There should be a way to set up a rule to allow emails from BCC to timeline from specific users be associated with specific accounts. This way if there is one contact associated with multiple accounts, it will map to the proper account depending on the sender.
BCC to Timeline Feature - contact on multiple accounts
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This can be solved using Gmail plugin which we have released. Please check out this link https://support.gainsight.com/Gainsight_NXT/Email_Assist/Chrome_Plug-in/Gainsight_Assist_Chrome_Plug-in_User_Guide for more details.
@john_apple activity association is still 1:1.