Issues with messages

If you try to create or update a signature in Outlook, you can't select an account. You might get this message: "This option is available only when Microsoft Outlook is running. Do you want to start Outlook?"

To disable the Microsoft roaming signatures feature that causes the issue:

1. Click StartRun (or press WIN+r).
2. Enter the following command:

   reg add HKCU\Software\Microsoft\Office\16.0\Outlook\Setup /v DisableRoamingSignaturesTemporaryToggle /t REG_DWORD /d 1

3. Restart Outlook.

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 & 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 & install GWSMO.

   Important: When you re-create 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, go to Large messages time out over slow connection.

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.

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.

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.

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.