diff --git a/internal/pkg/api/handleCheckin.go b/internal/pkg/api/handleCheckin.go
index 38cd78836..5f91515e4 100644
--- a/internal/pkg/api/handleCheckin.go
+++ b/internal/pkg/api/handleCheckin.go
@@ -521,6 +521,7 @@ func (ct *CheckinT) markUpgradeComplete(ctx context.Context, agent *model.Agent)
 		dl.FieldUpgradeStartedAt: nil,
 		dl.FieldUpgradeStatus:    nil,
 		dl.FieldUpgradedAt:       time.Now().UTC().Format(time.RFC3339),
+		dl.FieldUpgradeAttempts:  nil,
 	}
 	body, err := doc.Marshal()
 	if err != nil {
diff --git a/internal/pkg/dl/constants.go b/internal/pkg/dl/constants.go
index 73d382789..9c191955a 100644
--- a/internal/pkg/dl/constants.go
+++ b/internal/pkg/dl/constants.go
@@ -54,6 +54,7 @@ const (
 	FieldUpgradeStartedAt = "upgrade_started_at"
 	FieldUpgradeStatus    = "upgrade_status"
 	FieldUpgradeDetails   = "upgrade_details"
+	FieldUpgradeAttempts  = "upgrade_attempts"
 
 	FieldAuditUnenrolledTime   = "audit_unenrolled_time"
 	FieldAuditUnenrolledReason = "audit_unenrolled_reason"