Outlook sync tools exist because Outlook holds the calendar, contacts, and email history most businesses run on, yet it rarely stays in sync with everything else on its own. Sales teams need it talking to a CRM. Remote employees need their phone and desktop calendars to match. IT admins need shared mailboxes that behave the same way for everyone on the team. The ten tools below cover the different jobs businesses hire an Outlook sync tool to do: CRM sync, calendar sync, contact sync, mobile sync, team sync, and backup or migration sync. Each one is measured against the five criteria below.
How We Chose These Tools
- Sync reliability: Does the tool offer true two-way sync, and does it handle conflicts without duplicating or losing data?
- Ease of setup: Can a non-technical office manager get it running, or does it need an IT project?
- Outlook compatibility: Does it work with current Outlook (desktop, web, and New Outlook), not just an old legacy version?
- Security: How is data handled in transit and at rest, and does the vendor publish clear information about it?
- Pricing and value: Is the pricing model transparent, and does it match what a small or mid-sized business would actually pay?
1. HubSpot
HubSpot offers a free CRM platform that gives sales teams a central place to manage contacts, deals, and customer conversations without extra cost for the core tools. It's built for small businesses and sales reps who want CRM basics inside the inbox they already use every day, rather than a separate system to maintain.
HubSpot's Outlook integration keeps your inbox and CRM working together. Two-way email sync logs every message you send or receive in Outlook onto the matching contact's timeline in HubSpot, so the whole team can see the full conversation history. Email open and click tracking shows when a prospect engages with a message sent from Outlook.
The CRM sidebar inside Outlook puts contact details, deal stage, and activity history right next to your inbox, so reps never have to switch screens to check where a lead stands. Calendar sync connects Outlook Calendar to HubSpot's booking links, letting prospects schedule meetings directly, with updates syncing both ways. It needs a Microsoft 365 business subscription on the Outlook side. Core Outlook sync features are included on HubSpot's free CRM plan, but the free plan caps email templates at three and email sequences require a paid plan.
Key Features
- Two-way email logging — Messages sent and received in Outlook are recorded on the matching contact's timeline, so the whole team sees the full conversation history.
- CRM sidebar inside Outlook — Contact details, deal status, and activity history sit next to the inbox, so reps don't switch screens to check on a lead.
- Calendar sync with booking links — Outlook Calendar connects to HubSpot's meeting scheduler, and updates sync both ways. A Microsoft 365 business subscription is required on the Outlook side.
- Email open and click tracking — Shows when a prospect opens or clicks a message sent from Outlook.
- CRM email templates — Templates and personalization from the CRM are available inside Outlook. The free plan caps templates at three, and sequences need a paid plan.
2. Nutshell
Nutshell is a CRM platform that combines sales management, marketing automation, and reporting in a single system. It is built for small and mid-sized teams, and its Microsoft 365 integration connects directly with Outlook and Microsoft Teams.
Once an Office 365 or Exchange account is connected, Nutshell syncs email, calendar events, and Teams activity automatically. Email sync is two-way: messages can be sent, received, and tracked from either Nutshell or Outlook, and each one is logged to the matching contact or lead so the full conversation history stays visible to the team. Emails can be sent from a company domain, with outgoing messages saved to the Outlook sent folder. The initial sync brings in the last 45 days of email, and email and calendar sync can be turned on separately or together.
The Nutshell for Outlook add-in is available free from Microsoft AppSource and works with Office 365 accounts on web and desktop. It lets reps create contacts and tasks, view scheduled activities and timelines, add notes, and use email templates from the inbox. Two-way calendar sync keeps meetings, calls, and reminders current in both Nutshell and Outlook. Within Microsoft Teams, users can view and update lead details, and Teams meeting transcriptions sync into Nutshell with AI summaries. Contacts can also be imported from Office 365.
Key Features
- Two-way email sync — Send, receive, and track emails from both Nutshell and Outlook, with every message logged automatically to the right contact or lead.
- Outlook add-in — Reps can create contacts and tasks, view scheduled activities and timelines, add notes, and use email templates without leaving their inbox. It works on both PC and Mac.
- Two-way calendar sync — Meetings, calls, and reminders stay current in both Nutshell and Outlook. Email and calendar can be synced separately or together.
- Microsoft Teams integration — Teams users can view and update lead details inside Teams, and meeting transcriptions can sync into Nutshell with AI summaries.
- Included on every plan — Email and calendar sync, the Outlook add-in, and Teams integration work across all tiers. Email templates inside Outlook require the Business plan or higher.
3. Pipedrive
Pipedrive is a visual, pipeline-first CRM built for sales teams who think in deal stages rather than spreadsheets. It's designed to keep the sales process simple, with Outlook sync handling the email and calendar work reps would otherwise do by hand.
Pipedrive's two-way email sync logs every message sent from Outlook straight onto the matching deal, so there's no manual copy-pasting between inbox and CRM. Email open and link-click tracking shows exactly when a prospect engages with a message. One- or two-way calendar sync connects Pipedrive activities with Outlook, Office 365, or Exchange calendars, so meetings booked in either place show up in both.
Pipedrive's email sync works with Outlook.com, Microsoft Exchange, and IMAP accounts, not just Microsoft 365. The Pipedrive Marketplace also lists a Pipedrive for Outlook add-in that shows contacts, deals, activities, and notes in a sidebar. It's a separate app with its own trial, so check its pricing before counting on it. Calendar sync is included on every plan, but email sync isn't available on the entry-level plan.
Key Features
- Two-way email sync — Messages sent from Outlook log to the matching deal automatically, with no copy-pasting between inbox and CRM.
- One- or two-way calendar sync — Pipedrive activities connect with Outlook, Office 365, or Exchange calendars. Each user's sync covers only the activities they own.
- Email open and link-click tracking — Shows when a prospect engages with a message, without leaving the CRM.
- Wide account compatibility — Works with Outlook.com, Microsoft Exchange, and IMAP accounts. POP3 connections aren't supported.
- Pipedrive for Outlook add-in — A sidebar shows contacts, deals, activities, and notes, and lets reps create contacts, deals, and notes from the inbox. It's a separate Marketplace app with a 7-day free trial.
4. SyncGene
SyncGene is a cloud sync service built to keep Outlook, Google, and iCloud calendars and contacts matching across every device a person uses. It runs as a web app, so there's nothing to install on a work computer or company-managed device.
SyncGene's two-way sync keeps calendar events, contacts, and tasks aligned between Outlook, Google, and iCloud at once, which is useful for anyone splitting time between a work Outlook account and a personal Google or Apple setup. Duplicate detection prevents the same contact or calendar entry from piling up during sync, and syncing can run automatically in the background or manually on demand.
SyncGene also lets you share a calendar with someone else regardless of which platform they use, so a shared Outlook calendar stays visible to a colleague on Google without either side changing how they work. The free plan is limited to two sources and one manual sync a month, and automatic sync is only a seven-day preview. Premium removes the contact limit and supports up to five sources.
Key Features
- Three-way platform sync — Calendar events, contacts, and tasks stay aligned between Outlook (including Office 365, Outlook.com, and Exchange), Google, and iCloud.
- Duplicate prevention — Stops the same contact or calendar entry from piling up during sync.
- Folder and group mapping — Sync specific folders and groups, such as a Google contact group to an Exchange folder, instead of everything at once.
- Automatic or manual sync — Run syncs in the background on a schedule, or trigger them on demand.
- Cross-platform calendar sharing — Share an existing calendar with someone on any platform without creating a separate one.
5. gSyncit
gSyncit is a Windows-based Outlook add-in built to sync Outlook directly with Google in both directions. It installs straight into Outlook, so there's no separate application running alongside it.
gSyncit syncs Outlook calendars, contacts, notes, and tasks directly with a Google account, and it also connects to iCloud, Yahoo, AOL, and other CalDAV and CardDAV services beyond Google. Outlook categories map to Google calendar event colors automatically, keeping the same organization system visible on both sides.
The add-in supports multiple Outlook profiles and multiple Google accounts from a single install, which suits anyone managing more than one calendar or mailbox. A built-in duplicate-removal wizard cleans up Outlook folders of repeated entries created before or during sync. An unregistered version lets you try it first, with limits on sync mappings and item counts, and a full license is priced per computer rather than as a subscription.
Key Features
- One- and two-way sync — Outlook calendars, contacts, notes, and tasks sync with Google in whichever direction you choose.
- Services beyond Google — Also connects to iCloud, Yahoo, AOL, and other CalDAV and CardDAV services, plus task apps such as Todoist and Evernote.
- Category-to-color mapping — Outlook categories sync to Google calendar event colors, so the same organization system shows on both sides.
- Multiple profiles and accounts — Handles several Outlook profiles and multiple Google accounts from a single install.
- Duplicate matching and cleanup — Entries are matched automatically to avoid duplicates, and a removal wizard clears existing ones from Outlook folders.
6. CompanionLink for Outlook (DejaOffice)
CompanionLink pairs with the DejaOffice app to sync Outlook contacts, calendar, tasks, and notes directly to a phone, with no need to route data through Google or iCloud. It's built for business users who want Outlook data on their phone but prefer to keep client information off third-party cloud servers.
CompanionLink's two-way sync works over USB, local Wi-Fi, Bluetooth, or the optional DejaCloud service, giving businesses a choice of how directly their data travels between PC and device. It works with IMAP, POP3, and local Outlook folders, so an active Microsoft 365 subscription isn't required to keep a phone in sync.
Outlook's categories and color coding carry over to the synced device, and CompanionLink supports Outlook 2007 and newer, including the New Outlook. A 14-day free trial is available, and a single license covers up to three devices or PCs. It can be bought as a one-time license or a quarterly subscription.
Key Features
- Two-way device sync — Outlook contacts, calendar, tasks, notes, and categories sync with Android phones and tablets, iPhone, and iPad.
- Six sync methods — Choose USB, Wi-Fi, Bluetooth, DejaCloud, Google, or iCloud, and switch methods later on the same license.
- No Microsoft 365 required — Works with IMAP, POP3, and local Outlook folders, so no active subscription is needed.
- Categories and colors preserved — Outlook's category colors carry over to the synced device.
- Current Outlook support — Works with New Outlook and Classic Outlook, Microsoft 365 and Outlook.com accounts, and Outlook 2007 and newer.
7. Akruto
Akruto is Windows PC software that syncs Outlook calendar, contacts, tasks, and notes to a phone over a local or encrypted connection, without storing data on Akruto's own servers. It's built for businesses handling sensitive client information that want sync without a cloud middleman in between.
Akruto's two-way sync runs automatically between Outlook and unlimited iOS and Android devices under a single license, transferring data directly between the PC and device rather than through a third-party cloud. Calendar, contacts, tasks, and notes all sync together in one pass, and the connection is encrypted throughout.
Because sync runs whenever the PC and device are both connected, it works continuously in the background without manual triggering. A free trial is available before committing to a license.
Key Features
- Cloud-free sync — Data moves directly between the PC and the device, with nothing stored on Akruto's servers.
- Four data types in one pass — Calendar, contacts, tasks (reminders on iPhone), and notes sync together.
- Automatic wireless sync — Runs in the background over local Wi-Fi whenever the PC and device are both connected.
- Unlimited devices on one license — iPhone, iPad, and Android phones and tablets all sync under the same license.
- Encrypted connection — Sync travels over an encrypted connection built for privacy-conscious setups.
8. Microsoft 365 Shared Calendars and Shared Mailboxes
Microsoft 365's shared mailbox and shared calendar features, built on Exchange Online, let a team see and manage the same mailbox, calendar, or resource booking without adding any third-party software. For businesses already running Microsoft 365, this is sync that comes built into the platform rather than something layered on top. Because more people have access to the same inbox, shared mailboxes also raise the stakes on email security for Office 365.
Shared mailboxes are accessible from Outlook desktop, web, and mobile by any team member with permission, and shared or delegate calendars use configurable permission levels so colleagues can view or edit the same calendar directly instead of copying events between separate ones. Room and resource mailboxes extend the same system to booking meeting spaces or equipment.
Shared mailboxes under 50GB don't need their own license, and shared calendars and mailboxes work alongside Microsoft Teams. For teams standardized on Microsoft 365, this native option often covers team sync needs before any third-party tool becomes necessary.
Key Features
- Shared mailboxes — Team members with permission reach the same mailbox from Outlook on desktop, web, and mobile.
- Shared and delegate calendars — Configurable permission levels let colleagues view or edit the same calendar directly, with no copying between calendars.
- Room and resource mailboxes — Meeting spaces and equipment are booked through the same shared system.
- No separate license under 50GB — Shared mailboxes under 50GB don't need their own license.
- Teams compatibility — Shared calendars and mailboxes work alongside Microsoft Teams.
9. BitTitan MigrationWiz
BitTitan MigrationWiz is a cloud-based migration platform for moving mailboxes, calendars, contacts, and files between email platforms, most often into or out of Microsoft 365. It's built for one-time or periodic migration projects, such as a platform switch or company merger, rather than continuous day-to-day sync.
MigrationWiz performs full-fidelity mailbox migration, preserving calendar events and recurring meetings intact during the move, and it keeps contact address books intact at the same time. It supports Google Workspace, Microsoft 365, and a wide range of other source and destination platforms, along with public folder migration for shared emails, calendars, contacts, and files.
Delta sync passes catch changes made after the initial migration, and a single license covers them for 12 months, which keeps source and destination aligned during a gradual cutover. Licenses are priced per user for a single migration project rather than billed as a recurring subscription.
Key Features
- Full-fidelity mailbox migration — Mailbox contents move with calendar events, recurring meetings, and calendar permissions preserved.
- Contact migration — Address books stay intact during the move between platforms.
- Delta sync passes — Catch changes made after the first pass, for 12 months on a single license.
- Public folder migration — Moves emails, calendars, contacts, and files, with support for migrating into a shared mailbox.
- Cloud-based, no installation — Runs as a fully hosted service with one interface for mailbox, archive, and document projects.
10. cloudHQ
cloudHQ is a cloud-to-cloud sync and backup service that connects Outlook.com and Microsoft 365 with Google Workspace, Dropbox, and other cloud accounts in real time. Businesses running a mixed Microsoft and Google environment use it to keep both sides aligned automatically, without staff manually copying data between systems.
cloudHQ's two-way sync runs in real time rather than on a scheduled batch, and it can back up Microsoft 365 mail and files to a separate cloud destination, including Amazon S3, for an added layer of protection. A migration mode moves mail and files between platforms when a business switches providers.
Admin-level controls let IT manage syncing and backup for multiple users from one view, and point-in-time restore recovers data as it looked on a previous date rather than only the most recent version. A free plan covers personal, non-business cloud accounts, with Premium and Business plans scaling up from there.
Key Features
- Real-time two-way sync — Changes on either side sync continuously rather than in scheduled batches, with one-way sync also available.
- Cross-cloud coverage — Syncs between Microsoft 365, Outlook.com, Google Workspace, Dropbox, Box, OneDrive, SharePoint, and other cloud accounts.
- Real-time backup — Backs up Microsoft 365 mail and files to separate storage such as Amazon S3 or Glacier.
- Point-in-time restore — Recovers data as it looked on an earlier date, not just the latest version.
- Failover replica — Can keep a live copy of Microsoft 365 mail, OneDrive, and SharePoint in Google Workspace, ready to use if Microsoft 365 is unavailable.
How to Choose the Right Outlook Sync Tool
Start with what actually needs to sync, not with a list of features. A sales team mainly needs CRM sync (HubSpot, Nutshell, or Pipedrive); someone juggling Outlook with a personal Google or iCloud account needs calendar and contact sync (SyncGene or gSyncit); a business protecting sensitive data may prefer a no-cloud option (CompanionLink or Akruto).
Next, match the tool to your team's technical comfort. Cloud-based tools like SyncGene and cloudHQ are easier for non-technical staff to set up. Desktop tools like gSyncit, CompanionLink, and Akruto give more control but expect some comfort installing and configuring Windows software.
Finally, weigh ongoing cost against a one-time purchase. Subscription CRM tools bill monthly per user, and that adds up fast across a sales team. Several of the desktop sync tools on this list offer a one-time license instead, which can be cheaper for a small team that doesn't need frequent updates.
Conclusion
The right Outlook sync tool depends less on which one has the most features and more on what's actually breaking in your current setup. A sales team drowning in manual data entry needs CRM sync. A business with staff on mixed devices needs a calendar and contact sync that runs in the background. A company switching platforms needs a migration tool built for that one job, not a sync tool stretched past what it's meant to do. Pick the tool that closes your specific gap.