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 login
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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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Object owners can grant permissions on the objects they own. Principals that have CONTROL permission on a securable can grant permission on that securable.
Grantees of CONTROL SERVER permission, such as members of the sysadmin fixed server role, can grant any permission on any securable in the server.