diff --git a/lib/abstractimageoperation.cpp b/lib/abstractimageoperation.cpp
--- a/lib/abstractimageoperation.cpp
+++ b/lib/abstractimageoperation.cpp
@@ -52,14 +52,20 @@
         mOp->undo();
     }
 
+    void redo() override
+    {
+        mOp->redo();
+    }
+
 private:
     AbstractImageOperation* mOp;
 };
 
 struct AbstractImageOperationPrivate
 {
     QString mText;
     QUrl mUrl;
+    ImageOperationCommand* mCommand;
 };
 
 AbstractImageOperation::AbstractImageOperation()
@@ -75,7 +81,11 @@
 void AbstractImageOperation::applyToDocument(Document::Ptr doc)
 {
     d->mUrl = doc->url();
-    redo();
+
+    d->mCommand = new ImageOperationCommand(this);
+    d->mCommand->setText(d->mText);
+    // QUndoStack::push() executes command by calling its redo() function
+    doc->undoStack()->push(d->mCommand);
 }
 
 Document::Ptr AbstractImageOperation::document() const
@@ -88,12 +98,15 @@
 void AbstractImageOperation::finish(bool ok)
 {
     if (ok) {
-        ImageOperationCommand* command = new ImageOperationCommand(this);
-        command->setText(d->mText);
-        document()->undoStack()->push(command);
-        document()->imageOperationCompleted();
+        // Give QUndoStack time to update in case the redo/undo is executed immediately
+        // (e.g. undo crop just sets the previous image)
+        QTimer::singleShot(0, document().data(), &Document::imageOperationCompleted);
     } else {
-        deleteLater();
+#if QT_VERSION >= QT_VERSION_CHECK(5, 9, 0)
+        // Remove command from undo stack without executing undo()
+        d->mCommand->setObsolete(true);
+#endif
+        document()->undoStack()->undo();
     }
 }
 
diff --git a/tests/auto/documenttest.h b/tests/auto/documenttest.h
--- a/tests/auto/documenttest.h
+++ b/tests/auto/documenttest.h
@@ -129,6 +129,7 @@
     void testJobQueue();
     void testCheckDocumentEditor();
     void testUndoStackPush();
+    void testUndoRedo();
 
     void initTestCase();
     void init();
diff --git a/tests/auto/documenttest.cpp b/tests/auto/documenttest.cpp
--- a/tests/auto/documenttest.cpp
+++ b/tests/auto/documenttest.cpp
@@ -534,6 +534,7 @@
     QVERIFY(doc->editor());
     TestOperation* op = new TestOperation;
     op->applyToDocument(doc);
+    QTest::qWait(100);
     QVERIFY(doc->isModified());
     QCOMPARE(modifiedDocumentListChangedSpy.count(), 1);
     modifiedDocumentListChangedSpy.clear();
@@ -841,3 +842,66 @@
     QTest::qWait(100);
     QVERIFY(doc->undoStack()->isClean());
 }
+
+void DocumentTest::testUndoRedo()
+{
+    class SuccessOperation : public AbstractImageOperation
+    {
+    public:
+        int mRedoCount = 0;
+        int mUndoCount = 0;
+
+    protected:
+        virtual void redo()
+        {
+            mRedoCount++;
+            finish(true);
+        }
+
+        virtual void undo()
+        {
+            mUndoCount++;
+            finish(true);
+        }
+    };
+
+    Document::Ptr doc = DocumentFactory::instance()->load(urlForTestFile("orient6.jpg"));
+    QSignalSpy modifiedSpy(doc.data(), &Document::modified);
+    QSignalSpy savedSpy(doc.data(), &Document::saved);
+
+    SuccessOperation* op = new SuccessOperation;
+    QCOMPARE(op->mRedoCount, 0);
+    QCOMPARE(op->mUndoCount, 0);
+
+    // Apply (redo) operation
+    op->applyToDocument(doc);
+    QVERIFY(modifiedSpy.wait());
+    QCOMPARE(op->mRedoCount, 1);
+    QCOMPARE(op->mUndoCount, 0);
+    QCOMPARE(doc->undoStack()->count(), 1);
+    QVERIFY(!doc->undoStack()->isClean());
+
+    // Undo operation
+    doc->undoStack()->undo();
+    QVERIFY(savedSpy.wait());
+    QCOMPARE(op->mRedoCount, 1);
+    QCOMPARE(op->mUndoCount, 1);
+    QCOMPARE(doc->undoStack()->count(), 1);
+    QVERIFY(doc->undoStack()->isClean());
+
+    // Redo operation
+    doc->undoStack()->redo();
+    QVERIFY(modifiedSpy.wait());
+    QCOMPARE(op->mRedoCount, 2);
+    QCOMPARE(op->mUndoCount, 1);
+    QCOMPARE(doc->undoStack()->count(), 1);
+    QVERIFY(!doc->undoStack()->isClean());
+
+    // Undo operation again
+    doc->undoStack()->undo();
+    QVERIFY(savedSpy.wait());
+    QCOMPARE(op->mRedoCount, 2);
+    QCOMPARE(op->mUndoCount, 2);
+    QCOMPARE(doc->undoStack()->count(), 1);
+    QVERIFY(doc->undoStack()->isClean());
+}