diff --git a/src/structs/Item.js b/src/structs/Item.js
index 656f5e5b..874d2fff 100644
--- a/src/structs/Item.js
+++ b/src/structs/Item.js
@@ -22,7 +22,8 @@ import {
   readContentFormat,
   readContentType,
   addChangedTypeToTransaction,
-  UpdateDecoderV1, UpdateDecoderV2, UpdateEncoderV1, UpdateEncoderV2, ContentType, ContentDeleted, StructStore, ID, AbstractType, Transaction // eslint-disable-line
+  isDeleted,
+  DeleteSet, UpdateDecoderV1, UpdateDecoderV2, UpdateEncoderV1, UpdateEncoderV2, ContentType, ContentDeleted, StructStore, ID, AbstractType, Transaction // eslint-disable-line
 } from '../internals.js'
 
 import * as error from 'lib0/error'
@@ -125,7 +126,7 @@ export const splitItem = (transaction, leftItem, diff) => {
  * @param {Transaction} transaction The Yjs instance.
  * @param {Item} item
  * @param {Set<Item>} redoitems
- * @param {Array<Item>} itemsToDelete
+ * @param {DeleteSet} itemsToDelete
  *
  * @return {Item|null}
  *
@@ -143,42 +144,27 @@ export const redoItem = (transaction, item, redoitems, itemsToDelete) => {
   /**
    * @type {Item|null}
    */
-  let left
+  let left = null
   /**
    * @type {Item|null}
    */
   let right
+  // make sure that parent is redone
+  if (parentItem !== null && parentItem.deleted === true) {
+    // try to undo parent if it will be undone anyway
+    if (parentItem.redone === null && (!redoitems.has(parentItem) || redoItem(transaction, parentItem, redoitems, itemsToDelete) === null)) {
+      return null
+    }
+    while (parentItem.redone !== null) {
+      parentItem = getItemCleanStart(transaction, parentItem.redone)
+    }
+  }
+  const parentType = parentItem === null ? /** @type {AbstractType<any>} */ (item.parent) : /** @type {ContentType} */ (parentItem.content).type
+
   if (item.parentSub === null) {
     // Is an array item. Insert at the old position
     left = item.left
     right = item
-  } else {
-    // Is a map item. Insert as current value
-    left = item
-    while (left.right !== null) {
-      left = left.right
-      if (left.id.client !== ownClientID) {
-        // It is not possible to redo this item because it conflicts with a
-        // change from another client
-        return null
-      }
-    }
-    if (left.right !== null) {
-      left = /** @type {Item} */ (/** @type {AbstractType<any>} */ (item.parent)._map.get(item.parentSub))
-    }
-    right = null
-  }
-  // make sure that parent is redone
-  if (parentItem !== null && parentItem.deleted === true && parentItem.redone === null) {
-    // try to undo parent if it will be undone anyway
-    if (!redoitems.has(parentItem) || redoItem(transaction, parentItem, redoitems, itemsToDelete) === null) {
-      return null
-    }
-  }
-  if (parentItem !== null && parentItem.redone !== null) {
-    while (parentItem.redone !== null) {
-      parentItem = getItemCleanStart(transaction, parentItem.redone)
-    }
     // find next cloned_redo items
     while (left !== null) {
       /**
@@ -210,10 +196,32 @@ export const redoItem = (transaction, item, redoitems, itemsToDelete) => {
       }
       right = right.right
     }
-    // Iterate right while right is in itemsToDelete
-    // If it is intended to delete right while item is redone, we can expect that item should replace right.
-    while (left !== null && left.right !== null && left.right !== right && itemsToDelete.findIndex(d => d === /** @type {Item} */ (left).right) >= 0) {
-      left = left.right
+  } else {
+    right = null
+    if (item.right) {
+      left = item
+      // Iterate right while right is in itemsToDelete
+      // If it is intended to delete right while item is redone, we can expect that item should replace right.
+      while (left !== null && left.right !== null && isDeleted(itemsToDelete, left.right.id)) {
+        left = left.right
+      }
+      // follow redone
+      // trace redone until parent matches
+      while (left !== null && left.redone !== null) {
+        left = getItemCleanStart(transaction, left.redone)
+      }
+      // check wether we were allowed to follow right (indicating that originally this op was replaced by another item)
+      if (left === null || /** @type {AbstractType<any>} */ (left.parent)._item !== parentItem) {
+        // invalid parent; should never happen
+        return null
+      }
+      if (left && left.right !== null) {
+        // It is not possible to redo this item because it conflicts with a
+        // change from another client
+        return null
+      }
+    } else {
+      left = parentType._map.get(item.parentSub) || null
     }
   }
   const nextClock = getState(store, ownClientID)
@@ -222,7 +230,7 @@ export const redoItem = (transaction, item, redoitems, itemsToDelete) => {
     nextId,
     left, left && left.lastId,
     right, right && right.id,
-    parentItem === null ? item.parent : /** @type {ContentType} */ (parentItem.content).type,
+    parentType,
     item.parentSub,
     item.content.copy()
   )
diff --git a/src/utils/UndoManager.js b/src/utils/UndoManager.js
index 391f82ac..a7c45e9d 100644
--- a/src/utils/UndoManager.js
+++ b/src/utils/UndoManager.js
@@ -88,7 +88,7 @@ const popStackItem = (undoManager, stack, eventType) => {
         }
       })
       itemsToRedo.forEach(struct => {
-        performedChange = redoItem(transaction, struct, itemsToRedo, itemsToDelete) !== null || performedChange
+        performedChange = redoItem(transaction, struct, itemsToRedo, stackItem.insertions) !== null || performedChange
       })
       // We want to delete in reverse order so that children are deleted before
       // parents, so we have more information available when items are filtered.
diff --git a/tests/undo-redo.tests.js b/tests/undo-redo.tests.js
index b99df6c3..40e6a718 100644
--- a/tests/undo-redo.tests.js
+++ b/tests/undo-redo.tests.js
@@ -372,3 +372,158 @@ export const testUndoNestedUndoIssue = tc => {
   undoManager.redo()
   t.compare(design.toJSON(), { text: { blocks: { text: 'Something Else' } } })
 }
+
+/**
+ * This issue has been reported in https://github.com/yjs/yjs/issues/355
+ *
+ * @param {t.TestCase} tc
+ */
+export const testConsecutiveRedoBug = tc => {
+  const doc = new Y.Doc()
+  const yRoot = doc.getMap()
+  const undoMgr = new Y.UndoManager(yRoot)
+
+  let yPoint = new Y.Map()
+  yPoint.set('x', 0)
+  yPoint.set('y', 0)
+  yRoot.set('a', yPoint)
+  undoMgr.stopCapturing()
+
+  yPoint.set('x', 100)
+  yPoint.set('y', 100)
+  undoMgr.stopCapturing()
+
+  yPoint.set('x', 200)
+  yPoint.set('y', 200)
+  undoMgr.stopCapturing()
+
+  yPoint.set('x', 300)
+  yPoint.set('y', 300)
+  undoMgr.stopCapturing()
+
+  t.compare(yPoint.toJSON(), { x: 300, y: 300 })
+
+  undoMgr.undo() // x=200, y=200
+  t.compare(yPoint.toJSON(), { x: 200, y: 200 })
+  undoMgr.undo() // x=100, y=100
+  t.compare(yPoint.toJSON(), { x: 100, y: 100 })
+  undoMgr.undo() // x=0, y=0
+  t.compare(yPoint.toJSON(), { x: 0, y: 0 })
+  undoMgr.undo() // nil
+  t.compare(yRoot.get('a'), undefined)
+
+  undoMgr.redo() // x=0, y=0
+  yPoint = yRoot.get('a')
+
+  t.compare(yPoint.toJSON(), { x: 0, y: 0 })
+  undoMgr.redo() // x=100, y=100
+  t.compare(yPoint.toJSON(), { x: 100, y: 100 })
+  undoMgr.redo() // x=200, y=200
+  t.compare(yPoint.toJSON(), { x: 200, y: 200 })
+  undoMgr.redo() // expected x=300, y=300, actually nil
+  t.compare(yPoint.toJSON(), { x: 300, y: 300 })
+}
+
+/**
+ * This issue has been reported in https://github.com/yjs/yjs/issues/304
+ *
+ * @param {t.TestCase} tc
+ */
+export const testUndoXmlBug = tc => {
+  const origin = 'origin'
+  const doc = new Y.Doc()
+  const fragment = doc.getXmlFragment('t')
+  const undoManager = new Y.UndoManager(fragment, {
+    captureTimeout: 0,
+    trackedOrigins: new Set([origin])
+  })
+
+  // create element
+  doc.transact(() => {
+    const e = new Y.XmlElement('test-node')
+    e.setAttribute('a', '100')
+    e.setAttribute('b', '0')
+    fragment.insert(fragment.length, [e])
+  }, origin)
+
+  // change one attribute
+  doc.transact(() => {
+    const e = fragment.get(0)
+    e.setAttribute('a', '200')
+  }, origin)
+
+  // change both attributes
+  doc.transact(() => {
+    const e = fragment.get(0)
+    e.setAttribute('a', '180')
+    e.setAttribute('b', '50')
+  }, origin)
+
+  undoManager.undo()
+  undoManager.undo()
+  undoManager.undo()
+
+  undoManager.redo()
+  undoManager.redo()
+  undoManager.redo()
+  t.compare(fragment.toString(), '<test-node a="180" b="50"></test-node>')
+}
+
+/**
+ * This issue has been reported in https://github.com/yjs/yjs/issues/343
+ *
+ * @param {t.TestCase} tc
+ */
+export const testUndoBlockBug = tc => {
+  const doc = new Y.Doc({ gc: false })
+  const design = doc.getMap()
+
+  const undoManager = new Y.UndoManager(design, { captureTimeout: 0 })
+
+  const text = new Y.Map()
+
+  const blocks1 = new Y.Array()
+  const blocks1block = new Y.Map()
+  doc.transact(() => {
+    blocks1block.set('text', '1')
+    blocks1.push([blocks1block])
+
+    text.set('blocks', blocks1block)
+    design.set('text', text)
+  })
+
+  const blocks2 = new Y.Array()
+  const blocks2block = new Y.Map()
+  doc.transact(() => {
+    blocks2block.set('text', '2')
+    blocks2.push([blocks2block])
+    text.set('blocks', blocks2block)
+  })
+
+  const blocks3 = new Y.Array()
+  const blocks3block = new Y.Map()
+  doc.transact(() => {
+    blocks3block.set('text', '3')
+    blocks3.push([blocks3block])
+    text.set('blocks', blocks3block)
+  })
+
+  const blocks4 = new Y.Array()
+  const blocks4block = new Y.Map()
+  doc.transact(() => {
+    blocks4block.set('text', '4')
+    blocks4.push([blocks4block])
+    text.set('blocks', blocks4block)
+  })
+
+  // {"text":{"blocks":{"text":"4"}}}
+  undoManager.undo() // {"text":{"blocks":{"3"}}}
+  undoManager.undo() // {"text":{"blocks":{"text":"2"}}}
+  undoManager.undo() // {"text":{"blocks":{"text":"1"}}}
+  undoManager.undo() // {}
+  undoManager.redo() // {"text":{"blocks":{"text":"1"}}}
+  undoManager.redo() // {"text":{"blocks":{"text":"2"}}}
+  undoManager.redo() // {"text":{"blocks":{"text":"3"}}}
+  undoManager.redo() // {"text":{}}
+  t.compare(design.toJSON(), { text: { blocks: { text: '4' } } })
+}