diff --git a/administrator/components/com_joomlaupdate/src/Model/UpdateModel.php b/administrator/components/com_joomlaupdate/src/Model/UpdateModel.php
index 44f4e3b9bb6a2..041b57d21a472 100644
--- a/administrator/components/com_joomlaupdate/src/Model/UpdateModel.php
+++ b/administrator/components/com_joomlaupdate/src/Model/UpdateModel.php
@@ -1347,15 +1347,36 @@ public function getPhpOptions()
         $options[]         = $option;
         $updateInformation = $this->getUpdateInformation();
 
-        // Check if configured database is compatible with the next major version of Joomla
-        $nextMajorVersion = Version::MAJOR_VERSION + 1;
-
-        if (version_compare($updateInformation['latest'], (string) $nextMajorVersion, '>=')) {
+        // Extra checks when updating to the next major version of Joomla
+        if (version_compare($updateInformation['latest'], (string) Version::MAJOR_VERSION + 1, '>=')) {
+            // Check if configured database is compatible with the next major version of Joomla
             $option         = new \stdClass();
             $option->label  = Text::sprintf('INSTL_DATABASE_SUPPORTED', $this->getConfiguredDatabaseType());
             $option->state  = $this->isDatabaseTypeSupported();
             $option->notice = null;
             $options[]      = $option;
+
+            // Check if the Joomla 5 backwards compatibility plugin is disabled
+            $plugin = ExtensionHelper::getExtensionRecord('compat', 'plugin', 0, 'behaviour');
+
+            $this->translateExtensionName($plugin);
+
+            $option         = new \stdClass();
+            $option->label  = Text::sprintf('COM_JOOMLAUPDATE_VIEW_DEFAULT_PLUGIN_DISABLED_TITLE', $plugin->name);
+            $option->state  = !PluginHelper::isEnabled('behaviour', 'compat');
+            $option->notice = $option->state ? null : Text::sprintf('COM_JOOMLAUPDATE_VIEW_DEFAULT_PLUGIN_DISABLED_NOTICE', $plugin->folder, $plugin->element);
+            $options[]      = $option;
+
+            // Check if the Joomla 6 backwards compatibility plugin is enabled
+            $plugin = ExtensionHelper::getExtensionRecord('compat6', 'plugin', 0, 'behaviour');
+
+            $this->translateExtensionName($plugin);
+
+            $option         = new \stdClass();
+            $option->label  = Text::sprintf('COM_JOOMLAUPDATE_VIEW_DEFAULT_PLUGIN_ENABLED_TITLE', $plugin->name);
+            $option->state  = PluginHelper::isEnabled('behaviour', 'compat6');
+            $option->notice = $option->state ? null : Text::sprintf('COM_JOOMLAUPDATE_VIEW_DEFAULT_PLUGIN_ENABLED_NOTICE', $plugin->folder, $plugin->element);
+            $options[]      = $option;
         }
 
         // Check if database structure is up to date
diff --git a/administrator/language/en-GB/com_joomlaupdate.ini b/administrator/language/en-GB/com_joomlaupdate.ini
index 871c1f8243e12..c77d66f15d6a2 100644
--- a/administrator/language/en-GB/com_joomlaupdate.ini
+++ b/administrator/language/en-GB/com_joomlaupdate.ini
@@ -180,6 +180,10 @@ COM_JOOMLAUPDATE_VIEW_DEFAULT_PACKAGE_INFO="You can also download <a href=\"%s\"
 COM_JOOMLAUPDATE_VIEW_DEFAULT_PACKAGE_REINSTALL="Reinstall package URL"
 COM_JOOMLAUPDATE_VIEW_DEFAULT_PHP_VERSION_NOT_SUPPORTED="Your PHP version is not supported"
 COM_JOOMLAUPDATE_VIEW_DEFAULT_PHP_VERSION_NOT_SUPPORTED_DESC="An update to Joomla %1$s was found, but your currently installed PHP version does not match <a href=\"https://downloads.joomla.org/technical-requirements\">the minimum requirements for Joomla %1$s</a>."
+COM_JOOMLAUPDATE_VIEW_DEFAULT_PLUGIN_DISABLED_NOTICE="Go to <a href=\"index.php?option=com_plugins&view=plugins&filter[folder]=%1$s&filter[element]=%2$s\">'System - Manage - Plugins'</a> and disable the plugin."
+COM_JOOMLAUPDATE_VIEW_DEFAULT_PLUGIN_DISABLED_TITLE="The '%s' plugin is disabled"
+COM_JOOMLAUPDATE_VIEW_DEFAULT_PLUGIN_ENABLED_NOTICE="Go to <a href=\"index.php?option=com_plugins&view=plugins&filter[folder]=%1$s&filter[element]=%2$s\">'System - Manage - Plugins'</a> and enable the plugin."
+COM_JOOMLAUPDATE_VIEW_DEFAULT_PLUGIN_ENABLED_TITLE="The '%s' plugin is enabled"
 COM_JOOMLAUPDATE_VIEW_DEFAULT_POTENTIALLY_DANGEROUS_PLUGIN="Potential Upgrade Issue."
 COM_JOOMLAUPDATE_VIEW_DEFAULT_POTENTIALLY_DANGEROUS_PLUGIN_CONFIRM_MESSAGE="Are you sure you want to acknowledge the warnings about potentially incompatible extensions and proceed with the update?"
 COM_JOOMLAUPDATE_VIEW_DEFAULT_POTENTIALLY_DANGEROUS_PLUGIN_DESC="This extension includes a plugin that could cause the update to fail.<br><br>To perform the Joomla update safely you should either update this extension to a version compatible with your target version of Joomla or disable the relevant plugin(s) and check again."
diff --git a/libraries/src/Console/UpdateCoreCommand.php b/libraries/src/Console/UpdateCoreCommand.php
index 63a08ee4b28d6..b14c274c8b235 100644
--- a/libraries/src/Console/UpdateCoreCommand.php
+++ b/libraries/src/Console/UpdateCoreCommand.php
@@ -15,6 +15,8 @@
 use Joomla\CMS\Installer\InstallerHelper;
 use Joomla\CMS\Language\Text;
 use Joomla\CMS\Log\Log;
+use Joomla\CMS\Plugin\PluginHelper;
+use Joomla\CMS\Version;
 use Joomla\Console\Command\AbstractCommand;
 use Joomla\Database\DatabaseInterface;
 use Joomla\Filesystem\Exception\FilesystemException;
@@ -192,7 +194,6 @@ public function doExecute(InputInterface $input, OutputInterface $output): int
         $this->progressBar->display();
         $this->progressBar->advance();
 
-
         $errors = $this->checkSchema();
 
         if ($errors > 0) {
@@ -203,6 +204,22 @@ public function doExecute(InputInterface $input, OutputInterface $output): int
             return self::ERR_CHECKS_FAILED;
         }
 
+        // If upgrading to a new major version, check pre-conditions
+        if (version_compare($this->updateInfo['latest'], (string) Version::MAJOR_VERSION + 1, '>=')) {
+            $this->progressBar->clear();
+            $this->ioStyle->writeln('Check pre-conditions for a major upgrade to version ' . $this->updateInfo['latest'] . '...');
+            $this->progressBar->display();
+            $this->progressBar->advance();
+
+            if (!$this->checkMajorUpgrade()) {
+                $this->progressBar->finish();
+
+                $this->ioStyle->info('The pre-conditions for a major upgrade are not fulfilled.');
+
+                return self::ERR_CHECKS_FAILED;
+            }
+        }
+
         $this->progressBar->clear();
         $this->ioStyle->writeln('Starting Joomla! update ...');
         $this->progressBar->display();
@@ -502,4 +519,32 @@ public function checkSchema(): int
 
         return $changeInformation['errorsCount'];
     }
+
+    /**
+     * Check pre-conditions for major version upgrade
+     *
+     * @return  boolean  True if success
+     *
+     * @since __DEPLOY_VERSION__
+     */
+    public function checkMajorUpgrade(): bool
+    {
+        $return = true;
+
+        $language = Factory::getLanguage();
+        $language->load('plg_behaviour_compat.sys', JPATH_ADMINISTRATOR);
+        $language->load('plg_behaviour_compat6.sys', JPATH_ADMINISTRATOR);
+
+        if (PluginHelper::isEnabled('behaviour', 'compat')) {
+            $this->ioStyle->error('The \'' . Text::_('PLG_BEHAVIOUR_COMPAT') . '\' plugin is enabled.');
+            $return = false;
+        }
+
+        if (!PluginHelper::isEnabled('behaviour', 'compat6')) {
+            $this->ioStyle->error('The \'' . Text::_('PLG_BEHAVIOUR_COMPAT6') . '\' plugin is disabled.');
+            $return = false;
+        }
+
+        return $return;
+    }
 }