diff --git a/server/datastore/mysql/mdm.go b/server/datastore/mysql/mdm.go
index fa4a9e54525..95a406543ae 100644
--- a/server/datastore/mysql/mdm.go
+++ b/server/datastore/mysql/mdm.go
@@ -1999,7 +1999,7 @@ WHERE
     AND ncaa.renew_command_uuid IS NULL
     AND ne.enabled = true
 GROUP BY
-    host_uuid, ncaa.sha256, ncaa.cert_not_valid_after
+    host_uuid, ncaa.sha256, ncaa.cert_not_valid_after, ne.enrolled_from_migration, ne.type
 ORDER BY
     cert_not_valid_after ASC
 LIMIT ?`, expiryDays, limit)
diff --git a/server/datastore/mysql/microsoft_mdm.go b/server/datastore/mysql/microsoft_mdm.go
index a730d617996..aee567dc435 100644
--- a/server/datastore/mysql/microsoft_mdm.go
+++ b/server/datastore/mysql/microsoft_mdm.go
@@ -446,12 +446,17 @@ func (ds *Datastore) MDMWindowsDeleteEnrolledDeviceOnReenrollment(ctx context.Co
 		delActionsStmt  = "DELETE FROM host_mdm_actions WHERE host_id = (SELECT id FROM hosts WHERE uuid = ? LIMIT 1)"
 		delProfilesStmt = "DELETE FROM host_mdm_windows_profiles WHERE host_uuid = ?"
 		// setup_experience_status_results.host_uuid is keyed by fleet.HostUUIDForSetupExperience; for Windows that's the
-		// host's OsqueryHostID, NOT the Fleet host UUID stored on the MDM enrollment. Resolve via JOIN so we delete by
-		// whichever identifier matches (works for both shapes).
-		delSetupExpStmt = `DELETE ser FROM setup_experience_status_results ser
-			JOIN hosts h ON ser.host_uuid = h.osquery_host_id OR ser.host_uuid = h.uuid
-			WHERE h.uuid = ?`
-		delUpcomingStmt = `DELETE ua FROM upcoming_activities ua JOIN hosts h ON h.id = ua.host_id WHERE h.uuid = ?`
+		// host's OsqueryHostID, NOT the Fleet host UUID stored on the MDM enrollment. Resolve via the hosts table so we
+		// delete by whichever identifier matches (works for both shapes).
+		// Cross-dialect: avoid MySQL-only "DELETE alias FROM ... JOIN" syntax.
+		delSetupExpStmt = `DELETE FROM setup_experience_status_results
+			WHERE EXISTS (
+				SELECT 1 FROM hosts h
+				WHERE (setup_experience_status_results.host_uuid = h.osquery_host_id
+					OR setup_experience_status_results.host_uuid = h.uuid)
+				AND h.uuid = ?
+			)`
+		delUpcomingStmt = `DELETE FROM upcoming_activities WHERE host_id IN (SELECT id FROM hosts WHERE uuid = ?)`
 	)
 
 	return ds.withRetryTxx(ctx, func(tx sqlx.ExtContext) error {
@@ -3777,10 +3782,12 @@ LIMIT ?`
 // needs: a host that was offline when the profile was deleted keeps its host-profile row, which keeps the content alive until the
 // removal finally delivers. The NOT EXISTS is an index probe via host_mdm_windows_profiles(profile_uuid).
 func (ds *Datastore) CleanupWindowsMDMPendingDeleteProfiles(ctx context.Context) error {
+	// Cross-dialect: avoid MySQL-only "DELETE alias FROM table alias" syntax.
 	const stmt = `
-DELETE pd FROM mdm_windows_configuration_profiles_pending_delete pd
+DELETE FROM mdm_windows_configuration_profiles_pending_delete
 WHERE NOT EXISTS (
-	SELECT 1 FROM host_mdm_windows_profiles hmwp WHERE hmwp.profile_uuid = pd.profile_uuid
+	SELECT 1 FROM host_mdm_windows_profiles hmwp
+	WHERE hmwp.profile_uuid = mdm_windows_configuration_profiles_pending_delete.profile_uuid
 )`
 	if _, err := ds.writer(ctx).ExecContext(ctx, stmt); err != nil {
 		return ctxerr.Wrap(ctx, err, "cleanup windows mdm pending-delete profiles")
diff --git a/server/datastore/mysql/postgres_smoke_test.go b/server/datastore/mysql/postgres_smoke_test.go
index ce7ce79572d..a9abad0a7f3 100644
--- a/server/datastore/mysql/postgres_smoke_test.go
+++ b/server/datastore/mysql/postgres_smoke_test.go
@@ -555,3 +555,44 @@ func TestPostgresHostSoftwareUpdate(t *testing.T) {
 		assert.Empty(t, host.Software, "host inventory should be empty")
 	})
 }
+
+// TestPostgresMDMCleanupQueries is regression coverage for MDM statements that
+// previously used MySQL-only SQL and broke at runtime on PostgreSQL (the
+// cleanups_then_aggregation cron and Windows re-enrollment). Each subtest
+// executes the real statement against PG; a dialect regression fails here
+// instead of shipping silently (these paths are not otherwise in the
+// TestPostgres* suite).
+func TestPostgresMDMCleanupQueries(t *testing.T) {
+	ds := CreatePostgresDS(t)
+	ctx := context.Background()
+
+	t.Run("GetHostCertAssociationsToExpire", func(t *testing.T) {
+		// renew_scep_certificates cron: the expiry filter multiplies a bound
+		// param by INTERVAL '1 day' and must not be cast to timestamptz.
+		_, err := ds.GetHostCertAssociationsToExpire(ctx, 30, 100)
+		require.NoError(t, err, "GetHostCertAssociationsToExpire")
+	})
+
+	t.Run("CleanupWindowsMDMPendingDeleteProfiles", func(t *testing.T) {
+		require.NoError(t, ds.CleanupWindowsMDMPendingDeleteProfiles(ctx),
+			"CleanupWindowsMDMPendingDeleteProfiles")
+	})
+
+	t.Run("MDMWindowsDeleteEnrolledDeviceOnReenrollment", func(t *testing.T) {
+		device := &fleet.MDMWindowsEnrolledDevice{
+			MDMDeviceID:            "pg-mdm-device-1",
+			MDMHardwareID:          "pg-mdm-hwid-1-0123456789012345678901234567890123456789",
+			MDMDeviceState:         "2",
+			MDMDeviceType:          "CIMClient_Windows",
+			MDMDeviceName:          "PG-TEST-DESKTOP",
+			MDMEnrollType:          "ProgrammaticEnrollment",
+			MDMEnrollUserID:        "",
+			MDMEnrollProtoVersion:  "5.0",
+			MDMEnrollClientVersion: "10.0.19045.2965",
+			MDMNotInOOBE:           false,
+		}
+		require.NoError(t, ds.MDMWindowsInsertEnrolledDevice(ctx, device), "insert enrolled device")
+		require.NoError(t, ds.MDMWindowsDeleteEnrolledDeviceOnReenrollment(ctx, device.MDMHardwareID),
+			"MDMWindowsDeleteEnrolledDeviceOnReenrollment")
+	})
+}
diff --git a/server/platform/postgres/rebind_driver.go b/server/platform/postgres/rebind_driver.go
index 3517695b287..2b917556e2c 100644
--- a/server/platform/postgres/rebind_driver.go
+++ b/server/platform/postgres/rebind_driver.go
@@ -68,7 +68,9 @@ var (
 	// MySQL: INSERT INTO table () VALUES () — empty column/value lists for auto-increment-only inserts
 	reEmptyValues = regexp.MustCompile(`(?i)(INSERT\s+INTO\s+\S+\s+)\(\s*\)\s*VALUES\s*\(\s*\)`)
 	// PG can't infer $N type in interval arithmetic; cast to timestamptz
-	reParamBeforeInterval = regexp.MustCompile(`(\$\d+)\s+([-+*]\s*INTERVAL\b)`)
+	reParamBeforeInterval = regexp.MustCompile(`(\$\d+)\s+([-+]\s*INTERVAL\b)`)
+	// $N * INTERVAL scales the interval, so the param is a number, not a timestamp
+	reParamTimesInterval = regexp.MustCompile(`(\$\d+)\s*(\*\s*INTERVAL\b)`)
 	// JSON boolean comparison: MySQL ->> on JSON true returns '1', PG returns 'true'.
 	// Match: COALESCE(<expr>, '0') = '1' → COALESCE(<expr>, '0') IN ('1', 'true')
 	reJSONBoolCoalesce = regexp.MustCompile(`COALESCE\(([^)]+->>'[^']+'),\s*'0'\)\s*=\s*'1'`)
@@ -694,6 +696,7 @@ func rebindQuery(query string) string {
 	// PG can't infer the type of $N when used in interval arithmetic ($N - INTERVAL, $N + INTERVAL).
 	// Cast to timestamptz so the operator resolves correctly.
 	result = reParamBeforeInterval.ReplaceAllString(result, "${1}::timestamptz ${2}")
+	result = reParamTimesInterval.ReplaceAllString(result, "${1}::float8 ${2}")
 	return result
 }
 
diff --git a/server/platform/postgres/rebind_driver_test.go b/server/platform/postgres/rebind_driver_test.go
index c0c00803eb2..ef0572db3fc 100644
--- a/server/platform/postgres/rebind_driver_test.go
+++ b/server/platform/postgres/rebind_driver_test.go
@@ -301,6 +301,21 @@ func TestRewriteIntervalPlaceholder(t *testing.T) {
 			in:   "a >= NOW() - INTERVAL ? SECOND AND b <= NOW() + INTERVAL ? MINUTE",
 			want: "a >= NOW() - ($1::float8 * INTERVAL '1 second') AND b <= NOW() + ($2::float8 * INTERVAL '1 minute')",
 		},
+		{
+			name: "placeholder plus INTERVAL gets timestamptz cast",
+			in:   "expires_at <= ? + INTERVAL '1 hour'",
+			want: "expires_at <= $1::timestamptz + INTERVAL '1 hour'",
+		},
+		{
+			name: "placeholder minus INTERVAL gets timestamptz cast",
+			in:   "seen_at >= ? - INTERVAL '30 minutes'",
+			want: "seen_at >= $1::timestamptz - INTERVAL '30 minutes'",
+		},
+		{
+			name: "placeholder times INTERVAL gets float8 cast, not timestamptz",
+			in:   "cert_not_valid_after <= CURRENT_DATE + (? * INTERVAL '1 day')",
+			want: "cert_not_valid_after <= CURRENT_DATE + ($1::float8 * INTERVAL '1 day')",
+		},
 	}
 	for _, tc := range cases {
 		t.Run(tc.name, func(t *testing.T) {