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Troubleshoot synchronization issues

Google Workspace Sync for Microsoft Outlook

Here's how to troubleshoot synchronization issues you might have with Google Workspace Sync for Microsoft Outlook (GWSMO).

General sync issues  |  Mail sync issues  |  Calendar sync issues  |  Contact sync issues  |  Other sync issues

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General sync issues

GWSMO icon in the Microsoft Windows taskbar is showing offline

Either your network connection is down or Outlook has switched into offline mode (after a password reset, for example).

Getting sync errors or synchronization stopped altogether

Did you select an Unlimited mailbox size limit in GWSMO? If so, your local PST file might have reached its maximum size, which can cause errors or prevent GWSMO from syncing with Google Workspace. By default, Outlook limits the size of a local PST file to 20 GB (for Outlook 2007) or 50 GB (for Outlook 2010, 2013, 2016, or 2019). To fix the problem, you need to limit the mailbox size in GWSMO. For details, go to Set a local mailbox size.

Or, increase the size limit of your PST file in Outlook. For more information, consult this Microsoft article.

Dragged folders in Outlook cause synchronization issues

Dragging folders in Outlook to reorganize them can cause synchronization issues in GWSMO. Create a profile and data should sync correctly.

GWSMO doesn't return Windows Search results

GWSMO with Outlook running on certain versions of Microsoft Windows doesn't return Windows Search results. If you’re affected by this issue, apply the latest Microsoft Office updates for your version. For more information, consult the Outlook known issues in the June 2017 security updates, specifically Issue #5.

Mail sync issues

Local Outlook PST file larger than GWSMO mailbox

It's possible your PST file might exceed the size limit. This depends on your Outlook set up. For more information on how to configure the size limit for PST files in Outlook, consult this Microsoft article.

You can also try using Outlook to compact a local PST file. For more information on how to reduce the size of your mailbox and Outlook Data File, consult this Microsoft article.

Same message appears in multiple folders in Outlook

A message with multiple labels in Gmail appears in each corresponding folder in Outlook. It can look like there are multiple copies of the same message in Outlook, and the size of your local mailbox (PST file) can be larger as a result.

There's only one copy of the message. Deleting it from one folder deletes it from the other folders, too.

For details, go to Work with messages in Outlook Mail.

Executable file attachments aren't appearing

GWSMO doesn't allow sending executable (.exe) file attachments (including executables in compressed attachments) and some other types of file attachments. These attachments don't appear in Outlook or Gmail. There’s also limitations when you send .eml or .msg attachments to Outlook users. For details, go to Can't view EML or MSG files.

What type of files can't I send?

.ade, .adp, .bat, .chm, .cmd, .com, .cpl, .dll, .exe,
.hta, .ins, .isp, .jse, .lib, .mde, .msc, .msg, .msp,
.mst, .pif, .scr, .sct, .shb, .sys, .vb, .vbe,
.vbs, .vxd, .wsc, .wsf, .wsh

Outlook not showing older messages (but Gmail interface is)

Your local mailbox size (Outlook PST file) might not be large enough to store all your email messages. GWSMO stores the most recent messages locally (up to 1 GB by default). It stores all the messages (up to 25 GB) in the cloud, where they’re accessible from the Gmail interface.

If you want more messages stored locally, you can change your primary Outlook mailbox account size using the following methods:

Note: Although you can increase your Outlook mailbox size, this isn't normally recommended as it can affect sync performance.

Unable to move messages between folders in Outlook

If you're unable to move a message from one folder to another in Outlook, it could be because the destination folder doesn't have a corresponding label in Gmail. To fix the problem, try one of the following options:

  • Create a label in Gmail that corresponds to the folder you're moving the message to
  • Delete the folder in Outlook and recreate it

Note: You can't move messages directly into the Drafts folder. You have to save the message as a draft instead.

I'm getting sync errors, or synchronization has stopped altogether

Did you select an Unlimited mailbox size limit in GWSMO? If so, your local PST file might have reached its maximum size, which can cause errors or prevent GWSMO from syncing with Google Workspace. By default, Outlook limits the size of a local PST file to 20 GB (for Outlook 2007) or 50 GB (for Outlook 2010, 2013, 2016, or 2019). To fix the problem, you need to limit the mailbox size in GWSMO. For details, go to Set a local mailbox size.

Or, increase the size limit of your PST file in Outlook. For more information, consult this Microsoft article.

Large messages time out over slow connection

If you send a message with large attachments over a slow connection, the connection can time out. The message remains unsent in your Outbox. By default, the timeout is hard-coded to occur at 90 seconds.

You can extend this period by modifying your Windows registry. Add the following keys to override the default timeout values:

  • HKEY_CURRENT_USER\Software\Google\Google Apps Sync\Other\ResolveTimeoutSeconds > DWORD Value = 00000030
  • HKEY_CURRENT_USER\Software\Google\Google Apps Sync\Other\ConnectTimeoutSeconds > DWORD Value = 00000030
  • HKEY_CURRENT_USER\Software\Google\Google Apps Sync\Other\SendTimeoutSeconds > DWORD Value = 00000600
  • HKEY_CURRENT_USER\Software\Google\Google Apps Sync\Other\ReceiveTimeoutSeconds > DWORD Value = 00000600

Note: If you're running a 32-bit version of Outlook on a 64-bit version of Windows, you'll need to add these registry keys in the correct location for 32-bit applications. For details, go to Using a 32-bit version of Outlook on a 64-bit version of Windows.

Open the Registry Editor

  1. In the Start menu, click Windows Systemand thenRun.

    Note: Alternatively, press the Windows key + R.

  2. In the Run box, enter regedit.
  3. Click OK.

Note: If you're using a 32-bit version of Outlook on a 64-bit version of Windows, enter %systemroot%\syswow64\regedit instead in the Run dialog.

Add keys to the Windows registry

  1. Navigate to HKEY_CURRENT_USER\Software\Google\Google Apps Sync\.
  2. Click Edit and then New and then Key to create a new key folder.
  3. Enter Other as the name of the key, and press Enter.
  4. Select the Other folder you created.
  5. Click Edit and then New and then DWORD (32-bit) Value.
  6. Enter ResolveTimeoutSeconds as the new value, and press Enter.
  7. Right-click the ResolveTimeoutSeconds value you created and select Modify.
  8. In the Edit DWORD (32-bit) Value box, under Value data, enter the timeout value.
  9. Repeat the steps to create a DWORD (32-bit) value for the other timeout values (ConnectTimeoutSeconds, SendTimeoutSeconds, and ReceiveTimeoutSeconds).
Drafts saved in Outlook don't sync to Gmail

GWSMO doesn't synchronize email drafts with Gmail or other computers where you use Outlook. You must complete the email on the same client on which you started.

Sent messages not showing up in Outlook Sent Items folder

With the default Outlook settings, sent messages should appear in the Sent Items folder. If the original settings have been modified, restore them to the default settings. For more information on how to change where sent email messages are saved, consult this Microsoft article.

Messages moved from Outlook Sent Items folder reappear there

In Gmail, a message can later reappear with a Sent Mail label. If it does, it will try to sync back to Outlook's Sent Items folder.

This issue will resolve itself. It can take up to 24 hours to be synced correctly, however.

Can't view .eml or .msg files

If you attach an email message (using a .eml or .msg file) to a message in Outlook, recipients using Microsoft Exchange can't read the attachment. To avoid this issue, it's best to forward the message using Outlook, rather than forwarding it as an attachment. For details, go to Can't view EML or MSG files.

I get an "operation failed" error when sending email in Outlook

This issue can occur when you configure your GWSMO account and Exchange Server account in the same Outlook profile.

If you get this error, create separate Outlook profiles for the GWSMO and Exchange Server accounts.

Folders in Outlook don't always match labels in Gmail

This issue can occur if you rename a label in Gmail with nested labels underneath. Following a sync, you might get both the original label and the renamed label in Outlook.

I receive a "Google Workspace Sync has found problems in your profile" message

You might get this message if:

  • Your GWSMO profile was created using GWSMO version 4.0.17.0 or earlier.
  • You’re sending email from a secondary IMAP account (an IMAP account to the GWSMO Outlook profile). These email messages won't send.

The issue occurs when the name of a Google Workspace email label conflicts with an Outlook folder name. To resolve the issue, you should recreate your profile. For details, go to Create or replace your profile.

Messages moved between accounts in Outlook 2010 don't sync to Gmail

GWSMO doesn't synchronize emails to Gmail when moving messages between accounts in the GWSMO profile in Outlook 2010. To fix the problem, you need to copy the messages instead of moving them.

Hold the Ctrl key until you view a plus sign on your mouse pointer. You can then copy the messages between accounts and delete the originals. Note this method also works in later versions of Outlook.

Calendar sync issues

Invitations do not sync properly

This issue can occur if you're receiving calendar invitations not in iCalendar format. Check your Gmail interface to confirm if the invitation email contains a winmail.dat attachment. If it does, the sender needs to modify their Outlook settings to use iCal format when sending meeting requests outside of their organization. For more information on how to send meeting requests using the iCalendar format, consult this Microsoft article.

Note: This setting might be turned off if the sender is using GWSMO or is connected to an Exchange server.

Outlook adds events to primary calendar that belong on another calendar

Whenever Google Calendar sends you a notification about a new event, Outlook adds the event to your primary calendar—no matter what calendar the event actually belongs to.

If this is a frequent problem, you should avoid turning on New Event notifications for any calendar other than your primary calendar.

Events in Outlook show wrong time zone

In the Google Calendar interface, verify your time zone settings are correct:

  1. Go to Settings "" and then Settings.
  2. On the General tab, set the current time zone.
  3. On the Calendars tab, select any other calendars and set the time zone for them.
  4. Share these instructions with the people who invite you to meetings.

New events scheduled should now display the correct time zone. To ensure previously scheduled events display correctly, you must recreate your profile.

One-day events show up in Outlook across 2 days

Your time zone might not be correctly set in the Google Calendar interface. To check the setting and correct it:

  1. Go to Settings "" and then Settings to verify your time zone settings.
  2. Delete and resync your calendar data to correct any previously scheduled all-day events:
    1. In your Windows taskbar notification area, right-click GWSMO "" and click View sync status.
    2. In the Synchronization Status dialog, click Re-sync next to Google Calendar.
    3. In the Re-sync Google Calendar dialog, select the Delete and resync option to delete and resync your calendar data only.
    4. Click Re-sync.

This deletes Outlook-specific data from your calendar, such as colored categories you applied to events. For details on the Delete and resync option, go to Resync or repair Outlook data.

Outlook crashes when I refresh free/busy information

Are you using Outlook 2010? If so, ensure you got all the required hotfixes for Outlook 2010. Consult your Microsoft documentation for details.

Can't view other users' free/busy information in Outlook

There might be a problem with your Windows registry settings. Verify the following registry key is set exactly as shown below. If the key doesn't exist or if its value doesn't match what's shown below, create the key and edit its value.

  • Registry key: KEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Office\your_Outlook_version\Outlook\SchedulingInformation\FreeBusySupport
  • Value name: SMTP
  • Value type: REG_SZ (string value)
  • Value data: {0006F049-0000-0000-C000-000000000046}

Open the Registry Editor

  1. In the Start menu, click Windows Systemand thenRun.

    Note: Alternatively, press the Windows key + R.

  2. In the Run box, enter regedit.
  3. Click OK.

Note: If you're using a 32-bit version of Outlook on a 64-bit version of Windows, enter %systemroot%\syswow64\regedit instead in the Run dialog.

Modify this key in the Windows registry

  1. Navigate to HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Office\your_Outlook_version\Outlook\SchedulingInformation\

    where your_Outlook_version is:

    • 11.0 for Outlook 2003
    • 12.0 for Outlook 2007
    • 14.0 for Outlook 2010
    • 15.0 for Outlook 2013
    • 16.0 for Outlook 2016 and Outlook 2019
  2. If you don't find FreeBusySupport folder in the SchedulingInformation folder, click Edit and then New and then Key to create a new key folder.
  3. Enter FreeBusySupport as the name of the key, and press Enter.
  4. Select the FreeBusySupport folder you created.
  5. Click Edit and then New and then String Value.
  6. Enter SMTP as the new value, and press Enter.
  7. Right-click the SMTP value you created and select Modify.
  8. In the Edit String box, under Value data, enter {0006F049-0000-0000-C000-000000000046}.
Some calendar, contact, notes, or tasks folders aren't syncing

When creating folders in Outlook, make sure you create them under the appropriate Outlook app (Calendar, Contacts, and so on). If you don't, their contents won't sync with Google Workspace.

In addition, create all notes in your top-level Notes folder in Outlook. Notes placed elsewhere, such as in subfolders, won't sync with Google Docs, Sheets, and Slides.

Calendar resources added using the Outlook address book don't sync

If you add resource calendars and resource-room calendars from the Outlook address book to your Outlook Calendar, permissions aren't assigned to the Outlook calendar resources. Then, if a calendar event is created in Google Calendar and synced using GWSMO, the event doesn't appear in the Outlook calendar.

To fix the problem, a resource calendar can only be added using the Google Calendar web UI. For the recommended way to add a resource-room calendar, go to adding calendar resources using Google Calendar.

Contact sync issues

Does contact data still sync when you get a conflict error?

If you update a contact from both Outlook and Google Workspace or a separate mobile device, a conflict can occur because GWSMO retains 2 versions of the contact. You don't lose any data when this happens—both versions of the contact are retained.

To choose which version to keep:

  1. In Outlook Mail, open your Sync Issues and then Conflicts folder to find which contact has a conflicting version. Note that other issues might be reported here, too.
  2. Open the contact in Outlook to view the conflict message. Select which version to keep.

Solving other sync issues

  • Verify your version of Windows or Outlook meets all these system requirements.
  • Make sure you're using the latest release of GWSMO with the latest hotfixes. Learn more about the latest release.
  • Make sure your Outlook PST file isn't corrupt. For more information on how to repair Outlook data files, consult this Microsoft article.

Are there known issues?

To find out, go to Google Workspace Known Issues. Search under Data migration and sync and Device syncing.


Google, Google Workspace, and related marks and logos are trademarks of Google LLC. All other company and product names are trademarks of the companies with which they are associated.

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