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Have a client who started using Lightning for Outlook -- they have Office 365. Instead of creating a new account for each new contact, most of their contacts are associated with 1 bucket account that they use (e.g. "ABC Contacts").
In Outlook, when they display an email from a SF contact, the Opportunities for that contact don't appear in the SF sidepanel.  They have to search for it.  Is that because of the way the Account is being handled?