diff --git a/server/datastore/mysql/migrations/tables/20260729115013_AddDDMCustomActivations.go b/server/datastore/mysql/migrations/tables/20260729115013_AddDDMCustomActivations.go
new file mode 100644
index 0000000000..048235d65e
--- /dev/null
+++ b/server/datastore/mysql/migrations/tables/20260729115013_AddDDMCustomActivations.go
@@ -0,0 +1,101 @@
+package tables
+
+import (
+	"database/sql"
+	"fmt"
+)
+
+func init() {
+	MigrationClient.AddMigration(Up_20260729115013, Down_20260729115013)
+}
+
+func Up_20260729115013(tx *sql.Tx) error {
+	// This table was created alongside the original DDM tables to model
+	// many-to-many activation references, but was never written to by any code
+	// path. Custom activations are 1:1 with their configuration declaration, so
+	// drop it rather than carry it forward.
+	if _, err := tx.Exec(`DROP TABLE IF EXISTS mdm_apple_declaration_activation_references`); err != nil {
+		return fmt.Errorf("dropping mdm_apple_declaration_activation_references table: %w", err)
+	}
+
+	// Custom activations let admins override the activation Fleet otherwise
+	// generates for a DDM configuration declaration, mainly to attach a
+	// Predicate. The activation JSON is stored as-is (mediumtext, not json, so
+	// the generated token hashes the exact stored bytes) and is never
+	// interpreted by Fleet beyond validation of its envelope.
+	//
+	// declaration_uuid is the authoritative link to the configuration this
+	// activation gates: it is 1:1 (enforced by its unique key) and cascades on
+	// delete so removing a DDM profile removes its activation. The
+	// configuration_identifier column keeps the declaration's Identifier
+	// alongside it, since the activation JSON references its configuration by
+	// Identifier rather than by UUID.
+	_, err := tx.Exec(`
+CREATE TABLE mdm_apple_ddm_activations (
+	activation_uuid          varchar(37)  CHARACTER SET utf8mb4 COLLATE utf8mb4_unicode_ci NOT NULL DEFAULT '',
+	team_id                  int unsigned NOT NULL DEFAULT '0',
+	identifier               varchar(255) CHARACTER SET utf8mb4 COLLATE utf8mb4_unicode_ci NOT NULL,
+	raw_json                 mediumtext   CHARACTER SET utf8mb4 COLLATE utf8mb4_unicode_ci NOT NULL,
+	declaration_uuid         varchar(37)  CHARACTER SET utf8mb4 COLLATE utf8mb4_unicode_ci NOT NULL,
+	configuration_identifier varchar(255) CHARACTER SET utf8mb4 COLLATE utf8mb4_unicode_ci NOT NULL,
+	secrets_updated_at       datetime(6)  DEFAULT NULL,
+	created_at               timestamp(6) NOT NULL DEFAULT CURRENT_TIMESTAMP(6),
+	uploaded_at              timestamp(6) NULL DEFAULT NULL,
+	token                    binary(16) GENERATED ALWAYS AS
+		(unhex(md5(concat(raw_json, ifnull(secrets_updated_at, ''))))) STORED,
+
+	PRIMARY KEY (activation_uuid),
+	UNIQUE KEY idx_mdm_apple_ddm_activation_team_identifier (team_id, identifier),
+	UNIQUE KEY idx_mdm_apple_ddm_activation_team_config (team_id, configuration_identifier),
+	UNIQUE KEY idx_mdm_apple_ddm_activation_declaration (declaration_uuid),
+	CONSTRAINT fk_mdm_apple_ddm_activations_declaration_uuid
+		FOREIGN KEY (declaration_uuid) REFERENCES mdm_apple_declarations (declaration_uuid) ON DELETE CASCADE
+) ENGINE=InnoDB DEFAULT CHARSET=utf8mb4 COLLATE=utf8mb4_unicode_ci
+	`)
+	if err != nil {
+		return fmt.Errorf("creating mdm_apple_ddm_activations table: %w", err)
+	}
+
+	// Activations can carry Fleet variables, so they need an owner column in
+	// the profile variables table. The unique key is what makes that table's
+	// ON DUPLICATE KEY UPDATE write path work, and the check constraint has to
+	// be replaced to count the new column, otherwise every row setting it is
+	// rejected.
+	_, err = tx.Exec(`
+		ALTER TABLE mdm_configuration_profile_variables
+			ADD COLUMN apple_ddm_activation_uuid varchar(37) CHARACTER SET utf8mb4 COLLATE utf8mb4_unicode_ci DEFAULT NULL,
+			ADD UNIQUE KEY idx_mdm_config_profile_vars_ddm_activation_variable (apple_ddm_activation_uuid, fleet_variable_id),
+			ADD CONSTRAINT mdm_config_profile_variables_ddm_activation_fk
+				FOREIGN KEY (apple_ddm_activation_uuid) REFERENCES mdm_apple_ddm_activations (activation_uuid) ON DELETE CASCADE,
+			DROP CHECK ck_mdm_configuration_profile_variables_exactly_one,
+			ADD CONSTRAINT ck_mdm_configuration_profile_variables_exactly_one
+				CHECK ((
+					(IF(apple_profile_uuid IS NULL, 0, 1) +
+					 IF(windows_profile_uuid IS NULL, 0, 1) +
+					 IF(apple_declaration_uuid IS NULL, 0, 1) +
+					 IF(android_profile_uuid IS NULL, 0, 1) +
+					 IF(certificate_template_id IS NULL, 0, 1) +
+					 IF(android_app_configuration_id IS NULL, 0, 1) +
+					 IF(apple_ddm_activation_uuid IS NULL, 0, 1)) = 1
+				))
+	`)
+	if err != nil {
+		return fmt.Errorf("extending mdm_configuration_profile_variables for DDM activations: %w", err)
+	}
+
+	// Tracks when a host's activation last changed so the declaration's
+	// effective token can be regenerated, mirroring variables_updated_at and
+	// assets_updated_at. DATETIME(6) rather than TIMESTAMP because
+	// EffectiveDDMToken formats these values into the token string and
+	// TIMESTAMP would apply session timezone conversion on read.
+	_, err = tx.Exec(`ALTER TABLE host_mdm_apple_declarations ADD COLUMN activation_updated_at DATETIME(6) DEFAULT NULL`)
+	if err != nil {
+		return fmt.Errorf("adding activation_updated_at to host_mdm_apple_declarations: %w", err)
+	}
+
+	return nil
+}
+
+func Down_20260729115013(tx *sql.Tx) error {
+	return nil
+}
diff --git a/server/datastore/mysql/migrations/tables/20260729115013_AddDDMCustomActivations_test.go b/server/datastore/mysql/migrations/tables/20260729115013_AddDDMCustomActivations_test.go
new file mode 100644
index 0000000000..f105762a35
--- /dev/null
+++ b/server/datastore/mysql/migrations/tables/20260729115013_AddDDMCustomActivations_test.go
@@ -0,0 +1,117 @@
+package tables
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/require"
+)
+
+func TestUp_20260729115013(t *testing.T) {
+	db := applyUpToPrev(t)
+
+	// The stale activation references table is present before the migration.
+	var staleTableCount int
+	err := db.Get(&staleTableCount, `
+		SELECT COUNT(*) FROM information_schema.tables
+		WHERE table_schema = DATABASE() AND table_name = 'mdm_apple_declaration_activation_references'`)
+	require.NoError(t, err)
+	require.Equal(t, 1, staleTableCount)
+
+	// Seed a declaration and a profile variable row bound to it. Replacing the
+	// check constraint revalidates every existing row, so this guards against
+	// the migration failing (or dropping data) on a non-empty table.
+	const declUUID = "db7e0a0e6-0000-0000-0000-000000000001"
+	execNoErr(t, db, `
+		INSERT INTO mdm_apple_declarations (declaration_uuid, team_id, identifier, name, raw_json, uploaded_at)
+		VALUES (?, 0, 'com.fleet.test.config', 'Test config', '{"Type":"com.apple.configuration.passcode.settings"}', NOW(6))`,
+		declUUID)
+
+	var fleetVarID uint
+	require.NoError(t, db.Get(&fleetVarID, `SELECT id FROM fleet_variables ORDER BY id LIMIT 1`))
+	execNoErr(t, db, `
+		INSERT INTO mdm_configuration_profile_variables (apple_declaration_uuid, fleet_variable_id)
+		VALUES (?, ?)`, declUUID, fleetVarID)
+
+	applyNext(t, db)
+
+	// Stale table is gone, and the pre-existing variable row survived the
+	// check constraint swap.
+	err = db.Get(&staleTableCount, `
+		SELECT COUNT(*) FROM information_schema.tables
+		WHERE table_schema = DATABASE() AND table_name = 'mdm_apple_declaration_activation_references'`)
+	require.NoError(t, err)
+	require.Equal(t, 0, staleTableCount)
+
+	var existingVars int
+	require.NoError(t, db.Get(&existingVars, `
+		SELECT COUNT(*) FROM mdm_configuration_profile_variables WHERE apple_declaration_uuid = ?`, declUUID))
+	require.Equal(t, 1, existingVars)
+
+	// An activation can be attached to the declaration, and its token is
+	// generated from the stored JSON.
+	const actUUID = "ab7e0a0e6-0000-0000-0000-000000000001"
+	execNoErr(t, db, `
+		INSERT INTO mdm_apple_ddm_activations
+			(activation_uuid, team_id, identifier, raw_json, declaration_uuid, configuration_identifier, uploaded_at)
+		VALUES (?, 0, 'com.fleet.test.config.activation', ?, ?, 'com.fleet.test.config', NOW(6))`,
+		actUUID,
+		`{"Type":"com.apple.activation.simple","Payload":{"StandardConfigurations":["com.fleet.test.config"]}}`,
+		declUUID)
+
+	var token []byte
+	require.NoError(t, db.Get(&token, `SELECT token FROM mdm_apple_ddm_activations WHERE activation_uuid = ?`, actUUID))
+	require.Len(t, token, 16)
+
+	// Only one activation per declaration.
+	_, err = db.Exec(`
+		INSERT INTO mdm_apple_ddm_activations
+			(activation_uuid, team_id, identifier, raw_json, declaration_uuid, configuration_identifier)
+		VALUES ('a-dupe', 0, 'com.fleet.test.other.activation', '{}', ?, 'com.fleet.test.other')`, declUUID)
+	require.Error(t, err)
+
+	// An activation must reference a declaration that exists.
+	_, err = db.Exec(`
+		INSERT INTO mdm_apple_ddm_activations
+			(activation_uuid, team_id, identifier, raw_json, declaration_uuid, configuration_identifier)
+		VALUES ('a-orphan', 0, 'com.fleet.test.orphan.activation', '{}', 'd-does-not-exist', 'com.fleet.test.orphan')`)
+	require.Error(t, err)
+
+	// Fleet variables can be associated with an activation. This is the case
+	// the check constraint would reject if it hadn't been replaced.
+	execNoErr(t, db, `
+		INSERT INTO mdm_configuration_profile_variables (apple_ddm_activation_uuid, fleet_variable_id)
+		VALUES (?, ?)`, actUUID, fleetVarID)
+
+	// The constraint still requires exactly one owner: neither two nor zero.
+	_, err = db.Exec(`
+		INSERT INTO mdm_configuration_profile_variables (apple_ddm_activation_uuid, apple_declaration_uuid, fleet_variable_id)
+		VALUES (?, ?, ?)`, actUUID, declUUID, fleetVarID)
+	require.Error(t, err)
+
+	_, err = db.Exec(`INSERT INTO mdm_configuration_profile_variables (fleet_variable_id) VALUES (?)`, fleetVarID)
+	require.Error(t, err)
+
+	// host_mdm_apple_declarations tracks when the activation last changed.
+	execNoErr(t, db, `
+		INSERT INTO host_mdm_apple_declarations
+			(host_uuid, declaration_uuid, declaration_identifier, declaration_name, token, activation_updated_at)
+		VALUES ('host-uuid-1', ?, 'com.fleet.test.config', 'Test config', UNHEX(MD5('t')), NOW(6))`, declUUID)
+
+	var activationUpdatedAt *string
+	require.NoError(t, db.Get(&activationUpdatedAt, `
+		SELECT activation_updated_at FROM host_mdm_apple_declarations WHERE host_uuid = 'host-uuid-1'`))
+	require.NotNil(t, activationUpdatedAt)
+
+	// Deleting the declaration cascades to the activation and, through it, to
+	// the activation's variable rows.
+	execNoErr(t, db, `DELETE FROM mdm_apple_declarations WHERE declaration_uuid = ?`, declUUID)
+
+	var remainingActivations int
+	require.NoError(t, db.Get(&remainingActivations, `SELECT COUNT(*) FROM mdm_apple_ddm_activations`))
+	require.Equal(t, 0, remainingActivations)
+
+	var remainingVars int
+	require.NoError(t, db.Get(&remainingVars, `
+		SELECT COUNT(*) FROM mdm_configuration_profile_variables WHERE apple_ddm_activation_uuid = ?`, actUUID))
+	require.Equal(t, 0, remainingVars)
+}
diff --git a/server/datastore/mysql/schema.sql b/server/datastore/mysql/schema.sql
index bb9d31a609..31fa07e493 100644
--- a/server/datastore/mysql/schema.sql
+++ b/server/datastore/mysql/schema.sql
@@ -1006,6 +1006,7 @@ CREATE TABLE `host_mdm_apple_declarations` (
   `scope` enum('System','User') CHARACTER SET utf8mb4 COLLATE utf8mb4_unicode_ci NOT NULL DEFAULT 'System',
   `variables_updated_at` datetime(6) DEFAULT NULL,
   `assets_updated_at` datetime(6) DEFAULT NULL,
+  `activation_updated_at` datetime(6) DEFAULT NULL,
   PRIMARY KEY (`host_uuid`,`declaration_uuid`),
   KEY `status` (`status`),
   KEY `operation_type` (`operation_type`),
@@ -1832,13 +1833,22 @@ CREATE TABLE `mdm_apple_configuration_profiles` (
 /*!40101 SET character_set_client = @saved_cs_client */;
 /*!40101 SET @saved_cs_client     = @@character_set_client */;
 /*!50503 SET character_set_client = utf8mb4 */;
-CREATE TABLE `mdm_apple_declaration_activation_references` (
-  `declaration_uuid` varchar(37) CHARACTER SET utf8mb4 COLLATE utf8mb4_unicode_ci NOT NULL DEFAULT '',
-  `reference` varchar(37) CHARACTER SET utf8mb4 COLLATE utf8mb4_unicode_ci NOT NULL DEFAULT '',
-  PRIMARY KEY (`declaration_uuid`,`reference`),
-  KEY `reference` (`reference`),
-  CONSTRAINT `mdm_apple_declaration_activation_references_ibfk_1` FOREIGN KEY (`declaration_uuid`) REFERENCES `mdm_apple_declarations` (`declaration_uuid`) ON UPDATE CASCADE,
-  CONSTRAINT `mdm_apple_declaration_activation_references_ibfk_2` FOREIGN KEY (`reference`) REFERENCES `mdm_apple_declarations` (`declaration_uuid`) ON UPDATE CASCADE
+CREATE TABLE `mdm_apple_ddm_activations` (
+  `activation_uuid` varchar(37) CHARACTER SET utf8mb4 COLLATE utf8mb4_unicode_ci NOT NULL DEFAULT '',
+  `team_id` int unsigned NOT NULL DEFAULT '0',
+  `identifier` varchar(255) CHARACTER SET utf8mb4 COLLATE utf8mb4_unicode_ci NOT NULL,
+  `raw_json` mediumtext CHARACTER SET utf8mb4 COLLATE utf8mb4_unicode_ci NOT NULL,
+  `declaration_uuid` varchar(37) CHARACTER SET utf8mb4 COLLATE utf8mb4_unicode_ci NOT NULL,
+  `configuration_identifier` varchar(255) CHARACTER SET utf8mb4 COLLATE utf8mb4_unicode_ci NOT NULL,
+  `secrets_updated_at` datetime(6) DEFAULT NULL,
+  `created_at` timestamp(6) NOT NULL DEFAULT CURRENT_TIMESTAMP(6),
+  `uploaded_at` timestamp(6) NULL DEFAULT NULL,
+  `token` binary(16) GENERATED ALWAYS AS (unhex(md5(concat(`raw_json`,ifnull(`secrets_updated_at`,_utf8mb4''))))) STORED,
+  PRIMARY KEY (`activation_uuid`),
+  UNIQUE KEY `idx_mdm_apple_ddm_activation_team_identifier` (`team_id`,`identifier`),
+  UNIQUE KEY `idx_mdm_apple_ddm_activation_team_config` (`team_id`,`configuration_identifier`),
+  UNIQUE KEY `idx_mdm_apple_ddm_activation_declaration` (`declaration_uuid`),
+  CONSTRAINT `fk_mdm_apple_ddm_activations_declaration_uuid` FOREIGN KEY (`declaration_uuid`) REFERENCES `mdm_apple_declarations` (`declaration_uuid`) ON DELETE CASCADE
 ) ENGINE=InnoDB DEFAULT CHARSET=utf8mb4 COLLATE=utf8mb4_unicode_ci;
 /*!40101 SET character_set_client = @saved_cs_client */;
 /*!40101 SET @saved_cs_client     = @@character_set_client */;
@@ -2067,6 +2077,7 @@ CREATE TABLE `mdm_configuration_profile_variables` (
   `android_profile_uuid` varchar(37) CHARACTER SET utf8mb4 COLLATE utf8mb4_unicode_ci DEFAULT NULL,
   `certificate_template_id` int unsigned DEFAULT NULL,
   `android_app_configuration_id` int unsigned DEFAULT NULL,
+  `apple_ddm_activation_uuid` varchar(37) CHARACTER SET utf8mb4 COLLATE utf8mb4_unicode_ci DEFAULT NULL,
   PRIMARY KEY (`id`),
   UNIQUE KEY `idx_mdm_configuration_profile_variables_apple_variable` (`apple_profile_uuid`,`fleet_variable_id`),
   UNIQUE KEY `idx_mdm_configuration_profile_variables_windows_label_name` (`windows_profile_uuid`,`fleet_variable_id`),
@@ -2074,6 +2085,7 @@ CREATE TABLE `mdm_configuration_profile_variables` (
   UNIQUE KEY `idx_mdm_configuration_profile_variables_android_variable` (`android_profile_uuid`,`fleet_variable_id`),
   UNIQUE KEY `idx_mdm_configuration_profile_variables_cert_template_variable` (`certificate_template_id`,`fleet_variable_id`),
   UNIQUE KEY `idx_mdm_configuration_profile_variables_app_config_variable` (`android_app_configuration_id`,`fleet_variable_id`),
+  UNIQUE KEY `idx_mdm_config_profile_vars_ddm_activation_variable` (`apple_ddm_activation_uuid`,`fleet_variable_id`),
   KEY `mdm_configuration_profile_variables_fleet_variable_id` (`fleet_variable_id`),
   CONSTRAINT `fk_mdm_configuration_profile_variables_android_profile_uuid` FOREIGN KEY (`android_profile_uuid`) REFERENCES `mdm_android_configuration_profiles` (`profile_uuid`) ON DELETE CASCADE,
   CONSTRAINT `fk_mdm_configuration_profile_variables_app_config_id` FOREIGN KEY (`android_app_configuration_id`) REFERENCES `android_app_configurations` (`id`) ON DELETE CASCADE,
@@ -2081,8 +2093,9 @@ CREATE TABLE `mdm_configuration_profile_variables` (
   CONSTRAINT `fk_mdm_configuration_profile_variables_apple_profile_uuid` FOREIGN KEY (`apple_profile_uuid`) REFERENCES `mdm_apple_configuration_profiles` (`profile_uuid`) ON DELETE CASCADE,
   CONSTRAINT `fk_mdm_configuration_profile_variables_cert_template_id` FOREIGN KEY (`certificate_template_id`) REFERENCES `certificate_templates` (`id`) ON DELETE CASCADE,
   CONSTRAINT `fk_mdm_configuration_profile_variables_windows_profile_uuid` FOREIGN KEY (`windows_profile_uuid`) REFERENCES `mdm_windows_configuration_profiles` (`profile_uuid`) ON DELETE CASCADE,
+  CONSTRAINT `mdm_config_profile_variables_ddm_activation_fk` FOREIGN KEY (`apple_ddm_activation_uuid`) REFERENCES `mdm_apple_ddm_activations` (`activation_uuid`) ON DELETE CASCADE,
   CONSTRAINT `mdm_configuration_profile_variables_fleet_variable_id` FOREIGN KEY (`fleet_variable_id`) REFERENCES `fleet_variables` (`id`) ON DELETE CASCADE,
-  CONSTRAINT `ck_mdm_configuration_profile_variables_exactly_one` CHECK (((((((if((`apple_profile_uuid` is null),0,1) + if((`windows_profile_uuid` is null),0,1)) + if((`apple_declaration_uuid` is null),0,1)) + if((`android_profile_uuid` is null),0,1)) + if((`certificate_template_id` is null),0,1)) + if((`android_app_configuration_id` is null),0,1)) = 1))
+  CONSTRAINT `ck_mdm_configuration_profile_variables_exactly_one` CHECK ((((((((if((`apple_profile_uuid` is null),0,1) + if((`windows_profile_uuid` is null),0,1)) + if((`apple_declaration_uuid` is null),0,1)) + if((`android_profile_uuid` is null),0,1)) + if((`certificate_template_id` is null),0,1)) + if((`android_app_configuration_id` is null),0,1)) + if((`apple_ddm_activation_uuid` is null),0,1)) = 1))
 ) /*!50100 TABLESPACE `innodb_system` */ ENGINE=InnoDB DEFAULT CHARSET=utf8mb4 COLLATE=utf8mb4_unicode_ci;
 /*!40101 SET character_set_client = @saved_cs_client */;
 /*!40101 SET @saved_cs_client     = @@character_set_client */;
@@ -2223,9 +2236,9 @@ CREATE TABLE `migration_status_tables` (
   `is_applied` tinyint(1) NOT NULL,
   `tstamp` timestamp NULL DEFAULT CURRENT_TIMESTAMP,
   PRIMARY KEY (`id`)
-) /*!50100 TABLESPACE `innodb_system` */ ENGINE=InnoDB AUTO_INCREMENT=578 DEFAULT CHARSET=utf8mb4 COLLATE=utf8mb4_unicode_ci;
+) /*!50100 TABLESPACE `innodb_system` */ ENGINE=InnoDB AUTO_INCREMENT=579 DEFAULT CHARSET=utf8mb4 COLLATE=utf8mb4_unicode_ci;
 /*!40101 SET character_set_client = @saved_cs_client */;
-INSERT INTO `migration_status_tables` VALUES (1,0,1,'2020-01-01 01:01:01'),(2,20161118193812,1,'2020-01-01 01:01:01'),(3,20161118211713,1,'2020-01-01 01:01:01'),(4,20161118212436,1,'2020-01-01 01:01:01'),(5,20161118212515,1,'2020-01-01 01:01:01'),(6,20161118212528,1,'2020-01-01 01:01:01'),(7,20161118212538,1,'2020-01-01 01:01:01'),(8,20161118212549,1,'2020-01-01 01:01:01'),(9,20161118212557,1,'2020-01-01 01:01:01'),(10,20161118212604,1,'2020-01-01 01:01:01'),(11,20161118212613,1,'2020-01-01 01:01:01'),(12,20161118212621,1,'2020-01-01 01:01:01'),(13,20161118212630,1,'2020-01-01 01:01:01'),(14,20161118212641,1,'2020-01-01 01:01:01'),(15,20161118212649,1,'2020-01-01 01:01:01'),(16,20161118212656,1,'2020-01-01 01:01:01'),(17,20161118212758,1,'2020-01-01 01:01:01'),(18,20161128234849,1,'2020-01-01 01:01:01'),(19,20161230162221,1,'2020-01-01 01:01:01'),(20,20170104113816,1,'2020-01-01 01:01:01'),(21,20170105151732,1,'2020-01-01 01:01:01'),(22,20170108191242,1,'2020-01-01 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 /*!40101 SET @saved_cs_client     = @@character_set_client */;
 /*!50503 SET character_set_client = utf8mb4 */;
 CREATE TABLE `mobile_device_management_solutions` (