diff --git a/Userland/Applications/HexEditor/HexEditor.cpp b/Userland/Applications/HexEditor/HexEditor.cpp
index 9281bbe830f..fe82bec33af 100644
--- a/Userland/Applications/HexEditor/HexEditor.cpp
+++ b/Userland/Applications/HexEditor/HexEditor.cpp
@@ -377,8 +377,17 @@ void HexEditor::keydown_event(GUI::KeyEvent& event)
 {
     dbgln_if(HEX_DEBUG, "HexEditor::keydown_event key={}", static_cast<u8>(event.key()));
 
-    auto update_cursor_on_change = [&]() {
-        m_selection_start = m_selection_end = m_position;
+    auto move_and_update_cursor_by = [&](i64 cursor_location_change) {
+        size_t new_position = m_position + cursor_location_change;
+        if (event.modifiers() & Mod_Shift) {
+            size_t selection_pivot = m_position == m_selection_end ? m_selection_start : m_selection_end;
+            m_position = new_position;
+            m_selection_start = selection_pivot;
+            m_selection_end = m_position;
+            if (m_selection_start > m_selection_end)
+                swap(m_selection_start, m_selection_end);
+        } else
+            m_selection_start = m_selection_end = m_position = new_position;
         m_cursor_at_low_nibble = false;
         reset_cursor_blink_state();
         scroll_position_into_view(m_position);
@@ -386,64 +395,47 @@ void HexEditor::keydown_event(GUI::KeyEvent& event)
         update_status();
     };
 
-    auto advance_cursor_backwards = [this, update_cursor_on_change](size_t cursor_location_change) -> void {
-        m_position -= cursor_location_change;
-        update_cursor_on_change();
-    };
-
-    auto advance_cursor_forward = [this, update_cursor_on_change](size_t cursor_location_change) -> void {
-        m_position += cursor_location_change;
-        update_cursor_on_change();
-    };
-
     if (event.key() == KeyCode::Key_Up) {
-        if (m_position >= bytes_per_row()) {
-            advance_cursor_backwards(bytes_per_row());
-        }
+        if (m_position >= bytes_per_row())
+            move_and_update_cursor_by(-bytes_per_row());
         return;
     }
 
     if (event.key() == KeyCode::Key_Down) {
-        if (m_position + bytes_per_row() < m_document->size()) {
-            advance_cursor_forward(bytes_per_row());
-        }
+        if (m_position + bytes_per_row() < m_document->size())
+            move_and_update_cursor_by(bytes_per_row());
         return;
     }
 
     if (event.key() == KeyCode::Key_Left) {
-        if (m_position >= 1) {
-            advance_cursor_backwards(1);
-        }
+        if (m_position >= 1)
+            move_and_update_cursor_by(-1);
         return;
     }
 
     if (event.key() == KeyCode::Key_Right) {
-        if (m_position + 1 < m_document->size()) {
-            advance_cursor_forward(1);
-        }
+        if (m_position + 1 < m_document->size())
+            move_and_update_cursor_by(1);
         return;
     }
 
     if (event.key() == KeyCode::Key_Backspace) {
-        if (m_position > 0) {
-            advance_cursor_backwards(1);
-        }
+        if (m_position > 0)
+            move_and_update_cursor_by(-1);
         return;
     }
 
     if (event.key() == KeyCode::Key_PageUp) {
         auto cursor_location_change = min(bytes_per_row() * visible_content_rect().height(), m_position);
-        if (cursor_location_change > 0) {
-            advance_cursor_backwards(cursor_location_change);
-        }
+        if (cursor_location_change > 0)
+            move_and_update_cursor_by(-cursor_location_change);
         return;
     }
 
     if (event.key() == KeyCode::Key_PageDown) {
         auto cursor_location_change = min(bytes_per_row() * visible_content_rect().height(), m_document->size() - m_position);
-        if (cursor_location_change > 0) {
-            advance_cursor_forward(cursor_location_change);
-        }
+        if (cursor_location_change > 0)
+            move_and_update_cursor_by(cursor_location_change);
         return;
     }