diff --git a/src/test/java/org/opensearch/security/ssl/SslContextHandlerTest.java b/src/test/java/org/opensearch/security/ssl/SslContextHandlerTest.java
index c250b83583..803b1c846f 100644
--- a/src/test/java/org/opensearch/security/ssl/SslContextHandlerTest.java
+++ b/src/test/java/org/opensearch/security/ssl/SslContextHandlerTest.java
@@ -76,8 +76,11 @@ void writeCertificates(
     @Test
     public void failsIfCertificatesAreSame() throws Exception {
         final var sslContextHandler = sslContextHandler();
-        final var e = assertThrows(CertificateException.class, sslContextHandler::reloadSslContext);
-        assertThat(e.getMessage(), is("Existing certificates are the same as new one"));
+
+        final var sslContextBefore = sslContextHandler.sslContext();
+        sslContextHandler.reloadSslContext();
+
+        assertThat("SSL Context is the same", sslContextBefore.equals(sslContextHandler.sslContext()));
     }
 
     @Test
@@ -100,7 +103,7 @@ public void failsIfCertificatesNasNotValidDates() throws Exception {
         newAccessCertificate = certificatesRule.generateAccessCertificate(
             keyPair,
             accessCertificate.getNotBefore().toInstant().plus(10, ChronoUnit.DAYS),
-            accessCertificate.getNotAfter().toInstant()
+            accessCertificate.getNotAfter().toInstant().plus(20, ChronoUnit.DAYS)
         );
         writeCertificates(newCaCertificate, newAccessCertificate.v2(), newAccessCertificate.v1());
 
diff --git a/src/test/java/org/opensearch/security/ssl/config/SslCertificatesLoaderTest.java b/src/test/java/org/opensearch/security/ssl/config/SslCertificatesLoaderTest.java
index 04c65061bf..c2c6961430 100644
--- a/src/test/java/org/opensearch/security/ssl/config/SslCertificatesLoaderTest.java
+++ b/src/test/java/org/opensearch/security/ssl/config/SslCertificatesLoaderTest.java
@@ -25,6 +25,7 @@
 import static org.hamcrest.CoreMatchers.is;
 import static org.hamcrest.MatcherAssert.assertThat;
 import static org.hamcrest.Matchers.contains;
+import static org.hamcrest.Matchers.containsInAnyOrder;
 import static org.hamcrest.Matchers.notNullValue;
 
 public abstract class SslCertificatesLoaderTest extends RandomizedTest {
@@ -47,7 +48,7 @@ void assertTrustStoreConfiguration(
     ) {
         assertThat("Truststore configuration created", nonNull(trustStoreConfiguration));
         assertThat(trustStoreConfiguration.file(), is(expectedFile));
-        assertThat(trustStoreConfiguration.certificates(), contains(expectedCertificates));
+        assertThat(trustStoreConfiguration.certificates(), containsInAnyOrder(expectedCertificates));
         assertThat(trustStoreConfiguration.createTrustManagerFactory(), is(notNullValue()));
     }
 
@@ -58,7 +59,7 @@ void assertKeyStoreConfiguration(
     ) {
         assertThat("Keystore configuration created", nonNull(keyStoreConfiguration));
         assertThat(keyStoreConfiguration.files(), contains(expectedFiles.toArray(new Path[0])));
-        assertThat(keyStoreConfiguration.certificates(), contains(expectedCertificates));
+        assertThat(keyStoreConfiguration.certificates(), containsInAnyOrder(expectedCertificates));
         assertThat(keyStoreConfiguration.createKeyManagerFactory(), is(notNullValue()));
     }