diff --git a/autotests/chatmarkdownhelpertest.qml b/autotests/chatmarkdownhelpertest.qml
index 9ed992e3b..5f26e4d8f 100644
--- a/autotests/chatmarkdownhelpertest.qml
+++ b/autotests/chatmarkdownhelpertest.qml
@@ -77,8 +77,8 @@ TestCase {
             {tag: "inline code", input: "`c` ", outText: ["`", "c", "c`", "c "], outFormats: [[], [RichFormat.InlineCode], [RichFormat.InlineCode], []], unhandled: 0},
             {tag: "code", input: "``` ", outText: ["`", "``", "```", " "], outFormats: [[], [], [], []], unhandled: 1},
             {tag: "strikethrough", input: "~~s~~ ", outText: ["~", "~~", "s", "s~", "s~~", "s "], outFormats: [[], [], [RichFormat.Strikethrough], [RichFormat.Strikethrough], [RichFormat.Strikethrough], []], unhandled: 0},
-            {tag: "underline", input: "__u__ ", outText: ["_", "__", "u", "u_", "u__", "u "], outFormats: [[], [], [RichFormat.Underline], [RichFormat.Underline], [RichFormat.Underline], []], unhandled: 0},
-            {tag: "multiple closable", input: "***__~~t~~__*** ", outText: ["*", "**", "*", "_", "__", "~", "~~", "t", "t~", "t~~", "t_", "t__", "t*", "t**", "t*", "t "], outFormats: [[], [], [RichFormat.Bold], [RichFormat.Bold, RichFormat.Italic], [RichFormat.Bold, RichFormat.Italic], [RichFormat.Bold, RichFormat.Italic, RichFormat.Underline], [RichFormat.Bold, RichFormat.Italic, RichFormat.Underline], [RichFormat.Bold, RichFormat.Italic, RichFormat.Underline, RichFormat.Strikethrough], [RichFormat.Bold, RichFormat.Italic, RichFormat.Underline, RichFormat.Strikethrough], [RichFormat.Bold, RichFormat.Italic, RichFormat.Underline, RichFormat.Strikethrough], [RichFormat.Bold, RichFormat.Italic, RichFormat.Underline], [RichFormat.Bold, RichFormat.Italic, RichFormat.Underline], [RichFormat.Bold, RichFormat.Italic], [RichFormat.Bold, RichFormat.Italic], [RichFormat.Italic], []], unhandled: 0},
+            {tag: "underline", input: "_u_ ", outText: ["_", "u", "u_", "u "], outFormats: [[], [RichFormat.Underline], [RichFormat.Underline], []], unhandled: 0},
+            {tag: "multiple closable", input: "***_~~t~~_*** ", outText: ["*", "**", "*", "_", "~", "~~", "t", "t~", "t~~", "t_", "t*", "t**", "t*", "t "], outFormats: [[], [], [RichFormat.Bold], [RichFormat.Bold, RichFormat.Italic], [RichFormat.Bold, RichFormat.Italic, RichFormat.Underline], [RichFormat.Bold, RichFormat.Italic, RichFormat.Underline], [RichFormat.Bold, RichFormat.Italic, RichFormat.Underline, RichFormat.Strikethrough], [RichFormat.Bold, RichFormat.Italic, RichFormat.Underline, RichFormat.Strikethrough], [RichFormat.Bold, RichFormat.Italic, RichFormat.Underline, RichFormat.Strikethrough], [RichFormat.Bold, RichFormat.Italic, RichFormat.Underline], [RichFormat.Bold, RichFormat.Italic], [RichFormat.Bold, RichFormat.Italic], [RichFormat.Italic], []], unhandled: 0},
             {tag: "nonclosable closable", input: "* **b** ", outText: ["*", "* ", "*", "**", "b", "b*", "b**", "b "], outFormats: [[], [], [RichFormat.UnorderedList], [RichFormat.UnorderedList], [RichFormat.Bold, RichFormat.UnorderedList], [RichFormat.Bold, RichFormat.UnorderedList], [RichFormat.Bold, RichFormat.UnorderedList], [RichFormat.UnorderedList]], unhandled: 0},
             {tag: "not at line start", input: " 1) ", outText: [" ", " 1", " 1)", " 1) "], outFormats: [[], [], [], []], unhandled: 0},
         ]
@@ -96,4 +96,77 @@ TestCase {
 
         compare(spyUnhandledFormat.count, data.unhandled);
     }
+
+    function test_backspace(): void {
+        keyClick("*");
+        compare(chatMarkdownHelper.checkText("*"), true);
+        compare(chatMarkdownHelper.checkFormats([]), true);
+        keyClick("*");
+        compare(chatMarkdownHelper.checkText("**"), true);
+        compare(chatMarkdownHelper.checkFormats([]), true);
+        keyClick("b");
+        compare(chatMarkdownHelper.checkText("b"), true);
+        compare(chatMarkdownHelper.checkFormats([RichFormat.Bold]), true);
+        keyClick("o");
+        compare(chatMarkdownHelper.checkText("bo"), true);
+        compare(chatMarkdownHelper.checkFormats([RichFormat.Bold]), true);
+        keyClick("l");
+        compare(chatMarkdownHelper.checkText("bol"), true);
+        compare(chatMarkdownHelper.checkFormats([RichFormat.Bold]), true);
+        keyClick("d");
+        compare(chatMarkdownHelper.checkText("bold"), true);
+        compare(chatMarkdownHelper.checkFormats([RichFormat.Bold]), true);
+        keyClick(Qt.Key_Backspace);
+        compare(chatMarkdownHelper.checkText("bol"), true);
+        compare(chatMarkdownHelper.checkFormats([RichFormat.Bold]), true);
+        keyClick(Qt.Key_Backspace);
+        compare(chatMarkdownHelper.checkText("bo"), true);
+        compare(chatMarkdownHelper.checkFormats([RichFormat.Bold]), true);
+        keyClick("*");
+        compare(chatMarkdownHelper.checkText("bo*"), true);
+        compare(chatMarkdownHelper.checkFormats([RichFormat.Bold]), true);
+        keyClick("*");
+        compare(chatMarkdownHelper.checkText("bo**"), true);
+        compare(chatMarkdownHelper.checkFormats([RichFormat.Bold]), true);
+        keyClick(" ");
+        compare(chatMarkdownHelper.checkText("bo "), true);
+        compare(chatMarkdownHelper.checkFormats([]), true);
+    }
+
+    function test_cursorMove(): void {
+        keyClick("t");
+        keyClick("e");
+        keyClick("s");
+        keyClick("t");
+        compare(chatMarkdownHelper.checkText("test"), true);
+        compare(chatMarkdownHelper.checkFormats([]), true);
+        keyClick("*");
+        keyClick("*");
+        keyClick("b");
+        compare(chatMarkdownHelper.checkText("testb"), true);
+        compare(chatMarkdownHelper.checkFormats([RichFormat.Bold]), true);
+        textEdit.cursorPosition = 2;
+        keyClick("*");
+        keyClick("*");
+        keyClick("b");
+        compare(chatMarkdownHelper.checkText("tebstb"), true);
+        compare(chatMarkdownHelper.checkFormats([]), true);
+    }
+
+    function test_insertText(): void {
+        textEdit.insert(0, "test");
+        compare(chatMarkdownHelper.checkText("test"), true);
+        compare(chatMarkdownHelper.checkFormats([]), true);
+        textEdit.insert(4, "**b");
+        compare(chatMarkdownHelper.checkText("testb"), true);
+        compare(chatMarkdownHelper.checkFormats([RichFormat.Bold]), true);
+
+        textEdit.clear();
+        textEdit.insert(0, "test");
+        compare(chatMarkdownHelper.checkText("test"), true);
+        compare(chatMarkdownHelper.checkFormats([]), true);
+        textEdit.insert(2, "**b");
+        compare(chatMarkdownHelper.checkText("tebst"), true);
+        compare(chatMarkdownHelper.checkFormats([RichFormat.Bold]), true);
+    }
 }
diff --git a/autotests/chatmarkdownhelpertestwrapper.h b/autotests/chatmarkdownhelpertestwrapper.h
index e5b054b3d..c117f8a19 100644
--- a/autotests/chatmarkdownhelpertestwrapper.h
+++ b/autotests/chatmarkdownhelpertestwrapper.h
@@ -49,6 +49,7 @@ public:
         if (!doc) {
             return false;
         }
+        // qWarning() << doc->toPlainText() <<text;
         return text == doc->toPlainText();
     }
 
@@ -58,6 +59,7 @@ public:
         if (cursor.isNull()) {
             return false;
         }
+        // qWarning() << RichFormat::formatsAtCursor(cursor) <<formats;
         return RichFormat::formatsAtCursor(cursor) == formats;
     }
 
diff --git a/src/chatbar/ChatBar.qml b/src/chatbar/ChatBar.qml
index 59a101056..f62fe3f85 100644
--- a/src/chatbar/ChatBar.qml
+++ b/src/chatbar/ChatBar.qml
@@ -119,7 +119,7 @@ QQC2.Control {
 
     height: Math.max(Math.min(chatScrollView.contentHeight + bottomPadding + topPadding, Kirigami.Units.gridUnit * 10), Kirigami.Units.gridUnit * 5)
     leftPadding: rightPadding
-    rightPadding: (root.width - chatBarSizeHelper.availableWidth) / 2
+    rightPadding: (root.width - chatBarSizeHelper.availableWidth) / 2 + Kirigami.Units.largeSpacing
     topPadding: Kirigami.Units.smallSpacing
     bottomPadding: Kirigami.Units.smallSpacing
 
diff --git a/src/libneochat/chatmarkdownhelper.cpp b/src/libneochat/chatmarkdownhelper.cpp
index a880ebe4f..d7fd1b2a6 100644
--- a/src/libneochat/chatmarkdownhelper.cpp
+++ b/src/libneochat/chatmarkdownhelper.cpp
@@ -69,6 +69,20 @@ std::optional<bool> checkSequence(const QString &currentString, const QString &n
     return std::nullopt;
 }
 
+bool checkSequenceBackwards(const QString &currentString)
+{
+    auto it = syntax.cbegin();
+    while ((it = std::find_if(it,
+                              syntax.cend(),
+                              [currentString](const MarkdownSyntax &syntax) {
+                                  return syntax.sequence.endsWith(currentString);
+                              }))
+           != syntax.cend()) {
+        return true;
+    }
+    return false;
+}
+
 std::optional<MarkdownSyntax> syntaxForSequence(const QString &sequence)
 {
     const auto it = std::find_if(syntax.cbegin(), syntax.cend(), [sequence](const MarkdownSyntax &syntax) {
@@ -118,75 +132,93 @@ void ChatMarkdownHelper::setTextItem(ChatTextItemHelper *textItem)
 
 void ChatMarkdownHelper::updateStart()
 {
-    m_startPos = *m_textItem->cursorPosition();
-    m_endPos = m_startPos;
-    if (m_startPos == 0) {
-        m_currentState = Pre;
+    if (!m_textItem) {
+        return;
+    }
+    const auto newCursorPosition = m_textItem->cursorPosition();
+    if (newCursorPosition) {
+        updatePosition(*newCursorPosition);
     }
 }
 
 void ChatMarkdownHelper::checkMarkdown(int position, int charsRemoved, int charsAdded)
 {
+    updatePosition(position);
+
+    // This can happen when formatting is applied.
+    if (charsAdded == charsRemoved) {
+        return;
+    }
     auto cursor = m_textItem->textCursor();
     if (cursor.isNull()) {
         return;
     }
 
-    if (charsRemoved - charsAdded > 0) {
-        if (position < m_startPos) {
-            m_startPos = position;
-        }
-        m_endPos -= charsRemoved;
-        cursor.setPosition(m_endPos);
-        cursor.setPosition(m_endPos + (cursor.atBlockEnd() ? 0 : 1), QTextCursor::KeepAnchor);
-        const auto nextChar = cursor.selectedText();
-        m_currentState = m_startPos == 0 || nextChar == u' ' ? Pre : None;
+    if (charsRemoved > charsAdded) {
+        updatePosition(std::max(0, position - charsRemoved + charsAdded));
+    }
+
+    checkMarkdownForward(charsAdded - charsRemoved);
+}
+
+void ChatMarkdownHelper::updatePosition(int position)
+{
+    if (position == m_endPos) {
         return;
     }
 
-    for (auto i = 1; i <= charsAdded - charsRemoved; ++i) {
+    m_startPos = position;
+    m_endPos = position;
+
+    if (m_startPos <= 0) {
+        return;
+    }
+
+    auto cursor = m_textItem->textCursor();
+    if (cursor.isNull()) {
+        return;
+    }
+    cursor.setPosition(m_startPos);
+    cursor.movePosition(QTextCursor::PreviousCharacter, QTextCursor::KeepAnchor);
+    while (checkSequenceBackwards(cursor.selectedText()) && m_startPos > 0) {
+        --m_startPos;
+        cursor.movePosition(QTextCursor::PreviousCharacter, QTextCursor::KeepAnchor);
+    }
+}
+
+void ChatMarkdownHelper::checkMarkdownForward(int charsAdded)
+{
+    if (charsAdded <= 0) {
+        return;
+    }
+    auto cursor = m_textItem->textCursor();
+    if (cursor.isNull()) {
+        return;
+    }
+
+    for (auto i = 1; i <= charsAdded; ++i) {
         cursor.setPosition(m_startPos);
+        const auto atBlockStart = cursor.atBlockStart();
         cursor.setPosition(m_endPos, QTextCursor::KeepAnchor);
         const auto currentMarkdown = cursor.selectedText();
         cursor.setPosition(m_endPos);
         cursor.setPosition(m_endPos + 1, QTextCursor::KeepAnchor);
         const auto nextChar = cursor.selectedText();
-        cursor.setPosition(m_startPos);
 
-        const auto result = checkSequence(currentMarkdown, nextChar, cursor.atBlockStart());
-
-        switch (m_currentState) {
-        case None:
-            if (nextChar == u' ' || cursor.atBlockEnd()) {
-                m_currentState = Pre;
-            }
+        const auto result = checkSequence(currentMarkdown, nextChar, atBlockStart);
+        if (!result) {
             ++m_startPos;
             m_endPos = m_startPos;
-            break;
-        case Pre:
-            if (!result && RichFormat::formatsAtCursor(cursor).length() == 0) {
-                m_currentState = None;
-            } else if (result && !*result) {
-                m_currentState = Started;
-                ++m_endPos;
-                break;
-            }
-            ++m_startPos;
-            m_endPos = m_startPos;
-            break;
-        case Started:
-            if (!result) {
-                m_currentState = Pre;
-                ++m_startPos;
-                m_endPos = m_startPos;
-                break;
-            } else if (!*result) {
-                ++m_endPos;
-                break;
-            }
-            complete();
-            break;
+            continue;
+            ;
         }
+        if (!*result) {
+            ++m_endPos;
+            continue;
+            ;
+        }
+
+        complete();
     }
 }
 
@@ -200,29 +232,24 @@ void ChatMarkdownHelper::complete()
     cursor.setPosition(m_startPos);
     cursor.setPosition(m_endPos, QTextCursor::KeepAnchor);
     const auto syntax = syntaxForSequence(cursor.selectedText());
+    if (!syntax) {
+        return;
+    }
     cursor.removeSelectedText();
 
-    if (m_currentFormats.contains(syntax->format)) {
-        m_currentFormats.remove(syntax->format);
-    } else if (syntax->closable) {
-        m_currentFormats.insert(syntax->format, m_startPos);
-    }
-
     cursor.setPosition(m_startPos);
-    cursor.setPosition(m_startPos + 1, QTextCursor::KeepAnchor);
+    cursor.movePosition(QTextCursor::NextCharacter, QTextCursor::KeepAnchor);
     const auto nextChar = cursor.selectedText();
     const auto result = checkSequence({}, nextChar, cursor.atBlockStart());
-    m_currentState = result ? Started : Pre;
 
-    // cursor.setPosition(m_startPos + 1);
-    cursor.movePosition(QTextCursor::NextCharacter, QTextCursor::KeepAnchor);
-    if (syntax) {
-        const auto formatType = RichFormat::typeForFormat(syntax->format);
-        if (formatType == RichFormat::Block) {
-            Q_EMIT unhandledBlockFormat(syntax->format);
-        } else {
-            m_textItem->mergeFormatOnCursor(syntax->format, cursor);
-        }
+    cursor.setPosition(m_startPos);
+    cursor.movePosition(QTextCursor::NextWord, QTextCursor::KeepAnchor);
+
+    const auto formatType = RichFormat::typeForFormat(syntax->format);
+    if (formatType == RichFormat::Block) {
+        Q_EMIT unhandledBlockFormat(syntax->format);
+    } else {
+        m_textItem->mergeFormatOnCursor(syntax->format, cursor);
     }
 
     m_startPos = result ? m_startPos : m_startPos + 1;
@@ -231,14 +258,4 @@ void ChatMarkdownHelper::complete()
     cursor.endEditBlock();
 }
 
-void ChatMarkdownHelper::handleExternalFormatChange()
-{
-    auto cursor = m_textItem->textCursor();
-    if (cursor.isNull()) {
-        return;
-    }
-    cursor.setPosition(m_startPos);
-    m_currentState = RichFormat::formatsAtCursor(cursor).length() > 0 ? Pre : None;
-}
-
 #include "moc_chatmarkdownhelper.cpp"
diff --git a/src/libneochat/chatmarkdownhelper.h b/src/libneochat/chatmarkdownhelper.h
index 1cf785df7..3b33c541a 100644
--- a/src/libneochat/chatmarkdownhelper.h
+++ b/src/libneochat/chatmarkdownhelper.h
@@ -22,8 +22,6 @@ public:
     ChatTextItemHelper *textItem() const;
     void setTextItem(ChatTextItemHelper *textItem);
 
-    void handleExternalFormatChange();
-
 Q_SIGNALS:
     void textItemChanged();
 
@@ -36,21 +34,14 @@ Q_SIGNALS:
     void unhandledBlockFormat(RichFormat::Format format);
 
 private:
-    enum State {
-        None,
-        Pre,
-        Started,
-    };
-
     QPointer<ChatTextItemHelper> m_textItem;
 
-    State m_currentState = None;
     int m_startPos = 0;
     int m_endPos = 0;
     void updateStart();
 
-    QHash<RichFormat::Format, int> m_currentFormats;
-
     void checkMarkdown(int position, int charsRemoved, int charsAdded);
+    void updatePosition(int position);
+    void checkMarkdownForward(int charsAdded);
     void complete();
 };
diff --git a/src/libneochat/enums/richformat.cpp b/src/libneochat/enums/richformat.cpp
index a4d44d101..efdb4f13d 100644
--- a/src/libneochat/enums/richformat.cpp
+++ b/src/libneochat/enums/richformat.cpp
@@ -160,6 +160,14 @@ bool RichFormat::hasFormat(QTextCursor cursor, Format format)
     }
 }
 
+bool RichFormat::hasAnyFormat(QTextCursor cursor, QList<Format> formats)
+{
+    for (const auto &format : formats) {
+        return hasFormat(cursor, format);
+    }
+    return false;
+}
+
 QList<RichFormat::Format> RichFormat::formatsAtCursor(const QTextCursor &cursor)
 {
     QList<Format> formats;
diff --git a/src/libneochat/enums/richformat.h b/src/libneochat/enums/richformat.h
index 5e4c36354..894a51fdd 100644
--- a/src/libneochat/enums/richformat.h
+++ b/src/libneochat/enums/richformat.h
@@ -107,6 +107,13 @@ public:
      */
     static bool hasFormat(QTextCursor cursor, Format format);
 
+    /**
+     * @brief Whether the given QTextCursor has any of the given Formats.
+     *
+     * @sa Format, QTextCursor
+     */
+    static bool hasAnyFormat(QTextCursor cursor, QList<Format> formats);
+
     /**
      * @brief A lsit of Formats on the given QTextCursor.
      *