diff --git a/src/structs/ContentType.js b/src/structs/ContentType.js
index 96a731de..e9c11de1 100644
--- a/src/structs/ContentType.js
+++ b/src/structs/ContentType.js
@@ -108,7 +108,7 @@ export class ContentType {
     while (item !== null) {
       if (!item.deleted) {
         item.delete(transaction)
-      } else {
+      } else if (item.id.clock < (transaction.beforeState.get(item.id.client) || 0)) {
         // This will be gc'd later and we want to merge it if possible
         // We try to merge all deleted items after each transaction,
         // but we have no knowledge about that this needs to be merged
@@ -120,7 +120,7 @@ export class ContentType {
     this.type._map.forEach(item => {
       if (!item.deleted) {
         item.delete(transaction)
-      } else {
+      } else if (item.id.clock < (transaction.beforeState.get(item.id.client) || 0)) {
         // same as above
         transaction._mergeStructs.push(item)
       }
diff --git a/src/utils/Transaction.js b/src/utils/Transaction.js
index 35940595..5b93369f 100644
--- a/src/utils/Transaction.js
+++ b/src/utils/Transaction.js
@@ -166,18 +166,29 @@ export const addChangedTypeToTransaction = (transaction, type, parentSub) => {
 /**
  * @param {Array<AbstractStruct>} structs
  * @param {number} pos
+ * @return {number} # of merged structs
  */
-const tryToMergeWithLeft = (structs, pos) => {
-  const left = structs[pos - 1]
-  const right = structs[pos]
-  if (left.deleted === right.deleted && left.constructor === right.constructor) {
-    if (left.mergeWith(right)) {
-      structs.splice(pos, 1)
-      if (right instanceof Item && right.parentSub !== null && /** @type {AbstractType<any>} */ (right.parent)._map.get(right.parentSub) === right) {
-        /** @type {AbstractType<any>} */ (right.parent)._map.set(right.parentSub, /** @type {Item} */ (left))
+const tryToMergeWithLefts = (structs, pos) => {
+  let right = structs[pos]
+  let left = structs[pos - 1]
+  let i = pos
+  for (; i > 0; right = left, left = structs[--i - 1]) {
+    if (left.deleted === right.deleted && left.constructor === right.constructor) {
+      if (left.mergeWith(right)) {
+        if (right instanceof Item && right.parentSub !== null && /** @type {AbstractType<any>} */ (right.parent)._map.get(right.parentSub) === right) {
+          /** @type {AbstractType<any>} */ (right.parent)._map.set(right.parentSub, /** @type {Item} */ (left))
+        }
+        continue
       }
     }
+    break
   }
+  const merged = pos - i
+  if (merged) {
+    // remove all merged structs from the array
+    structs.splice(pos + 1 - merged, merged)
+  }
+  return merged
 }
 
 /**
@@ -224,9 +235,9 @@ const tryMergeDeleteSet = (ds, store) => {
       for (
         let si = mostRightIndexToCheck, struct = structs[si];
         si > 0 && struct.id.clock >= deleteItem.clock;
-        struct = structs[--si]
+        struct = structs[si]
       ) {
-        tryToMergeWithLeft(structs, si)
+        si -= 1 + tryToMergeWithLefts(structs, si)
       }
     }
   })
@@ -318,23 +329,25 @@ const cleanupTransactions = (transactionCleanups, i) => {
           const structs = /** @type {Array<GC|Item>} */ (store.clients.get(client))
           // we iterate from right to left so we can safely remove entries
           const firstChangePos = math.max(findIndexSS(structs, beforeClock), 1)
-          for (let i = structs.length - 1; i >= firstChangePos; i--) {
-            tryToMergeWithLeft(structs, i)
+          for (let i = structs.length - 1; i >= firstChangePos;) {
+            i -= 1 + tryToMergeWithLefts(structs, i)
           }
         }
       })
       // try to merge mergeStructs
       // @todo: it makes more sense to transform mergeStructs to a DS, sort it, and merge from right to left
       //        but at the moment DS does not handle duplicates
-      for (let i = 0; i < mergeStructs.length; i++) {
+      for (let i = mergeStructs.length - 1; i >= 0; i--) {
         const { client, clock } = mergeStructs[i].id
         const structs = /** @type {Array<GC|Item>} */ (store.clients.get(client))
         const replacedStructPos = findIndexSS(structs, clock)
         if (replacedStructPos + 1 < structs.length) {
-          tryToMergeWithLeft(structs, replacedStructPos + 1)
+          if (tryToMergeWithLefts(structs, replacedStructPos + 1) > 1) {
+            continue // no need to perform next check, both are already merged
+          }
         }
         if (replacedStructPos > 0) {
-          tryToMergeWithLeft(structs, replacedStructPos)
+          tryToMergeWithLefts(structs, replacedStructPos)
         }
       }
       if (!transaction.local && transaction.afterState.get(doc.clientID) !== transaction.beforeState.get(doc.clientID)) {