diff --git a/packages/tiptap-commands/src/commands/removeMark.js b/packages/tiptap-commands/src/commands/removeMark.js
index 158caf47a..4c967a698 100644
--- a/packages/tiptap-commands/src/commands/removeMark.js
+++ b/packages/tiptap-commands/src/commands/removeMark.js
@@ -2,8 +2,9 @@ import { getMarkRange } from 'tiptap-utils'
 
 export default function (type) {
   return (state, dispatch) => {
-    let { from, to } = state.selection
-    const { $from, empty } = state.selection
+    const { tr, selection } = state
+    let { from, to } = selection
+    const { $from, empty } = selection
 
     if (empty) {
       const range = getMarkRange($from, type)
@@ -12,6 +13,8 @@ export default function (type) {
       to = range.to
     }
 
-    return dispatch(state.tr.removeMark(from, to, type))
+    tr.removeMark(from, to, type)
+
+    return dispatch(tr)
   }
 }
diff --git a/packages/tiptap-commands/src/commands/updateMark.js b/packages/tiptap-commands/src/commands/updateMark.js
index 4c217cf1f..0082ae260 100644
--- a/packages/tiptap-commands/src/commands/updateMark.js
+++ b/packages/tiptap-commands/src/commands/updateMark.js
@@ -2,8 +2,9 @@ import { getMarkRange } from 'tiptap-utils'
 
 export default function (type, attrs) {
   return (state, dispatch) => {
-    let { from, to } = state.selection
-    const { $from, empty } = state.selection
+    const { tr, selection, doc } = state
+    let { from, to } = selection
+    const { $from, empty } = selection
 
     if (empty) {
       const range = getMarkRange($from, type)
@@ -12,6 +13,14 @@ export default function (type, attrs) {
       to = range.to
     }
 
-    return dispatch(state.tr.addMark(from, to, type.create(attrs)))
+    const hasMark = doc.rangeHasMark(from, to, type)
+
+    if (hasMark) {
+      tr.removeMark(from, to, type)
+    }
+
+    tr.addMark(from, to, type.create(attrs))
+
+    return dispatch(tr)
   }
 }