diff --git a/.upgrade.yml b/.upgrade.yml
index a2d4baa0e..09f6ed7e0 100644
--- a/.upgrade.yml
+++ b/.upgrade.yml
@@ -205,8 +205,6 @@ mappings:
   FunctionalTest: SilverStripe\Dev\FunctionalTest
   InstallerTest: SilverStripe\Dev\InstallerTest
   MigrationTask: SilverStripe\Dev\MigrationTask
-  SapphireInfo: SilverStripe\Dev\SapphireInfo
-  SapphireREPL: SilverStripe\Dev\SapphireREPL
   SapphireTest: SilverStripe\Dev\SapphireTest
   TaskRunner: SilverStripe\Dev\TaskRunner
   TestMailer: SilverStripe\Dev\TestMailer
@@ -1018,6 +1016,14 @@ warnings:
       message: 'Use SilverStripe\CMS\BatchActions\CMSBatchAction_Archive instead'
     'EncryptAllPasswordsTask':
       message: 'Removed'
+    'SapphireInfo':
+      message: 'Removed'
+    'SilverStripe\Dev\SapphireREPL':
+      message: 'Removed'
+    'SilverStripe\Dev\SapphireInfo':
+      message: 'Deprecated'
+    'SilverStripe\Dev\InstallerTest':
+      message: 'Deprecated'
   methods:
     'SilverStripe\Security\Authenticator::register()':
       message: 'Custom authenticators work differently now'
diff --git a/_config/routes.yml b/_config/routes.yml
index 6d1368c95..990b68551 100644
--- a/_config/routes.yml
+++ b/_config/routes.yml
@@ -14,10 +14,6 @@ SilverStripe\Control\Director:
     'Security//$Action/$ID/$OtherID': SilverStripe\Security\Security
     'CMSSecurity//$Action/$ID/$OtherID': SilverStripe\Security\CMSSecurity
     'dev': SilverStripe\Dev\DevelopmentAdmin
-    'interactive': SilverStripe\Dev\SapphireREPL
-    'InstallerTest//$Action/$ID/$OtherID': SilverStripe\Dev\InstallerTest
-    'SapphireInfo//$Action/$ID/$OtherID': SilverStripe\Dev\SapphireInfo
-    'SapphireREPL//$Action/$ID/$OtherID': SilverStripe\Dev\SapphireREPL
 ---
 Name: security-limited
 After:
diff --git a/src/Dev/InstallerTest.php b/src/Dev/InstallerTest.php
index ba9b1b871..76f349cb8 100644
--- a/src/Dev/InstallerTest.php
+++ b/src/Dev/InstallerTest.php
@@ -6,6 +6,7 @@ use SilverStripe\Control\Controller;
 
 /**
  * Simple controller that the installer uses to test that URL rewriting is working.
+ * @deprecated 4.4.7 This class will be removed in Silverstripe Framework 5.
  */
 class InstallerTest extends Controller
 {
diff --git a/src/Dev/SapphireInfo.php b/src/Dev/SapphireInfo.php
index f915749ee..3b5868288 100644
--- a/src/Dev/SapphireInfo.php
+++ b/src/Dev/SapphireInfo.php
@@ -9,6 +9,7 @@ use SilverStripe\Security\Security;
 
 /**
  * Returns information about the current site instance.
+ * @deprecated 4.4.7 This class will be removed in Silverstripe Framework 5.
  */
 class SapphireInfo extends Controller
 {
diff --git a/src/Dev/SapphireREPL.php b/src/Dev/SapphireREPL.php
deleted file mode 100644
index 5b181fcb5..000000000
--- a/src/Dev/SapphireREPL.php
+++ /dev/null
@@ -1,110 +0,0 @@
-<?php
-
-namespace SilverStripe\Dev;
-
-use SilverStripe\Control\Controller;
-use SilverStripe\Control\Director;
-use Exception;
-
-/* Don't actually define these, since it'd clutter up the namespace.
-define('1',E_ERROR);
-define('2',E_WARNING);
-define('4',E_PARSE);
-define('8',E_NOTICE);
-define('16',E_CORE_ERROR);
-define('32',E_CORE_WARNING);
-define('64',E_COMPILE_ERROR);
-define('128',E_COMPILE_WARNING);
-define('256',E_USER_ERROR);
-define('512',E_USER_WARNING);
-define('1024',E_USER_NOTICE);
-define('2048',E_STRICT);
-define('4096',E_RECOVERABLE_ERROR);
-define('8192',E_DEPRECATED);
-define('16384',E_USER_DEPRECATED);
-define('30719',E_ALL);
-*/
-/**
- */
-class SapphireREPL extends Controller
-{
-
-    private static $allowed_actions = array(
-        'index'
-    );
-
-    public function error_handler($errno, $errstr, $errfile, $errline, $errctx)
-    {
-        // Ignore unless important error
-        if (($errno & ~( 2048 | 8192 | 16384 )) == 0) {
-            return ;
-        }
-        // Otherwise throw exception to handle in REPL loop
-        throw new Exception(sprintf("%s:%d\r\n%s", $errfile, $errline, $errstr));
-    }
-
-    public function index()
-    {
-        if (!Director::is_cli()) {
-            return "The SilverStripe Interactive Command-line doesn't work in a web browser."
-                . " Use 'sake interactive' from the command-line to run.";
-        }
-
-
-        /* Try using PHP_Shell if it exists */
-        @include 'php-shell-cmd.php' ;
-
-        /* Fall back to our simpler interface */
-        if (empty($__shell)) {
-            set_error_handler(array($this, 'error_handler'));
-
-            echo "SilverStripe Interactive Command-line (REPL interface). Type help for hints.\n\n";
-            while (true) {
-                echo CLI::text("?> ", "cyan");
-                echo CLI::start_colour("yellow");
-                $command = trim(fgets(STDIN, 4096));
-                echo CLI::end_colour();
-
-                if ($command == 'help' || $command == '?') {
-                    print "help or ? to exit\n" ;
-                    print "quit or \q to exit\n" ;
-                    print "install PHP_Shell for a more advanced interface with"
-                        . " auto-completion and readline support\n\n" ;
-                    continue ;
-                }
-
-                if ($command == 'quit' || $command == '\q') {
-                    break ;
-                }
-
-                // Simple command processing
-                if (substr($command, -1) == ';') {
-                    $command = substr($command, 0, -1);
-                }
-                $is_print = preg_match('/^\s*print/i', $command);
-                $is_return = preg_match('/^\s*return/i', $command);
-                if (!$is_print && !$is_return) {
-                    $command = "return ($command)";
-                }
-                $command .= ";";
-
-                try {
-                    $result = eval($command);
-                    if (!$is_print) {
-                        print_r($result);
-                    }
-                    echo "\n";
-                } catch (Exception $__repl_exception) {
-                    echo CLI::start_colour("red");
-                    printf(
-                        '%s (code: %d) got thrown' . PHP_EOL,
-                        get_class($__repl_exception),
-                        $__repl_exception->getCode()
-                    );
-                    print $__repl_exception;
-                    echo "\n";
-                }
-            }
-        }
-    }
-}