diff --git a/client/src/main/java/envoy/client/ui/controller/ChatScene.java b/client/src/main/java/envoy/client/ui/controller/ChatScene.java
index c431aad..c261ed6 100644
--- a/client/src/main/java/envoy/client/ui/controller/ChatScene.java
+++ b/client/src/main/java/envoy/client/ui/controller/ChatScene.java
@@ -355,6 +355,7 @@ public final class ChatScene implements Restorable {
 			try {
 				final var fileBytes = Files.readAllBytes(file.toPath());
 				pendingAttachment = new Attachment(fileBytes, type);
+				checkPostConditions(false);
 				// Setting the preview image as image of the attachmentView
 				if (type == AttachmentType.PICTURE)
 					attachmentView.setImage(new Image(new ByteArrayInputStream(fileBytes), DEFAULT_ICON_SIZE, DEFAULT_ICON_SIZE, true, true));
@@ -413,9 +414,9 @@ public final class ChatScene implements Restorable {
 				|| !settings.isEnterToSend() && e.getCode() == KeyCode.ENTER && e.isControlDown());
 	}
 
-	private void checkPostConditions(boolean sendKeyPressed) {
+	private void checkPostConditions(boolean postMessage) {
 		if (!postingPermanentlyDisabled) {
-			if (!postButton.isDisabled() && sendKeyPressed) postMessage();
+			if (!postButton.isDisabled() && postMessage) postMessage();
 			postButton.setDisable(messageTextArea.getText().isBlank() && pendingAttachment == null || currentChat == null);
 		} else {
 			final var noMoreMessaging = "Go online to send messages";