The grantor (or the principal specified with the AS option) must have either the permission itself with GRANT OPTION, or a higher permission that implies the permission being granted.
If you are using the AS option, the following additional requirements apply.
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AS granting_principal
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Additional permission required
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Database user
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IMPERSONATE permission on the user, membership in the db_securityadmin fixed database role, membership in the db_owner fixed database role, or membership in the sysadmin fixed server role.
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Database user mapped to a Windows User
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IMPERSONATE permission on the user, membership in the db_securityadmin fixed database role, membership in the db_owner fixed database role, or membership in the sysadmin fixed server role.
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Database user mapped to a Windows Group
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Membership in the Windows group, membership in the db_securityadmin fixed database role, membership in the db_owner fixed database role, or membership in the sysadmin fixed server role.
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Database user mapped to a certificate
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Membership in the db_securityadmin fixed database role, membership in the db_owner fixed database role, or membership in the sysadmin fixed server role.
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Database user mapped to an asymmetric key
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Membership in the db_securityadmin fixed database role, membership in the db_owner fixed database role, or membership in the sysadmin fixed server role.
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Database user not mapped to any server principal
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IMPERSONATE permission on the user, membership in the db_securityadmin fixed database role, membership in the db_owner fixed database role, or membership in the sysadmin fixed server role.
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Database role
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ALTER permission on the role, membership in the db_securityadmin fixed database role, membership in the db_owner fixed database role, or membership in the sysadmin fixed server role.
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Application role
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ALTER permission on the role, membership in the db_securityadmin fixed database role, membership in the db_owner fixed database role, or membership in the sysadmin fixed server role.
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Principals that have CONTROL permission on a securable can grant permission on that securable.
Grantees of CONTROL permission on a database, such as members of the db_owner fixed database role, can grant any permission on any securable in the database.