Refetch host mdm enrollment status until unenrolled (#11740)

changes/issue-11695-webhook-migrate-mdm

@@ -1 +1,2 @@
 - Added device-authenticated endpoint to signal the Fleet server to send a webbook request with the device UUID and serial number to the webhook URL configured for MDM migration.
+- Added mechanism to refetch MDM enrollment status of a host pending unenrollment (due to a migration to Fleet) at a high interval.

ee/server/service/devices.go

@@ -18,6 +18,12 @@ func (svc *Service) RequestEncryptionKeyRotation(ctx context.Context, hostID uin
 	return svc.ds.SetDiskEncryptionResetStatus(ctx, hostID, true)
 }
 
+const refetchMDMUnenrollCriticalQueryDuration = 3 * time.Minute
+
+// TriggerMigrateMDMDevice triggers the webhook associated with the MDM
+// migration to Fleet configuration. It is located in the ee package instead of
+// the server/webhooks one because it is a Fleet Premium only feature and for
+// licensing reasons this needs to live under this package.
 func (svc *Service) TriggerMigrateMDMDevice(ctx context.Context, host *fleet.Host) error {
 	ac, err := svc.ds.AppConfig(ctx)
 	if err != nil {
@@ -35,9 +41,12 @@ func (svc *Service) TriggerMigrateMDMDevice(ctx context.Context, host *fleet.Hos
 		bre.InternalErr = ctxerr.New(ctx, "macOS migration webhook URL not configured")
 	case !host.IsOsqueryEnrolled(), !host.MDMInfo.IsDEPCapable(), !host.MDMInfo.IsEnrolledInThirdPartyMDM():
 		bre.InternalErr = ctxerr.New(ctx, "host not eligible for macOS migration")
+	case host.RefetchCriticalQueriesUntil != nil && host.RefetchCriticalQueriesUntil.After(svc.clock.Now()):
+		// the webhook has already been triggered successfully recently (within the
+		// refetch critical queries delay), so do as if it did send it successfully
+		// but do not re-send.
+		return nil
 	}
-	// TODO: add case to check if webhok has already been sent (if host refetchUntil is not zero?)
-
 	if bre.InternalErr != nil {
 		return &bre
 	}
@@ -52,6 +61,15 @@ func (svc *Service) TriggerMigrateMDMDevice(ctx context.Context, host *fleet.Hos
 		return ctxerr.Wrap(ctx, err, "posting macOS migration webhook")
 	}
 
+	// if the webhook was successfully triggered, we update the host to
+	// constantly run the query to check if it has been unenrolled from its
+	// existing third-party MDM.
+	refetchUntil := svc.clock.Now().Add(refetchMDMUnenrollCriticalQueryDuration)
+	host.RefetchCriticalQueriesUntil = &refetchUntil
+	if err := svc.ds.UpdateHost(ctx, host); err != nil {
+		return ctxerr.Wrap(ctx, err, "save host with refetch critical queries timestamp")
+	}
+
 	return nil
 }
 

server/datastore/mysql/hosts.go

@@ -61,9 +61,10 @@ func (ds *Datastore) NewHost(ctx context.Context, host *fleet.Host) (*fleet.Host
 			logger_tls_period,
 			config_tls_refresh,
 			refetch_requested,
-			hardware_serial
+			hardware_serial,
+			refetch_critical_queries_until
 		)
-		VALUES (?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?)
+		VALUES (?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?)
 		`
 		result, err := tx.ExecContext(
 			ctx,
@@ -87,6 +88,7 @@ func (ds *Datastore) NewHost(ctx context.Context, host *fleet.Host) (*fleet.Host
 			host.ConfigTLSRefresh,
 			host.RefetchRequested,
 			host.HardwareSerial,
+			host.RefetchCriticalQueriesUntil,
 		)
 		if err != nil {
 			return ctxerr.Wrap(ctx, err, "new host")
@@ -426,6 +428,7 @@ SELECT
   h.label_updated_at,
   h.last_enrolled_at,
   h.refetch_requested,
+  h.refetch_critical_queries_until,
   h.team_id,
   h.policy_updated_at,
   h.public_ip,
@@ -621,6 +624,7 @@ func (ds *Datastore) ListHosts(ctx context.Context, filter fleet.TeamFilter, opt
     h.label_updated_at,
     h.last_enrolled_at,
     h.refetch_requested,
+    h.refetch_critical_queries_until,
     h.team_id,
     h.policy_updated_at,
     h.public_ip,
@@ -1402,6 +1406,7 @@ func (ds *Datastore) EnrollHost(ctx context.Context, isMDMEnabled bool, osqueryH
         h.label_updated_at,
         h.last_enrolled_at,
         h.refetch_requested,
+        h.refetch_critical_queries_until,
         h.team_id,
         h.policy_updated_at,
         h.public_ip,
@@ -1483,6 +1488,7 @@ func (ds *Datastore) LoadHostByNodeKey(ctx context.Context, nodeKey string) (*fl
       h.label_updated_at,
       h.last_enrolled_at,
       h.refetch_requested,
+      h.refetch_critical_queries_until,
       h.team_id,
       h.policy_updated_at,
       h.public_ip,
@@ -1557,6 +1563,7 @@ func (ds *Datastore) LoadHostByOrbitNodeKey(ctx context.Context, nodeKey string)
       h.label_updated_at,
       h.last_enrolled_at,
       h.refetch_requested,
+      h.refetch_critical_queries_until,
       h.team_id,
       h.policy_updated_at,
       h.public_ip,
@@ -1650,6 +1657,7 @@ func (ds *Datastore) LoadHostByDeviceAuthToken(ctx context.Context, authToken st
       h.label_updated_at,
       h.last_enrolled_at,
       h.refetch_requested,
+      h.refetch_critical_queries_until,
       h.team_id,
       h.policy_updated_at,
       h.public_ip,
@@ -1795,6 +1803,7 @@ func (ds *Datastore) SearchHosts(ctx context.Context, filter fleet.TeamFilter, m
     h.label_updated_at,
     h.last_enrolled_at,
     h.refetch_requested,
+    h.refetch_critical_queries_until,
     h.team_id,
     h.policy_updated_at,
     h.public_ip,
@@ -1890,7 +1899,8 @@ SELECT
 	label_updated_at,
 	last_enrolled_at,
 	policy_updated_at,
-	refetch_requested
+	refetch_requested,
+	refetch_critical_queries_until
 FROM hosts
 WHERE uuid IN (?) AND %s
 		`, ds.whereFilterHostsByTeams(filter, "hosts"),
@@ -1947,6 +1957,7 @@ func (ds *Datastore) HostByIdentifier(ctx context.Context, identifier string) (*
       h.label_updated_at,
       h.last_enrolled_at,
       h.refetch_requested,
+      h.refetch_critical_queries_until,
       h.team_id,
       h.policy_updated_at,
       h.public_ip,
@@ -3350,6 +3361,7 @@ func (ds *Datastore) HostLite(ctx context.Context, id uint) (*fleet.Host, error)
 		"last_enrolled_at",
 		"policy_updated_at",
 		"refetch_requested",
+		"refetch_critical_queries_until",
 	).Where(goqu.I("id").Eq(id)).ToSQL()
 	if err != nil {
 		return nil, ctxerr.Wrap(ctx, err, "sql build")
@@ -3432,7 +3444,8 @@ func (ds *Datastore) UpdateHost(ctx context.Context, host *fleet.Host) error {
 			primary_mac = ?,
 			public_ip = ?,
 			refetch_requested = ?,
-			orbit_node_key = ?
+			orbit_node_key = ?,
+			refetch_critical_queries_until = ?
 		WHERE id = ?
 	`
 	_, err := ds.writer.ExecContext(ctx, sqlStatement,
@@ -3469,6 +3482,7 @@ func (ds *Datastore) UpdateHost(ctx context.Context, host *fleet.Host) error {
 		host.PublicIP,
 		host.RefetchRequested,
 		host.OrbitNodeKey,
+		host.RefetchCriticalQueriesUntil,
 		host.ID,
 	)
 	if err != nil {

server/datastore/mysql/hosts_test.go

@@ -182,6 +182,10 @@ func testUpdateHost(t *testing.T, ds *Datastore, updateHostFunc func(context.Con
 	err = updateHostFunc(context.Background(), host)
 	require.NoError(t, err)
 
+	host.RefetchCriticalQueriesUntil = ptr.Time(time.Now().UTC().Add(time.Hour))
+	err = updateHostFunc(context.Background(), host)
+	require.NoError(t, err)
+
 	host, err = ds.Host(context.Background(), host.ID)
 	require.NoError(t, err)
 
@@ -189,6 +193,8 @@ func testUpdateHost(t *testing.T, ds *Datastore, updateHostFunc func(context.Con
 	assert.Equal(t, "192.168.1.1", host.PrimaryIP)
 	assert.Equal(t, "30-65-EC-6F-C4-58", host.PrimaryMac)
 	assert.Equal(t, policyUpdatedAt.UTC(), host.PolicyUpdatedAt)
+	assert.NotNil(t, host.RefetchCriticalQueriesUntil)
+	assert.True(t, time.Now().Before(*host.RefetchCriticalQueriesUntil))
 
 	additionalJSON := json.RawMessage(`{"foobar": "bim"}`)
 	err = ds.SaveHostAdditional(context.Background(), host.ID, &additionalJSON)
@@ -203,9 +209,14 @@ func testUpdateHost(t *testing.T, ds *Datastore, updateHostFunc func(context.Con
 	err = updateHostFunc(context.Background(), host)
 	require.NoError(t, err)
 
+	host.RefetchCriticalQueriesUntil = nil
+	err = updateHostFunc(context.Background(), host)
+	require.NoError(t, err)
+
 	host, err = ds.Host(context.Background(), host.ID)
 	require.NoError(t, err)
 	require.NotNil(t, host)
+	require.Nil(t, host.RefetchCriticalQueriesUntil)
 
 	p, err := ds.NewPack(context.Background(), &fleet.Pack{
 		Name:    t.Name(),

server/datastore/mysql/labels.go

@@ -497,24 +497,25 @@ func (ds *Datastore) ListHostsInLabel(ctx context.Context, filter fleet.TeamFilt
       h.label_updated_at,
       h.last_enrolled_at,
       h.refetch_requested,
+      h.refetch_critical_queries_until,
       h.team_id,
       h.policy_updated_at,
       h.public_ip,
       COALESCE(hd.gigs_disk_space_available, 0) as gigs_disk_space_available,
       COALESCE(hd.percent_disk_space_available, 0) as percent_disk_space_available,
       COALESCE(hst.seen_time, h.created_at) as seen_time,
-	  COALESCE(hu.software_updated_at, h.created_at) AS software_updated_at,
+      COALESCE(hu.software_updated_at, h.created_at) AS software_updated_at,
       (SELECT name FROM teams t WHERE t.id = h.team_id) AS team_name
       %s
-	  %s
+      %s
     FROM label_membership lm
     JOIN hosts h ON (lm.host_id = h.id)
     LEFT JOIN host_seen_times hst ON (h.id=hst.host_id)
-	LEFT JOIN host_updates hu ON (h.id = hu.host_id)
+    LEFT JOIN host_updates hu ON (h.id = hu.host_id)
     LEFT JOIN host_disks hd ON (h.id=hd.host_id)
     %s
-	%s
-	`
+    %s
+`
 	failingPoliciesSelect := `,
 		COALESCE(failing_policies.count, 0) AS failing_policies_count,
 		COALESCE(failing_policies.count, 0) AS total_issues_count
@@ -631,6 +632,7 @@ func (ds *Datastore) ListUniqueHostsInLabels(ctx context.Context, filter fleet.T
         h.label_updated_at,
         h.last_enrolled_at,
         h.refetch_requested,
+        h.refetch_critical_queries_until,
         h.team_id,
         h.policy_updated_at,
         h.public_ip,
@@ -641,7 +643,7 @@ func (ds *Datastore) ListUniqueHostsInLabels(ctx context.Context, filter fleet.T
       JOIN hosts h ON lm.host_id = h.id
       LEFT JOIN host_disks hd ON hd.host_id = h.id
       WHERE lm.label_id IN (?) AND %s
-		`, ds.whereFilterHostsByTeams(filter, "h"),
+`, ds.whereFilterHostsByTeams(filter, "h"),
 	)
 
 	query, args, err := sqlx.In(sqlStatement, labels)

server/datastore/mysql/migrations/tables/20230517152807_AddRefetchCriticalQueriesUntilToHosts.go

@@ -0,0 +1,22 @@
+package tables
+
+import (
+	"database/sql"
+
+	"github.com/pkg/errors"
+)
+
+func init() {
+	MigrationClient.AddMigration(Up_20230517152807, Down_20230517152807)
+}
+
+func Up_20230517152807(tx *sql.Tx) error {
+	_, err := tx.Exec(`
+ALTER TABLE hosts ADD COLUMN refetch_critical_queries_until TIMESTAMP NULL;
+`)
+	return errors.Wrap(err, "add refetch_critical_queries_until")
+}
+
+func Down_20230517152807(tx *sql.Tx) error {
+	return nil
+}

server/datastore/mysql/migrations/tables/20230517152807_AddRefetchCriticalQueriesUntilToHosts_test.go

@@ -0,0 +1,79 @@
+package tables
+
+import (
+	"testing"
+	"time"
+
+	"github.com/fleetdm/fleet/v4/server"
+	"github.com/stretchr/testify/require"
+)
+
+func TestUp_20230517152807(t *testing.T) {
+	db := applyUpToPrev(t)
+
+	someString := func() string {
+		s, err := server.GenerateRandomText(16)
+		require.NoError(t, err)
+		return s
+	}
+
+	insertStmt := `
+		INSERT INTO hosts (
+			osquery_host_id,
+			detail_updated_at,
+			label_updated_at,
+			policy_updated_at,
+			node_key,
+			hostname,
+			computer_name,
+			uuid,
+			platform,
+			osquery_version,
+			os_version,
+			uptime,
+			memory,
+			team_id,
+			distributed_interval,
+			logger_tls_period,
+			config_tls_refresh,
+			refetch_requested,
+			hardware_serial
+		)
+		VALUES (?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?)`
+
+	newHostArgs := func() []any {
+		return []any{
+			someString(),
+			time.Now(),
+			time.Now(),
+			time.Now(),
+			someString(),
+			someString(),
+			someString(),
+			someString(),
+			someString(),
+			someString(),
+			someString(),
+			1337,
+			1337,
+			nil,
+			1337,
+			1337,
+			1337,
+			true,
+			someString(),
+		}
+	}
+
+	args := newHostArgs()
+	execNoErr(t, db, insertStmt, args...)
+
+	// Apply current migration.
+	applyNext(t, db)
+
+	// existing host has a null refetch_critical_queries_until
+	var until *time.Time
+	err := db.Get(&until, "SELECT refetch_critical_queries_until FROM hosts WHERE osquery_host_id = ?", args[0])
+	require.NoError(t, err)
+	require.Nil(t, until)
+}

server/fleet/hosts.go

@@ -281,6 +281,22 @@ type Host struct {
 	// other host fields, it is not filled in by all host-returning datastore
 	// methods.
 	MDMInfo *HostMDM `json:"-" csv:"-"`
+
+	// RefetchCriticalQueriesUntil can be set to a timestamp up to which the
+	// "critical" queries will be constantly reported to the host that checks in
+	// to be re-executed until a condition is met (or the timestamp expires). The
+	// notion of "critical query" is voluntarily loosely defined so that future
+	// requirements may use this mechanism. The difference with RefetchRequested
+	// is that the latter is a one-time request, while this one is a persistent
+	// until the timestamp expires. The initial use-case is to check for a host
+	// to be unenrolled from its old MDM solution, in the "migrate to Fleet MDM"
+	// workflow.
+	//
+	// In the future, if we want to use it for more than one use-case, we could
+	// add a "reason" field with well-known labels so we know what condition(s)
+	// are expected to clear the timestamp. For now there's a single use-case
+	// so we don't need this.
+	RefetchCriticalQueriesUntil *time.Time `json:"-" db:"refetch_critical_queries_until" csv:"-"`
 }
 
 type MDMHostData struct {

server/service/integration_mdm_test.go

@@ -3172,7 +3172,9 @@ func (s *integrationMDMTestSuite) TestMigrateMDMDeviceWebhook() {
 
 	h := createHostAndDeviceToken(t, s.ds, "good-token")
 
+	var webhookCalled bool
 	webhookSrv := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		webhookCalled = true
 		w.WriteHeader(http.StatusOK)
 		switch r.URL.Path {
 		case "/test_mdm_migration":
@@ -3200,7 +3202,7 @@ func (s *integrationMDMTestSuite) TestMigrateMDMDeviceWebhook() {
 				"enable": true,
 				"mode": "voluntary",
 				"webhook_url": "%s/test_mdm_migration"
-		      }
+			}
 		}
 	}`, webhookSrv.URL)), http.StatusOK, &acResp)
 	require.True(t, acResp.MDM.MacOSMigration.Enable)
@@ -3213,25 +3215,63 @@ func (s *integrationMDMTestSuite) TestMigrateMDMDeviceWebhook() {
 	// host is a server so migration is not allowed
 	require.NoError(t, s.ds.SetOrUpdateMDMData(context.Background(), h.ID, isServer, enrolled, mdmURL, installedFromDEP, mdmName))
 	s.Do("POST", fmt.Sprintf("/api/v1/fleet/device/%s/migrate_mdm", "good-token"), nil, http.StatusBadRequest)
+	require.False(t, webhookCalled)
 
 	// host is not DEP so migration is not allowed
 	require.NoError(t, s.ds.SetOrUpdateMDMData(context.Background(), h.ID, !isServer, enrolled, mdmURL, !installedFromDEP, mdmName))
 	s.Do("POST", fmt.Sprintf("/api/v1/fleet/device/%s/migrate_mdm", "good-token"), nil, http.StatusBadRequest)
+	require.False(t, webhookCalled)
 
 	// host is not enrolled to MDM so migration is not allowed
 	require.NoError(t, s.ds.SetOrUpdateMDMData(context.Background(), h.ID, !isServer, !enrolled, mdmURL, installedFromDEP, mdmName))
 	s.Do("POST", fmt.Sprintf("/api/v1/fleet/device/%s/migrate_mdm", "good-token"), nil, http.StatusBadRequest)
+	require.False(t, webhookCalled)
 
 	// host is already enrolled to Fleet MDM so migration is not allowed
 	require.NoError(t, s.ds.SetOrUpdateMDMData(context.Background(), h.ID, !isServer, enrolled, mdmURL, installedFromDEP, fleet.WellKnownMDMFleet))
 	s.Do("POST", fmt.Sprintf("/api/v1/fleet/device/%s/migrate_mdm", "good-token"), nil, http.StatusBadRequest)
+	require.False(t, webhookCalled)
+
+	// up to this point, the refetch critical queries timestamp has not been set
+	// on the host.
+	h, err := s.ds.Host(context.Background(), h.ID)
+	require.NoError(t, err)
+	require.Nil(t, h.RefetchCriticalQueriesUntil)
 
 	// host is enrolled to a third-party MDM so migration is allowed
 	require.NoError(t, s.ds.SetOrUpdateMDMData(context.Background(), h.ID, !isServer, enrolled, mdmURL, installedFromDEP, mdmName))
 	s.Do("POST", fmt.Sprintf("/api/v1/fleet/device/%s/migrate_mdm", "good-token"), nil, http.StatusNoContent)
+	require.True(t, webhookCalled)
+	webhookCalled = false
+
+	// the refetch critical queries timestamp has been set in the future
+	h, err = s.ds.Host(context.Background(), h.ID)
+	require.NoError(t, err)
+	require.NotNil(t, h.RefetchCriticalQueriesUntil)
+	require.True(t, h.RefetchCriticalQueriesUntil.After(time.Now()))
+
+	// calling again works but does not trigger the webhook, as it was called recently
+	s.Do("POST", fmt.Sprintf("/api/v1/fleet/device/%s/migrate_mdm", "good-token"), nil, http.StatusNoContent)
+	require.False(t, webhookCalled)
+
+	// setting the refetch critical queries timestamp in the past triggers the webhook again
+	h.RefetchCriticalQueriesUntil = ptr.Time(time.Now().Add(-1 * time.Minute))
+	err = s.ds.UpdateHost(context.Background(), h)
+	require.NoError(t, err)
+
+	s.Do("POST", fmt.Sprintf("/api/v1/fleet/device/%s/migrate_mdm", "good-token"), nil, http.StatusNoContent)
+	require.True(t, webhookCalled)
+	webhookCalled = false
+
+	// the refetch critical queries timestamp has been updated to the future
+	h, err = s.ds.Host(context.Background(), h.ID)
+	require.NoError(t, err)
+	require.NotNil(t, h.RefetchCriticalQueriesUntil)
+	require.True(t, h.RefetchCriticalQueriesUntil.After(time.Now()))
 
 	// bad token
 	s.Do("POST", fmt.Sprintf("/api/v1/fleet/device/%s/migrate_mdm", "bad-token"), nil, http.StatusUnauthorized)
+	require.False(t, webhookCalled)
 
 	// disable macos migration
 	s.DoJSON("PATCH", "/api/latest/fleet/config", json.RawMessage(`{
@@ -3247,6 +3287,7 @@ func (s *integrationMDMTestSuite) TestMigrateMDMDeviceWebhook() {
 
 	// expect error if macos migration is not configured
 	s.Do("POST", fmt.Sprintf("/api/v1/fleet/device/%s/migrate_mdm", "good-token"), nil, http.StatusBadRequest)
+	require.False(t, webhookCalled)
 }
 
 func (s *integrationMDMTestSuite) TestMDMMacOSSetup() {

server/service/osquery.go

@@ -608,11 +608,24 @@ func (svc *Service) GetDistributedQueries(ctx context.Context) (queries map[stri
 
 const alwaysTrueQuery = "SELECT 1"
 
+// list of detail queries that are returned when only the critical queries
+// should be returned (due to RefetchCriticalQueriesUntil timestamp being set).
+var criticalDetailQueries = map[string]bool{
+	"mdm": true,
+}
+
 // detailQueriesForHost returns the map of detail+additional queries that should be executed by
 // osqueryd to fill in the host details.
 func (svc *Service) detailQueriesForHost(ctx context.Context, host *fleet.Host) (queries map[string]string, discovery map[string]string, err error) {
+	var criticalQueriesOnly bool
 	if !svc.shouldUpdate(host.DetailUpdatedAt, svc.config.Osquery.DetailUpdateInterval, host.ID) && !host.RefetchRequested {
-		return nil, nil, nil
+		// would not return anything, check if critical queries should be returned
+		if host.RefetchCriticalQueriesUntil != nil && host.RefetchCriticalQueriesUntil.After(svc.clock.Now()) {
+			// return only those critical queries
+			criticalQueriesOnly = true
+		} else {
+			return nil, nil, nil
+		}
 	}
 
 	appConfig, err := svc.ds.AppConfig(ctx)
@@ -630,6 +643,10 @@ func (svc *Service) detailQueriesForHost(ctx context.Context, host *fleet.Host)
 
 	detailQueries := osquery_utils.GetDetailQueries(ctx, svc.config, appConfig, features)
 	for name, query := range detailQueries {
+		if criticalQueriesOnly && !criticalDetailQueries[name] {
+			continue
+		}
+
 		if query.RunsForPlatform(host.Platform) {
 			queryName := hostDetailQueryPrefix + name
 			queries[queryName] = query.Query
@@ -641,7 +658,7 @@ func (svc *Service) detailQueriesForHost(ctx context.Context, host *fleet.Host)
 		}
 	}
 
-	if features.AdditionalQueries == nil {
+	if features.AdditionalQueries == nil || criticalQueriesOnly {
 		// No additional queries set
 		return queries, discovery, nil
 	}
@@ -833,6 +850,7 @@ func (svc *Service) SubmitDistributedQueryResults(
 	additionalUpdated := false
 	labelResults := map[uint]*bool{}
 	policyResults := map[uint]*bool{}
+	refetchCriticalSet := host.RefetchCriticalQueriesUntil != nil
 
 	svc.maybeDebugHost(ctx, host, results, statuses, messages)
 
@@ -936,8 +954,9 @@ func (svc *Service) SubmitDistributedQueryResults(
 	if refetchRequested {
 		host.RefetchRequested = false
 	}
+	refetchCriticalCleared := refetchCriticalSet && host.RefetchCriticalQueriesUntil == nil
 
-	if refetchRequested || detailUpdated {
+	if refetchRequested || detailUpdated || refetchCriticalCleared {
 		appConfig, err := svc.ds.AppConfig(ctx)
 		if err != nil {
 			logging.WithErr(ctx, err)

server/service/osquery_test.go

@@ -519,6 +519,7 @@ func verifyDiscovery(t *testing.T, queries, discovery map[string]string) {
 }
 
 func TestHostDetailQueries(t *testing.T) {
+	ctx := context.Background()
 	ds := new(mock.Store)
 	additional := json.RawMessage(`{"foobar": "select foo", "bim": "bam"}`)
 	ds.AppConfigFunc = func(ctx context.Context) (*fleet.AppConfig, error) {
@@ -553,23 +554,26 @@ func TestHostDetailQueries(t *testing.T) {
 		jitterH:  make(map[time.Duration]*jitterHashTable),
 	}
 
-	queries, discovery, err := svc.detailQueriesForHost(context.Background(), &host)
+	// detail_updated_at is now, so nothing gets returned by default
+	queries, discovery, err := svc.detailQueriesForHost(ctx, &host)
 	require.NoError(t, err)
 	assert.Empty(t, queries)
 	verifyDiscovery(t, queries, discovery)
 
 	// With refetch requested detail queries should be returned
 	host.RefetchRequested = true
-	queries, discovery, err = svc.detailQueriesForHost(context.Background(), &host)
+	queries, discovery, err = svc.detailQueriesForHost(ctx, &host)
 	require.NoError(t, err)
-	assert.NotEmpty(t, queries)
+	// +2: additional queries: bim, foobar
+	require.Equal(t, len(expectedDetailQueriesForPlatform(host.Platform))+2, len(queries), distQueriesMapKeys(queries))
 	verifyDiscovery(t, queries, discovery)
 	host.RefetchRequested = false
 
 	// Advance the time
 	mockClock.AddTime(1*time.Hour + 1*time.Minute)
 
-	queries, discovery, err = svc.detailQueriesForHost(context.Background(), &host)
+	// all queries returned now that detail udpated at is in the past
+	queries, discovery, err = svc.detailQueriesForHost(ctx, &host)
 	require.NoError(t, err)
 	// +2: additional queries: bim, foobar
 	require.Equal(t, len(expectedDetailQueriesForPlatform(host.Platform))+2, len(queries), distQueriesMapKeys(queries))
@@ -581,6 +585,31 @@ func TestHostDetailQueries(t *testing.T) {
 	}
 	assert.Equal(t, "bam", queries[hostAdditionalQueryPrefix+"bim"])
 	assert.Equal(t, "select foo", queries[hostAdditionalQueryPrefix+"foobar"])
+
+	host.DetailUpdatedAt = mockClock.Now()
+
+	// detail_updated_at is now, so nothing gets returned
+	queries, discovery, err = svc.detailQueriesForHost(ctx, &host)
+	require.NoError(t, err)
+	assert.Empty(t, queries)
+	verifyDiscovery(t, queries, discovery)
+
+	// setting refetch_critical_queries_until in the past still returns nothing
+	host.RefetchCriticalQueriesUntil = ptr.Time(mockClock.Now().Add(-1 * time.Minute))
+	queries, discovery, err = svc.detailQueriesForHost(ctx, &host)
+	require.NoError(t, err)
+	assert.Empty(t, queries)
+	verifyDiscovery(t, queries, discovery)
+
+	// setting refetch_critical_queries_until in the future returns only the critical queries
+	host.RefetchCriticalQueriesUntil = ptr.Time(mockClock.Now().Add(1 * time.Minute))
+	queries, discovery, err = svc.detailQueriesForHost(ctx, &host)
+	require.NoError(t, err)
+	require.Equal(t, len(criticalDetailQueries), len(queries), distQueriesMapKeys(queries))
+	for name := range criticalDetailQueries {
+		assert.Contains(t, queries, hostDetailQueryPrefix+name)
+	}
+	verifyDiscovery(t, queries, discovery)
 }
 
 func TestQueriesAndHostFeatures(t *testing.T) {

server/service/osquery_utils/queries.go

@@ -1250,13 +1250,20 @@ func directIngestMDMMac(ctx context.Context, logger log.Logger, host *fleet.Host
 		}
 	}
 
+	mdmSolutionName := deduceMDMNameMacOS(rows[0])
+	if !enrolled && installedFromDep && mdmSolutionName != fleet.WellKnownMDMFleet && host.RefetchCriticalQueriesUntil != nil {
+		// the host was unenrolled from a non-Fleet DEP MDM solution, and the
+		// refetch critical queries timestamp was set, so clear it.
+		host.RefetchCriticalQueriesUntil = nil
+	}
+
 	return ds.SetOrUpdateMDMData(ctx,
 		host.ID,
 		false,
 		enrolled,
 		rows[0]["server_url"],
 		installedFromDep,
-		deduceMDMNameMacOS(rows[0]),
+		mdmSolutionName,
 	)
 }