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In Eloqua, can you send out an email to a contact list but version the "hero" image headline for each segment using dynamic content blocks? And then can you do the reverse, have the main image remain the same, and dynamically populate products below that they've purchased in the past?

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For scenario 1, yes that is possible out of the box.

Scenario 2 however is a bit more complicated and would generally require a 3rd party tool to provide this type of dynamic code generation based upon a lookup table (in this case a line item inventory or purchases). Because a contact could have zero or more products (commonly as individual records in a CDO), you would generally need to aggregate or count the number of related records, and then generate your HTML table and formatting around those record values, and be contextually aware if it is the first or last record (to begin and close the table). Dynamic content does not have mathematical functions and would not be able to count those related records - this is something usually provided by a B2C system like SFMC using ampscript or dynamically generated through custom code and sent through a transactional SMTP service. You could have multiple dynamic content on top of each other, but your biggest limitation becomes the field merge, with only lets you select a record based upon earliest/last creation date, or last modified. This is not suitable if you have more than 2 records. A third party service that provides a cloud content module for your email is your best bet.