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The Add Email to Salesforce button allows you to push any emails you receive in your inbox to your Salesforce account from Outlook or Gmail. We do the look up based on the sender of the email, so we can currently only use this button for emails you received.

We are working on changing the functionality to allow to log emails you've already sent, but in the meantime, if it didn't automatically log when sent or show up in your failed activities in the activity log, you can forward it to your Salesforce BCC email address.

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