Troubleshoot issues with messages

Google Workspace Sync for Microsoft Outlook

Here's how to troubleshoot problems you might have with message content in Google Workspace Sync for Microsoft Outlook (GWSMO).

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Issues with messages

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Get MIME conversion error after message fails to send

If you receive the following error message when trying to send a message from Outlook, it might mean the GWSMO message-conversion process is corrupted and needs repair:

This email message was not sent because we were unable to convert the message into Internet format (MIME). Removing attachments or removing forwarded text from the message might let you to send the message.

To fix this issue:

  1. Restart your computer.
  2. If the problem persists, reinstall both Outlook and GWSMO.

You won't lose any of your mail, calendar events, contacts, notes, or tasks. However, you have to set up your Outlook options again.

How do I reinstall Outlook and GWSMO?

Important: Before completing these steps, make sure you have access to your Outlook installation disk or files.

  1. Go to the Program management section of your Microsoft Windows Control Panel (called Programs and Features in Windows 7, for example) and uninstall GWSMO just like you'd uninstall any other program.
  2. From the same place in your Windows Control Panel, uninstall Outlook.
  3. Reinstall Outlook from the disk or installation files.
  4. Recreate your profile in Outlook to synchronize with your Google Account. For details, go to Download and install GWSMO.

    Important: When you recreate your profile, don't import data from your old Outlook profile. Your data is already in your Google Account.

  5. Restart your computer.
Large messages time out over slow connection

If you send a message with a large attachment over a slow connection, the connection can time out, leaving the message unsent in your Outbox. To troubleshoot this issue, go to Large messages time out over slow connection.

Text files corrupted when emailed to own email account or non-Google Workspace user

If you attach a text file and send it to yourself, or to a non-Google Workspace user within Outlook, the attachment might be corrupted in the received message.

To avoid this issue, add the attachment to Google Drive instead of emailing a file to yourself. Or, you can send an attachment to yourself from the Gmail web interface.

Bullet points not correctly rendered when using Outlook with GWSMO

If you send an email message with bullet and sub-bullet points through Outlook by GWSMO, the bullet structure might be corrupted in the received message.

To report this issue, we recommend you contact Microsoft support.

Add a Microsoft Exchange account to a profile and get errors

Although it's possible to add an Exchange Server account to your profile in GWSMO, we don't recommend it. Using Exchange and GWSMO in the same profile can cause sending errors and other problems. Create separate Outlook profiles for the GWSMO and Exchange Server accounts.

Can't view EML or MSG files

If you attach an email message (.eml or .msg) file to a message in Outlook synced with GWSMO or IMAP, recipients using Exchange or other non-Gmail mail services can't read the attachment (the attachment appears blank). Avoid this issue by forwarding the original message with the non-Gmail mail service, instead of attaching the original message as a .eml or .msg file.

Email message attachments sent from Outlook directly to the Gmail web UI are read differently, depending on the type:

  • .eml attachments are readable with Gmail's EML Viewer.
  • .msg attachments are not readable.

GWSMO automatically converts .eml and .msg attachments to a format that Gmail can read (message/rfc822 format). So a .eml or .msg attachment sent from one GWSMO user to another GWSMO user, or from a GWSMO user to the Gmail web UI, is readable by the recipient.

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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