diff --git a/oak-upgrade/src/main/java/org/apache/jackrabbit/oak/upgrade/cli/node/SegmentFactory.java b/oak-upgrade/src/main/java/org/apache/jackrabbit/oak/upgrade/cli/node/SegmentFactory.java
index 94aeb49..78bb638 100644
--- a/oak-upgrade/src/main/java/org/apache/jackrabbit/oak/upgrade/cli/node/SegmentFactory.java
+++ b/oak-upgrade/src/main/java/org/apache/jackrabbit/oak/upgrade/cli/node/SegmentFactory.java
@@ -43,11 +43,18 @@ public class SegmentFactory implements NodeStoreFactory {
     public SegmentFactory(String directory, boolean mmap) {
         this.dir = new File(directory);
         this.mmap = mmap;
+        createDirectoryIfMissing(dir);
         if (!dir.isDirectory()) {
             throw new IllegalArgumentException("Not a directory: " + dir.getPath());
         }
     }
 
+    private void createDirectoryIfMissing(File directory) {
+        if (!directory.exists()) {
+            directory.mkdirs();
+        }
+    }
+
     @Override
     public NodeStore create(BlobStore blobStore, Closer closer) throws IOException {
         Builder builder = FileStore.builder(new File(dir, "segmentstore"));
diff --git a/oak-upgrade/src/main/java/org/apache/jackrabbit/oak/upgrade/cli/node/SegmentTarFactory.java b/oak-upgrade/src/main/java/org/apache/jackrabbit/oak/upgrade/cli/node/SegmentTarFactory.java
index c96f37b..c75da87 100644
--- a/oak-upgrade/src/main/java/org/apache/jackrabbit/oak/upgrade/cli/node/SegmentTarFactory.java
+++ b/oak-upgrade/src/main/java/org/apache/jackrabbit/oak/upgrade/cli/node/SegmentTarFactory.java
@@ -43,11 +43,18 @@ public class SegmentTarFactory implements NodeStoreFactory {
     public SegmentTarFactory(String directory, boolean mmap) {
         this.dir = new File(directory);
         this.mmap = mmap;
+        createDirectoryIfMissing(dir);
         if (!dir.isDirectory()) {
             throw new IllegalArgumentException("Not a directory: " + dir.getPath());
         }
     }
 
+    private void createDirectoryIfMissing(File directory) {
+        if (!directory.exists()) {
+            directory.mkdirs();
+        }
+    }
+
     @Override
     public NodeStore create(BlobStore blobStore, Closer closer) throws IOException {
         final FileStoreBuilder builder = fileStoreBuilder(new File(dir, "segmentstore"));
diff --git a/oak-upgrade/src/test/java/org/apache/jackrabbit/oak/upgrade/UpgradeOldSegmentTest.java b/oak-upgrade/src/test/java/org/apache/jackrabbit/oak/upgrade/UpgradeOldSegmentTest.java
index 79870b0..0359337 100644
--- a/oak-upgrade/src/test/java/org/apache/jackrabbit/oak/upgrade/UpgradeOldSegmentTest.java
+++ b/oak-upgrade/src/test/java/org/apache/jackrabbit/oak/upgrade/UpgradeOldSegmentTest.java
@@ -56,7 +56,6 @@ public class UpgradeOldSegmentTest {
         File oldRepo = new File(testFolder, "test-repo-1.0");
         File newRepo = new File(testFolder, "test-repo-new");
         oldRepo.mkdirs();
-        newRepo.mkdirs();
         try (InputStream in = UpgradeOldSegmentTest.class.getResourceAsStream("/test-repo-1.0.zip")) {
             Util.unzip(in, oldRepo);
         }
diff --git a/oak-upgrade/src/test/java/org/apache/jackrabbit/oak/upgrade/cli/SegmentToSegmentTarWithMissingDestinationDirectoryTest.java b/oak-upgrade/src/test/java/org/apache/jackrabbit/oak/upgrade/cli/SegmentToSegmentTarWithMissingDestinationDirectoryTest.java
new file mode 100644
index 0000000..465b355
--- /dev/null
+++ b/oak-upgrade/src/test/java/org/apache/jackrabbit/oak/upgrade/cli/SegmentToSegmentTarWithMissingDestinationDirectoryTest.java
@@ -0,0 +1,59 @@
+/*
+ * Licensed to the Apache Software Foundation (ASF) under one or more
+ * contributor license agreements.  See the NOTICE file distributed with
+ * this work for additional information regarding copyright ownership.
+ * The ASF licenses this file to You under the Apache License, Version 2.0
+ * (the "License"); you may not use this file except in compliance with
+ * the License.  You may obtain a copy of the License at
+ *
+ *      http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+package org.apache.jackrabbit.oak.upgrade.cli;
+
+import org.apache.jackrabbit.oak.upgrade.cli.container.NodeStoreContainer;
+import org.apache.jackrabbit.oak.upgrade.cli.container.SegmentNodeStoreContainer;
+import org.apache.jackrabbit.oak.upgrade.cli.container.SegmentTarNodeStoreContainer;
+
+public class SegmentToSegmentTarWithMissingDestinationDirectoryTest  extends AbstractOak2OakTest {
+
+    private final NodeStoreContainer source;
+
+    private final NodeStoreContainer destination;
+
+    public SegmentToSegmentTarWithMissingDestinationDirectoryTest() {
+        source = new SegmentNodeStoreContainer();
+        destination = getSegmentTarNodeStoreContainerWithMissingDirectory();
+    }
+
+    private SegmentTarNodeStoreContainer getSegmentTarNodeStoreContainerWithMissingDirectory() {
+        SegmentTarNodeStoreContainer segmentTarNodeStoreContainer = new SegmentTarNodeStoreContainer();
+        segmentTarNodeStoreContainer.getDirectory().delete();
+        return segmentTarNodeStoreContainer;
+    }
+
+    @Override
+    protected NodeStoreContainer getSourceContainer() {
+        return source;
+    }
+
+    @Override
+    protected NodeStoreContainer getDestinationContainer() {
+        return destination;
+    }
+
+    @Override
+    protected String[] getArgs() {
+        return new String[] { source.getDescription(), destination.getDescription() };
+    }
+
+    @Override
+    protected boolean supportsCheckpointMigration() {
+        return true;
+    }
+}
diff --git a/oak-upgrade/src/test/java/org/apache/jackrabbit/oak/upgrade/cli/SegmentToSegmentWithMissingDestinationDirectoryTest.java b/oak-upgrade/src/test/java/org/apache/jackrabbit/oak/upgrade/cli/SegmentToSegmentWithMissingDestinationDirectoryTest.java
new file mode 100644
index 0000000..567c97b
--- /dev/null
+++ b/oak-upgrade/src/test/java/org/apache/jackrabbit/oak/upgrade/cli/SegmentToSegmentWithMissingDestinationDirectoryTest.java
@@ -0,0 +1,58 @@
+/*
+ * Licensed to the Apache Software Foundation (ASF) under one or more
+ * contributor license agreements.  See the NOTICE file distributed with
+ * this work for additional information regarding copyright ownership.
+ * The ASF licenses this file to You under the Apache License, Version 2.0
+ * (the "License"); you may not use this file except in compliance with
+ * the License.  You may obtain a copy of the License at
+ *
+ *      http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+package org.apache.jackrabbit.oak.upgrade.cli;
+
+import org.apache.jackrabbit.oak.upgrade.cli.container.NodeStoreContainer;
+import org.apache.jackrabbit.oak.upgrade.cli.container.SegmentNodeStoreContainer;
+
+public class SegmentToSegmentWithMissingDestinationDirectoryTest extends AbstractOak2OakTest {
+    private final NodeStoreContainer source;
+
+    private final NodeStoreContainer destination;
+
+    public SegmentToSegmentWithMissingDestinationDirectoryTest() {
+        source = new SegmentNodeStoreContainer();
+        destination = getSegmentNodeStoreContainerWithMissingDirectory();
+    }
+
+    private SegmentNodeStoreContainer getSegmentNodeStoreContainerWithMissingDirectory() {
+        SegmentNodeStoreContainer segmentNodeStoreContainer = new SegmentNodeStoreContainer();
+        segmentNodeStoreContainer.getDirectory().delete();
+        return segmentNodeStoreContainer;
+    }
+
+    @Override
+    protected NodeStoreContainer getSourceContainer() {
+        return source;
+    }
+
+    @Override
+    protected NodeStoreContainer getDestinationContainer() {
+        return destination;
+    }
+
+    @Override
+    protected String[] getArgs() {
+        return new String[] { source.getDescription(), destination.getDescription() };
+    }
+
+    @Override
+    protected boolean supportsCheckpointMigration() {
+        return true;
+    }
+
+}
diff --git a/oak-upgrade/src/test/java/org/apache/jackrabbit/oak/upgrade/cli/container/SegmentNodeStoreContainer.java b/oak-upgrade/src/test/java/org/apache/jackrabbit/oak/upgrade/cli/container/SegmentNodeStoreContainer.java
index a2a4ee2..6731cd3 100644
--- a/oak-upgrade/src/test/java/org/apache/jackrabbit/oak/upgrade/cli/container/SegmentNodeStoreContainer.java
+++ b/oak-upgrade/src/test/java/org/apache/jackrabbit/oak/upgrade/cli/container/SegmentNodeStoreContainer.java
@@ -78,4 +78,8 @@ public class SegmentNodeStoreContainer implements NodeStoreContainer {
         return SEGMENT_OLD_PREFIX + directory.getPath();
     }
 
+    public File getDirectory() {
+        return directory;
+    }
+
 }
diff --git a/oak-upgrade/src/test/java/org/apache/jackrabbit/oak/upgrade/cli/container/SegmentTarNodeStoreContainer.java b/oak-upgrade/src/test/java/org/apache/jackrabbit/oak/upgrade/cli/container/SegmentTarNodeStoreContainer.java
index 4993f5a..43fc25a 100644
--- a/oak-upgrade/src/test/java/org/apache/jackrabbit/oak/upgrade/cli/container/SegmentTarNodeStoreContainer.java
+++ b/oak-upgrade/src/test/java/org/apache/jackrabbit/oak/upgrade/cli/container/SegmentTarNodeStoreContainer.java
@@ -78,4 +78,8 @@ public class SegmentTarNodeStoreContainer implements NodeStoreContainer {
         return directory.getPath();
     }
 
+    public File getDirectory() {
+        return directory;
+    }
+
 }