diff --git a/admin/class-convertkit-admin-deactivation.php b/admin/class-convertkit-admin-deactivation.php
new file mode 100644
index 000000000..aec9ce2bc
--- /dev/null
+++ b/admin/class-convertkit-admin-deactivation.php
@@ -0,0 +1,141 @@
+<?php
+/**
+ * ConvertKit Admin Deactivation class.
+ *
+ * @package ConvertKit
+ * @author ConvertKit
+ */
+
+/**
+ * Displays a modal requesting an optional reason for the user deactivating
+ * the Plugin.
+ *
+ * @package ConvertKit
+ * @author ConvertKit
+ */
+class ConvertKit_Admin_Deactivation {
+
+	/**
+	 * Registers action and filter hooks.
+	 *
+	 * @since   2.0.2
+	 */
+	public function __construct() {
+
+		add_action( 'admin_enqueue_scripts', array( $this, 'enqueue_scripts' ) );
+		add_action( 'admin_enqueue_scripts', array( $this, 'enqueue_styles' ) );
+		add_action( 'wp_ajax_convertkit_deactivation_modal_submit', array( $this, 'deactivation_modal_submit' ) );
+
+	}
+
+	/**
+	 * Enqueue JavaScript on the Plugins screen to handle displaying
+	 * and submitting the deactivation modal.
+	 *
+	 * @since   2.0.2
+	 *
+	 * @param   string $hook   Hook.
+	 */
+	public function enqueue_scripts( $hook ) {
+
+		// Bail if we are not on the Plugin screen.
+		if ( $hook !== 'plugins.php' ) {
+			return;
+		}
+
+		// Enqueue scripts.
+		wp_enqueue_script( 'convertkit-admin-deactivation', CONVERTKIT_PLUGIN_URL . 'resources/backend/js/deactivation.js', array( 'jquery' ), CONVERTKIT_PLUGIN_VERSION, true );
+		wp_localize_script(
+			'convertkit-admin-deactivation',
+			'convertkit_deactivation',
+			array(
+				'plugin' => array(
+					'name'    => strtolower( CONVERTKIT_PLUGIN_NAME ),
+					'version' => CONVERTKIT_PLUGIN_VERSION,
+				),
+			)
+		);
+
+		// Output deactivation modal view in admin footer.
+		add_action( 'admin_footer', array( $this, 'output_deactivation_modal' ) );
+
+	}
+
+	/**
+	 * Enqueue CSS on the Plugins screen to handle displaying
+	 * the deactivation modal.
+	 *
+	 * @since   2.0.2
+	 *
+	 * @param   string $hook   Hook.
+	 */
+	public function enqueue_styles( $hook ) {
+
+		// Bail if we are not on the Plugin screen.
+		if ( $hook !== 'plugins.php' ) {
+			return;
+		}
+
+		// Enqueue styles.
+		wp_enqueue_style( 'convertkit-admin-deactivation', CONVERTKIT_PLUGIN_URL . 'resources/backend/css/deactivation.css', array(), CONVERTKIT_PLUGIN_VERSION );
+
+	}
+
+	/**
+	 * Outputs the Deactivation Modal HTML, which is displayed by Javascript.
+	 *
+	 * @since   2.0.2
+	 */
+	public function output_deactivation_modal() {
+
+		// Define the deactivation reasons.
+		$reasons = array(
+			'temporary'          => array(
+				'label'       => __( 'This is temporary / debugging an issue.', 'convertkit' ),
+				'placeholder' => __( 'What problem are you experiencing?', 'convertkit' ),
+			),
+			'not_working'        => array(
+				'label'       => __( 'Could not get the plugin to work.', 'convertkit' ),
+				'placeholder' => __( 'What problem are you experiencing?', 'convertkit' ),
+			),
+			'better_alternative' => array(
+				'label'       => __( 'Found a better plugin.', 'convertkit' ),
+				'placeholder' => __( 'What\'s the plugin\'s name?', 'convertkit' ),
+			),
+			'not_required'       => array(
+				'label'       => __( 'Don\'t need this plugin.', 'convertkit' ),
+				'placeholder' => __( 'What\'s one thing we could improve?', 'convertkit' ),
+			),
+			'other'              => array(
+				'label'       => __( 'Other.', 'convertkit' ),
+				'placeholder' => __( 'What can we do better?', 'convertkit' ),
+			),
+		);
+
+		// Output modal, which will be displayed when the user clicks deactivate on this plugin.
+		require_once CONVERTKIT_PLUGIN_PATH . '/views/backend/deactivation/modal.php';
+
+	}
+
+	/**
+	 * Sends the deactivation reason.
+	 *
+	 * @since   2.0.2
+	 */
+	public function deactivation_modal_submit() {
+
+		// Build args.
+		// phpcs:disable WordPress.Security.NonceVerification
+		$args = array(
+			'product'     => sanitize_text_field( $_REQUEST['product'] ),
+			'version'     => sanitize_text_field( $_REQUEST['version'] ),
+			'reason'      => sanitize_text_field( $_REQUEST['reason'] ),
+			'reason_text' => sanitize_text_field( $_REQUEST['reason_text'] ),
+			'site_url'    => str_replace( wp_parse_url( get_bloginfo( 'url' ), PHP_URL_SCHEME ) . '://', '', get_bloginfo( 'url' ) ),
+		);
+		// phpcs:enable
+
+		// Send deactivation reason.
+	}
+
+}
diff --git a/includes/class-wp-convertkit.php b/includes/class-wp-convertkit.php
index cb21aa538..b724bdc28 100644
--- a/includes/class-wp-convertkit.php
+++ b/includes/class-wp-convertkit.php
@@ -67,6 +67,7 @@ private function initialize_admin() {
 		$this->classes['admin_bulk_edit']                     = new ConvertKit_Admin_Bulk_Edit();
 		$this->classes['admin_cache_plugins']                 = new ConvertKit_Admin_Cache_Plugins();
 		$this->classes['admin_category']                      = new ConvertKit_Admin_Category();
+		$this->classes['admin_deactivation']                  = new ConvertKit_Admin_Deactivation();
 		$this->classes['admin_landing_page']                  = new ConvertKit_Admin_Landing_Page();
 		$this->classes['admin_notices']                       = new ConvertKit_Admin_Notices();
 		$this->classes['admin_post']                          = new ConvertKit_Admin_Post();
diff --git a/resources/backend/css/deactivation.css b/resources/backend/css/deactivation.css
new file mode 100644
index 000000000..a97fe784e
--- /dev/null
+++ b/resources/backend/css/deactivation.css
@@ -0,0 +1,60 @@
+.convertkit-modal-overlay {
+	display: none;
+	position: fixed;
+	z-index: 99999999;
+	top: 0;
+	left: 0;
+	opacity: 0.5;
+	width: 100vw;
+	height: 100vh;
+	background-color: #000;
+}
+.convertkit-modal {
+	display: none;
+	position: absolute;
+	white-space: normal;
+	width: 400px;
+
+	z-index: 100000000;
+	box-sizing: border-box;
+	background-color: #f7f7f7;
+	box-shadow: 0 0 15px -5px rgba(0, 0, 0, .5);
+	transition: all .3s ease-out;
+}
+.convertkit-modal header {
+	position: relative;
+	height: 40px;
+	background: url(../images/logomark-red.svg) 20px 50% no-repeat;
+	background-size: 20px auto;
+	background-color: #212f4f;
+}
+.convertkit-modal header::before {
+	content: "";
+	display: block;
+	position: absolute;
+	top: 50%;
+	transform: translateY(-50%);
+	left: -10px;
+	border-top: 20px solid transparent;
+	border-right: 20px solid #212f4f;
+	border-bottom: 20px solid transparent;
+}
+.convertkit-modal header h2 {
+	font-size: 16px;
+	line-height: 40px;
+	font-weight: 400;
+	margin: 0;
+	padding: 0 20px 0 50px;
+	color: #fff;
+}
+.convertkit-modal form {
+	padding: 20px;
+}
+.convertkit-modal form ul {
+	margin: 0 0 20px 0;
+	padding: 0;
+}
+.convertkit-modal form input[type="text"] {
+	display: none;
+	margin: 0 0 20px 0;
+}
diff --git a/resources/backend/js/deactivation.js b/resources/backend/js/deactivation.js
new file mode 100644
index 000000000..b48e881f2
--- /dev/null
+++ b/resources/backend/js/deactivation.js
@@ -0,0 +1,125 @@
+/**
+ * Shows the deactivation modal window when the Plugin is deactivated
+ * through the Plugins screen, giving the user an option to specify
+ * why they are deactivating.
+ *
+ * @package ConvertKit
+ * @author ConvertKit
+ */
+
+var convertkit_deactivation_url;
+
+jQuery( document ).ready(
+	function( $ ) {
+
+		/**
+		 * Show deactivation modal if the user is deactivating our plugin.
+		 */
+		$( 'span.deactivate a' ).on(
+			'click',
+			function( e ) {
+
+				// If the link slug doesn't exist, let the request through.
+				var plugin_name = $( this ).closest( 'tr' ).data( 'slug' );
+				if ( typeof plugin_name === 'undefined' ) {
+					return true;
+				}
+
+				// If the Plugin being deactivated isn't our one, let the request through.
+				if ( plugin_name != convertkit_deactivation.plugin.name ) {
+					return true;
+				}
+
+				// If here, we're deactivating our plugin.
+				e.preventDefault();
+
+				// Store the target URL.
+				convertkit_deactivation_url = $( this ).attr( 'href' );
+
+				// Position the modal.
+				$( '#convertkit-deactivation-modal' ).css(
+					{
+						top: ( $( this ).offset().top - $( this ).height() - 25 ) + 'px',
+						left: ( $( this ).offset().left + $( this ).width() + 20 ) + 'px'
+					}
+				);
+
+				// Show the modal.
+				$( '#convertkit-deactivation-modal, #convertkit-deactivation-modal-overlay' ).show();
+
+			}
+		);
+
+		/**
+		 * Update input text field's placeholder when a reason radio button is clicked
+		 */
+		$( 'input[name="convertkit-deactivation-reason"]' ).on(
+			'change',
+			function( e ) {
+
+				$( 'input[name="convertkit-deactivation-reason-text"]' ).attr(
+					'placeholder',
+					$( this ).data( 'placeholder' )
+				).show();
+
+			}
+		);
+
+		/**
+		 * Send the result of the deactivation modal when the submit button is clicked,
+		 * and load the deactivation URL so that the plugin gets deactivated.
+		 */
+		$( 'form#convertkit-deactivation-modal-form' ).on(
+			'submit',
+			function( e ) {
+
+				e.preventDefault();
+
+				var convertkit_deactivation_reason  = $( 'input[name=convertkit-deactivation-reason]:checked', $( this ) ).val(),
+				convertkit_deactivation_reason_text = $( 'input[name=convertkit-deactivation-reason-text]', $( this ) ).val();
+
+				// Submit the form via AJAX if a reason was given.
+				if ( typeof convertkit_deactivation_reason !== 'undefined' ) {
+					$.ajax(
+						{
+							url: 		ajaxurl,
+							type: 		'POST',
+							async:    	true,
+							data: 		{
+								action: 		'convertkit_deactivation_modal_submit',
+								product: 		convertkit_deactivation.plugin.name,
+								version: 		convertkit_deactivation.plugin.version,
+								reason: 		convertkit_deactivation_reason,
+								reason_text: 	convertkit_deactivation_reason_text
+							},
+							error: function( a, b, c ) {
+							},
+							success: function( result ) {
+							}
+						}
+					);
+				}
+
+				// Hide the modal.
+				$( '#convertkit-deactivation-modal, #convertkit-deactivation-modal-overlay' ).hide();
+
+				// Load the deactivation URL.
+				window.location.href = convertkit_deactivation_url;
+
+			}
+		);
+
+		/**
+		 * Hide the overlay and modal when the overlay is clicked.
+		 */
+		$( '#convertkit-deactivation-modal-overlay' ).on(
+			'click',
+			function( e ) {
+
+				$( '#convertkit-deactivation-modal, #convertkit-deactivation-modal-overlay' ).hide();
+
+			}
+		);
+
+	}
+);
diff --git a/tests/acceptance/general/ActivateDeactivatePluginCest.php b/tests/acceptance/general/ActivateDeactivatePluginCest.php
index a7d4f3192..ab27ecb3b 100644
--- a/tests/acceptance/general/ActivateDeactivatePluginCest.php
+++ b/tests/acceptance/general/ActivateDeactivatePluginCest.php
@@ -43,7 +43,85 @@ public function testPluginActivationAndDeactivationWithOtherPlugins(AcceptanceTe
 
 		// Use API by loading Settings screen, which will use WordPress Libraries and show errors
 		// if there's a conflict e.g. an older WordPress Library was loaded from another ConvertKit Plugin.
-		$I->loadConvertKitSettingsGeneralScreen($I);
+		$I->setupConvertKitPlugin($I);
+
+		// Deactivate this Plugin.
+		$I->deactivateConvertKitPlugin($I);
+	}
+
+	/**
+	 * Test that the ConvertKit Plugin deactivates when clicking the Deactivate link on the Plugins
+	 * screen, completing the form fields on the deactivational modal and then submitting.
+	 *
+	 * @since   2.2.3
+	 *
+	 * @param   AcceptanceTester $I  Tester.
+	 */
+	public function testPluginDeactivationModal(AcceptanceTester $I)
+	{
+		$I->activateConvertKitPlugin($I);
+
+		// Deactivate using the 'Deactivate' link on the Plugins screen, which will trigger
+		// ConvertKit's deactivation modal.
+		$I->click('a#deactivate-convertkit');
+
+		// Wait for modal to appear.
+		$I->waitForElementVisible('#convertkit-deactivation-modal');
+
+		// Select each reason, ensuring the text input's placeholder updates.
+		$reasons = [
+			'temporary'          => 'What problem are you experiencing?',
+			'not_working'        => 'What problem are you experiencing?',
+			'better_alternative' => 'What\'s the plugin\'s name?',
+			'not_required'       => 'What\'s one thing we could improve?',
+			'other'              => 'What can we do better?',
+		];
+		foreach ($reasons as $reason => $placeholder) {
+			// Confirm reason can be selected as a radio button.
+			$I->selectOption('#convertkit-deactivation-modal input[name="convertkit-deactivation-reason"]', $reason);
+
+			// Confirm input field's placeholder has updated, based on the selected reason.
+			$I->assertEquals(
+				$I->grabAttributeFrom('input[name="convertkit-deactivation-reason-text"]', 'placeholder'),
+				$placeholder
+			);
+		}
+
+		// Complete the input field and submit.
+		$I->fillField('convertkit-deactivation-reason-text', 'Testing');
+		$I->click('#convertkit-deactivation-modal input[type="submit"]');
+
+		// Check that the Plugin deactivated successfully.
+		$I->seePluginDeactivated('convertkit');
+
+		// Check that no PHP warnings or notices were output.
+		$I->checkNoWarningsAndNoticesOnScreen($I);
+	}
+
+	/**
+	 * Test that the ConvertKit Plugin deactivates when clicking the Deactivate link on the Plugins
+	 * screen, ignoring the form fields on the deactivational modal and then submitting.
+	 *
+	 * @since   2.2.3
+	 *
+	 * @param   AcceptanceTester $I  Tester.
+	 */
+	public function testPluginDeactivationModalWithNoFormFieldValues(AcceptanceTester $I)
+	{
+		$I->activateConvertKitPlugin($I);
+
+		// Deactivate using the 'Deactivate' link on the Plugins screen, which will trigger
+		// ConvertKit's deactivation modal.
+		$I->click('a#deactivate-convertkit');
+
+		// Wait for modal to appear.
+		$I->waitForElementVisible('#convertkit-deactivation-modal');
+
+		// Submit deactivation modal.
+		$I->click('#convertkit-deactivation-modal input[type="submit"]');
+
+		// Check that the Plugin deactivated successfully.
+		$I->seePluginDeactivated('convertkit');
 
 		// Click the Save Changes button.
 		$I->click('Save Changes');
diff --git a/views/backend/deactivation/modal.php b/views/backend/deactivation/modal.php
new file mode 100644
index 000000000..7f1d2042e
--- /dev/null
+++ b/views/backend/deactivation/modal.php
@@ -0,0 +1,42 @@
+<?php
+/**
+ * Deactivation Modal view, displayed when a Plugin is deactivated.
+ *
+ * @package ConvertKit
+ * @author ConvertKit
+ */
+
+?>
+<div id="convertkit-deactivation-modal-overlay" class="convertkit-modal-overlay"></div>
+<div id="convertkit-deactivation-modal" class="convertkit-modal">
+	<header>
+		<h2 class="title">
+			<?php echo esc_html_e( 'What went wrong?', 'convertkit' ); ?>
+		</h2>
+	</header>
+
+	<form method="post" action="<?php echo esc_url( admin_url( 'plugins.php' ) ); ?>" id="convertkit-deactivation-modal-form">
+		<ul>
+			<?php
+			if ( is_array( $reasons ) && count( $reasons ) > 0 ) {
+				foreach ( $reasons as $reason => $labels ) {
+					?>
+					<li>
+						<label>
+							<span>
+								<input type="radio" name="convertkit-deactivation-reason" value="<?php echo esc_attr( $reason ); ?>" data-placeholder="<?php echo esc_attr( $labels['placeholder'] ); ?>" />
+							</span>
+							<span><?php echo esc_html( $labels['label'] ); ?></span>
+						</label>
+					</li>
+					<?php
+				}
+			}
+			?>
+		</ul>
+
+		<input type="text" name="convertkit-deactivation-reason-text" placeholder="" class="widefat" />
+
+		<input type="submit" name="submit" value="<?php esc_attr_e( 'Deactivate', 'convertkit' ); ?>" class="button" />
+	</form>
+</div>
diff --git a/wp-convertkit.php b/wp-convertkit.php
index 24ab686c5..71e71e567 100644
--- a/wp-convertkit.php
+++ b/wp-convertkit.php
@@ -117,6 +117,7 @@
 	require_once CONVERTKIT_PLUGIN_PATH . '/admin/class-convertkit-admin-quick-edit.php';
 	require_once CONVERTKIT_PLUGIN_PATH . '/admin/class-convertkit-admin-cache-plugins.php';
 	require_once CONVERTKIT_PLUGIN_PATH . '/admin/class-convertkit-admin-category.php';
+	require_once CONVERTKIT_PLUGIN_PATH . '/admin/class-convertkit-admin-deactivation.php';
 	require_once CONVERTKIT_PLUGIN_PATH . '/admin/class-convertkit-admin-notices.php';
 	require_once CONVERTKIT_PLUGIN_PATH . '/admin/class-convertkit-admin-post.php';
 	require_once CONVERTKIT_PLUGIN_PATH . '/admin/class-convertkit-admin-refresh-resources.php';