diff --git a/src/main/java/edu/harvard/iq/dataverse/DatasetVersion.java b/src/main/java/edu/harvard/iq/dataverse/DatasetVersion.java
index 3be005a252d..437c42ba8b3 100644
--- a/src/main/java/edu/harvard/iq/dataverse/DatasetVersion.java
+++ b/src/main/java/edu/harvard/iq/dataverse/DatasetVersion.java
@@ -52,6 +52,8 @@
         uniqueConstraints = @UniqueConstraint(columnNames = {"dataset_id,versionnumber,minorversionnumber"}))
 public class DatasetVersion implements Serializable {
 
+    private static final Logger logger = Logger.getLogger(DatasetVersion.class.getCanonicalName());
+
     /**
      * Convenience comparator to compare dataset versions by their version number.
      * The draft version is considered the latest.
@@ -1034,6 +1036,26 @@ public Set<ConstraintViolation> validate() {
                 }
             }
         }
+        List<FileMetadata> dsvfileMetadatas = this.getFileMetadatas();
+        if (dsvfileMetadatas != null) {
+            for (FileMetadata fileMetadata : dsvfileMetadatas) {
+                Set<ConstraintViolation<FileMetadata>> constraintViolations = validator.validate(fileMetadata);
+                if (constraintViolations.size() > 0) {
+                    // currently only support one message
+                    ConstraintViolation<FileMetadata> violation = constraintViolations.iterator().next();
+                    /**
+                     * @todo How can we expose this more detailed message
+                     * containing the invalid value to the user?
+                     */
+                    String message = "Constraint violation found in FileMetadata. "
+                            + violation.getMessage() + " "
+                            + "The invalid value is \"" + violation.getInvalidValue().toString() + "\".";
+                    logger.info(message);
+                    returnSet.add(violation);
+                    break; // currently only support one message, so we can break out of the loop after the first constraint violation
+                }
+            }
+        }
         return returnSet;
     }
 }
diff --git a/src/main/java/edu/harvard/iq/dataverse/engine/command/impl/CreateDatasetCommand.java b/src/main/java/edu/harvard/iq/dataverse/engine/command/impl/CreateDatasetCommand.java
index 25d2231708a..3a8973c7845 100644
--- a/src/main/java/edu/harvard/iq/dataverse/engine/command/impl/CreateDatasetCommand.java
+++ b/src/main/java/edu/harvard/iq/dataverse/engine/command/impl/CreateDatasetCommand.java
@@ -100,6 +100,7 @@ public Dataset execute(CommandContext ctxt) throws CommandException {
             String validationFailedString = "Validation failed:";
             for (ConstraintViolation constraintViolation : constraintViolations) {
                 validationFailedString += " " + constraintViolation.getMessage();
+                validationFailedString += " Invalid value: '" + constraintViolation.getInvalidValue() + "'.";
             }
             throw new IllegalCommandException(validationFailedString, this);
         }
diff --git a/src/test/java/edu/harvard/iq/dataverse/api/FileMetadataIT.java b/src/test/java/edu/harvard/iq/dataverse/api/FileMetadataIT.java
index 8f243451c68..3f279de4c2f 100644
--- a/src/test/java/edu/harvard/iq/dataverse/api/FileMetadataIT.java
+++ b/src/test/java/edu/harvard/iq/dataverse/api/FileMetadataIT.java
@@ -32,8 +32,10 @@
 import java.util.UUID;
 
 import static com.jayway.restassured.RestAssured.given;
+import static javax.ws.rs.core.Response.Status.BAD_REQUEST;
 import static junit.framework.Assert.assertEquals;
 import static junit.framework.Assert.fail;
+import static org.hamcrest.CoreMatchers.equalTo;
 
 /**
  * FileMetadata Integration Tests
@@ -138,15 +140,18 @@ public void testJsonParserWithDirectoryLabels() {
         try {
 
             // try to create a dataset with directory labels that contain both leading and trailing file separators
-            Response resp = given()
+            Response shouldFailDueToLeadingAndTrailingSeparators = given()
                     .header(keyString, token)
                     .body(IOUtils.toString(classLoader.getResourceAsStream(
                             "json/complete-dataset-with-files-invalid-directory-labels.json")))
                     .contentType("application/json")
                     .post("/api/dataverses/" + testName + "/datasets");
-            // this request should fail since a @Pattern constraint exists in FileMetadata to prevent this 
-            assertEquals(resp.getStatusCode(), 500);
-            
+            shouldFailDueToLeadingAndTrailingSeparators.prettyPrint();
+            shouldFailDueToLeadingAndTrailingSeparators.then().assertThat()
+                    // Note that the JSON under test actually exercises leading too but only the first (trailing) is exercised here.
+                    .body("message", equalTo("Validation failed: Directory Name cannot contain leading or trailing file separators. Invalid value: 'data/subdir1/'."))
+                    .statusCode(BAD_REQUEST.getStatusCode());
+
             // create dataset and set id
             dsId = given()
                     .header(keyString, token)
diff --git a/src/test/java/edu/harvard/iq/dataverse/ingest/IngestServiceBeanHelperTest.java b/src/test/java/edu/harvard/iq/dataverse/ingest/IngestServiceBeanHelperTest.java
index 09d0b045b6c..20099d654fd 100644
--- a/src/test/java/edu/harvard/iq/dataverse/ingest/IngestServiceBeanHelperTest.java
+++ b/src/test/java/edu/harvard/iq/dataverse/ingest/IngestServiceBeanHelperTest.java
@@ -20,6 +20,8 @@
 import java.util.List;
 
 import static edu.harvard.iq.dataverse.mocks.MocksFactory.makeDataset;
+import java.util.Set;
+import javax.validation.ConstraintViolation;
 
 /**
  * Tests against IngestServiceBean helper methods.
@@ -367,4 +369,40 @@ public void testCheckForDuplicateFileNamesTabular() throws Exception {
         assertEquals(file2NameAltered, true);
     }
 
+    @Test
+    public void testDirectoryLabels() {
+
+        DatasetVersion datasetVersion = new DatasetVersion();
+        FileMetadata fileMetadata = new FileMetadata();
+        fileMetadata.setLabel("foo.png");
+        fileMetadata.setDirectoryLabel("/has/leading/slash");
+        datasetVersion.getFileMetadatas().add(fileMetadata);
+
+        Set<ConstraintViolation> violations1 = datasetVersion.validate();
+        assertEquals(1, violations1.size());
+        ConstraintViolation violation1 = violations1.iterator().next();
+        assertEquals("Directory Name cannot contain leading or trailing file separators.", violation1.getMessage());
+
+        // reset
+        datasetVersion.setFileMetadatas(new ArrayList<>());
+        Set<ConstraintViolation> violations2 = datasetVersion.validate();
+        assertEquals(0, violations2.size());
+
+        fileMetadata.setDirectoryLabel("has/trailing/slash/");
+        datasetVersion.getFileMetadatas().add(fileMetadata);
+        Set<ConstraintViolation> violations3 = datasetVersion.validate();
+        assertEquals(1, violations3.size());
+        assertEquals("Directory Name cannot contain leading or trailing file separators.", violations3.iterator().next().getMessage());
+
+        // reset
+        datasetVersion.setFileMetadatas(new ArrayList<>());
+        Set<ConstraintViolation> violations4 = datasetVersion.validate();
+        assertEquals(0, violations4.size());
+
+        fileMetadata.setDirectoryLabel("just/right");
+        datasetVersion.getFileMetadatas().add(fileMetadata);
+        Set<ConstraintViolation> violations5 = datasetVersion.validate();
+        assertEquals(0, violations5.size());
+    }
+
 }