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 912076a..42e9f87 100644
--- a/client/src/main/java/envoy/client/ui/controller/ChatScene.java
+++ b/client/src/main/java/envoy/client/ui/controller/ChatScene.java
@@ -542,16 +542,20 @@ public final class ChatScene implements EventListener, Restorable {
 	 */
 	@FXML
 	private void checkKeyCombination(KeyEvent e) {
+
 		// Checks whether the text is too long
 		messageTextUpdated();
+
 		// Sending an IsTyping event if none has been sent for
 		// IsTyping#millisecondsActive
 		if (currentChat.getLastWritingEvent() + IsTyping.millisecondsActive <= System.currentTimeMillis()) {
 			eventBus.dispatch(new SendEvent(new IsTyping(getChatID(), currentChat.getRecipient().getID())));
 			currentChat.lastWritingEventWasNow();
 		}
-		// Automatic sending of messages via (ctrl +) enter
-		checkPostConditions(e);
+
+		// 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) checkPostConditions(e);
 	}
 
 	/**
@@ -572,8 +576,16 @@ public final class ChatScene implements EventListener, Restorable {
 	 */
 	@FXML
 	private void checkPostConditions(KeyEvent e) {
-		checkPostConditions(settings.isEnterToSend() && e.getCode() == KeyCode.ENTER
-				|| !settings.isEnterToSend() && e.getCode() == KeyCode.ENTER && e.isControlDown());
+		final var messagePosted = settings.isEnterToSend() && e.getCode() == KeyCode.ENTER
+				|| !settings.isEnterToSend() && e.getCode() == KeyCode.ENTER && e.isControlDown();
+		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());
+		}
+		checkPostConditions(messagePosted);
 	}
 
 	private void checkPostConditions(boolean postMessage) {