diff --git a/x-pack/plugin/core/src/test/resources/org/elasticsearch/xpack/security/transport/ssl/certs/simple/samba4.crt b/x-pack/plugin/core/src/test/resources/org/elasticsearch/xpack/security/transport/ssl/certs/simple/samba4.crt
index 59ecbd22e8b23..a1f78231fa3c4 100644
--- a/x-pack/plugin/core/src/test/resources/org/elasticsearch/xpack/security/transport/ssl/certs/simple/samba4.crt
+++ b/x-pack/plugin/core/src/test/resources/org/elasticsearch/xpack/security/transport/ssl/certs/simple/samba4.crt
@@ -1,22 +1,20 @@
 -----BEGIN CERTIFICATE-----
-MIIDoDCCAoigAwIBAgIUMVGoHuyNTjTFaoRmqFELz75jzDEwDQYJKoZIhvcNAQEL
-BQAwNDEyMDAGA1UEAxMpRWxhc3RpYyBDZXJ0aWZpY2F0ZSBUb29sIEF1dG9nZW5l
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 -----END CERTIFICATE-----
diff --git a/x-pack/plugin/security/src/test/java/org/elasticsearch/xpack/security/authc/ldap/LdapSessionFactoryTests.java b/x-pack/plugin/security/src/test/java/org/elasticsearch/xpack/security/authc/ldap/LdapSessionFactoryTests.java
index 873fb5d1ce08f..e2151b027e6cb 100644
--- a/x-pack/plugin/security/src/test/java/org/elasticsearch/xpack/security/authc/ldap/LdapSessionFactoryTests.java
+++ b/x-pack/plugin/security/src/test/java/org/elasticsearch/xpack/security/authc/ldap/LdapSessionFactoryTests.java
@@ -10,6 +10,7 @@
 import com.unboundid.ldap.sdk.LDAPException;
 import com.unboundid.ldap.sdk.LDAPURL;
 import com.unboundid.ldap.sdk.SimpleBindRequest;
+import org.apache.lucene.util.LuceneTestCase;
 import org.elasticsearch.common.network.NetworkAddress;
 import org.elasticsearch.common.settings.SecureString;
 import org.elasticsearch.common.settings.Settings;
@@ -244,6 +245,7 @@ public void testGroupLookupBase() throws Exception {
      * If the realm's CA path is monitored for changes and the underlying SSL context is reloaded, then we will get two different outcomes
      * (one failure, one success) depending on which file content is in place.
      */
+    @LuceneTestCase.AwaitsFix(bugUrl = "https://github.com/elastic/elasticsearch/issues/68995")
     public void testSslTrustIsReloaded() throws Exception {
         assumeFalse("NPE thrown in BCFIPS JSSE - addressed in " +
             "https://github.com/bcgit/bc-java/commit/5aed687e17a3cd63f34373cafe92699b90076fb6#diff-8e5d8089bc0d504d93194a1e484d3950R179",
diff --git a/x-pack/plugin/security/src/test/resources/org/elasticsearch/xpack/security/authc/ldap/support/ADtrust.jks b/x-pack/plugin/security/src/test/resources/org/elasticsearch/xpack/security/authc/ldap/support/ADtrust.jks
index 5ad7981b83ed7..ab82846740752 100644
Binary files a/x-pack/plugin/security/src/test/resources/org/elasticsearch/xpack/security/authc/ldap/support/ADtrust.jks and b/x-pack/plugin/security/src/test/resources/org/elasticsearch/xpack/security/authc/ldap/support/ADtrust.jks differ
diff --git a/x-pack/plugin/security/src/test/resources/org/elasticsearch/xpack/security/authc/ldap/support/smb_ca.crt b/x-pack/plugin/security/src/test/resources/org/elasticsearch/xpack/security/authc/ldap/support/smb_ca.crt
index be5a6d0264579..df7b319d1e313 100644
--- a/x-pack/plugin/security/src/test/resources/org/elasticsearch/xpack/security/authc/ldap/support/smb_ca.crt
+++ b/x-pack/plugin/security/src/test/resources/org/elasticsearch/xpack/security/authc/ldap/support/smb_ca.crt
@@ -1,22 +1,20 @@
 -----BEGIN CERTIFICATE-----
-MIIDmzCCAoOgAwIBAgIUdwsnIxjgSneHNVKT6JNCCsrQ3T0wDQYJKoZIhvcNAQEL
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 -----END CERTIFICATE-----
diff --git a/x-pack/plugin/security/src/test/resources/org/elasticsearch/xpack/security/authc/ldap/support/smb_cert.crt b/x-pack/plugin/security/src/test/resources/org/elasticsearch/xpack/security/authc/ldap/support/smb_cert.crt
index 59ecbd22e8b23..a1f78231fa3c4 100644
--- a/x-pack/plugin/security/src/test/resources/org/elasticsearch/xpack/security/authc/ldap/support/smb_cert.crt
+++ b/x-pack/plugin/security/src/test/resources/org/elasticsearch/xpack/security/authc/ldap/support/smb_cert.crt
@@ -1,22 +1,20 @@
 -----BEGIN CERTIFICATE-----
-MIIDoDCCAoigAwIBAgIUMVGoHuyNTjTFaoRmqFELz75jzDEwDQYJKoZIhvcNAQEL
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 -----END CERTIFICATE-----
diff --git a/x-pack/test/smb-fixture/src/main/resources/certs/README.asciidoc b/x-pack/test/smb-fixture/src/main/resources/certs/README.asciidoc
new file mode 100644
index 0000000000000..5e0e447998d12
--- /dev/null
+++ b/x-pack/test/smb-fixture/src/main/resources/certs/README.asciidoc
@@ -0,0 +1,47 @@
+= Key material details
+This document details the steps used to create the certificate and key files in this directory.
+
+== Instructions on generating certificates
+
+The certificates in this directory have been generated using elasticsearch-certutil (8.0.0 SNAPSHOT)
+
+=== Generate certificates for the Samba server
+
+These keys and certificates are copied by installsmb.sh for the Samba server to use for TLS. See `../provision/installsmb.sh`
+
+[source,shell]
+-----------------------------------------------------------------------------------------------------------
+elasticsearch-certutil ca --pem --out=${PWD}/samba-ca.zip
+
+unzip samba-ca.zip
+mv ca/ca.crt ./ca.pem
+mv ca/ca.key ./ca.key
+
+rm samba-ca.zip
+rm -r ca
+-----------------------------------------------------------------------------------------------------------
+
+[source,shell]
+-----------------------------------------------------------------------------------------------------------
+elasticsearch-certutil cert  --pem --ca-cert ${PWD}/ca.pem --ca-key ${PWD}/ca.key \
+   --dns localhost --ip 127.0.0.1,0:0:0:0:0:0:0:1 --name samba4 --out ${PWD}/samba4.zip
+
+unzip samba4.zip
+mv samba4/samba4.crt ./cert.pem
+mv samba4/samba4.key ./key.pem
+
+rm samba4.zip
+rm -r samba4
+-----------------------------------------------------------------------------------------------------------
+
+
+== Ensure that all tests are aware of the certificate and keys
+
+[source,shell]
+-----------------------------------------------------------------------------------------------------------
+cp ./ca.pem ../../../../../../../x-pack/plugin/security/src/test/resources/org/elasticsearch/xpack/security/authc/ldap/support/smb_ca.crt
+cp ./cert.pem ../../../../../../../x-pack/plugin/security/src/test/resources/org/elasticsearch/xpack/security/authc/ldap/support/smb_cert.crt
+cp ./cert.pem ../../../../../../../x-pack/plugin/core/src/test/resources/org/elasticsearch/xpack/security/transport/ssl/certs/simple/samba4.crt
+
+keytool -keystore ../../../../../../../x-pack/plugin/security/src/test/resources/org/elasticsearch/xpack/security/authc/ldap/support/ADtrust.jks -storepass changeit -delete -noprompt -alias smb_ca
+keytool -keystore ../../../../../../../x-pack/plugin/security/src/test/resources/org/elasticsearch/xpack/security/authc/ldap/support/ADtrust.jks -storepass changeit -importcert -file ca.pem -alias smb_ca -noprompt
diff --git a/x-pack/test/smb-fixture/src/main/resources/certs/ca.key b/x-pack/test/smb-fixture/src/main/resources/certs/ca.key
index b755b758914ee..c490e0477f8f5 100644
--- a/x-pack/test/smb-fixture/src/main/resources/certs/ca.key
+++ b/x-pack/test/smb-fixture/src/main/resources/certs/ca.key
@@ -1,27 +1,27 @@
 -----BEGIN RSA PRIVATE KEY-----
-MIIEogIBAAKCAQEApAA/+F2xZ27cKT9m16iyK3KeZclMKeR5wFhIu2OBiH2s8MWm
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 -----END RSA PRIVATE KEY-----
diff --git a/x-pack/test/smb-fixture/src/main/resources/certs/ca.pem b/x-pack/test/smb-fixture/src/main/resources/certs/ca.pem
index 082882be57f79..df7b319d1e313 100644
--- a/x-pack/test/smb-fixture/src/main/resources/certs/ca.pem
+++ b/x-pack/test/smb-fixture/src/main/resources/certs/ca.pem
@@ -1,22 +1,20 @@
 -----BEGIN CERTIFICATE-----
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 -----END CERTIFICATE-----
diff --git a/x-pack/test/smb-fixture/src/main/resources/certs/cert.pem b/x-pack/test/smb-fixture/src/main/resources/certs/cert.pem
index 34f12d8605184..a1f78231fa3c4 100644
--- a/x-pack/test/smb-fixture/src/main/resources/certs/cert.pem
+++ b/x-pack/test/smb-fixture/src/main/resources/certs/cert.pem
@@ -1,22 +1,20 @@
 -----BEGIN CERTIFICATE-----
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 -----END CERTIFICATE-----
diff --git a/x-pack/test/smb-fixture/src/main/resources/certs/key.pem b/x-pack/test/smb-fixture/src/main/resources/certs/key.pem
index 4d5c3a2026733..2def63ef63914 100644
--- a/x-pack/test/smb-fixture/src/main/resources/certs/key.pem
+++ b/x-pack/test/smb-fixture/src/main/resources/certs/key.pem
@@ -1,27 +1,27 @@
 -----BEGIN RSA PRIVATE KEY-----
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+qt/MXIOtlgjx1hMqfsM3QoMxxyAvwY3tC8vevm3k8yzGfe7Vxb8=
 -----END RSA PRIVATE KEY-----