diff --git a/spring-cloud-aws-parameter-store-config/src/main/java/org/springframework/cloud/aws/paramstore/AwsParamStorePropertySourceLocator.java b/spring-cloud-aws-parameter-store-config/src/main/java/org/springframework/cloud/aws/paramstore/AwsParamStorePropertySourceLocator.java
index 4caa4ed32..0d1cc215f 100644
--- a/spring-cloud-aws-parameter-store-config/src/main/java/org/springframework/cloud/aws/paramstore/AwsParamStorePropertySourceLocator.java
+++ b/spring-cloud-aws-parameter-store-config/src/main/java/org/springframework/cloud/aws/paramstore/AwsParamStorePropertySourceLocator.java
@@ -124,9 +124,9 @@ private AwsParamStorePropertySource create(String context) {
 
 	private void addProfiles(Set<String> contexts, String baseContext,
 			List<String> profiles) {
-		for (String profile : profiles) {
-			contexts.add(
-					baseContext + this.properties.getProfileSeparator() + profile + "/");
+		for (int index = profiles.size() - 1; index >= 0; --index) {
+			contexts.add(baseContext + this.properties.getProfileSeparator()
+					+ profiles.get(index) + "/");
 		}
 	}
 
diff --git a/spring-cloud-aws-parameter-store-config/src/test/java/org/springframework/cloud/aws/paramstore/AwsParamStorePropertySourceLocatorTest.java b/spring-cloud-aws-parameter-store-config/src/test/java/org/springframework/cloud/aws/paramstore/AwsParamStorePropertySourceLocatorTest.java
index d6ab4041d..82a4d3950 100644
--- a/spring-cloud-aws-parameter-store-config/src/test/java/org/springframework/cloud/aws/paramstore/AwsParamStorePropertySourceLocatorTest.java
+++ b/spring-cloud-aws-parameter-store-config/src/test/java/org/springframework/cloud/aws/paramstore/AwsParamStorePropertySourceLocatorTest.java
@@ -25,10 +25,12 @@
 import com.amazonaws.services.simplesystemsmanagement.model.Parameter;
 import org.junit.Test;
 
+import org.springframework.core.env.PropertySource;
 import org.springframework.mock.env.MockEnvironment;
 
 import static org.assertj.core.api.Assertions.assertThat;
 import static org.mockito.ArgumentMatchers.any;
+import static org.mockito.ArgumentMatchers.eq;
 import static org.mockito.Mockito.mock;
 import static org.mockito.Mockito.when;
 
@@ -36,6 +38,7 @@
  * Unit test for {@link AwsParamStorePropertySourceLocator}.
  *
  * @author Matej Nedic
+ * @author Pete Guyatt
  */
 public class AwsParamStorePropertySourceLocatorTest {
 
@@ -91,28 +94,92 @@ public void contextSpecificOrderExpected() {
 
 		AwsParamStorePropertySourceLocator locator = new AwsParamStorePropertySourceLocator(
 				ssmClient, properties);
-		env.setActiveProfiles("test");
+		env.setActiveProfiles("test", "more-specific", "most-specific");
 		locator.locate(env);
 
 		List<String> contextToBeTested = new ArrayList<>(locator.getContexts());
 
 		assertThat(contextToBeTested.get(0))
+				.isEqualTo("application/messaging-service_most-specific/");
+		assertThat(contextToBeTested.get(1))
+				.isEqualTo("application/messaging-service_more-specific/");
+		assertThat(contextToBeTested.get(2))
 				.isEqualTo("application/messaging-service_test/");
-		assertThat(contextToBeTested.get(1)).isEqualTo("application/messaging-service/");
-		assertThat(contextToBeTested.get(2)).isEqualTo("application/application_test/");
-		assertThat(contextToBeTested.get(3)).isEqualTo("application/application/");
+		assertThat(contextToBeTested.get(3)).isEqualTo("application/messaging-service/");
+		assertThat(contextToBeTested.get(4))
+				.isEqualTo("application/application_most-specific/");
+		assertThat(contextToBeTested.get(5))
+				.isEqualTo("application/application_more-specific/");
+		assertThat(contextToBeTested.get(6)).isEqualTo("application/application_test/");
+		assertThat(contextToBeTested.get(7)).isEqualTo("application/application/");
+	}
+
+	@Test
+	public void contextWithMultipleProfilesValidatePropertyPrecedence() {
+		AwsParamStoreProperties properties = new AwsParamStorePropertiesBuilder()
+				.withDefaultContext("context").withName("application").build();
+
+		String[] activeProfiles = { "test", "more-specific", "most-specific" };
+		String propertyKey = "my-test-value";
+
+		when(ssmClient.getParametersByPath(
+				eq(newGetParametersByPathRequest("context/application/")))).thenReturn(
+						newGetParametersByPathResult("context/application/" + propertyKey,
+								""));
+
+		for (String profile : activeProfiles) {
+			String path = String.format("context/application_%s/", profile);
+			when(ssmClient.getParametersByPath(eq(newGetParametersByPathRequest(path))))
+					.thenReturn(
+							newGetParametersByPathResult(path + propertyKey, profile));
+		}
+
+		AwsParamStorePropertySourceLocator locator = new AwsParamStorePropertySourceLocator(
+				ssmClient, properties);
+		env.setActiveProfiles(activeProfiles);
+		PropertySource<?> propertySource = locator.locate(env);
+
+		assertThat(propertySource.getProperty(propertyKey))
+				.isEqualTo(activeProfiles[activeProfiles.length - 1]);
+
+		List<String> contexts = locator.getContexts();
+		assertThat(contexts).hasSize(4);
+
+		assertThat(contexts.get(0)).isEqualTo("context/application_most-specific/");
+		assertThat(contexts.get(1)).isEqualTo("context/application_more-specific/");
+		assertThat(contexts.get(2)).isEqualTo("context/application_test/");
+		assertThat(contexts.get(3)).isEqualTo("context/application/");
+	}
+
+	private static GetParametersByPathResult newGetParametersByPathResult(String name,
+			String value) {
+		return newGetParametersByPathResult(newParameter(name, value));
+	}
+
+	private static GetParametersByPathResult newGetParametersByPathResult(
+			Parameter... parameters) {
+		return new GetParametersByPathResult().withParameters(parameters);
+	}
+
+	private static GetParametersByPathRequest newGetParametersByPathRequest(String path) {
+		return new GetParametersByPathRequest().withPath(path).withRecursive(true)
+				.withWithDecryption(true);
+	}
+
+	public static Parameter newParameter(String name, String value) {
+		return new Parameter().withName(name).withValue(value);
 	}
 
 	private static GetParametersByPathResult getNextResult() {
-		return new GetParametersByPathResult().withParameters(
-				new Parameter().withName("/config/myservice/key3").withValue("value3"),
-				new Parameter().withName("/config/myservice/key4").withValue("value4"));
+		return newGetParametersByPathResult(
+				newParameter("/config/myservice/key3", "value3"),
+				newParameter("/config/myservice/key4", "value3"));
 	}
 
 	private static GetParametersByPathResult getFirstResult() {
-		return new GetParametersByPathResult().withParameters(
-				new Parameter().withName("/config/myservice/key3").withValue("value3"),
-				new Parameter().withName("/config/myservice/key4").withValue("value4"));
+		return newGetParametersByPathResult(
+				newParameter("/config/myservice/key3", "value3"),
+				newParameter("/config/myservice/key4", "value3"));
 	}
 
 	private static final class AwsParamStorePropertiesBuilder {