diff --git a/.env.example.complete b/.env.example.complete
index 3f1a8ab94..cfc968192 100644
--- a/.env.example.complete
+++ b/.env.example.complete
@@ -219,7 +219,7 @@ LDAP_USER_FILTER=false
 LDAP_VERSION=false
 LDAP_START_TLS=false
 LDAP_TLS_INSECURE=false
-LDAP_TLS_CACERTFILE=false
+LDAP_TLS_CA_CERT=false
 LDAP_ID_ATTRIBUTE=uid
 LDAP_EMAIL_ATTRIBUTE=mail
 LDAP_DISPLAY_NAME_ATTRIBUTE=cn
diff --git a/app/Access/LdapService.php b/app/Access/LdapService.php
index 56e7aba04..e0d7f2615 100644
--- a/app/Access/LdapService.php
+++ b/app/Access/LdapService.php
@@ -209,10 +209,10 @@ class LdapService
             $this->ldap->setOption(null, LDAP_OPT_X_TLS_REQUIRE_CERT, LDAP_OPT_X_TLS_NEVER);
         }
 
-        // Specify CA Cert file for LDAP.
+        // Configure any user-provided CA cert files for LDAP.
         // This option works globally and must be set before a connection is created.
-        if ($this->config['tls_cacertfile']) {
-            $this->ldap->setOption(null, LDAP_OPT_X_TLS_CACERTFILE, $this->config['tls_cacertfile']);
+        if ($this->config['tls_ca_cert']) {
+            $this->configureTlsCaCerts($this->config['tls_ca_cert']);
         }
 
         $ldapHost = $this->parseServerString($this->config['server']);
@@ -229,7 +229,14 @@ class LdapService
 
         // Start and verify TLS if it's enabled
         if ($this->config['start_tls']) {
-            $started = $this->ldap->startTls($ldapConnection);
+            try {
+                $started = $this->ldap->startTls($ldapConnection);
+            } catch (\Exception $exception) {
+                $error = $exception->getMessage() . ' :: ' . ldap_error($ldapConnection);
+                ldap_get_option($ldapConnection, LDAP_OPT_DIAGNOSTIC_MESSAGE, $detail);
+                Log::info("LDAP STARTTLS failure: {$error} {$detail}");
+                throw new LdapException('Could not start TLS connection. Further details in the application log.');
+            }
             if (!$started) {
                 throw new LdapException('Could not start TLS connection');
             }
@@ -240,6 +247,33 @@ class LdapService
         return $this->ldapConnection;
     }
 
+    /**
+     * Configure TLS CA certs globally for ldap use.
+     * This will detect if the given path is a directory or file, and set the relevant
+     * LDAP TLS options appropriately otherwise throw an exception if no file/folder found.
+     *
+     * Note: When using a folder, certificates are expected to be correctly named by hash
+     * which can be done via the c_rehash utility.
+     *
+     * @throws LdapException
+     */
+    protected function configureTlsCaCerts(string $caCertPath): void
+    {
+        $errMessage = "Provided path [{$caCertPath}] for LDAP TLS CA certs could not be resolved to an existing location";
+        $path = realpath($caCertPath);
+        if ($path === false) {
+            throw new LdapException($errMessage);
+        }
+
+        if (is_dir($path)) {
+            $this->ldap->setOption(null, LDAP_OPT_X_TLS_CACERTDIR, $path);
+        } else if (is_file($path)) {
+            $this->ldap->setOption(null, LDAP_OPT_X_TLS_CACERTFILE, $path);
+        } else {
+            throw new LdapException($errMessage);
+        }
+    }
+
     /**
      * Parse an LDAP server string and return the host suitable for a connection.
      * Is flexible to formats such as 'ldap.example.com:8069' or 'ldaps://ldap.example.com'.
diff --git a/app/Config/services.php b/app/Config/services.php
index a407b5dc8..f93ca44f6 100644
--- a/app/Config/services.php
+++ b/app/Config/services.php
@@ -133,7 +133,7 @@ return [
         'group_attribute'        => env('LDAP_GROUP_ATTRIBUTE', 'memberOf'),
         'remove_from_groups'     => env('LDAP_REMOVE_FROM_GROUPS', false),
         'tls_insecure'           => env('LDAP_TLS_INSECURE', false),
-        'tls_cacertfile'   	     => env('LDAP_TLS_CACERTFILE', false),
+        'tls_ca_cert'            => env('LDAP_TLS_CA_CERT', false),
         'start_tls'              => env('LDAP_START_TLS', false),
         'thumbnail_attribute'    => env('LDAP_THUMBNAIL_ATTRIBUTE', null),
     ],
diff --git a/tests/Auth/LdapTest.php b/tests/Auth/LdapTest.php
index 34900ce6f..717167729 100644
--- a/tests/Auth/LdapTest.php
+++ b/tests/Auth/LdapTest.php
@@ -4,6 +4,7 @@ namespace Tests\Auth;
 
 use BookStack\Access\Ldap;
 use BookStack\Access\LdapService;
+use BookStack\Exceptions\LdapException;
 use BookStack\Users\Models\Role;
 use BookStack\Users\Models\User;
 use Illuminate\Testing\TestResponse;
@@ -35,6 +36,7 @@ class LdapTest extends TestCase
             'services.ldap.user_filter'            => '(&(uid=${user}))',
             'services.ldap.follow_referrals'       => false,
             'services.ldap.tls_insecure'           => false,
+            'services.ldap.tls_ca_cert'            => false,
             'services.ldap.thumbnail_attribute'    => null,
         ]);
         $this->mockLdap = $this->mock(Ldap::class);
@@ -767,4 +769,34 @@ EBEQCgwSExIQEw8QEBD/yQALCAABAAEBAREA/8wABgAQEAX/2gAIAQEAAD8A0s8g/9k=')],
         $this->assertNotNull($user->avatar);
         $this->assertEquals('8c90748342f19b195b9c6b4eff742ded', md5_file(public_path($user->avatar->path)));
     }
+
+    public function test_tls_ca_cert_option_throws_if_set_to_invalid_location()
+    {
+        $path = 'non_found_' . time();
+        config()->set(['services.ldap.tls_ca_cert' => $path]);
+
+        $this->commonLdapMocks(0, 0, 0, 0, 0);
+
+        $this->assertThrows(function () {
+            $this->withoutExceptionHandling()->mockUserLogin();
+        }, LdapException::class, "Provided path [{$path}] for LDAP TLS CA certs could not be resolved to an existing location");
+    }
+
+    public function test_tls_ca_cert_option_used_if_set_to_a_folder()
+    {
+        $path = $this->files->testFilePath('');
+        config()->set(['services.ldap.tls_ca_cert' => $path]);
+
+        $this->mockLdap->shouldReceive('setOption')->once()->with(null, LDAP_OPT_X_TLS_CACERTDIR, rtrim($path, '/'))->andReturn(true);
+        $this->runFailedAuthLogin();
+    }
+
+    public function test_tls_ca_cert_option_used_if_set_to_a_file()
+    {
+        $path = $this->files->testFilePath('test-file.txt');
+        config()->set(['services.ldap.tls_ca_cert' => $path]);
+
+        $this->mockLdap->shouldReceive('setOption')->once()->with(null, LDAP_OPT_X_TLS_CACERTFILE, $path)->andReturn(true);
+        $this->runFailedAuthLogin();
+    }
 }