Connectivity

SmarterMail provides a variety of options that allow users to manage and access third-party, external accounts directly within SmarterMail. When accessing your connectivity settings, the following options will be available:

Jump To:

Email Retrieval - Download emails from third-party accounts directly into SmarterMail
SMTP Accounts - Send emails from third-party accounts directly within SmarterMail
Synchronized Devices - Review the syncing connections for your user
Authenticated IPs - The IP addresses being used by any device connecting to your SmarterMail account. These can be clients on mobile or desktop clients, etc.
Mailbox Migration - Importing email, contacts, calendars, tasks, and notes from third-party accounts

Regarding Gmail, Microsoft and Email Retrieval / SMTP Accounts

Google transitioned to their "Sign in with Google" authentication method as a part of their roll-out of 2-Step Verification and as a way to ensure that any product or service you're connecting to your Google account is secure enough to do so. However, not every application or service can, much less wants to, integrate with Google using "Sign in with Google". As such, when using Mailbox Migration to migrate a Gmail account to SmarterMail, or when adding a Gmail account to the Email Retrieval card, you will be required to use an "app password." App passwords are 16-digit passcodes that can be used in place of your existing Gmail password that allow applications and/or devices to access your Gmail account. For the time being, Google allows the use of app passwords for connecting accounts to third-party services. However, Google's policies around integration with third parties are likely to change, becoming more rigid and restrictive.

In the case of connecting Google Drive as a Cloud Storage Connection, SmarterMail uses "Google Picker" as a way to validate your connection. You log into Google with your account, then when adding links to files, a separate Google modal opens. Here, you can select the various files you want to link to right from Google Drive itself.

Microsoft is retiring Exchange Web Services (EWS) for Microsoft 365 (Exchange Online). Microsoft began blocking EWS in Exchange Online on October 1, 2026, and shuts it off completely on April 1, 2027. As a result, SmarterMail no longer uses EWS to connect to Microsoft 365 or Outlook.com mailboxes. You can connect these accounts using Microsoft Graph or IMAP instead, and both use Microsoft sign-in (OAuth 2.0) rather than a password saved in SmarterMail:

Microsoft Graph - Select Microsoft Graph as the Type and you're taken to Microsoft to sign in. There's no server address, port, encryption setting or password to enter. When migrating a mailbox, Graph can bring over contacts, calendars, tasks and notes in addition to email.
IMAP - Enter the account's email address (there's no Password field) and you're taken to Microsoft to sign in. IMAP transfers email only.

Microsoft sign-in works for both work or school accounts (Microsoft 365) and personal accounts (Outlook.com, Hotmail, Live and MSN). EWS is still available for on-premises Exchange servers and other servers that support it.

Email Retrieval

These days it's rare for someone to have, and use, a single email address. That's why SmarterMail's Email Retrieval feature is so great: it allows users to pull email from another account directly into the SmarterMail web interface. This means users can add their Gmail, Hotmail, Yahoo! or any other mail account to SmarterMail so that they can have all of their emails, from a number of different accounts, within a single web-based email client

In addition, a nice complement to Email Retrieval is SMTP Accounts. When used together, users can send and receive email from external accounts directly within the SmarterMail webmail client.

Note: By default, Email Retrieval simply pulls messages from the retrieval account and delivers them straight to your mailbox, bypassing the usual mail processing pipeline — so things like spam filtering, autoresponders, and virus checking are not performed on retrieved messages. However, this only holds true as long as the "Enable content filtering" (or "Enable spam and content filtering") option is left off for that retrieval account. If you turn that option on, retrieved messages are routed through the same delivery pipeline as normal incoming mail, and spam filtering and autoresponders can apply to them just like any other message.

Using Email Retrieval

To establish a connection with an external email account, click New Retrieval Task on the Connectivity page of your account settings. You'll see a list of email services and providers, much like you see during a mailbox migration. Regardless of the type of account you are setting up (POP, IMAP, EWS or Microsoft Graph) or which service you're connecting to, several pieces of information are required in order for SmarterMail to connect to the account and start retrieving messages. If these settings are unknown, it's a good idea to contact your IT or email administrator with the list below that corresponds to the type of connection you want.

Note: When setting up Email Retrieval and connecting to another SmarterMail account (as opposed to any other email provider), that SmarterMail account needs to have MAPI/EWS enabled in order to pull over all relevant folders. This includes Calendars, Contacts, Tasks, and Notes, in addition to email.

Microsoft 365 and Outlook.com Retrieval

Microsoft no longer allows basic authentication (a username and password) for Microsoft 365 and Outlook.com mailboxes, and SmarterMail no longer retrieves from them using EWS. When you select Microsoft 365 (Office) or Outlook.com from the list of providers, you can choose Microsoft Graph or IMAP as the Type. Microsoft Graph is selected by default. Both use Microsoft sign-in: when you click Save, a Microsoft window opens where you sign in to the account you're retrieving and complete any secondary verification set up for it. (E.g., Entering a code sent to a backup email address.)

Email Retrieval brings over email only, whichever Type you choose. SmarterMail's access through Microsoft Graph is read-only, so nothing is changed or deleted in the Microsoft mailbox. Messages in the Outbox, Sync Issues and RSS feed folders aren't retrieved.

When adding a Microsoft 365 or Outlook.com retrieval task, the following options are available:

Type - Select Microsoft Graph or IMAP. With Microsoft Graph, there's no server address, port, encryption setting or password to enter. With IMAP, SmarterMail fills in the server address for you. That address works for Microsoft 365, Outlook.com, Hotmail and Live.com accounts, so it shouldn't be changed. The Type can't be changed after the task is saved.
Email Address - The full email address of the account you'll be adding. For example, my_name@outlook.com.
Retrieval Method - The method by which SmarterMail checks for new messages, either Manual or Automatic. If you choose to manually retrieve messages, you will have to navigate to the Connectivity page, click on the retrieval task, then click Retrieve Messages Now in order to check for new messages. If you choose to automatically retrieve messages, SmarterMail checks for new messages on a schedule set by your system administrator, which is every 10 minutes by default.
Folder Transfer Method - This is how you want the folders within your account to be transferred into SmarterMail. You can add them as root level folders, meaning they will appear intermingled with any existing folders in your primary account, or as subfolders. When adding them as subfolders, you'll select a Destination Folder to import into, so it's a good idea to create a folder specifically for the account you're retrieving. For example, create a "M365" folder and then use that.
Enable content filtering (Inbox only) - Select this option to apply your SmarterMail content filtering settings to messages retrieved into the Inbox.

Note: To switch an existing retrieval task between Microsoft Graph and IMAP, delete the task and add it again.

Converting Microsoft 365 Retrieval Tasks That Use EWS

Recurring retrieval tasks that connect to Microsoft 365 using EWS are suspended when SmarterMail is upgraded to a version that supports Microsoft Graph. You'll receive an "Email retrieval suspended" notification for each one, and the task shows "Suspended: conversion required" on the Connectivity page. A suspended task doesn't retrieve messages and can't be edited until it's converted.

To convert a suspended task, do the following:

On the Connectivity page, click the suspended retrieval task.
Click Convert to Microsoft Graph.
Sign in to the Microsoft account in the window that opens.

The conversion runs in the background and keeps the task's existing settings, such as its Retrieval Method and Folder Transfer Method. SmarterMail also carries over its record of the messages already retrieved, so they aren't downloaded again. When the conversion finishes, you'll receive a notification. If any previously retrieved messages couldn't be matched, the notification says how many, and those messages may be retrieved a second time. If the conversion fails, the task stays suspended and you can try again.

Microsoft Exchange (On-Premises) Retrieval

Exchange servers you host or manage yourself, whether on-premises or remotely hosted, still connect using EWS. Select Microsoft Exchange from the list of providers and fill in the server address and account information for that server. The Microsoft Exchange provider can't be used for Microsoft 365 or Outlook.com mailboxes. If you enter a Microsoft 365 server address (such as outlook.office365.com), or an Outlook.com, Hotmail, Live or MSN email address, SmarterMail won't save the task and directs you to the Microsoft 365 or Outlook.com provider instead.

POP Retrieval

SmarterMail's POP retrieval service will download email messages from the Inbox of another server via POP3 and deliver them to your SmarterMail mailbox. One primary difference between POP and IMAP is that a POP account will generally retrieve the messages then delete them from the originating server. While SmarterMail's POP Retrieval DOES allow you to leave messages on the server, users need to make sure they enable it. Otherwise, POP retrieval will delete the messages from the server after they are downloaded to your mailbox. The other primary difference is that IMAP allows the retrieval of ALL messages in the external mailbox, while POP will only download the contents from the Inbox.

In addition, some services (e.g., outlook.com) do not offer POP as a retrieval method. Instead, they default to IMAP or they use a different protocol.

When creating a new account for POP message retrieval, the following options are available:

Type - Select POP.
Server Address - The address for the email server for which you want to connect. This will most likely be the URL to the mail server. (E.g., mail.example.com).
Port - The port used to connect to the email server. By default, the port is 110. However, some mail providers may require a separate port be used for POP retrieval.
Username - The identifier used to authenticate with the email server. This will most likely be the full email address you want to bring into SmarterMail.
Password - The password used to log into the mail account.
Retrieval Method - The method by which SmarterMail checks for new messages on the server, either Manual or Automatic. If you choose to manually retrieve messages, you will have to navigate to the Connectivity page, click on the retrieval task, then click Retrieve Messages Now in order to check for new messages. If you choose to automatically retrieve messages, you will not need to return to the Connectivity page, as messages would be automatically retrieved every 10 minutes.
Destination Folder - The folder where messages from the external account should be downloaded.
Enable APOP authentication - Select this option if the server requires additional login security.
Leave messages on server - Select this option to keep your messages on the server after they are downloaded to your SmarterMail mailbox.
Require SSL - Select this option if the connection to the server must be SSL.
Enable spam and content filtering - Select this option to apply your SmarterMail spam and content filtering settings to any messages downloaded from this server. If the antispam solution being used for the account you're retrieving is good, this may not be necessary.

Note: After you've added your information, when you click the Save button, the connection is tested prior to actually being saved by SmarterMail. If an error occurs during the test, you will receive a notification that an error occurred and will need to correct it prior to being able to save the connection.

IMAP Retrieval

SmarterMail's IMAP retrieval service will download email messages from another server via IMAP and deliver them to your SmarterMail mailbox. One primary difference between IMAP and POP is that an IMAP account will leave the original messages on the original mail server by default. The other primary difference is that IMAP allows the retrieval of ALL messages in all folders of the external mailbox, while POP will only download the contents from the Inbox.

When creating a new account for IMAP message retrieval, the following options are available:

Type - Select IMAP.
Server Address - The address for the email server you want to connect to. This will most likely be the URL to the mail server. (E.g., mail.example.com).
Port - The port used to connect to the email server. By default, the port is 143. However, some mail providers may require a separate port be used for IMAP retrieval.
Username - The identifier used to authenticate with the email server. This will most likely be the full email address you want to bring into SmarterMail.
Password - The password used to log into the mail account.
Retrieval Method - The method by which SmarterMail checks for new messages on the server, either Manual or Automatic. If you choose to manually retrieve messages, you will have to navigate to the Connectivity page, click on the retrieval task, then click Retrieve Messages Now in order to check for new messages. If you choose to automatically retrieve messages, you will not need to return to the Connectivity page, as messages would be automatically retrieved every 10 minutes.
Folder Transfer Method - The method by which SmarterMail imports emails from the server. The advantage of creating an IMAP connection, rather than POP, is that IMAP allows existing folders to be brought into SmarterMail. Users can choose to add their external account folders as root folders or append them as subfolders on an existing SmarterMail folder.
Requires SSL - Select this option if the connection to the server must be SSL.
Enable spam and content filtering (Inbox only) - Select this option to apply your SmarterMail spam and content filtering settings to any messages downloaded from this server. If the antispam solution being used for the account you're retrieving is good, this may not be necessary.

Removing a Retrieval Task

To remove a retrieval task, click on the account from the list of retrieval tasks. Then click Delete.

SMTP Accounts

These days it's rare for someone to have, and use, a single email address. That's why SmarterMail's SMTP Accounts feature is so great: it allows users to send email from another account directly within the SmarterMail Web interface. This means users can add their Gmail, Hotmail, Yahoo! or any other mail account to SmarterMail so that they can send all of their emails, from a number of different accounts, from within a single interface.

A nice complement to SMTP Accounts is Email Retrieval. When used together, users can send and receive email from external accounts directly within SmarterMail.

Connecting an SMTP Account

To establish a connection with an external email account, click New SMTP Account. Several pieces of information are required in order for SmarterMail to connect to the account. If these settings are unknown, it's a good idea to contact your IT or email administrator with the list below.

When creating a new SMTP account, the following options are available:

Display Name - The name that should appear in the From field of emails sent using this account.
Server Address - The address for the external email server for which you want to connect. This usually takes the form of mail.example.com.
Server Port - The port used to connect to the email server. By default, the port is 25. However, some ISPs block port 25 by default. Therefore, it's a good idea to check with your email provider or email administrator to ensure that you're using the proper port for this account.
Encryption - The type of encryption required by the external email server. Many ISPs and service providers require you use SSL to send emails.
Email Address - The full email address that corresponds to the external email server. For example, jdoe@example.com.
Enable Authentication - Select this option if SMTP authentication is required to send mail from this email address. What that means is that, once you attempt to send a message using this account, SmarterMail will pass your credentials back to the sending server to authenticate your address and let the sending mail server know that you're authorized to send mail from that account.
Username - The identifier used to authenticate with the external email server. In many cases, this and the Email Address will need to be identical.
Password - The password used to authenticate with the external email server.

Removing an SMTP Account

To remove an SMTP account, or to simply reset the connection, click on the account from the list of SMTP Accounts. Then click Delete.

Synchronized Devices

In the Synchronized Devices section, a user can review the syncing connections that are configured for their user. SmarterMail will show the type of connection being made (generally, the protocol being used) and, in most cases, the device/client and protocol, except for IMAP or POP connections as these are not listed. For example, "Outlook (MAPI)" or "WindowsMail (EAS)". SmarterMail Enterprise uses multiple data synchronization technologies to sync user data with email clients and mobile devices, including:

MAPI is an optional add-on that syncs SmarterMail mailboxes with Microsoft Outlook for Windows and that allows Outlook users the same features and functionality that's available within Outlook when using Microsoft Exchange.
EAS is an optional add-on that is the standard for syncing with most smartphones and tablets.
EWS is an optional add-on that seamlessly syncs SmarterMail messages, contacts, calendars and tasks to third-party email clients that support the protocol, including Microsoft Outlook for Mac, Apple Mail, the Outlook client for iPad and eM Client.
CalDAV is an extension of the WebDAV protocol that syncs SmarterMail calendars with Macs, iPads, iPhones, and other devices/applications that use the technology.
CardDAV is an extension of the WebDAV protocol that syncs SmarterMail contacts with Macs, iPads, iPhones, Thunderbird and other devices/applications that use the technology.

(For more information regarding the different synchronization methods available for SmarterMail and/or your device, please refer to Synchronizing with SmarterMail.)

Deleting a Connection

In general, users should not delete a sync connection as this may cause the device/application to stop functioning with SmarterMail. Deleting a connection is only recommended if you are no longer utilizing that device or if you are experiencing issues and want to completely resync the device's connection to SmarterMail.

When reconfiguring a device's connection, you should:

Remove your SmarterMail account from the device.
Delete the connection from the Synchronized Devices section.
Then add the account configuration back to the device.

Resync all Devices

There may be instances where a user who has multiple different clients set up will want to manually force all of those clients to resync. This should generally be done at the request of the domain administrator, but it can be done any time there is at least one device listed. Forcing a resync of one or more clients can help resolve issues, such as emails appearing in one client and not another.

That said, resyncing all clients can take some time to complete, especially for particularly busy/active users. Therefore, it should only be done during off hours, when possible.

When pressing the Resync all Devices button, the user is presented with a confirmation dialog warning them of the time that may be necessary to complete the action. Once acknowledged, a toast notification appears letting them know the process has begun. From there, notifications are used to let the user know when the process completes, and if there are any issues. Resyncing of clients is logged, so if an issue presents itself, the user should contact their domain administrator, who can then help further troubleshoot the issue.

Authenticated IPs

This section displays all of the authenticated logins, by IP address, over the previous 3 days for your user. These IPs may be associated with email clients, webmail clients, mobile devices or any other type of connection that accesses your SmarterMail user, and can include private/internal IP addresses if you connect from within your own network.

Where possible, the associated protocol is listed as well, which can be used to help identify what is connecting and from where. For example, EAS connections are most likely mobile devices. The same IP address may show up multiple times if, for example, you're logged in via webmail as well as Outlook on the same computer.

Mailbox Migration

The mailbox migration tool moves an account from an email provider like Microsoft 365 or Yahoo!, or from another email server like MailEnable or Open-Xchange, into SmarterMail. Depending on whether the provider allows it, Mailbox Migration can import email, contacts, calendars, tasks and notes into a SmarterMail account.

Note: When migrating from one SmarterMail server to another SmarterMail server, the account(s) on the source SmarterMail server need(s) to have MAPI/EWS enabled in order to pull over all relevant folders. This includes Calendars, Contacts, Tasks, and Notes, in addition to email. Otherwise, IMAP can be used to migrate just email.

Migrating a Mailbox

To import data from a third-party mail server, do the following:

Note: Not every setting, below, will be available as they're based on the product migrating from. For example, Zimbra migrations give you the option to select "Items to Import" but MDaemon does not as it only supports migrating email.

Log into SmarterMail as a user.
Click the Settings icon.
Click on Connectivity in the navigation pane.
On the Mailbox Migration card, click the Migrate button.
The Mailbox Migration modal appears. Here, you will select which service or mail server you want to migrate data from. Find your appropriate starting point and click on its icon.
The information required will vary based on the service or server you're migrating from, and in some cases SmarterMail already knows information such as the Server Address. For example, when migrating from Microsoft 365 or Outlook.com, you'll only need your email address before signing in at Microsoft. However, if migrating from another email server, such as MailEnable, you'll need more detailed information. Depending on the source, the following settings may be available:
- Items to Import - You'll be able to select what you want to migrate over to SmarterMail: Email, Contacts, Calendars, Tasks or Notes, or all of them. In some cases the provider makes the choice for you, so this may not always be available, especially if migrating from another mail server like Zimbra or MailEnable.
- Server Address - This will be the URL you use to log in to the mail server, or the mail server address you use when connecting to an email client. For example, mail.your-domain.com. Whenever possible, SmarterMail pre-fills the server address to make it easier for you to start the migration.
- Type - POP, IMAP, EWS or Microsoft Graph, depending on the source. POP imports only the messages in the Inbox. IMAP imports email from all folders, but not contacts, calendars, tasks or notes. EWS and Microsoft Graph import every item type the source supports. Microsoft Graph is available only for Microsoft 365 and Outlook.com accounts, where it's selected by default, and EWS can't be used for them. (For more information, see Migrating from Microsoft 365 or Outlook.com, below.)
- Port - The port that's associated with the Type you've selected. Not used with Microsoft Graph.
- Email Address - This is the full email address you're migrating over. For example, jdoe@outlook.com.
- Password - This is the password you use to log into the account you're migrating over.
  Note: Some services, such as Microsoft 365 and Outlook.com, require you to sign in to the account at the service itself. For these services, the Password field is hidden and a sign-in window from the service opens instead.
- Encryption - For POP and IMAP, the type of encryption the server requires (None, SSL or TLS).
- Leave messages on server - Available for POP only. Enable this to leave migrated messages on the originating server.
- Require SSL - Available for some EWS sources. Select this option if the connection to the server must be SSL.
- Delete existing SmarterMail mailbox items - Enabling this deletes all of your existing items of each type you're importing (email, contacts, calendar entries, etc.) before the migration starts, so the end result is that only the migrated data remains. If this is not enabled, the migrated data is added alongside your existing data. Keep in mind this isn't a duplicate-detecting merge: if you run the same migration more than once with this option off, you can end up with duplicate items.
Once you've filled out the necessary information, and selected the items you want to migrate over, the mailbox migration will start. You can track its progress as the data is imported. The total time needed to migrate your data depends on how much data there is, your internet connection and other factors.

Note: It may take some time for your mailbox data to import. You can continue using SmarterMail during this time as the migration process happens in the background. In addition, the type of items available for migration depends entirely on the service you're migrating from. SmarterMail cannot migrate any item that is not allowed by the service provider.

Our knowledge base offers a couple of different articles that walk through the migration process. Please see:

Migrating from Microsoft 365 or Outlook.com

Microsoft 365 and Outlook.com mailboxes can be migrated using Microsoft Graph or IMAP. Use Microsoft Graph when you want contacts, calendars, tasks and notes brought over along with email. IMAP migrates email only. EWS can no longer be used for these mailboxes: choosing the Microsoft Exchange provider with a Microsoft server address, or with an Outlook.com-style email address, is rejected with a message directing you to the Microsoft 365 or Outlook.com provider. EWS remains available for on-premises Exchange and other servers.

Microsoft Graph always uses Microsoft sign-in. When you click Start, a Microsoft window opens where you sign in to the account and approve SmarterMail's access to it. There's no server address, port, encryption setting or password to enter. Sign-in works for both work or school accounts (Microsoft 365) and personal accounts (Outlook.com, Hotmail, Live and MSN).

SmarterMail asks Microsoft for read-only access to the account's profile, mail, contacts, calendars, Microsoft To Do tasks and mailbox settings. Nothing is changed or deleted in the Microsoft mailbox during the migration.

Note: Some Microsoft 365 organizations don't allow users to approve third-party applications on their own. If the Microsoft window says administrator approval is required, your Microsoft 365 administrator will need to grant consent for SmarterMail before the migration can continue.

Microsoft Graph doesn't expose everything stored in a Microsoft mailbox, so some items are imported differently, or not at all:

Contact groups (personal distribution lists) aren't imported because Graph doesn't expose them. Individual contacts are imported normally, and the migration summary notes that contact groups were skipped.
Contact notes are imported as plain text, since Graph doesn't expose a contact's rich-text notes.
Deleted occurrences of a recurring event are reproduced from the start of the series through two years after the migration date, or through the end of the series if that's sooner. A deleted occurrence that falls after that window appears again in SmarterMail.
Tasks come from Microsoft To Do, which doesn't track percent complete, actual or total work, mileage, billing or company. Percent complete is set to 100 for completed tasks and 0 for all others, and the remaining fields are left empty. The Flagged Emails list isn't imported as tasks because its items are email messages.
Notes kept in additional notes folders, such as folders created in classic Outlook, are imported into the default Notes folder. Graph doesn't expose those folders, so their names and structure can't be reproduced.
Messages in the Outbox, Sync Issues and RSS feed folders aren't imported.

A few quick notes regarding Mailbox Migration:

The mailbox migration tool will only transfer email, contacts, calendars, tasks, and notes (if supported) from a single third-party mailbox to your SmarterMail mailbox. System administrators can use mail server conversion tools to migrate multiple mailboxes or entire domains from mail server applications like MailEnable, Merak, MailMax, or Imail quickly and easily. System administrators can also use Web services to run migrations for multiple accounts.
SmarterMail is typically able to keep date and time stamps when importing from other email servers as long as they follow the standard time and date format in the email header.
Some services, such as Yahoo! and Gmail, require changes to your account's security settings (for example, creating an app password) before a third-party application can connect. Make any necessary security changes to your account before you start the migration.
There may be a discrepancy in the number of items in the Deleted Items folder after a migration. This is because some email providers, notably Microsoft, don't restrict the type of item that gets stored in Deleted Items. For example, a Microsoft 365 account may have contacts, calendar appointments, notes, and tasks in Deleted Items. SmarterMail only allows mail messages in Deleted Items, so other item types in that folder aren't imported.
Finally, if there are issues with a migration, SmarterMail logs all migration activity. Therefore, a system administrator can check the Mailbox Importing logs for a user to see what happened, and find a resolution.