diff --git a/wp-admin/admin-ajax.php b/wp-admin/admin-ajax.php
index 30e9a414b5..087a11993d 100644
--- a/wp-admin/admin-ajax.php
+++ b/wp-admin/admin-ajax.php
@@ -164,6 +164,8 @@ if ( ! empty( $_POST['action'] ) && in_array( $_POST['action'], $core_actions_po
 	add_action( 'wp_ajax_' . $_POST['action'], 'wp_ajax_' . str_replace( '-', '_', $_POST['action'] ), 1 );
 }
 
+add_action( 'wp_ajax_nopriv_generate-password', 'wp_ajax_nopriv_generate_password' );
+
 add_action( 'wp_ajax_nopriv_heartbeat', 'wp_ajax_nopriv_heartbeat', 1 );
 
 $action = ( isset( $_REQUEST['action'] ) ) ? $_REQUEST['action'] : '';
diff --git a/wp-admin/includes/ajax-actions.php b/wp-admin/includes/ajax-actions.php
index 06c09f6e92..6f91c3a7ea 100644
--- a/wp-admin/includes/ajax-actions.php
+++ b/wp-admin/includes/ajax-actions.php
@@ -12,8 +12,7 @@
 //
 
 /**
- * Ajax handler for the Heartbeat API in
- * the no-privilege context.
+ * Ajax handler for the Heartbeat API in the no-privilege context.
  *
  * Runs when the user is not logged in.
  *
@@ -3976,6 +3975,15 @@ function wp_ajax_generate_password() {
 	wp_send_json_success( wp_generate_password( 24 ) );
 }
 
+/**
+ * Ajax handler for generating a password in the no-privilege context.
+ *
+ * @since 5.7.0
+ */
+function wp_ajax_nopriv_generate_password() {
+	wp_send_json_success( wp_generate_password( 24 ) );
+}
+
 /**
  * Ajax handler for saving the user's WordPress.org username.
  *
diff --git a/wp-admin/js/user-profile.js b/wp-admin/js/user-profile.js
index c8f8d03261..dfec0fdba2 100644
--- a/wp-admin/js/user-profile.js
+++ b/wp-admin/js/user-profile.js
@@ -157,7 +157,7 @@
 		var $generateButton,
 			$cancelButton;
 
-		$pass1Row = $( '.user-pass1-wrap, .user-pass-wrap' );
+		$pass1Row = $( '.user-pass1-wrap, .user-pass-wrap, .reset-pass-submit' );
 
 		// Hide the confirm password field when JavaScript support is enabled.
 		$('.user-pass2-wrap').hide();
@@ -461,4 +461,15 @@
 		}
 	} );
 
+	/*
+	 * We need to generate a password as soon as the Reset Password page is loaded,
+	 * to avoid double clicking the button to retrieve the first generated password.
+	 * See ticket #39638.
+	 */
+	$( document ).ready( function() {
+		if ( $( '.reset-pass-submit' ).length ) {
+			$( '.reset-pass-submit button.wp-generate-pw' ).trigger( 'click' );
+		}
+	});
+
 })(jQuery);
diff --git a/wp-admin/js/user-profile.min.js b/wp-admin/js/user-profile.min.js
index a43f6ab9e1..521356f36b 100644
--- a/wp-admin/js/user-profile.min.js
+++ b/wp-admin/js/user-profile.min.js
@@ -1,2 +1,2 @@
 /*! This file is auto-generated */
-!function(r){var e,a,n,t,i,o,d,l,p,c,u=!1,h=wp.i18n.__;function f(){"function"==typeof zxcvbn?(!a.val()||c.hasClass("is-open")?(a.val(a.data("pw")),a.trigger("pwupdate")):b(),g(),1!==parseInt(o.data("start-masked"),10)?a.attr("type","text"):o.trigger("click"),r("#pw-weak-text-label").text(h("Confirm use of weak password"))):setTimeout(f,50)}function w(s){o.attr({"aria-label":h(s?"Show password":"Hide password")}).find(".text").text(h(s?"Show":"Hide")).end().find(".dashicons").removeClass(s?"dashicons-hidden":"dashicons-visibility").addClass(s?"dashicons-visibility":"dashicons-hidden")}function m(s,e,a){var n=r("<div />");n.addClass("notice inline"),n.addClass("notice-"+(e?"success":"error")),n.text(r(r.parseHTML(a)).text()).wrapInner("<p />"),s.prop("disabled",e),s.siblings(".notice").remove(),s.before(n)}function v(){var s;e=r(".user-pass1-wrap, .user-pass-wrap"),r(".user-pass2-wrap").hide(),l=r("#submit, #wp-submit").on("click",function(){u=!1}),d=l.add(" #createusersub"),t=r(".pw-weak"),(i=t.find(".pw-checkbox")).on("change",function(){d.prop("disabled",!i.prop("checked"))}),(a=r("#pass1")).length?(p=a.val(),1===parseInt(a.data("reveal"),10)&&f(),a.on("input pwupdate",function(){a.val()!==p&&(p=a.val(),a.removeClass("short bad good strong"),g())})):a=r("#user_pass"),n=r("#pass2").on("input",function(){0<n.val().length&&(a.val(n.val()),n.val(""),p="",a.trigger("pwupdate"))}),a.is(":hidden")&&(a.prop("disabled",!0),n.prop("disabled",!0)),c=e.find(".wp-pwd"),s=e.find("button.wp-generate-pw"),(o=e.find(".wp-hide-pw")).show().on("click",function(){"password"===a.attr("type")?(a.attr("type","text"),w(!1)):(a.attr("type","password"),w(!0))}),s.show(),s.on("click",function(){u=!0,s.attr("aria-expanded","true"),c.show().addClass("is-open"),a.attr("disabled",!1),n.attr("disabled",!1),f(),w(!1),wp.ajax.post("generate-password").done(function(s){a.data("pw",s)})}),e.find("button.wp-cancel-pw").on("click",function(){u=!1,a.prop("disabled",!0),n.prop("disabled",!0),a.val("").trigger("pwupdate"),w(!1),c.hide().removeClass("is-open"),d.prop("disabled",!1)}),e.closest("form").on("submit",function(){u=!1,a.prop("disabled",!1),n.prop("disabled",!1),n.val(a.val())})}function b(){var s=r("#pass1").val();if(r("#pass-strength-result").removeClass("short bad good strong empty"),s&&""!==s.trim())switch(wp.passwordStrength.meter(s,wp.passwordStrength.userInputDisallowedList(),s)){case-1:r("#pass-strength-result").addClass("bad").html(pwsL10n.unknown);break;case 2:r("#pass-strength-result").addClass("bad").html(pwsL10n.bad);break;case 3:r("#pass-strength-result").addClass("good").html(pwsL10n.good);break;case 4:r("#pass-strength-result").addClass("strong").html(pwsL10n.strong);break;case 5:r("#pass-strength-result").addClass("short").html(pwsL10n.mismatch);break;default:r("#pass-strength-result").addClass("short").html(pwsL10n.short)}else r("#pass-strength-result").addClass("empty").html("&nbsp;")}function g(){var s=r("#pass-strength-result")[0];s.className&&(a.addClass(s.className),r(s).is(".short, .bad")?(i.prop("checked")||d.prop("disabled",!0),t.show()):(r(s).is(".empty")?(d.prop("disabled",!0),i.prop("checked",!1)):d.prop("disabled",!1),t.hide()))}r(document).ready(function(){var s,a,n,t,i=r("#display_name"),e=i.val(),o=r("#wp-admin-bar-my-account").find(".display-name");r("#pass1").val("").on("input pwupdate",b),r("#pass-strength-result").show(),r(".color-palette").on("click",function(){r(this).siblings('input[name="admin_color"]').prop("checked",!0)}),i.length&&(r("#first_name, #last_name, #nickname").on("blur.user_profile",function(){var a=[],n={display_nickname:r("#nickname").val()||"",display_username:r("#user_login").val()||"",display_firstname:r("#first_name").val()||"",display_lastname:r("#last_name").val()||""};n.display_firstname&&n.display_lastname&&(n.display_firstlast=n.display_firstname+" "+n.display_lastname,n.display_lastfirst=n.display_lastname+" "+n.display_firstname),r.each(r("option",i),function(s,e){a.push(e.value)}),r.each(n,function(s,e){e&&(e=e.replace(/<\/?[a-z][^>]*>/gi,""),n[s].length&&-1===r.inArray(e,a)&&(a.push(e),r("<option />",{text:e}).appendTo(i)))})}),i.on("change",function(){var s;n===t&&(s=r.trim(this.value)||e,o.text(s))})),s=r("#color-picker"),a=r("#colors-css"),n=r("input#user_id").val(),t=r('input[name="checkuser_id"]').val(),s.on("click.colorpicker",".color-option",function(){var s,e=r(this);if(!e.hasClass("selected")&&(e.siblings(".selected").removeClass("selected"),e.addClass("selected").find('input[type="radio"]').prop("checked",!0),n===t)){if((a=0===a.length?r('<link rel="stylesheet" />').appendTo("head"):a).attr("href",e.children(".css_url").val()),"undefined"!=typeof wp&&wp.svgPainter){try{s=r.parseJSON(e.children(".icon_colors").val())}catch(s){}s&&(wp.svgPainter.setColors(s),wp.svgPainter.paint())}r.post(ajaxurl,{action:"save-user-color-scheme",color_scheme:e.children('input[name="admin_color"]').val(),nonce:r("#color-nonce").val()}).done(function(s){s.success&&r("body").removeClass(s.data.previousScheme).addClass(s.data.currentScheme)})}}),v(),r("#generate-reset-link").on("click",function(){var e=r(this),s={user_id:userProfileL10n.user_id,nonce:userProfileL10n.nonce};e.parent().find(".notice-error").remove();s=wp.ajax.post("send-password-reset",s);s.done(function(s){m(e,!0,s)}),s.fail(function(s){m(e,!1,s)})})}),r("#destroy-sessions").on("click",function(s){var e=r(this);wp.ajax.post("destroy-sessions",{nonce:r("#_wpnonce").val(),user_id:r("#user_id").val()}).done(function(s){e.prop("disabled",!0),e.siblings(".notice").remove(),e.before('<div class="notice notice-success inline"><p>'+s.message+"</p></div>")}).fail(function(s){e.siblings(".notice").remove(),e.before('<div class="notice notice-error inline"><p>'+s.message+"</p></div>")}),s.preventDefault()}),window.generatePassword=f,r(window).on("beforeunload",function(){if(!0===u)return h("Your new password has not been saved.")})}(jQuery);
\ No newline at end of file
+!function(o){var e,a,t,n,i,r,d,p,l,c,u=!1,h=wp.i18n.__;function f(){"function"==typeof zxcvbn?(!a.val()||c.hasClass("is-open")?(a.val(a.data("pw")),a.trigger("pwupdate")):b(),g(),1!==parseInt(r.data("start-masked"),10)?a.attr("type","text"):r.trigger("click"),o("#pw-weak-text-label").text(h("Confirm use of weak password"))):setTimeout(f,50)}function w(s){r.attr({"aria-label":h(s?"Show password":"Hide password")}).find(".text").text(h(s?"Show":"Hide")).end().find(".dashicons").removeClass(s?"dashicons-hidden":"dashicons-visibility").addClass(s?"dashicons-visibility":"dashicons-hidden")}function m(s,e,a){var t=o("<div />");t.addClass("notice inline"),t.addClass("notice-"+(e?"success":"error")),t.text(o(o.parseHTML(a)).text()).wrapInner("<p />"),s.prop("disabled",e),s.siblings(".notice").remove(),s.before(t)}function v(){var s;e=o(".user-pass1-wrap, .user-pass-wrap, .reset-pass-submit"),o(".user-pass2-wrap").hide(),p=o("#submit, #wp-submit").on("click",function(){u=!1}),d=p.add(" #createusersub"),n=o(".pw-weak"),(i=n.find(".pw-checkbox")).on("change",function(){d.prop("disabled",!i.prop("checked"))}),(a=o("#pass1")).length?(l=a.val(),1===parseInt(a.data("reveal"),10)&&f(),a.on("input pwupdate",function(){a.val()!==l&&(l=a.val(),a.removeClass("short bad good strong"),g())})):a=o("#user_pass"),t=o("#pass2").on("input",function(){0<t.val().length&&(a.val(t.val()),t.val(""),l="",a.trigger("pwupdate"))}),a.is(":hidden")&&(a.prop("disabled",!0),t.prop("disabled",!0)),c=e.find(".wp-pwd"),s=e.find("button.wp-generate-pw"),(r=e.find(".wp-hide-pw")).show().on("click",function(){"password"===a.attr("type")?(a.attr("type","text"),w(!1)):(a.attr("type","password"),w(!0))}),s.show(),s.on("click",function(){u=!0,s.attr("aria-expanded","true"),c.show().addClass("is-open"),a.attr("disabled",!1),t.attr("disabled",!1),f(),w(!1),wp.ajax.post("generate-password").done(function(s){a.data("pw",s)})}),e.find("button.wp-cancel-pw").on("click",function(){u=!1,a.prop("disabled",!0),t.prop("disabled",!0),a.val("").trigger("pwupdate"),w(!1),c.hide().removeClass("is-open"),d.prop("disabled",!1)}),e.closest("form").on("submit",function(){u=!1,a.prop("disabled",!1),t.prop("disabled",!1),t.val(a.val())})}function b(){var s=o("#pass1").val();if(o("#pass-strength-result").removeClass("short bad good strong empty"),s&&""!==s.trim())switch(wp.passwordStrength.meter(s,wp.passwordStrength.userInputDisallowedList(),s)){case-1:o("#pass-strength-result").addClass("bad").html(pwsL10n.unknown);break;case 2:o("#pass-strength-result").addClass("bad").html(pwsL10n.bad);break;case 3:o("#pass-strength-result").addClass("good").html(pwsL10n.good);break;case 4:o("#pass-strength-result").addClass("strong").html(pwsL10n.strong);break;case 5:o("#pass-strength-result").addClass("short").html(pwsL10n.mismatch);break;default:o("#pass-strength-result").addClass("short").html(pwsL10n.short)}else o("#pass-strength-result").addClass("empty").html("&nbsp;")}function g(){var s=o("#pass-strength-result")[0];s.className&&(a.addClass(s.className),o(s).is(".short, .bad")?(i.prop("checked")||d.prop("disabled",!0),n.show()):(o(s).is(".empty")?(d.prop("disabled",!0),i.prop("checked",!1)):d.prop("disabled",!1),n.hide()))}o(document).ready(function(){var s,a,t,n,i=o("#display_name"),e=i.val(),r=o("#wp-admin-bar-my-account").find(".display-name");o("#pass1").val("").on("input pwupdate",b),o("#pass-strength-result").show(),o(".color-palette").on("click",function(){o(this).siblings('input[name="admin_color"]').prop("checked",!0)}),i.length&&(o("#first_name, #last_name, #nickname").on("blur.user_profile",function(){var a=[],t={display_nickname:o("#nickname").val()||"",display_username:o("#user_login").val()||"",display_firstname:o("#first_name").val()||"",display_lastname:o("#last_name").val()||""};t.display_firstname&&t.display_lastname&&(t.display_firstlast=t.display_firstname+" "+t.display_lastname,t.display_lastfirst=t.display_lastname+" "+t.display_firstname),o.each(o("option",i),function(s,e){a.push(e.value)}),o.each(t,function(s,e){e&&(e=e.replace(/<\/?[a-z][^>]*>/gi,""),t[s].length&&-1===o.inArray(e,a)&&(a.push(e),o("<option />",{text:e}).appendTo(i)))})}),i.on("change",function(){var s;t===n&&(s=o.trim(this.value)||e,r.text(s))})),s=o("#color-picker"),a=o("#colors-css"),t=o("input#user_id").val(),n=o('input[name="checkuser_id"]').val(),s.on("click.colorpicker",".color-option",function(){var s,e=o(this);if(!e.hasClass("selected")&&(e.siblings(".selected").removeClass("selected"),e.addClass("selected").find('input[type="radio"]').prop("checked",!0),t===n)){if((a=0===a.length?o('<link rel="stylesheet" />').appendTo("head"):a).attr("href",e.children(".css_url").val()),"undefined"!=typeof wp&&wp.svgPainter){try{s=o.parseJSON(e.children(".icon_colors").val())}catch(s){}s&&(wp.svgPainter.setColors(s),wp.svgPainter.paint())}o.post(ajaxurl,{action:"save-user-color-scheme",color_scheme:e.children('input[name="admin_color"]').val(),nonce:o("#color-nonce").val()}).done(function(s){s.success&&o("body").removeClass(s.data.previousScheme).addClass(s.data.currentScheme)})}}),v(),o("#generate-reset-link").on("click",function(){var e=o(this),s={user_id:userProfileL10n.user_id,nonce:userProfileL10n.nonce};e.parent().find(".notice-error").remove();s=wp.ajax.post("send-password-reset",s);s.done(function(s){m(e,!0,s)}),s.fail(function(s){m(e,!1,s)})})}),o("#destroy-sessions").on("click",function(s){var e=o(this);wp.ajax.post("destroy-sessions",{nonce:o("#_wpnonce").val(),user_id:o("#user_id").val()}).done(function(s){e.prop("disabled",!0),e.siblings(".notice").remove(),e.before('<div class="notice notice-success inline"><p>'+s.message+"</p></div>")}).fail(function(s){e.siblings(".notice").remove(),e.before('<div class="notice notice-error inline"><p>'+s.message+"</p></div>")}),s.preventDefault()}),window.generatePassword=f,o(window).on("beforeunload",function(){if(!0===u)return h("Your new password has not been saved.")}),o(document).ready(function(){o(".reset-pass-submit").length&&o(".reset-pass-submit button.wp-generate-pw").trigger("click")})}(jQuery);
\ No newline at end of file
diff --git a/wp-includes/version.php b/wp-includes/version.php
index 76ccea18fb..9c39501714 100644
--- a/wp-includes/version.php
+++ b/wp-includes/version.php
@@ -13,7 +13,7 @@
  *
  * @global string $wp_version
  */
-$wp_version = '5.7-alpha-50152';
+$wp_version = '5.7-alpha-50153';
 
 /**
  * Holds the WordPress DB revision, increments when changes are made to the WordPress DB schema.
diff --git a/wp-login.php b/wp-login.php
index 128e3b254c..301424f687 100644
--- a/wp-login.php
+++ b/wp-login.php
@@ -852,7 +852,7 @@ switch ( $action ) {
 		wp_enqueue_script( 'utils' );
 		wp_enqueue_script( 'user-profile' );
 
-		login_header( __( 'Reset Password' ), '<p class="message reset-pass">' . __( 'Enter your new password below.' ) . '</p>', $errors );
+		login_header( __( 'Reset Password' ), '<p class="message reset-pass">' . __( 'Enter your new password below or generate one.' ) . '</p>', $errors );
 
 		?>
 		<form name="resetpassform" id="resetpassform" action="<?php echo esc_url( network_site_url( 'wp-login.php?action=resetpass', 'login_post' ) ); ?>" method="post" autocomplete="off">
@@ -898,8 +898,9 @@ switch ( $action ) {
 
 			?>
 			<input type="hidden" name="rp_key" value="<?php echo esc_attr( $rp_key ); ?>" />
-			<p class="submit">
-				<input type="submit" name="wp-submit" id="wp-submit" class="button button-primary button-large" value="<?php esc_attr_e( 'Reset Password' ); ?>" />
+			<p class="submit reset-pass-submit">
+				<button type="button" class="button wp-generate-pw hide-if-no-js" aria-expanded="true"><?php _e( 'Generate Password' ); ?></button>
+				<input type="submit" name="wp-submit" id="wp-submit" class="button button-primary button-large" value="<?php esc_attr_e( 'Save Password' ); ?>" />
 			</p>
 		</form>