Should you wish to manually append files to your contacts, initially you will require a custom field type dedicated to files.
1. Select "Settings"

2. Select "Custom Fields"

3. Click "Add Field"

4. Select "File Upload"

5. Click "Choose File"

6. Click "Next"

7. Provide "Field Name"

8. Choose Object from the drop down list

9. Choose group from the drop down list

10. Tick box/es of file format you want to allow
Select the kind of files you'd like to have the ability to attach, or simply pick 'any' if you desire the flexibility to attach all types of files.

11. Tick Allow Multiple Files
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12. Set Max File Limit
Establish a maximum limit for the file you wish to attach.
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13. Click "Additional Preferences"

14. Provide Unique Key

15. Add Description

16. Click Save once done setting up
