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I don't believe there is anyway to do this in Gmail. When an email is sent it appears in the "Sent Mail" folder (or rather is assigned the sent label) and there does not appear to be anyway to change this behaviour. "Filters" only act on incoming email. However, you can do this in some other email clients, by essentially not saving the sent email: ...


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Google consumer accounts can't be upgraded to a Google Apps account, but if a Google consumer account use as primary email address one from a custom domain a conflicting account will be created. During the signup process for that account, Google will offer the user to migrate some of the data. References Resolve conflicting accounts - Google Apps Help


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At this time is not possible, but recently Google added more controls for multi-domain organizations, so the hangouts web address mapping could be added "soon" (could take several months). References Feature parity for multi-domain Google Apps instances



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