Troubleshoot issues with messages

The following error message indicates that GSSMO's message-conversion process might be corrupted and needs to be repaired:

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 may enable you to send the message.

To fix this issue:

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

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

How do I reinstall GSSMO and Outlook?

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 Windows Control Panel (called Programs and Features in Windows 7, for example) and uninstall GSSMO 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 GSSMO profile in Outlook and synchronize with your Google Account. For details, see Download and install GSSMO.

   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.

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, see Sending large messages over a slow connection.

If you attach and email a text file and send it to yourself or to a non-G Suite 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.

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

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

Although it's possible to add an Exchange account to your profile in GSSMO, we don't recommend it. Using Exchange and GSSMO in the same profile can cause sending errors and other problems.