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I'm trying to migrate a client from an on-site Exchange 2010 server to Google Apps. Every email address has multiple aliases, and each user needs to be able to send mail from each alias. To complicate matters, users will be accessing their Gmail account through Outlook.

Google Apps Sync for Outlook can sync your delegated accounts in Gmail with Outlook, so that when you send a new message you can select which of the delegated accounts you would like to send from. However, installing Google Apps Sync on everyone's computer and entering their account info will cause serious complications during the rollout.

Is there a way to send a message as a delegated Gmail account from Outlook without using Google Apps Sync for Outlook?

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While it's still not great, you can use a direct "send as" approach instead of delegation.

This involves defining a second account in Outlook, but at least it doesn't require installing anything. You can either straight up define the needed SMTP server/username/password or just duplicate each user's original account except changing the "from" field into the needed address.

If you choose the latter, you have to enable it in each user's Gmail settings as explained in https://support.google.com/mail/answer/22370:

  1. Define the SMTP server/username/password in each user's Gmail settings.
  2. Have the second address' owner click on the confirmations he/she'll be getting.
  3. Duplicate each user's Outlook account and just change the "from" field like we said.

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