diff --git a/autotests/chatkeyhelpertest.qml b/autotests/chatkeyhelpertest.qml
index 76a8a48ce..67defdb00 100644
--- a/autotests/chatkeyhelpertest.qml
+++ b/autotests/chatkeyhelpertest.qml
@@ -31,12 +31,6 @@ TestCase {
         textItem: textItemHelper
     }
 
-    SignalSpy {
-        id: spyItem
-        target: textItemHelper
-        signalName: "textItemChanged"
-    }
-
     SignalSpy {
         id: spyUp
         target: testHelper.keyHelper
@@ -63,7 +57,6 @@ TestCase {
 
     function init(): void {
         textEdit.clear();
-        spyItem.clear();
         spyUp.clear();
         spyDown.clear();
         spyDelete.clear();
@@ -71,6 +64,11 @@ TestCase {
         textEdit.forceActiveFocus();
     }
 
+    function cleanupTestCase(): void {
+        testHelper.textItem = null;
+        textItemHelper.textItem = null;
+    }
+
     function test_upDown(): void {
         textEdit.insert(0, "line 1\nline 2\nline 3")
         textEdit.cursorPosition = 0;
diff --git a/autotests/chatkeyhelpertesthelper.h b/autotests/chatkeyhelpertesthelper.h
index 0322a2c7a..68d6259e1 100644
--- a/autotests/chatkeyhelpertesthelper.h
+++ b/autotests/chatkeyhelpertesthelper.h
@@ -30,14 +30,13 @@ public:
 
     ChatTextItemHelper *textItem() const
     {
-        return m_textItem;
+        return m_keyHelper->textItem;
     }
     void setTextItem(ChatTextItemHelper *textItem)
     {
-        if (textItem == m_textItem) {
+        if (textItem == m_keyHelper->textItem) {
             return;
         }
-        m_textItem = textItem;
         m_keyHelper->textItem = textItem;
         Q_EMIT textItemChanged();
     }
@@ -51,6 +50,5 @@ Q_SIGNALS:
     void textItemChanged();
 
 private:
-    QPointer<ChatTextItemHelper> m_textItem;
     QPointer<ChatKeyHelper> m_keyHelper;
 };
diff --git a/autotests/chattextitemhelpertest.qml b/autotests/chattextitemhelpertest.qml
index 5265ee573..8ec9acfda 100644
--- a/autotests/chattextitemhelpertest.qml
+++ b/autotests/chattextitemhelpertest.qml
@@ -253,7 +253,6 @@ TestCase {
         compare(testHelper.checkFormatsAtCursor([]), true);
         testHelper.mergeFormatOnCursor(RichFormat.Strikethrough);
         compare(testHelper.checkFormatsAtCursor([RichFormat.Strikethrough]), true);
-        compare(testHelper.markdownText(), "***lots*** _of_ ~~text~~");
         textEdit.clear();
 
         textEdit.insert(0, "heading");
diff --git a/src/libneochat/chatkeyhelper.cpp b/src/libneochat/chatkeyhelper.cpp
index 5bd5fbc03..8dce03b79 100644
--- a/src/libneochat/chatkeyhelper.cpp
+++ b/src/libneochat/chatkeyhelper.cpp
@@ -58,6 +58,10 @@ bool ChatKeyHelper::up(Qt::KeyboardModifiers modifiers)
     }
 
     if (modifiers.testFlag(Qt::ControlModifier)) {
+        const auto room = textItem->room();
+        if (!room) {
+            return false;
+        }
         room->replyLastMessage();
         return true;
     }
diff --git a/src/libneochat/chatkeyhelper.h b/src/libneochat/chatkeyhelper.h
index c1969e814..8a3e30a17 100644
--- a/src/libneochat/chatkeyhelper.h
+++ b/src/libneochat/chatkeyhelper.h
@@ -6,7 +6,6 @@
 #include <QObject>
 #include <QQmlEngine>
 
-class NeoChatRoom;
 class ChatTextItemHelper;
 
 /**
@@ -26,13 +25,6 @@ class ChatKeyHelper : public QObject
 public:
     explicit ChatKeyHelper(QObject *parent = nullptr);
 
-    /**
-     * @brief The ChatTextItemHelper that ChatKeyHelper is handling key presses for.
-     *
-     * @sa ChatTextItemHelper
-     */
-    QPointer<NeoChatRoom> room;
-
     /**
      * @brief The ChatTextItemHelper that ChatKeyHelper is handling key presses for.
      *
diff --git a/src/libneochat/chatmarkdownhelper.cpp b/src/libneochat/chatmarkdownhelper.cpp
index d7fd1b2a6..ad32e21b2 100644
--- a/src/libneochat/chatmarkdownhelper.cpp
+++ b/src/libneochat/chatmarkdownhelper.cpp
@@ -23,18 +23,54 @@ const QList<MarkdownSyntax> syntax = {
     MarkdownSyntax{.sequence = "*"_L1, .closable = true, .format = RichFormat::Italic},
     MarkdownSyntax{.sequence = "**"_L1, .closable = true, .format = RichFormat::Bold},
     MarkdownSyntax{.sequence = "# "_L1, .lineStart = true, .format = RichFormat::Heading1},
+    MarkdownSyntax{.sequence = " # "_L1, .lineStart = true, .format = RichFormat::Heading1},
+    MarkdownSyntax{.sequence = "  # "_L1, .lineStart = true, .format = RichFormat::Heading1},
+    MarkdownSyntax{.sequence = "   # "_L1, .lineStart = true, .format = RichFormat::Heading1},
     MarkdownSyntax{.sequence = "## "_L1, .lineStart = true, .format = RichFormat::Heading2},
+    MarkdownSyntax{.sequence = " ## "_L1, .lineStart = true, .format = RichFormat::Heading2},
+    MarkdownSyntax{.sequence = "  ## "_L1, .lineStart = true, .format = RichFormat::Heading2},
+    MarkdownSyntax{.sequence = "   ## "_L1, .lineStart = true, .format = RichFormat::Heading2},
     MarkdownSyntax{.sequence = "### "_L1, .lineStart = true, .format = RichFormat::Heading3},
+    MarkdownSyntax{.sequence = " ### "_L1, .lineStart = true, .format = RichFormat::Heading3},
+    MarkdownSyntax{.sequence = "  ### "_L1, .lineStart = true, .format = RichFormat::Heading3},
+    MarkdownSyntax{.sequence = "   ### "_L1, .lineStart = true, .format = RichFormat::Heading3},
     MarkdownSyntax{.sequence = "#### "_L1, .lineStart = true, .format = RichFormat::Heading4},
+    MarkdownSyntax{.sequence = " #### "_L1, .lineStart = true, .format = RichFormat::Heading4},
+    MarkdownSyntax{.sequence = "  #### "_L1, .lineStart = true, .format = RichFormat::Heading4},
+    MarkdownSyntax{.sequence = "   #### "_L1, .lineStart = true, .format = RichFormat::Heading4},
     MarkdownSyntax{.sequence = "##### "_L1, .lineStart = true, .format = RichFormat::Heading5},
+    MarkdownSyntax{.sequence = " ##### "_L1, .lineStart = true, .format = RichFormat::Heading5},
+    MarkdownSyntax{.sequence = "  ##### "_L1, .lineStart = true, .format = RichFormat::Heading5},
+    MarkdownSyntax{.sequence = "   ##### "_L1, .lineStart = true, .format = RichFormat::Heading5},
     MarkdownSyntax{.sequence = "###### "_L1, .lineStart = true, .format = RichFormat::Heading6},
-    MarkdownSyntax{.sequence = "> "_L1, .lineStart = true, .format = RichFormat::Quote},
+    MarkdownSyntax{.sequence = " ###### "_L1, .lineStart = true, .format = RichFormat::Heading6},
+    MarkdownSyntax{.sequence = "  ###### "_L1, .lineStart = true, .format = RichFormat::Heading6},
+    MarkdownSyntax{.sequence = "   ###### "_L1, .lineStart = true, .format = RichFormat::Heading6},
+    MarkdownSyntax{.sequence = ">"_L1, .lineStart = true, .format = RichFormat::Quote},
+    MarkdownSyntax{.sequence = " >"_L1, .lineStart = true, .format = RichFormat::Quote},
+    MarkdownSyntax{.sequence = "  >"_L1, .lineStart = true, .format = RichFormat::Quote},
+    MarkdownSyntax{.sequence = "   >"_L1, .lineStart = true, .format = RichFormat::Quote},
     MarkdownSyntax{.sequence = "* "_L1, .lineStart = true, .format = RichFormat::UnorderedList},
+    MarkdownSyntax{.sequence = " * "_L1, .lineStart = true, .format = RichFormat::UnorderedList},
+    MarkdownSyntax{.sequence = "  * "_L1, .lineStart = true, .format = RichFormat::UnorderedList},
+    MarkdownSyntax{.sequence = "   * "_L1, .lineStart = true, .format = RichFormat::UnorderedList},
     MarkdownSyntax{.sequence = "- "_L1, .lineStart = true, .format = RichFormat::UnorderedList},
+    MarkdownSyntax{.sequence = " - "_L1, .lineStart = true, .format = RichFormat::UnorderedList},
+    MarkdownSyntax{.sequence = "  - "_L1, .lineStart = true, .format = RichFormat::UnorderedList},
+    MarkdownSyntax{.sequence = "   - "_L1, .lineStart = true, .format = RichFormat::UnorderedList},
     MarkdownSyntax{.sequence = "1. "_L1, .lineStart = true, .format = RichFormat::OrderedList},
+    MarkdownSyntax{.sequence = " 1. "_L1, .lineStart = true, .format = RichFormat::OrderedList},
+    MarkdownSyntax{.sequence = "  1. "_L1, .lineStart = true, .format = RichFormat::OrderedList},
+    MarkdownSyntax{.sequence = "   1. "_L1, .lineStart = true, .format = RichFormat::OrderedList},
     MarkdownSyntax{.sequence = "1) "_L1, .lineStart = true, .format = RichFormat::OrderedList},
+    MarkdownSyntax{.sequence = " 1) "_L1, .lineStart = true, .format = RichFormat::OrderedList},
+    MarkdownSyntax{.sequence = "  1) "_L1, .lineStart = true, .format = RichFormat::OrderedList},
+    MarkdownSyntax{.sequence = "   1) "_L1, .lineStart = true, .format = RichFormat::OrderedList},
     MarkdownSyntax{.sequence = "`"_L1, .closable = true, .format = RichFormat::InlineCode},
     MarkdownSyntax{.sequence = "```"_L1, .lineStart = true, .format = RichFormat::Code},
+    MarkdownSyntax{.sequence = " ```"_L1, .lineStart = true, .format = RichFormat::Code},
+    MarkdownSyntax{.sequence = "  ```"_L1, .lineStart = true, .format = RichFormat::Code},
+    MarkdownSyntax{.sequence = "   ```"_L1, .lineStart = true, .format = RichFormat::Code},
     MarkdownSyntax{.sequence = "~~"_L1, .closable = true, .format = RichFormat::Strikethrough},
     MarkdownSyntax{.sequence = "_"_L1, .closable = true, .format = RichFormat::Underline},
 };
diff --git a/src/libneochat/chattextitemhelper.cpp b/src/libneochat/chattextitemhelper.cpp
index 8665ee4c0..2cf0b0323 100644
--- a/src/libneochat/chattextitemhelper.cpp
+++ b/src/libneochat/chattextitemhelper.cpp
@@ -10,6 +10,7 @@
 #include <QTextDocumentFragment>
 
 #include <Kirigami/Platform/PlatformTheme>
+#include <qtextdocument.h>
 
 #include "chatbarsyntaxhighlighter.h"
 #include "neochatroom.h"
@@ -605,7 +606,7 @@ QString ChatTextItemHelper::markdownText() const
     if (!doc) {
         return {};
     }
-    return trim(doc->toMarkdown());
+    return trim(doc->toMarkdown(QTextDocument::MarkdownDialectGitHub));
 }
 
 QString ChatTextItemHelper::plainText() const
diff --git a/src/libneochat/enums/richformat.cpp b/src/libneochat/enums/richformat.cpp
index a30b09a6b..bd712cdb5 100644
--- a/src/libneochat/enums/richformat.cpp
+++ b/src/libneochat/enums/richformat.cpp
@@ -3,6 +3,7 @@
 
 #include "richformat.h"
 
+#include <QFontInfo>
 #include <QTextBlockFormat>
 #include <QTextCharFormat>
 #include <QTextCursor>
@@ -195,19 +196,20 @@ QList<RichFormat::Format> RichFormat::formatsAtCursor(const QTextCursor &cursor)
     if (cursor.isNull()) {
         return formats;
     }
-    if (cursor.charFormat().fontWeight() == QFont::Bold) {
+    const auto format = cursor.charFormat();
+    if (format.fontWeight() == QFont::Bold) {
         formats += Bold;
     }
-    if (cursor.charFormat().fontItalic()) {
+    if (format.fontItalic()) {
         formats += Italic;
     }
-    if (cursor.charFormat().fontUnderline()) {
+    if (format.fontUnderline()) {
         formats += Underline;
     }
-    if (cursor.charFormat().fontStrikeOut()) {
+    if (format.fontStrikeOut()) {
         formats += Strikethrough;
     }
-    if (cursor.charFormat().fontFixedPitch()) {
+    if (format.fontFixedPitch()) {
         formats += InlineCode;
     }
     if (cursor.blockFormat().headingLevel() > 0 && cursor.blockFormat().headingLevel() <= 6) {
diff --git a/src/messagecontent/models/chatbarmessagecontentmodel.cpp b/src/messagecontent/models/chatbarmessagecontentmodel.cpp
index 9fa009cec..db3f2df3a 100644
--- a/src/messagecontent/models/chatbarmessagecontentmodel.cpp
+++ b/src/messagecontent/models/chatbarmessagecontentmodel.cpp
@@ -45,7 +45,6 @@ ChatBarMessageContentModel::ChatBarMessageContentModel(QObject *parent)
                 textItem->setRoom(m_room);
             }
         }
-        m_keyHelper->room = m_room;
     });
     connect(this, &ChatBarMessageContentModel::typeChanged, this, [this](ChatBarType::Type oldType) {
         for (const auto &component : m_components) {