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 c022ac7..fbec656 100644
--- a/client/src/main/java/envoy/client/ui/controller/ChatScene.java
+++ b/client/src/main/java/envoy/client/ui/controller/ChatScene.java
@@ -562,7 +562,7 @@ public final class ChatScene implements EventListener, Restorable {
 		// KeyPressed will be called before the char has been added to the text, hence
 		// this is needed for the first char
 		if (messageTextArea.getText().length() == 1 && e != null) checkPostConditions(e);
-		
+
 		// This is needed for the messageTA context menu
 		else if (e == null) checkPostConditions(false);
 	}
@@ -585,14 +585,23 @@ public final class ChatScene implements EventListener, Restorable {
 	 */
 	@FXML
 	private void checkPostConditions(KeyEvent e) {
-		final var messagePosted = settings.isEnterToSend() && e.getCode() == KeyCode.ENTER
-				|| !settings.isEnterToSend() && e.getCode() == KeyCode.ENTER && e.isControlDown();
+		final var	enterPressed	= e.getCode() == KeyCode.ENTER;
+		final var	messagePosted	= enterPressed ? settings.isEnterToSend() ? !e.isControlDown() : e.isControlDown() : false;
 		if (messagePosted) {
 
 			// Removing an inserted line break if added by pressing enter
 			final var	text			= messageTextArea.getText();
-			final var	caretPosition	= messageTextArea.getCaretPosition();
-			if (text.charAt(caretPosition - 1) == '\n') messageTextArea.setText(new StringBuilder(text).deleteCharAt(caretPosition - 1).toString());
+			final var	textPosition	= messageTextArea.getCaretPosition() - 1;
+			if (!e.isControlDown() && !text.isEmpty() && text.charAt(textPosition) == '\n')
+				messageTextArea.setText(new StringBuilder(text).deleteCharAt(textPosition).toString());
+		}
+
+		// if control is pressed, the enter press is originally invalidated. Here it'll
+		// be inserted again
+		else if (enterPressed && e.isControlDown()) {
+			var caretPosition = messageTextArea.getCaretPosition();
+			messageTextArea.setText(new StringBuilder(messageTextArea.getText()).insert(caretPosition, '\n').toString());
+			messageTextArea.positionCaret(++caretPosition);
 		}
 		checkPostConditions(messagePosted);
 	}