diff --git a/Block/Adminhtml/System/Config/AutoUploadMapping.php b/Block/Adminhtml/System/Config/AutoUploadMapping.php
new file mode 100644
index 00000000..55837d21
--- /dev/null
+++ b/Block/Adminhtml/System/Config/AutoUploadMapping.php
@@ -0,0 +1,97 @@
+<?php
+
+namespace Cloudinary\Cloudinary\Block\Adminhtml\System\Config;
+
+use Cloudinary\Cloudinary\Core\ConfigurationInterface;
+use Magento\Backend\Block\Template\Context;
+use Magento\Config\Block\System\Config\Form\Field;
+use Magento\Framework\Data\Form\Element\AbstractElement;
+
+class AutoUploadMapping extends Field
+{
+    /**
+     * @var string
+     */
+    protected $_template = 'Cloudinary_Cloudinary::config/auto-upload-mapping-btn.phtml';
+
+    /**
+     * @var ConfigurationInterface
+     */
+    private $configuration;
+
+    /**
+     * @method __construct
+     * @param  Context                $context
+     * @param  ConfigurationInterface $configuration
+     * @param  array                  $data
+     */
+    public function __construct(
+        Context $context,
+        ConfigurationInterface $configuration,
+        array $data = []
+    ) {
+        $this->configuration = $configuration;
+        parent::__construct($context, $data);
+    }
+
+    /**
+     * Remove scope label
+     *
+     * @param  AbstractElement $element
+     * @return string
+     */
+    public function render(AbstractElement $element)
+    {
+        $element->unsScope()->unsCanUseWebsiteValue()->unsCanUseDefaultValue();
+        return parent::render($element);
+    }
+
+    /**
+     * Return element html
+     *
+     * @param  AbstractElement $element
+     * @return string
+     */
+    protected function _getElementHtml(AbstractElement $element)
+    {
+        return $this->_toHtml();
+    }
+
+    /**
+     * Return ajax url for collect button
+     *
+     * @return string
+     */
+    public function getAjaxUrl()
+    {
+        return $this->getUrl('cloudinary/ajax_system_config/autoUploadMapping');
+    }
+
+    /**
+     * @return bool
+     */
+    public function isEnabled()
+    {
+        return $this->configuration->isEnabled();
+    }
+
+    /**
+    * Generate collect button html
+    *
+    * @return string
+    */
+    public function getButtonHtml()
+    {
+        $button = $this->getLayout()->createBlock(
+            'Magento\Backend\Block\Widget\Button'
+        )->setData(
+            [
+               'id' => 'auto-upload-mapping-btn',
+               'label' => __('Map media directory'),
+               'disabled' => !$this->configuration->isEnabled(),
+           ]
+       );
+
+        return $button->toHtml();
+    }
+}
diff --git a/Controller/Adminhtml/Ajax/System/Config/AutoUploadMapping.php b/Controller/Adminhtml/Ajax/System/Config/AutoUploadMapping.php
new file mode 100644
index 00000000..4512f8a1
--- /dev/null
+++ b/Controller/Adminhtml/Ajax/System/Config/AutoUploadMapping.php
@@ -0,0 +1,130 @@
+<?php
+
+namespace Cloudinary\Cloudinary\Controller\Adminhtml\Ajax\System\Config;
+
+use Cloudinary\Cloudinary\Core\AutoUploadMapping\RequestProcessor;
+use Cloudinary\Cloudinary\Model\Configuration;
+use Magento\Backend\App\Action;
+use Magento\Backend\App\Action\Context;
+use Magento\Framework\App\Cache\TypeListInterface;
+use Magento\Framework\App\Config\ReinitableConfigInterface;
+use Magento\Framework\App\Config\ScopeConfigInterface;
+use Magento\Framework\App\Filesystem\DirectoryList;
+use Magento\Framework\Controller\Result\JsonFactory;
+use Magento\Framework\Controller\ResultInterface;
+use Magento\Framework\Message\ManagerInterface;
+
+/**
+ * @SuppressWarnings(PHPMD.CouplingBetweenObjects)
+ */
+class AutoUploadMapping extends Action
+{
+    const AUTO_UPLOAD_SETUP_FAIL_MESSAGE = 'Error. Unable to setup auto upload mapping.';
+
+    /**
+     * @var JsonFactory
+     */
+    private $jsonResultFactory;
+
+    /**
+     * @var RequestProcessor
+     */
+    protected $requestProcessor;
+
+    /**
+     * @var ManagerInterface
+     */
+    protected $messageManager;
+
+    /**
+     * @var Configuration
+     */
+    protected $configuration;
+
+    /**
+     * Application config
+     *
+     * @var ScopeConfigInterface
+     */
+    protected $appConfig;
+
+    /**
+     * @var TypeListInterface
+     */
+    protected $cacheTypeList;
+
+    /**
+     * @method __construct
+     * @param  Context                   $context
+     * @param  JsonFactory               $jsonResultFactory
+     * @param  RequestProcessor          $requestProcessor
+     * @param  ManagerInterface          $messageManager
+     * @param  Configuration             $configuration
+     * @param  TypeListInterface         $cacheTypeList
+     * @param  ReinitableConfigInterface $config
+     */
+    public function __construct(
+        Context $context,
+        JsonFactory $jsonResultFactory,
+        RequestProcessor $requestProcessor,
+        ManagerInterface $messageManager,
+        Configuration $configuration,
+        TypeListInterface $cacheTypeList,
+        ReinitableConfigInterface $config
+    ) {
+        parent::__construct($context);
+        $this->jsonResultFactory = $jsonResultFactory;
+        $this->requestProcessor = $requestProcessor;
+        $this->messageManager = $messageManager;
+        $this->configuration = $configuration;
+        $this->cacheTypeList = $cacheTypeList;
+        $this->appConfig = $config;
+    }
+
+    /**
+     * @return ResultInterface
+     */
+    public function execute()
+    {
+        try {
+            $this->validateAjaxRequest();
+            $this->cleanConfigCache();
+
+            if ($this->configuration->isEnabled()) {
+                if (!$this->requestProcessor->handle(DirectoryList::MEDIA, $this->configuration->getMediaBaseUrl(), true)) {
+                    throw new \Exception(self::AUTO_UPLOAD_SETUP_FAIL_MESSAGE);
+                }
+            }
+        } catch (\Exception $e) {
+            return $this->jsonResultFactory->create()
+                ->setHttpResponseCode(500)
+                ->setData(['error' => 1, 'message' => "ERROR during the mapping process: " . $e->getMessage(), 'errorcode' => $e->getCode()]);
+        }
+
+        return $this->jsonResultFactory->create()
+            ->setHttpResponseCode(\Magento\Framework\Webapi\Response::HTTP_OK)
+            ->setData(['error' => 0, 'message' => 'Successfully mapped media directory!']);
+    }
+
+    protected function cleanConfigCache()
+    {
+        $this->cacheTypeList->cleanType(\Magento\Framework\App\Cache\Type\Config::TYPE_IDENTIFIER);
+        $this->appConfig->reinit();
+        return $this;
+    }
+
+    protected function _isAllowed()
+    {
+        return $this->_authorization->isAllowed('Cloudinary_Cloudinary::config_cloudinary');
+    }
+
+    /**
+     * @throws \Exception
+     */
+    private function validateAjaxRequest()
+    {
+        if (!$this->getRequest()->isAjax()) {
+            throw new \Exception(self::NON_AJAX_REQUEST);
+        }
+    }
+}
diff --git a/Model/Observer/Configuration.php b/Model/Observer/Configuration.php
deleted file mode 100644
index 9164d19c..00000000
--- a/Model/Observer/Configuration.php
+++ /dev/null
@@ -1,104 +0,0 @@
-<?php
-
-namespace Cloudinary\Cloudinary\Model\Observer;
-
-use Cloudinary\Cloudinary\Core\AutoUploadMapping\RequestProcessor;
-use Magento\Framework\App\Cache\TypeListInterface;
-use Magento\Framework\App\Config\ReinitableConfigInterface;
-use Magento\Framework\App\Config\ScopeConfigInterface;
-use Magento\Framework\App\Filesystem\DirectoryList;
-use Magento\Framework\Event\Observer;
-use Magento\Framework\Event\ObserverInterface;
-use Magento\Framework\Message\ManagerInterface;
-
-class Configuration implements ObserverInterface
-{
-    const AUTO_UPLOAD_SETUP_FAIL_MESSAGE = 'Error. Unable to setup auto upload mapping.';
-
-    /**
-     * @var RequestProcessor
-     */
-    protected $requestProcessor;
-
-    /**
-     * @var ManagerInterface
-     */
-    protected $messageManager;
-
-    /**
-     * @var \Cloudinary\Cloudinary\Model\Configuration
-     */
-    protected $configuration;
-
-    /**
-     * Application config
-     *
-     * @var ScopeConfigInterface
-     */
-    protected $appConfig;
-
-    /**
-     * @var TypeListInterface
-     */
-    protected $cacheTypeList;
-
-    protected $changedPaths = [];
-
-    /**
-     * @param RequestProcessor                           $requestProcessor
-     * @param ManagerInterface                           $messageManager
-     * @param \Cloudinary\Cloudinary\Model\Configuration $configuration
-     * @param TypeListInterface                          $cacheTypeList
-     * @param ReinitableConfigInterface                  $config
-     */
-    public function __construct(
-        RequestProcessor $requestProcessor,
-        ManagerInterface $messageManager,
-        \Cloudinary\Cloudinary\Model\Configuration $configuration,
-        TypeListInterface $cacheTypeList,
-        ReinitableConfigInterface $config
-    ) {
-        $this->requestProcessor = $requestProcessor;
-        $this->messageManager = $messageManager;
-        $this->configuration = $configuration;
-        $this->cacheTypeList = $cacheTypeList;
-        $this->appConfig = $config;
-    }
-
-    /**
-     * @param Observer $observer
-     */
-    public function execute(Observer $observer)
-    {
-        //Clear config cache if needed
-        $this->changedPaths = (array) $observer->getEvent()->getChangedPaths();
-        if (count(
-            array_intersect(
-                $this->changedPaths,
-                [
-                \Cloudinary\Cloudinary\Model\Configuration::CONFIG_PATH_ENABLED,
-                \Cloudinary\Cloudinary\Model\Configuration::CONFIG_PATH_ENVIRONMENT_VARIABLE,
-                \Cloudinary\Cloudinary\Model\AutoUploadMapping\AutoUploadConfiguration::REQUEST_PATH
-                ]
-            )
-        ) > 0
-        ) {
-            $this->cleanConfigCache();
-        }
-
-        if (!$this->configuration->isEnabled()) {
-            return $this;
-        }
-
-        if (!$this->requestProcessor->handle(DirectoryList::MEDIA, $this->configuration->getMediaBaseUrl(), true)) {
-            $this->messageManager->addErrorMessage(self::AUTO_UPLOAD_SETUP_FAIL_MESSAGE);
-        }
-    }
-
-    protected function cleanConfigCache()
-    {
-        $this->cacheTypeList->cleanType(\Magento\Framework\App\Cache\Type\Config::TYPE_IDENTIFIER);
-        $this->appConfig->reinit();
-        return $this;
-    }
-}
diff --git a/composer.json b/composer.json
index d6cf5314..1cf35def 100644
--- a/composer.json
+++ b/composer.json
@@ -2,7 +2,7 @@
     "name": "cloudinary/cloudinary-magento2",
     "description": "Cloudinary Magento 2 Integration.",
     "type": "magento2-module",
-    "version": "1.15.2",
+    "version": "1.16.0",
     "license": "MIT",
     "require": {
         "cloudinary/cloudinary_php": "^1.20.0"
diff --git a/etc/adminhtml/events.xml b/etc/adminhtml/events.xml
index a9c2ee94..748cd58a 100644
--- a/etc/adminhtml/events.xml
+++ b/etc/adminhtml/events.xml
@@ -14,8 +14,4 @@
         <observer name="delete_images_from_cloudinary" instance="Cloudinary\Cloudinary\Model\Observer\DeleteProductImage" />
     </event>
 
-    <event name="admin_system_config_changed_section_cloudinary">
-        <observer name="cloudinary_configuration_observer" instance="Cloudinary\Cloudinary\Model\Observer\Configuration" />
-    </event>
-
 </config>
diff --git a/etc/adminhtml/system.xml b/etc/adminhtml/system.xml
index 3cf4f357..af50f581 100644
--- a/etc/adminhtml/system.xml
+++ b/etc/adminhtml/system.xml
@@ -42,9 +42,16 @@
                 </field>
                 <field id="cloudinary_auto_upload_mapping_request" translate="label comment" type="select" sortOrder="3" showInDefault="1" showInWebsite="0" showInStore="0" canRestore="1">
                     <label>Enable auto-upload</label>
-                    <comment>Automatically upload your existing Magento images to your Cloudinary account when an image is requested by a user.</comment>
+                    <comment>Automatically upload your existing Magento images to your Cloudinary account when an image is requested by a user. Once enabled, click the button below to map your Magento media directory to your Cloudinary account.</comment>
                     <source_model>Magento\Config\Model\Config\Source\Yesno</source_model>
                 </field>
+                <field id="cloudinary_auto_upload_mapping_button" translate="label comment" type="button" sortOrder="5" showInDefault="1" showInWebsite="0" showInStore="0">
+                    <frontend_model>Cloudinary\Cloudinary\Block\Adminhtml\System\Config\AutoUploadMapping</frontend_model>
+                    <depends>
+                        <field id="cloudinary_enabled">1</field>
+                        <field id="cloudinary_auto_upload_mapping_request">1</field>
+                    </depends>
+                </field>
             </group>
             <group id="transformations" translate="label" sortOrder="4" showInDefault="1" showInWebsite="0" showInStore="0">
                 <label>Default Image Transformations</label>
diff --git a/etc/module.xml b/etc/module.xml
index 73ad1044..2b436328 100644
--- a/etc/module.xml
+++ b/etc/module.xml
@@ -1,6 +1,6 @@
 <?xml version="1.0"?>
 <config xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xsi:noNamespaceSchemaLocation="urn:magento:framework:Module/etc/module.xsd">
-  <module name="Cloudinary_Cloudinary" setup_version="1.15.2">
+  <module name="Cloudinary_Cloudinary" setup_version="1.16.0">
       <sequence>
           <module name="Magento_ProductVideo"/>
           <module name="Magento_PageBuilder"/>
diff --git a/marketplace.composer.json b/marketplace.composer.json
index 2909bdbe..a9c687e3 100644
--- a/marketplace.composer.json
+++ b/marketplace.composer.json
@@ -2,7 +2,7 @@
     "name": "cloudinary/cloudinary",
     "description": "Cloudinary Magento 2 Integration.",
     "type": "magento2-module",
-    "version": "1.15.2",
+    "version": "1.16.0",
     "license": "MIT",
     "require": {
         "cloudinary/cloudinary_php": "^1.20.0"
diff --git a/view/adminhtml/templates/config/auto-upload-mapping-btn.phtml b/view/adminhtml/templates/config/auto-upload-mapping-btn.phtml
new file mode 100644
index 00000000..b7a8551a
--- /dev/null
+++ b/view/adminhtml/templates/config/auto-upload-mapping-btn.phtml
@@ -0,0 +1,43 @@
+<?php
+/**
+ * @var $block Cloudinary\Cloudinary\Block\Adminhtml\System\Config\AutoUploadMapping
+ */
+?>
+<?php echo $block->getButtonHtml() ?>
+<div id="auto-upload-mapping-message"></div>
+
+<?php if ($block->isEnabled()): ?>
+    <script>
+        require([
+            'jquery'
+        ], function($){
+            $(document).on('click', '#auto-upload-mapping-btn', function () {
+                $('body').trigger('processStart');
+                $('#auto-upload-mapping-message').html("");
+                $.getJSON('<?php echo $block->getAjaxUrl() ?>')
+                    .done(function(res) {
+                        if(res && !res.error){
+                            $('#auto-upload-mapping-message').html(
+                                '<p><div class="messages"><div class="message message-success success">' + (res.message || res) + '</div></div></p>'
+                            );
+                        }else{
+                            $('#auto-upload-mapping-message').html(
+                                '<p><div class="messages"><div class="message message-error error">' + (res.message || 'Unknown ERROR during the mapping process.') + '</div></div></p>'
+                            );
+                        }
+                    })
+                    .fail(function(e) {
+                        console.error(e);
+                        $('#auto-upload-mapping-message').html(
+                            '<p><div class="messages"><div class="message message-error error">' + (e.message || e || 'Unknown ERROR during the mapping process.') + '</div></div></p>'
+                        );
+                    })
+                    .always(function(res) {
+                        $('body').trigger('processStop');
+                    });
+            });
+        });
+    </script>
+<?php else: ?>
+    <p class="note"><?= __('This button would be available after enabling the module with a valid environment variable.') ?></p>
+<?php endif; ?>