How to make a list of case studies with a thumbnail image?

Unless it’s a problem with copying it here, your indentation seems to be wrong for the cover key. And you want this to be a field, not a section, so you have to create a new fields section first, like this:

title: Default Page

columns:
  main:
    width: 2/3
    sections:
      fields:
        image_content: 
          type: files
        menu_name: 
          type: text
        description_meta_tag:
          type: text     
        heading:
          type: text
        subheading:
          type: text
        text:
          type: textarea
          size: large

  sidebar:
    width: 1/3
    sections:
      pages: # this is a pages section
        type: pages
        template: default
      files: # this is a files section
        type: files
      filesfield: # this is a new fields section
        type: fields
        fields:
          cover: # this is the select field for your thumbnail
            type: files
            required: true

So always two spaces for each indentation level.

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