diff --git a/backend/plugins/jira/api/connection_api.go b/backend/plugins/jira/api/connection_api.go
index aee973ef8ba..2a0fe3e32a5 100644
--- a/backend/plugins/jira/api/connection_api.go
+++ b/backend/plugins/jira/api/connection_api.go
@@ -54,22 +54,22 @@ func testConnection(ctx context.Context, connection models.JiraConn) (*JiraTestC
 	// serverInfo checking
 	res, err := apiClient.Get("api/2/serverInfo", nil, nil)
 	if err != nil {
+		// check if `/rest/` was missing
+		if strings.Contains(err.Error(), "status code 404") && !strings.HasSuffix(connection.Endpoint, "/rest/") {
+			endpointUrl, err := url.Parse(connection.Endpoint)
+			if err != nil {
+				return nil, errors.Convert(err)
+			}
+			refUrl, err := url.Parse("/rest/")
+			if err != nil {
+				return nil, errors.Convert(err)
+			}
+			restUrl := endpointUrl.ResolveReference(refUrl)
+			return nil, errors.NotFound.New(fmt.Sprintf("Seems like an invalid Endpoint URL, please try %s", restUrl.String()))
+		}
 		return nil, err
 	}
 	serverInfoFail := "Failed testing the serverInfo: [ " + res.Request.URL.String() + " ]"
-	// check if `/rest/` was missing
-	if res.StatusCode == http.StatusNotFound && !strings.HasSuffix(connection.Endpoint, "/rest/") {
-		endpointUrl, err := url.Parse(connection.Endpoint)
-		if err != nil {
-			return nil, errors.Convert(err)
-		}
-		refUrl, err := url.Parse("/rest/")
-		if err != nil {
-			return nil, errors.Convert(err)
-		}
-		restUrl := endpointUrl.ResolveReference(refUrl)
-		return nil, errors.NotFound.New(fmt.Sprintf("Seems like an invalid Endpoint URL, please try %s", restUrl.String()))
-	}
 	if res.StatusCode == http.StatusUnauthorized {
 		return nil, errors.HttpStatus(http.StatusBadRequest).New("Error username/password")
 	}