diff --git a/app/src/main/java/eu/faircode/email/FragmentCompose.java b/app/src/main/java/eu/faircode/email/FragmentCompose.java
index c7d92fe068..bdd1a66177 100644
--- a/app/src/main/java/eu/faircode/email/FragmentCompose.java
+++ b/app/src/main/java/eu/faircode/email/FragmentCompose.java
@@ -1029,12 +1029,35 @@ public class FragmentCompose extends FragmentBase {
                     return true;
                 } else {
                     PopupMenuLifecycle popupMenu = new PopupMenuLifecycle(getContext(), getViewLifecycleOwner(), block_bar.findViewById(action));
+
                     if (action == R.id.menu_alignment)
                         popupMenu.inflate(R.menu.popup_style_alignment);
                     else if (action == R.id.menu_list)
                         popupMenu.inflate(R.menu.popup_style_list);
                     else if (action == R.id.menu_indentation)
                         popupMenu.inflate(R.menu.popup_style_indentation);
+
+                    Menu menu = popupMenu.getMenu();
+                    Editable edit = etBody.getText();
+
+                    Pair<Integer, Integer> b = StyleHelper.getParagraph(etBody, true);
+                    BulletSpan[] bullets = (b == null ? null : edit.getSpans(b.first, b.second, BulletSpan.class));
+                    IndentSpan[] indents = (b == null ? null : edit.getSpans(b.first, b.second, IndentSpan.class));
+                    if (b == null ||
+                            (action == R.id.menu_list && indents.length > 0) ||
+                            (action == R.id.menu_indentation && bullets.length > 0)) {
+                        for (int i = 0; i < menu.size(); i++)
+                            menu.getItem(i).setEnabled(false);
+                    } else {
+                        if (action == R.id.menu_list) {
+                            Pair<Integer, Integer> p = StyleHelper.getParagraph(etBody, false);
+                            Integer maxLevel = (p == null ? null : StyleHelper.getMaxListLevel(edit, p.first, p.second));
+                            menu.findItem(R.id.menu_style_list_increase).setEnabled(maxLevel != null);
+                            menu.findItem(R.id.menu_style_list_decrease).setEnabled(maxLevel != null && maxLevel > 0);
+                        } else if (action == R.id.menu_indentation)
+                            popupMenu.getMenu().findItem(R.id.menu_style_indentation_decrease).setEnabled(indents.length > 0);
+                    }
+
                     popupMenu.insertIcons(getContext());
                     popupMenu.setOnMenuItemClickListener(new PopupMenu.OnMenuItemClickListener() {
                         @Override
diff --git a/app/src/main/java/eu/faircode/email/StyleHelper.java b/app/src/main/java/eu/faircode/email/StyleHelper.java
index 0893ac706c..f407e2baf1 100644
--- a/app/src/main/java/eu/faircode/email/StyleHelper.java
+++ b/app/src/main/java/eu/faircode/email/StyleHelper.java
@@ -201,18 +201,15 @@ public class StyleHelper {
                 smenu.add(R.id.group_style_font_standard, fonts.size(), 0, R.string.title_style_font_default)
                         .setIntent(new Intent());
 
-                int level = -1;
-                BulletSpan[] spans = edit.getSpans(start, end, BulletSpan.class);
-                for (BulletSpan span : spans)
-                    if (span instanceof NumberSpan)
-                        level = ((NumberSpan) span).getLevel();
-                    else if (span instanceof BulletSpanEx)
-                        level = ((BulletSpanEx) span).getLevel();
-
-                popupMenu.getMenu().findItem(R.id.menu_style_list_increase).setVisible(level >= 0);
-                popupMenu.getMenu().findItem(R.id.menu_style_list_decrease).setVisible(level > 0);
-
+                Integer maxLevel = getMaxListLevel(edit, start, end);
                 IndentSpan[] indents = edit.getSpans(start, end, IndentSpan.class);
+
+                popupMenu.getMenu().findItem(R.id.menu_style_list_bullets).setEnabled(indents.length == 0);
+                popupMenu.getMenu().findItem(R.id.menu_style_list_numbered).setEnabled(indents.length == 0);
+                popupMenu.getMenu().findItem(R.id.menu_style_list_increase).setEnabled(indents.length == 0 && maxLevel != null);
+                popupMenu.getMenu().findItem(R.id.menu_style_list_decrease).setEnabled(indents.length == 0 && maxLevel != null && maxLevel > 0);
+
+                popupMenu.getMenu().findItem(R.id.menu_style_indentation_increase).setEnabled(maxLevel == null);
                 popupMenu.getMenu().findItem(R.id.menu_style_indentation_decrease).setEnabled(indents.length > 0);
 
                 popupMenu.getMenu().findItem(R.id.menu_style_parenthesis).setEnabled(BuildConfig.DEBUG);
@@ -966,6 +963,21 @@ public class StyleHelper {
             throw new IllegalArgumentException(type.getName());
     }
 
+    static Integer getMaxListLevel(Editable edit, int start, int end) {
+        Integer maxLevel = null;
+        BulletSpan[] bullets = edit.getSpans(start, end, BulletSpan.class);
+        for (BulletSpan span : bullets) {
+            Integer level = null;
+            if (span instanceof NumberSpan)
+                level = ((NumberSpan) span).getLevel();
+            else if (span instanceof BulletSpanEx)
+                level = ((BulletSpanEx) span).getLevel();
+            if (level != null && (maxLevel == null || level > maxLevel))
+                maxLevel = level;
+        }
+        return maxLevel;
+    }
+
     static void renumber(Editable text, boolean clean, Context context) {
         int bulletGap = context.getResources().getDimensionPixelSize(R.dimen.bullet_gap_size);
         int bulletIndent = context.getResources().getDimensionPixelSize(R.dimen.bullet_indent_size);