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In addition to what mentioned by @Mayur Jadhav on the process, if you are moving a checkbox field values and mapping it to the new multi-select dropdown list field via CSV, you need to create multiple columns to transform your existing assigned checkbox field value(s) to individual columns.
Example - ABC-123 issue's checkbox field value(s) contains "One", "Two", and "Three". In your CSV file for bulk update (via Systems > External System Import), the CSV file needs separate column for each one of those values
|This is a test||ABC-123||One||Two||Three|
In the bulk update process, map Option1, Option2, and Option3 to your new multi-select dropdown list field.
Hope this helps.
Best, Joseph Chung Yin
Jira/JSM Functional Lead, Global Infrastructure Applications Team
No You can't change the field's type (for example, making a single-select field into a multi-select field). To change a field's type, recreate the field using the desired type.
But You can follow these method to migrate data of custom field to another custom field.
Migrating Custom Field content to another field using CSV import:
4. Open in an Excel editor
5. Import the CSV, mapping:
Migrating Custom Field content to another field using bulk operation
This approach is done with the use of bulk edit operations to migrate content manually from one field to another:
Why not just reference the JIRA Knowledge Base article from where these words were taken? (dated as Last modified on Apr 30, 2021)