diff --git a/flink-state-backends/flink-statebackend-rocksdb/src/main/java/org/apache/flink/contrib/streaming/state/RocksDBOperationUtils.java b/flink-state-backends/flink-statebackend-rocksdb/src/main/java/org/apache/flink/contrib/streaming/state/RocksDBOperationUtils.java
index 45df7283ade9e..1455c1bbebe91 100644
--- a/flink-state-backends/flink-statebackend-rocksdb/src/main/java/org/apache/flink/contrib/streaming/state/RocksDBOperationUtils.java
+++ b/flink-state-backends/flink-statebackend-rocksdb/src/main/java/org/apache/flink/contrib/streaming/state/RocksDBOperationUtils.java
@@ -24,6 +24,7 @@
 import org.apache.flink.runtime.state.RegisteredStateMetaInfoBase;
 import org.apache.flink.util.FlinkRuntimeException;
 import org.apache.flink.util.IOUtils;
+import org.apache.flink.util.OperatingSystem;
 import org.apache.flink.util.Preconditions;
 import org.apache.flink.util.function.LongFunctionWithException;
 
@@ -80,6 +81,10 @@ public static RocksDB openDB(
 		} catch (RocksDBException e) {
 			IOUtils.closeQuietly(columnFamilyOptions);
 			columnFamilyDescriptors.forEach((cfd) -> IOUtils.closeQuietly(cfd.getOptions()));
+
+			// improve error reporting on Windows
+			throwExceptionIfPathLengthExceededOnWindows(path, e);
+
 			throw new IOException("Error while opening RocksDB instance.", e);
 		}
 
@@ -207,4 +212,16 @@ public static OpaqueMemoryResource<RocksDBSharedResources> allocateSharedCachesI
 			throw new IOException("Failed to acquire shared cache resource for RocksDB", e);
 		}
 	}
+
+	private static void throwExceptionIfPathLengthExceededOnWindows(String path, Exception cause) throws IOException {
+		// max directory path length on Windows is 247.
+		// the maximum path length is 260, subtracting one file name length (12 chars) and one NULL terminator.
+		final int maxWinDirPathLen = 247;
+
+		if (path.length() > maxWinDirPathLen && OperatingSystem.isWindows()) {
+			throw new IOException(String.format(
+				"The directory path length (%d) is longer than the directory path length limit for Windows (%d): %s",
+				path.length(), maxWinDirPathLen, path), cause);
+		}
+	}
 }
diff --git a/flink-state-backends/flink-statebackend-rocksdb/src/test/java/org/apache/flink/contrib/streaming/state/RocksDBOperationsUtilsTest.java b/flink-state-backends/flink-statebackend-rocksdb/src/test/java/org/apache/flink/contrib/streaming/state/RocksDBOperationsUtilsTest.java
new file mode 100644
index 0000000000000..ac0a68e88f865
--- /dev/null
+++ b/flink-state-backends/flink-statebackend-rocksdb/src/test/java/org/apache/flink/contrib/streaming/state/RocksDBOperationsUtilsTest.java
@@ -0,0 +1,88 @@
+/*
+ * 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.flink.contrib.streaming.state;
+
+import org.apache.flink.util.OperatingSystem;
+
+import org.junit.BeforeClass;
+import org.junit.ClassRule;
+import org.junit.Test;
+import org.junit.rules.TemporaryFolder;
+import org.rocksdb.ColumnFamilyOptions;
+import org.rocksdb.DBOptions;
+import org.rocksdb.NativeLibraryLoader;
+import org.rocksdb.RocksDB;
+
+import java.io.File;
+import java.io.IOException;
+import java.nio.file.Files;
+import java.util.Collections;
+
+import static org.hamcrest.Matchers.containsString;
+import static org.junit.Assert.assertThat;
+import static org.junit.Assume.assumeTrue;
+
+/**
+ * Tests for the {@link RocksDBOperationUtils}.
+ */
+public class RocksDBOperationsUtilsTest {
+
+	@ClassRule
+	public static final TemporaryFolder TMP_DIR = new TemporaryFolder();
+
+	@BeforeClass
+	public static void loadRocksLibrary() throws Exception {
+		NativeLibraryLoader.getInstance().loadLibrary(TMP_DIR.newFolder().getAbsolutePath());
+	}
+
+	@Test
+	public void testPathExceptionOnWindows() throws Exception {
+		assumeTrue(OperatingSystem.isWindows());
+
+		final File folder = TMP_DIR.newFolder();
+		final File rocksDir = new File(folder, getLongString(247 - folder.getAbsolutePath().length()));
+
+		Files.createDirectories(rocksDir.toPath());
+
+		try (DBOptions dbOptions = new DBOptions().setCreateIfMissing(true);
+			ColumnFamilyOptions colOptions = new ColumnFamilyOptions()) {
+
+			RocksDB rocks = RocksDBOperationUtils.openDB(
+					rocksDir.getAbsolutePath(),
+					Collections.emptyList(),
+					Collections.emptyList(),
+					colOptions, dbOptions);
+			rocks.close();
+
+			// do not provoke a test failure if this passes, because some setups may actually
+			// support long paths, in which case: great!
+		}
+		catch (IOException e) {
+			assertThat(e.getMessage(), containsString("longer than the directory path length limit for Windows"));
+		}
+	}
+
+	private static String getLongString(int numChars) {
+		final StringBuilder builder = new StringBuilder();
+		for (int i = numChars; i > 0; --i) {
+			builder.append('a');
+		}
+		return builder.toString();
+	}
+}