Why can't I type more than 255 characters into a field? [All editions]
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Retain 3.6 allows you to set fields to be as long as you want, within the limits of your database platform, however older versions of Retain restricted you to 255 characters due to the size of the text boxes.

Retain is not designed to display very large pieces of text in fields about jobs, resources or bookings. If you need to include information such as a resume about a resource, then you can designate that field as a 'document link' in Retain Manager, Setup | Field Properties, which allows you to define a link to a text document which can be accessed through a button which will appear next to that field in Retain.