diff --git a/pkg/api/dashboard_permission.go b/pkg/api/dashboard_permission.go
index 4ae1ce4d36e16..c4fbbbdd13d41 100644
--- a/pkg/api/dashboard_permission.go
+++ b/pkg/api/dashboard_permission.go
@@ -126,6 +126,10 @@ func (hs *HTTPServer) UpdateDashboardPermissions(c *models.ReqContext) response.
 				return response.Error(400, err.Error(), err)
 			}
 
+			if err == guardian.ErrGuardianOverrideDuplicate {
+				return response.Error(409, err.Error(), err)
+			}
+
 			return response.Error(500, "Error while checking dashboard permissions", err)
 		}
 
diff --git a/pkg/services/dashboards/database/acl.go b/pkg/services/dashboards/database/acl.go
index 940a2ab7aad16..37eb9dd79347a 100644
--- a/pkg/services/dashboards/database/acl.go
+++ b/pkg/services/dashboards/database/acl.go
@@ -63,15 +63,20 @@ func (d *DashboardStore) GetDashboardAclInfoList(ctx context.Context, query *mod
 				d.is_folder,
 				CASE WHEN (da.dashboard_id = -1 AND d.folder_id > 0) OR da.dashboard_id = d.folder_id THEN ` + d.dialect.BooleanStr(true) + ` ELSE ` + falseStr + ` END AS inherited
 			FROM dashboard as d
+				-- get folder dashboards for reference purposes
 				LEFT JOIN dashboard folder on folder.id = d.folder_id
+				-- get the acls under the following conditions
 				LEFT JOIN dashboard_acl AS da ON
+				-- if it is for this dashboard
 				da.dashboard_id = d.id OR
+				-- or if it is for the parent folder
 				da.dashboard_id = d.folder_id OR
 				(
-					-- include default permissions -->
-					da.org_id = -1 AND (
-					  (folder.id IS NOT NULL AND folder.has_acl = ` + falseStr + `) OR
-					  (folder.id IS NULL AND d.has_acl = ` + falseStr + `)
+					-- include default permissions if dashboard has no acl AND ((folder is set without acl)
+					-- OR ( folder is NOT set and dashboard has no acl set ))
+					da.org_id = -1 AND d.has_acl = ` + falseStr + ` AND (
+						(folder.id IS NOT NULL AND folder.has_acl = ` + falseStr + `) OR
+				  		(folder.id IS NULL)
 					)
 				)
 				LEFT JOIN ` + d.dialect.Quote("user") + ` AS u ON u.id = da.user_id
diff --git a/pkg/services/dashboards/database/database.go b/pkg/services/dashboards/database/database.go
index 847654c416c23..c5bc462b6352d 100644
--- a/pkg/services/dashboards/database/database.go
+++ b/pkg/services/dashboards/database/database.go
@@ -201,6 +201,8 @@ func (d *DashboardStore) UpdateDashboardACL(ctx context.Context, dashboardID int
 			return fmt.Errorf("deleting from dashboard_acl failed: %w", err)
 		}
 
+		hasAcl := false
+
 		for _, item := range items {
 			if item.UserID == 0 && item.TeamID == 0 && (item.Role == nil || !item.Role.IsValid()) {
 				return models.ErrDashboardAclInfoMissing
@@ -214,10 +216,12 @@ func (d *DashboardStore) UpdateDashboardACL(ctx context.Context, dashboardID int
 			if _, err := sess.Insert(item); err != nil {
 				return err
 			}
+
+			hasAcl = true
 		}
 
 		// Update dashboard HasAcl flag
-		dashboard := models.Dashboard{HasAcl: true}
+		dashboard := models.Dashboard{HasAcl: hasAcl}
 		_, err = sess.Cols("has_acl").Where("id=?", dashboardID).Update(&dashboard)
 		return err
 	})
diff --git a/pkg/services/guardian/guardian.go b/pkg/services/guardian/guardian.go
index fcf278642efc5..506ba9d584a13 100644
--- a/pkg/services/guardian/guardian.go
+++ b/pkg/services/guardian/guardian.go
@@ -12,8 +12,9 @@ import (
 )
 
 var (
-	ErrGuardianPermissionExists = errors.New("permission already exists")
-	ErrGuardianOverride         = errors.New("you can only override a permission to be higher")
+	ErrGuardianPermissionExists  = errors.New("permission already exists")
+	ErrGuardianOverride          = errors.New("you can only override a permission to be higher")
+	ErrGuardianOverrideDuplicate = errors.New("you can not override with duplicate permissions")
 )
 
 // DashboardGuardian to be used for guard against operations without access on dashboard and acl
@@ -205,9 +206,15 @@ func (g *dashboardGuardianImpl) CheckPermissionBeforeUpdate(permission models.Pe
 				continue
 			}
 
-			if a.IsDuplicateOf(existingPerm) && a.Permission <= existingPerm.Permission {
-				return false, ErrGuardianOverride
+			if a.IsDuplicateOf(existingPerm) {
+				return false, ErrGuardianOverrideDuplicate
 			}
+			// Disabling the following check because it goes against the way we are using permissions https://soracom.slack.com/archives/C9PHDH1QB/p1555664739066900
+			// existing permissions returned by GetAcl above include default parent folder permissions if this dashboard has never had permissions set before
+			// and is inside a folder.  That could possibly cause an error _before_ we are able to set the permissions catch 22.
+			// if a.Permission <= existingPerm.Permission {
+			// 	return false, ErrGuardianOverride
+			// }
 		}
 	}