diff --git a/desktop/src/main/java/bisq/desktop/main/support/dispute/DisputeChatPopup.java b/desktop/src/main/java/bisq/desktop/main/support/dispute/DisputeChatPopup.java
index c184234444b..d87a1f1c238 100644
--- a/desktop/src/main/java/bisq/desktop/main/support/dispute/DisputeChatPopup.java
+++ b/desktop/src/main/java/bisq/desktop/main/support/dispute/DisputeChatPopup.java
@@ -121,6 +121,7 @@ public void openChat(Dispute selectedDispute, DisputeSession concreteDisputeSess
                 MenuItem menuItem1 = new MenuItem(Res.get("support.uploadTraderChat"));
                 MenuItem menuItem2 = new MenuItem(Res.get("support.sendLogFiles"));
                 menuItem1.setOnAction(e -> doTextAttachment(chatView));
+                setChatUploadEnabledState(menuItem1);
                 menuItem2.setOnAction(e -> chatCallback.onSendLogsFromChatWindow(selectedDispute));
                 menuButton.getItems().addAll(menuItem1, menuItem2);
                 menuButton.getStyleClass().add("jfx-button");
@@ -196,4 +197,12 @@ private void doTextAttachment(ChatView chatView) {
             }
         });
     }
+
+    private void setChatUploadEnabledState(MenuItem menuItem) {
+        disputeManager.findTrade(selectedDispute).ifPresentOrElse(t -> {
+            menuItem.setDisable(t.getChatMessages().size() == 0);
+        }, () -> {
+            menuItem.setDisable(true);
+        });
+    }
 }