test thoroughly.
Communicate changes – Train end users on appropriate alias usage and new configurations.
Troubleshoot patiently – Expect hiccups early on. Allow time for caching and dependencies.
Backup always – Don’t assume aliases are safeguarded. Include in business continuity planning.

Aliases unlock new ways to segment and manage email communications. But thoughtful change management and governance is required to avoid pitfalls. When in doubt, start small and build up alias capabilities cautiously.

Frequently Asked Questions about Sending Emails from Aliases

Can I customize the name displayed with an alias?

By default, aliases show the same name as your primary email address when sending. However, there are some options to customize this:

Change user name in Exchange Online – Modify the mailbox properties to update the displayed name. This changes the name for all emails.
Create directory contacts – Make a contact for the alias with a unique name, and use that as the From address. Contacts don’t count against license limits.
Use a distribution group – Shared mailboxes and distribution groups can have custom display names and be used for sending.
Register external domains – Verify your own domains in Office 365 and manage display names fully with external accounts.

So in short, there are workarounds to change the display name for aliases, but this does come with administrative tradeoffs. Many organizations decide consistent naming is preferable for governance and compliance.

Does send as alias work for external recipients?

Yes, there are no restrictions on sending emails from an alias to recipients outside your Office 365 organization. The process is the same – configure the alias in the From field when composing a new message.

Emails will be delivered and received by any external address with your alias appearing as the sender. Some caveats:

If email passes through on-premises Exchange, aliases may get overwritten. Cloud-only is best.
Some compliance policies restrict external sending from aliases, check your settings.
Replies from outside your organization may not maintain the alias properly in all cases.

But in general, aliases can be leveraged for external communication as well as internal – just be aware of potential email routing complexities.

Is this feature available for on-premises Exchange?

Microsoft has mentioned that send as alias functionality works only for Exchange Online cloud mailboxes as of now. The feature is not supported out-of-the-box for Exchange Server or hybrid configurations.

On-premises Exchange deployments would need to utilize some workaround methods:

Create separate mailboxes for aliases and configure forwarding.
Develop custom scripts to overwrite aliases during transport.
Route mail through a cloud service that supports alias rewriting.

So unfortunately native send as alias is only available in the Office 365 cloud currently. On-premises Exchange users have more limited options. This may improve in the future as Microsoft reaches parity with hybrid features.

What are the limits for the number of aliases?

Office 365 lets you create up to 400 aliases per mailbox. However, just because you can have that many doesn’t mean you should! When planning your alias strategy:

Audit existing aliases and remove unused ones first.
Start with 1-3 validated aliases per user maximum.
Enforce alias creation policies and document business need.
Get manager approval for adding more than 5 aliases.
Monitor growth and keep under 50 aliases per mailbox.
Require aliases to be deactivated after period of inactivity.

While the technical limit is 400, restraint is wise when handing out multiple email addresses. Keep aliases purpose-driven and tightly governed to maximize the value while minimizing potential issues.

The key is having enough aliases to improve email management without going overboard. Aim for quality over quantity, with a less is more approach.

Let’s review some frequently asked questions about using aliases in Outlook:

Q: How many aliases can I create for my email address?

A: Office 365 allows up to 400 aliases per mailbox. However, it’s recommended to start with 1-3 and obtain approval for additional aliases based on need.

Q: Can I customize the name that displays with an alias?

A: By default it matches your primary email name, but workarounds exist like contacts or groups to set custom names.

Q: Do recipients receive the email from my alias address?

A: Yes, recipients will see the email as coming directly from your alias with no indication it’s rerouted.

Q: Can I reply to a message from the same alias?

A: Yes, by default Outlook will maintain the original alias address when replying back and forth.

Q: Does send as alias work externally outside my organization?

A: Yes, there are no restrictions on sending emails from aliases to external recipients.

Q: Is this feature supported for on-premises Exchange?

A: Currently it is only supported for Exchange Online Office 365 accounts, not Exchange Server.

Q: Where do I configure aliases in Outlook?

A: In the From field when composing a new message – enter the alias you want to send from.

Q: How do I view all my email aliases?

A: In Office 365 admin portal, under a user’s Mail tab. Or with PowerShell using Get-Mailbox.

Q: What permissions do I need to send from an alias?

A: Global admin can enable the feature tenant-wide. Users need access to aliases and Send As rights.

Q: If I change an alias, will previous emails remain linked?

A: Yes, existing alias email history will stay connected to your mailbox when modifying.

Q: Can aliases be used for sending to distribution groups?

A: Yes, there are no restrictions on sending to individuals or groups from an alias.

Let us know any other common alias questions in the comments!