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Synchronizing with SmarterMail

Overview

SmarterMail is a powerful collaboration mail server that supports the synchronization of calendars, tasks, notes, and contacts on desktop applications like Microsoft Outlook and over-the-air synchronization for most popular mobile devices.

It should be noted that synchronization capabilities may vary depending on the edition of SmarterMail that you are using:

  • For full synchronization capabilities, SmarterTools recommends upgrading to SmarterMail Enterprise. SmarterMail Enterprise users have the ability to synchronize their mailboxes using any of the protocols discussed in this document.
  • SmarterMail Professional users can download their email using IMAP or POP3 retrieval, and sync calendars and contacts using free protocols like CalDAV and CardDAV. However, they cannot sync calendars, contacts, tasks or notes using either EAS or MAPI/EWS and so miss out on a more complete user experience.
  • SmarterMail Free users have the ability to synchronize their mailboxes using any of the protocols discussed in this document except EAS and MAPI/EWS, which are only available as add-ons to SmarterMail Enterprise.

For information on how to sync a specific device or client to SmarterMail please go to the Desktop and Mobile Synchronization section of the SmarterTools knowledge base . That section of the knowledge base contains a number of articles that offer step-by-step instructions that cover things such as connecting Outlook 2019 to a MAPI mailbox, using Autodiscover on Android devices, setting up Adium with XMPP and much more.

This document covers the synchronization methods and processes for the following applications and devices:

Note: This is not an exhaustive list of all compatible applications and mobile devices. SmarterTools recommends contacting the manufacturer for details regarding the available synchronization protocols for applications and/or mobile devices not listed in this document.

Who Should Use This Document

This document is intended to be used in conjunction with the SmarterMail Online Help, Knowledge Base articles (KBs), and other SmarterTools reference sources as part of an overall solution. It should be used by:

  • Hosting companies, Internet Service Providers (ISPs) and IT professionals as part of a complete SmarterMail communications solution for their customers
  • Individual users of SmarterMail seeking to maximize the functionality and features of the SmarterMail account

Synchronization Protocols

SmarterMail uses multiple synchronization technologies to sync mailbox items with email clients and mobile devices:

  • EAS is an optional add-on that syncs SmarterMail mailboxes, calendars, contacts — including contact pictures — with mobile devices as well as the default clients installed with Windows 10/11, such as Windows Mail, Calendars, and People.
  • MAPI/EWS are optional add-ons that sync SmarterMail messages, contacts, calendars and tasks to third-party email clients that support the protocol, including Microsoft Outlook 2016 and above for Windows, Outlook for Mac, Apple Mail and eM Client. SmarterMail is the ONLY mail server on the market, other than Microsoft Exchange, that fully supports the MAPI protocol. As a result, Microsoft Outlook users can get the same level of features and functionality they do with Microsoft Exchange when using SmarterMail and MAPI/EWS.
  • CalDAV is an extension of the WebDAV protocol that syncs SmarterMail calendars natively with Macs, iPads, iPhones, Thunderbird, and other devices/applications that use the technology. Note that some Android devices require the use of third-party apps that support CalDAV. More information on CalDAV implementations can be found by reviewing Implementations of CalDAV and CardDAV .
  • CardDAV is an extension of the WebDAV protocol that syncs SmarterMail contacts — including contact pictures — natively with Macs, iPads, iPhones, and other devices/applications that use the technology. Note that some Android devices require the use of third-party apps that support CardDAV. More information on CardDAV implementations can be found by reviewing Implementations of CalDAV and CardDAV .
  • Add to Outlook is a synchronization method based on Microsoft's Sharepoint platform. However, Microsoft no longer supports the synchronization features within SharePoint that are used by the Add to Outlook connector. Therefore, Add to Outlook is becoming less and less secure, and less and less reliable as there is no more assistance from Microsoft for it. As a result, Add to Outlook is offered "As Is". For a more feature-rich experience, EAS (for mobile devices and Windows Mail) or MAPI/EWS (for Outlook for Mac or Windows, and Apple Mail) should be used.

Synchronized Devices

SmarterMail makes it easy to view the devices and protocols used to synchronize your mailbox to desktop and mobile clients. The Connectivity page, available in a user's Settings area, shows users a variety of information about the devices that are synced to their accounts, including the last successful synchronization. Users also have the ability to reset the synchronization state of devices on the Synchronized Devices card.

Desktop Applications

SmarterMail supports synchronization with many desktop applications and email clients, including:

macOS

macOS is the primary operating system for the MacBook, Mac mini, iMac and Mac Pro lines of desktops and laptops.

Apple Contacts

Apple Contacts is the default application for macOS users built for managing contact data. It is intended to be used in conjunction with Apple's Mail and Calendar programs to provide Mac users with full email, calendar, and contact management.

MAPI/EWS

The MAPI/EWS add-on is available as an optional add-on for SmarterMail Enterprise and can be purchased from the SmarterTools website. Users can use EWS to sync contact data with Apple Contacts on computers running Mac OS 10.6 and above.

CardDAV

Users can synchronize their SmarterMail contacts — including contact pictures — with Address Book using EWS or the CardDAV protocol. Support for CardDAV is built into both products, so there is no need to download and install additional applications to sync contact data.

For more information, refer to our Knowledge Base.

Apple Calendar

Apple Calendar is the default application for macOS users built for managing calendar data. It is intended to be used in conjunction with Apple's Mail and Address Book programs to provide Mac users with full email, calendar, and contact management.

MAPI/EWS

The MAPI/EWS add-on is available as an optional add-on for SmarterMail Enterprise and can be purchased from the SmarterTools website. Users can use EWS to sync calendar data with Apple Calendar on computers running Mac OS 10.6 and above.

CalDAV

Users can synchronize their SmarterMail calendars with iCal using the CalDAV protocol. Support for CalDAV is built into both products, so there is no need to download and install additional applications to sync calendar data. For more information, refer to our Knowledge Base.

Apple Mail

Apple Mail is the default email client for macOS users. It is intended to be used in conjunction with Apple's Address Book and iCal programs to provide Mac users with full email, calendar, and contact management.

MAPI/EWS

The MAPI/EWS add-on is available as an optional add-on for SmarterMail Enterprise and can be purchased from the SmarterTools website. Users can use EWS to sync messages with Apple Mail on computers running Mac OS 10.6 or later.

Once the MAPI/EWS add-on has been purchased, the system administrator will need to reactivate SmarterMail and enable the add-on for the domain. For more information, see the Licensing and Activation page of our help documentation.

Once the add-on is activated for the domain, users can sync to Apple Mail using the protocol. For more information, refer to the KB article How To Synchronize SmarterMail with Apple Mail Using MAPI/EWS .

Message Retrieval

For SmarterMail users with MAPI/EWS, messages will automatically be synchronized with Apple Mail. SmarterMail users without the MAPI/EWS option should set up an account within Apple Mail using either IMAP or POP3.

IMAP is a robust protocol that easily handles mailboxes that process and/or store large volumes of email. In addition, IMAP IDLE is an optional feature of the IMAP protocol that pushes all new messages out as they are received by the mail server. Unlike POP, IMAP offers two-way communication between your SmarterMail mailbox and your email client(s). This means when you log in to the SmarterMail Web interface, actions you performed on email clients and mobile devices will automatically appear in the Web interface (and vice versa). In addition, IMAP keeps all messages and folders on the server whereas POP downloads all messages to an email client.

With POP3, your mail is saved in a mailbox on the remote server until you check your mail. When you check your mail, all the mail is downloaded to your computer and is no longer maintained on the server. If you use POP3 and are traveling or check your mail from multiple locations, you will not be able to view any of your old mail because the messages only exist on the computer on which you originally received your mail. That is, unless you have the option to leave the messages on the server.

Microsoft Windows Mail, People, Calendar

Windows 10/11 is the latest operating system offered by Microsoft that is available for a variety of desktops, laptops and the Microsoft Surface tablet. Windows includes an email client (Mail) as well as both calendar (Calendar) and contacts (People) applications as part of its default installation, similar to those same features offered by Apple's operating system.

Windows Mail

Windows Mail is an email client that comes pre-installed with Windows. It allows users to set up accounts using a variety of methods.

EAS

The EAS add-on is available as an optional add-on for SmarterMail Enterprise and can be purchased from the SmarterTools website. Unlike the other synchronization methods, EAS uses direct push technology to sync email, calendars, and contacts in real time, ensuring any changes to collaboration data are automatically recorded in both SmarterMail and within Windows Mail.

With the release of Windows, Microsoft integrated EAS with the Windows Mail application that comes as part of the Windows installation. Therefore, administrators and end users can Windows Mail using the EAS add-on as well as via IMAP or POP.

note: EAS is not supported for use with any version of Outlook.

Once the EAS add-on has been purchased, the system administrator will need to reactivate SmarterMail and enable the add-on for the user's mailbox. For more information, refer to the KB article How To Activate EAS .

If SmarterMail is running under IIS, the system administrator will also need to disable Windows authentication before adding EAS to specific mailboxes. For more information, refer to the KB article How To Configure IIS for EAS.

Message Retrieval

For SmarterMail users with EAS, messages will automatically be synchronized with Windows Mail. SmarterMail users without the EAS option should set up an account within Windows Mail using either IMAP or POP3, where possible.

IMAP is a robust protocol that easily handles mailboxes that process and/or store large volumes of email. In addition, IMAP IDLE is an optional feature of the IMAP protocol that pushes all new messages out as they are received by the mail server. Unlike POP, IMAP offers two-way communication between your SmarterMail mailbox and your email client(s). This means when you log in to the SmarterMail Web interface, actions you performed on email clients and mobile devices will automatically appear in the Web interface (and vice versa). In addition, IMAP keeps all messages and folders on the server whereas POP downloads all messages to an email client.

With POP3, your mail is saved in a mailbox on the remote server until you check your mail. When you check your mail, all the mail is downloaded to your computer and is no longer maintained on the server. If you use POP3 and are traveling or check your mail from multiple locations, you will not be able to view any of your old mail because the messages only exist on the computer on which you originally received your mail.

note: If you have enabled Outlook to keep messages on the server, you will be able to access your messages and folders from any computer via the SmarterMail Web interface or your mobile device.

Windows People

Windows People is a contacts system that comes pre-installed with Windows. It allows users to set up contacts within Windows that can be used for a variety of purposes (e.g., emailing).

EAS

The EAS add-on is available as an optional add-on for SmarterMail Enterprise and can be purchased from the SmarterTools website. Unlike the other synchronization methods, EAS uses direct push technology to sync email, calendars, and contacts — including contact pictures — in real time, ensuring any changes to collaboration data are automatically recorded in both SmarterMail and within Windows Mail.

With the release of Windows 10, Microsoft integrated EAS with the Windows Mail, People and Calendar applications that come as part of the Windows installation. Therefore, administrators and end users can set up Windows Mail using the EAS add-on as well as via IMAP or POP.

Once the EAS add-on has been purchased, the system administrator will need to reactivate SmarterMail and enable the add-on for the user's mailbox. For more information, refer to the KB article How To Activate EAS .

If SmarterMail is running under IIS, the system administrator will also need to disable Windows authentication before adding EAS to specific mailboxes. For more information, refer to the KB article How To Configure IIS for EAS .

Windows Calendar

Windows Calendar is a calendar application that comes pre-installed with Windows. It allows users to set up calendars within Windows that can be used for a variety of purposes (e.g., keeping track of appointments).

EAS

The EAS add-on is available as an optional add-on for SmarterMail Enterprise and can be purchased from the SmarterTools website. Unlike the other synchronization methods, EAS uses direct push technology to sync email, calendars, and contacts in real time, ensuring any changes to collaboration data are automatically recorded in both SmarterMail and within Windows Mail.

Once the EAS add-on has been purchased, the system administrator will need to reactivate SmarterMail and enable the add-on for the user's mailbox. For more information, refer to the KB article How to Activate EAS .

If SmarterMail is running under IIS, the system administrator will also need to disable Windows authentication before adding EAS to specific mailboxes. For more information, refer to the KB article How To Configure IIS for EAS .

Cross Platform Options

Microsoft Outlook

Microsoft Outlook is an email client developed by Microsoft, Inc. for managing messages, contacts, notes, tasks, and appointments and is commonly distributed as part of the Microsoft Office suite. Outlook is offered on both the Windows and macOS platforms. SmarterMail supports synchronization of email, contacts, calendars, tasks and notes both on Windows and macOS.

MAPI/EWS

The MAPI/EWS add-on is available as an optional add-on for SmarterMail Enterprise and can be purchased from the SmarterTools website. Users can currently use MAPI/EWS to sync messages, contacts, calendars and tasks with Outlook from Microsoft 365 and Outlook 2016 and above for both Windows and Mac, and Apple Mail.

note: The MAPI/EWS bundle is comprised of 2 different protocols: Outlook for Windows connects using MAPI while Outlook for Mac connects using EWS.

Once the MAPI/EWS add-on has been purchased, the system administrator will need to reactivate SmarterMail and enable the add-on for the domain.

Add to Outlook

The Add to Outlook (Sharepoint Sync) feature allows for two-way synchronization of calendars, contacts (but not contact pictures) and tasks with Outlook 2007 or higher, including a user's shared resources. Calendars and contacts shared at the domain level are not supported. For more information, refer to the KB article How To Synchronize SmarterMail with Outlook Using the Add to Outlook Feature . However, Sharepoint Sync does not support notification features, so items like SmarterMail calendar reminders will not be available within Outlook. For full integration, EAS (for mobile devices and Outlook 13 and above for Windows) or EWS (for Outlook for Mac and Apple Mail) should be used.

Message Retrieval

For SmarterMail users with MAPI/EWS, messages will automatically be synchronized with Outlook. SmarterMail users without the MAPI/EWS option should set up an account within Outlook using either IMAP or POP3.

IMAP is a robust protocol that easily handles mailboxes that process and/or store large volumes of email. In addition, IMAP IDLE is an optional feature of the IMAP protocol that pushes all new messages out as they are received by the mail server. Unlike POP, IMAP offers two-way communication between your SmarterMail mailbox and your email client(s). This means when you log in to the SmarterMail Web interface, actions you performed on email clients and mobile devices will automatically appear in the Web interface (and vice versa). In addition, IMAP keeps all messages and folders on the server whereas POP downloads all messages to an email client.

With POP3, your mail is saved in a mailbox on the remote server until you check your mail. When you check your mail, all the mail is downloaded to your computer and is no longer maintained on the server. If you use POP3 and are traveling or check your mail from multiple locations, you will not be able to view any of your old mail because the messages only exist on the computer on which you originally received your mail.

note: If you have enabled Outlook to keep messages on the server, you will be able to access your messages and folders from any computer via the SmarterMail Web interface or your mobile device.)

eM Client

eM Client is a cross-platform client for managing messages, contacts, notes, tasks, and appointments, and includes an integrated XMPP chat client. eM Client is offered on both the Windows and macOS platforms. SmarterMail supports synchronization of email, contacts, calendars, tasks and notes, as well as live chat, on both on Windows and OS X.

MAPI/EWS

The MAPI/EWS add-on is available as an optional add-on for SmarterMail Enterprise and can be purchased from the SmarterTools website. Users can currently use MAPI/EWS to sync messages, contacts, calendars and tasks with eM Client for both Windows and Mac. The chat client that comes with eM Client uses the XMPP protocol.

Once the MAPI/EWS add-on has been purchased, the system administrator will need to reactivate SmarterMail and enable the add-on for the domain.

Message Retrieval

For SmarterMail users with MAPI/EWS, messages will automatically be synchronized with eM Client. SmarterMail users without the MAPI/EWS option should set up an account within eM Client using either IMAP or POP3.

Mozilla Thunderbird

Mozilla Thunderbird is a free, open source email client developed by the Mozilla Foundation. SmarterMail supports synchronization of email, contacts and calendars with Thunderbird.

CalDAV

Users can also synchronize their SmarterMail calendars with Thunderbird using the CalDAV protocol and the Lightning add-on.

Message Retrieval

For messages, users should set up an account within Thunderbird using either IMAP or POP3.

IMAP is a robust protocol that easily handles mailboxes that process and/or store large volumes of email. In addition, IMAP IDLE is an optional feature of the IMAP protocol that pushes all new messages out as they are received by the mail server. Unlike POP, IMAP offers two-way communication between your SmarterMail mailbox and your email client(s). This means when you log in to the SmarterMail Web interface, actions you performed on email clients and mobile devices will automatically appear in the Web interface (and vice versa). In addition, IMAP keeps all messages and folders on the server whereas POP downloads all messages to an email client.

With POP3, your mail is saved in a mailbox on the remote server until you check your mail. When you check your mail, all the mail is downloaded to your computer and is no longer maintained on the server. If you use POP3 and are traveling or check your mail from multiple locations, you will not be able to view any of your old mail because the messages only exist on the computer on which you originally received your mail.

Mobile Devices

SmarterMail supports synchronization with most mobile devices on the market, including:

Apple iOS

Apple iOS devices include the iPod Touch, iPhone and the iPad. SmarterMail supports synchronization of email, contacts, and calendars with iOS devices.

EAS

The EAS add-on is available as an optional add-on for SmarterMail Enterprise and can be purchased from the SmarterTools website. Unlike the other synchronization methods, EAS uses direct push technology to sync email, calendars, and contacts — including contact pictures — in real time, ensuring any changes to collaboration data are automatically recorded in both SmarterMail and the mobile device.

Once the EAS add-on has been purchased, the system administrator will need to reactivate SmarterMail and enable the add-on for the user's mailbox. For more information, refer to the KB article How To Activate EAS .

If SmarterMail is running under IIS, the system administrator will also need to disable Windows authentication before adding EAS to specific mailboxes. For more information, refer to the KB article How To Configure IIS for EAS .

For synchronization instructions for a specific mobile device, refer to the manufacturer's website. Additional information may be available in the SmarterTools Knowledge Base.

CardDAV and CalDAV

SmarterMail users that choose not to purchase the EAS add-on can synchronize their SmarterMail contacts — including contact pictures — and calendars with iOS devices using the CardDAV and CalDAV protocols. Support for CardDAV and CalDAV is built into these products, so there is no need to download and install additional applications to sync contact and calendar data.

Google Android

Android is an operating system designed for use in a variety of smartphones and mobile devices. Examples of devices that run on Google Android include the Google Pixel line, the Samsung Galaxy line, and devices from other manufacturers. In addition, the Kindle Fire runs on a modified version of the Android operating system. SmarterMail supports synchronization of email, contacts, and calendars with Android devices.

EAS

The EAS add-on is available as an optional add-on for SmarterMail Enterprise and can be purchased from the SmarterTools website. Unlike the other synchronization methods, EAS uses direct push technology to sync email, calendars, and contacts — including contact pictures — in real time, ensuring any changes to collaboration data are automatically recorded in both SmarterMail and the mobile device.

Note: Only Android devices running version 2.0 or later support synchronization via EAS. Support for EAS may also vary by device. For example, EAS does not support Corporate Calendar or email applications for the Motorola Droid, Droid 2 or Droid X because they are custom applications that do not comply with EAS specifications.

Once the EAS add-on has been purchased, the system administrator will need to reactivate SmarterMail and enable the add-on for the user's mailbox. For more information, refer to the KB article How To Activate EAS .

If SmarterMail is running under IIS, the system administrator will also need to disable Windows authentication before adding EAS to specific mailboxes. For more information, refer to the KB article How To Configure IIS for EAS .

For synchronization instructions for a specific mobile device, refer to the manufacturer's website. Additional information may be available in the SmarterTools Knowledge Base.

CardDAV and CalDAV

SmarterMail users that choose not to purchase the EAS add-on can synchronize their SmarterMail contacts and calendars with Android devices using the CardDAV and CalDAV protocols. While the default calendar and contacts apps may NOT support either protocol, there are some Android apps that do support both. IN addition, there are CalDAV and CardDAV specific apps that can facilitate synchronization, though these may be paid apps. More information and implementations of CalDAV and CardDAV can be found by reviewing Implementations of CalDAV and CardDAV .

Message Retrieval

For SmarterMail users with EAS mailboxes, messages will automatically be pushed to their mobile devices as they are received. SmarterMail users without the EAS option should set up an account within the mail application provided on the mobile device using either IMAP or POP3.

IMAP is a robust protocol that easily handles mailboxes that process and/or store large volumes of email. In addition, IMAP IDLE is an optional feature of the IMAP protocol that pushes all new messages out as they are received by the mail server. Unlike POP, IMAP offers two-way communication between your SmarterMail mailbox and your email client(s). This means when you log in to the SmarterMail Web interface, actions you performed on email clients and mobile devices will automatically appear in the Web interface (and vice versa). In addition, IMAP keeps all messages and folders on the server whereas POP downloads all messages to an email client.

With POP3, your mail is saved in a mailbox on the remote server until you check your mail. When you check your mail, all the mail is downloaded to your computer and is no longer maintained on the server. If you use POP3 and are traveling or check your mail from multiple locations, you will not be able to view any of your old mail because the messages only exist on the computer on which you originally received your mail.

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