diff --git a/src/main/java/com/marklogic/mgmt/api/security/RoleObjectNodesSorter.java b/src/main/java/com/marklogic/mgmt/api/security/RoleObjectNodesSorter.java
index 194a36ac4..6bbcfc357 100644
--- a/src/main/java/com/marklogic/mgmt/api/security/RoleObjectNodesSorter.java
+++ b/src/main/java/com/marklogic/mgmt/api/security/RoleObjectNodesSorter.java
@@ -78,7 +78,15 @@ else if (index > -1) {
 			}
 		}
 
-		String[] sortedRoleNames = sorter.sort();
+		String[] sortedRoleNames;
+		try {
+			sortedRoleNames = sorter.sort();
+		} catch (IllegalStateException ex) {
+			throw new IllegalArgumentException("Unable to deploy roles due to circular dependencies " +
+				"between two or more roles; please remove these circular dependencies in order to deploy" +
+				" your roles");
+		}
+
 		roles = new ArrayList<>();
 		for (String name : sortedRoleNames) {
 			roles.add(map.get(name));
diff --git a/src/test/java/com/marklogic/appdeployer/command/security/DeployRolesWithDependenciesTest.java b/src/test/java/com/marklogic/appdeployer/command/security/DeployRolesWithDependenciesTest.java
index 3f84b997c..bac58197a 100644
--- a/src/test/java/com/marklogic/appdeployer/command/security/DeployRolesWithDependenciesTest.java
+++ b/src/test/java/com/marklogic/appdeployer/command/security/DeployRolesWithDependenciesTest.java
@@ -6,7 +6,7 @@
 
 import java.io.File;
 
-import static org.junit.jupiter.api.Assertions.assertTrue;
+import static org.junit.jupiter.api.Assertions.*;
 
 /**
  * Each of these tests verifies that the roles in the given config dir can be deployed successfully based on their
@@ -73,6 +73,22 @@ public void anotherSortingTest() {
 		}
 	}
 
+	@Test
+	void circularDependencies() {
+		appConfig.getFirstConfigDir().setBaseDir(new File("src/test/resources/sample-app/roles-with-circular-dependencies"));
+		initializeAppDeployer(new DeployRolesCommand());
+		try {
+			deploySampleApp();
+			fail("Expected an error due to a circular dependency between the two roles");
+		} catch (IllegalArgumentException ex) {
+			assertEquals("Unable to deploy roles due to circular dependencies between two or more roles; " +
+					"please remove these circular dependencies in order to deploy your roles",
+				ex.getMessage());
+		} finally {
+			undeploySampleApp();
+		}
+	}
+
 	@Test
 	public void test() {
 		appConfig.getFirstConfigDir().setBaseDir(new File("src/test/resources/sample-app/roles-with-dependencies"));
diff --git a/src/test/resources/sample-app/roles-with-circular-dependencies/security/roles/role0.json b/src/test/resources/sample-app/roles-with-circular-dependencies/security/roles/role0.json
new file mode 100644
index 000000000..f2120b8df
--- /dev/null
+++ b/src/test/resources/sample-app/roles-with-circular-dependencies/security/roles/role0.json
@@ -0,0 +1,6 @@
+{
+	"role-name": "sample-app-role0",
+	"role": [
+		"sample-app-role1"
+	]
+}
diff --git a/src/test/resources/sample-app/roles-with-circular-dependencies/security/roles/role1.json b/src/test/resources/sample-app/roles-with-circular-dependencies/security/roles/role1.json
new file mode 100644
index 000000000..526f6decd
--- /dev/null
+++ b/src/test/resources/sample-app/roles-with-circular-dependencies/security/roles/role1.json
@@ -0,0 +1,6 @@
+{
+	"role-name": "sample-app-role1",
+	"role": [
+		"sample-app-role0"
+	]
+}