diff --git a/novelwriter/gui/doceditor.py b/novelwriter/gui/doceditor.py
index 13525ded..0b0e7568 100644
--- a/novelwriter/gui/doceditor.py
+++ b/novelwriter/gui/doceditor.py
@@ -1470,7 +1470,7 @@ class GuiDocEditor(QPlainTextEdit):
     #  Internal Functions : Text Manipulation
     ##
 
-    def _toggleFormat(self, fLen: int, fChar: str) -> bool:
+    def _toggleFormat(self, fLen: int, fChar: str) -> None:
         """Toggle the formatting of a specific type for a piece of text.
         If more than one block is selected, the formatting is applied to
         the first block.
@@ -1488,12 +1488,12 @@ class GuiDocEditor(QPlainTextEdit):
 
         posS = cursor.selectionStart()
         posE = cursor.selectionEnd()
-        if self._qDocument.characterAt(posO - 1) == fChar:
+        if posS == posE and self._qDocument.characterAt(posO - 1) == fChar:
             logger.warning("Format repetition, cancelling action")
             cursor.clearSelection()
             cursor.setPosition(posO)
             self.setTextCursor(cursor)
-            return False
+            return
 
         blockS = self._qDocument.findBlock(posS)
         blockE = self._qDocument.findBlock(posE)
@@ -1519,7 +1519,6 @@ class GuiDocEditor(QPlainTextEdit):
                 break
 
         if fLen == min(numA, numB):
-            cursor.clearSelection()
             cursor.beginEditBlock()
             cursor.setPosition(posS)
             for i in range(fLen):
@@ -1528,17 +1527,19 @@ class GuiDocEditor(QPlainTextEdit):
             for i in range(fLen):
                 cursor.deletePreviousChar()
             cursor.endEditBlock()
-            cursor.clearSelection()
-            cursor.setPosition(posO - fLen)
-            self.setTextCursor(cursor)
+
+            if select != _SelectAction.KEEP_SELECTION:
+                cursor.clearSelection()
+                cursor.setPosition(posO - fLen)
+                self.setTextCursor(cursor)
 
         else:
             self._wrapSelection(fChar*fLen, pos=posO, select=select)
 
-        return True
+        return
 
     def _wrapSelection(self, before: str, after: str | None = None, pos: int | None = None,
-                       select: _SelectAction = _SelectAction.NO_DECISION) -> bool:
+                       select: _SelectAction = _SelectAction.NO_DECISION) -> None:
         """Wrap the selected text in whatever is in tBefore and tAfter.
         If there is no selection, the autoSelect setting decides the
         action. AutoSelect will select the word under the cursor before
@@ -1578,21 +1579,21 @@ class GuiDocEditor(QPlainTextEdit):
         if select == _SelectAction.MOVE_AFTER:
             cursor.setPosition(posE + len(before + after))
         elif select == _SelectAction.KEEP_SELECTION:
-            cursor.setPosition(posE + len(before), QtMoveAnchor)
-            cursor.setPosition(posS + len(before), QtKeepAnchor)
+            cursor.setPosition(posS + len(before), QtMoveAnchor)
+            cursor.setPosition(posE + len(before), QtKeepAnchor)
         elif select == _SelectAction.KEEP_POSITION:
             cursor.setPosition(posO + len(before))
 
         self.setTextCursor(cursor)
 
-        return True
+        return
 
-    def _replaceQuotes(self, sQuote: str, oQuote: str, cQuote: str) -> bool:
+    def _replaceQuotes(self, sQuote: str, oQuote: str, cQuote: str) -> None:
         """Replace all straight quotes in the selected text."""
         cursor = self.textCursor()
         if not cursor.hasSelection():
             SHARED.error(self.tr("Please select some text before calling replace quotes."))
-            return False
+            return
 
         posS = cursor.selectionStart()
         posE = cursor.selectionEnd()
@@ -1632,7 +1633,7 @@ class GuiDocEditor(QPlainTextEdit):
 
         self._allowAutoReplace(True)
 
-        return True
+        return
 
     def _processBlockFormat(
         self, action: nwDocAction, text: str, toggle: bool = True