diff --git a/spring-boot-cli/samples/actuator.groovy b/spring-boot-cli/samples/actuator.groovy
index 21e4df8f9a..ffad280f9d 100644
--- a/spring-boot-cli/samples/actuator.groovy
+++ b/spring-boot-cli/samples/actuator.groovy
@@ -2,14 +2,11 @@ package org.test
 
 @Grab("spring-boot-starter-actuator")
 
-@Controller
+@RestController
 class SampleController {
 
 	@RequestMapping("/")
-	@ResponseBody
 	public def hello() {
 		[message: "Hello World!"]
 	}
 }
-
-
diff --git a/spring-boot-cli/samples/secure.groovy b/spring-boot-cli/samples/secure.groovy
new file mode 100644
index 0000000000..6615bc144f
--- /dev/null
+++ b/spring-boot-cli/samples/secure.groovy
@@ -0,0 +1,13 @@
+package org.test
+
+@Grab("spring-boot-starter-security")
+@Grab("spring-boot-starter-actuator")
+
+@RestController
+class SampleController {
+
+	@RequestMapping("/")
+	public def hello() {
+		[message: "Hello World!"]
+	}
+}
diff --git a/spring-boot-cli/src/test/java/org/springframework/boot/cli/ReproIntegrationTests.java b/spring-boot-cli/src/test/java/org/springframework/boot/cli/ReproIntegrationTests.java
index 51644f3362..223833d2c7 100644
--- a/spring-boot-cli/src/test/java/org/springframework/boot/cli/ReproIntegrationTests.java
+++ b/spring-boot-cli/src/test/java/org/springframework/boot/cli/ReproIntegrationTests.java
@@ -39,4 +39,20 @@ public class ReproIntegrationTests {
 				containsString("{\"message\":\"Hello World\"}"));
 	}
 
+	// Security depends on old versions of Spring so if the dependencies aren't pinned
+	// this will fail
+	@Test
+	public void securityDependencies() throws Exception {
+		this.cli.run("secure.groovy");
+		assertThat(this.cli.getHttpOutput(),
+				containsString("{\"message\":\"Hello World\"}"));
+	}
+
+	@Test
+	public void shellDependencies() throws Exception {
+		this.cli.run("crsh.groovy");
+		assertThat(this.cli.getHttpOutput(),
+				containsString("{\"message\":\"Hello World\"}"));
+	}
+
 }
diff --git a/spring-boot-cli/src/test/resources/repro-samples/crsh.groovy b/spring-boot-cli/src/test/resources/repro-samples/crsh.groovy
new file mode 100644
index 0000000000..9d827ad1b7
--- /dev/null
+++ b/spring-boot-cli/src/test/resources/repro-samples/crsh.groovy
@@ -0,0 +1,14 @@
+package org.test
+
+@Grab("spring-boot-starter-shell-remote")
+
+@RestController
+class SampleController {
+
+	@RequestMapping("/")
+	public def hello() {
+		[message: "Hello World!"]
+	}
+}
+
+
diff --git a/spring-boot-cli/src/test/resources/repro-samples/secure.groovy b/spring-boot-cli/src/test/resources/repro-samples/secure.groovy
new file mode 100644
index 0000000000..a03471d452
--- /dev/null
+++ b/spring-boot-cli/src/test/resources/repro-samples/secure.groovy
@@ -0,0 +1,15 @@
+package org.test
+
+// No security features added just a test that the dependencies are resolved
+@Grab("spring-boot-starter-security")
+
+@RestController
+class SampleController {
+
+	@RequestMapping("/")
+	public def hello() {
+		[message: "Hello World!"]
+	}
+}
+
+