diff --git a/wp-admin/about.php b/wp-admin/about.php
index 22ea828fe1..20a3932147 100644
--- a/wp-admin/about.php
+++ b/wp-admin/about.php
@@ -69,7 +69,7 @@ include( ABSPATH . 'wp-admin/admin-header.php' );
 			);
 			require_once ABSPATH . 'wp-admin/includes/class-wp-upgrader.php';
 			$updater = new WP_Automatic_Updater;
-			$can_auto_update = wp_http_supports( 'ssl' ) && $updater->should_update( 'core', $future_minor_update, ABSPATH );
+			$can_auto_update = wp_http_supports( array( 'ssl' ) ) && $updater->should_update( 'core', $future_minor_update, ABSPATH );
 
 			if ( $can_auto_update ) {
 				echo '<p class="about-auto-update cool">' . __( 'This site <strong>is</strong> able to apply these updates automatically. Cool!' ). '</p>';
diff --git a/wp-admin/includes/plugin-install.php b/wp-admin/includes/plugin-install.php
index 7f1e0f2c62..58a9e9bab7 100644
--- a/wp-admin/includes/plugin-install.php
+++ b/wp-admin/includes/plugin-install.php
@@ -60,17 +60,23 @@ function plugins_api($action, $args = null) {
 	$res = apply_filters( 'plugins_api', false, $action, $args );
 
 	if ( false === $res ) {
-		$url = 'http://api.wordpress.org/plugins/info/1.0/';
-		if ( wp_http_supports( array( 'ssl' ) ) )
+		$url = $http_url = 'http://api.wordpress.org/plugins/info/1.0/';
+		if ( $ssl = wp_http_supports( array( 'ssl' ) ) )
 			$url = set_url_scheme( $url, 'https' );
 
-		$request = wp_remote_post( $url, array(
+		$args = array(
 			'timeout' => 15,
 			'body' => array(
 				'action' => $action,
 				'request' => serialize( $args )
 			)
-		) );
+		);
+		$request = wp_remote_post( $url, $args );
+
+		if ( $ssl && is_wp_error( $request ) ) {
+			trigger_error( __( 'An unexpected error occurred. Something may be wrong with WordPress.org or this server&#8217;s configuration. If you continue to have problems, please try the <a href="http://wordpress.org/support/">support forums</a>.' ) . ' ' . '(WordPress could not establish a secure connection to WordPress.org. Please contact your server administrator.)', headers_sent() || WP_DEBUG ? E_USER_WARNING : E_USER_NOTICE );
+			$request = wp_remote_post( $http_url, $args );
+		}
 
 		if ( is_wp_error($request) ) {
 			$res = new WP_Error('plugins_api_failed', __( 'An unexpected error occurred. Something may be wrong with WordPress.org or this server&#8217;s configuration. If you continue to have problems, please try the <a href="http://wordpress.org/support/">support forums</a>.' ), $request->get_error_message() );
diff --git a/wp-admin/includes/theme.php b/wp-admin/includes/theme.php
index 0e48bac887..9ea69f2faa 100644
--- a/wp-admin/includes/theme.php
+++ b/wp-admin/includes/theme.php
@@ -282,16 +282,22 @@ function themes_api($action, $args = null) {
 	$res = apply_filters('themes_api', false, $action, $args); //NOTE: Allows a theme to completely override the builtin WordPress.org API.
 
 	if ( ! $res ) {
-		$url = 'http://api.wordpress.org/themes/info/1.0/';
-		if ( wp_http_supports( array( 'ssl' ) ) )
+		$url = $http_url = 'http://api.wordpress.org/themes/info/1.0/';
+		if ( $ssl = wp_http_supports( array( 'ssl' ) ) )
 			$url = set_url_scheme( $url, 'https' );
 
-		$request = wp_remote_post( $url, array(
+		$args = array(
 			'body' => array(
 				'action' => $action,
 				'request' => serialize( $args )
 			)
-		) );
+		);
+		$request = wp_remote_post( $url, $args );
+
+		if ( $ssl && is_wp_error( $request ) ) {
+			trigger_error( __( 'An unexpected error occurred. Something may be wrong with WordPress.org or this server&#8217;s configuration. If you continue to have problems, please try the <a href="http://wordpress.org/support/">support forums</a>.' ) . ' ' . '(WordPress could not establish a secure connection to WordPress.org. Please contact your server administrator.)', headers_sent() || WP_DEBUG ? E_USER_WARNING : E_USER_NOTICE );
+			$request = wp_remote_post( $http_url, $args );
+		}
 
 		if ( is_wp_error($request) ) {
 			$res = new WP_Error('themes_api_failed', __( 'An unexpected error occurred. Something may be wrong with WordPress.org or this server&#8217;s configuration. If you continue to have problems, please try the <a href="http://wordpress.org/support/">support forums</a>.' ), $request->get_error_message() );
diff --git a/wp-admin/includes/update.php b/wp-admin/includes/update.php
index 147ce4a10f..feafd94b87 100644
--- a/wp-admin/includes/update.php
+++ b/wp-admin/includes/update.php
@@ -103,9 +103,9 @@ function find_core_auto_update() {
 function get_core_checksums( $version, $locale ) {
 	$return = array();
 
-	$url = 'http://api.wordpress.org/core/checksums/1.0/?' . http_build_query( compact( 'version', 'locale' ), null, '&' );
+	$url = $http_url = 'http://api.wordpress.org/core/checksums/1.0/?' . http_build_query( compact( 'version', 'locale' ), null, '&' );
 
-	if ( wp_http_supports( array( 'ssl' ) ) )
+	if ( $ssl = wp_http_supports( array( 'ssl' ) ) )
 		$url = set_url_scheme( $url, 'https' );
 
 	$options = array(
@@ -113,6 +113,10 @@ function get_core_checksums( $version, $locale ) {
 	);
 
 	$response = wp_remote_get( $url, $options );
+	if ( $ssl && is_wp_error( $response ) ) {
+		trigger_error( __( 'An unexpected error occurred. Something may be wrong with WordPress.org or this server&#8217;s configuration. If you continue to have problems, please try the <a href="http://wordpress.org/support/">support forums</a>.' ) . ' ' . '(WordPress could not establish a secure connection to WordPress.org. Please contact your server administrator.)', headers_sent() || WP_DEBUG ? E_USER_WARNING : E_USER_NOTICE );
+		$response = wp_remote_get( $http_url, $options );
+	}
 
 	if ( is_wp_error( $response ) || 200 != wp_remote_retrieve_response_code( $response ) )
 		return false;
diff --git a/wp-admin/update-core.php b/wp-admin/update-core.php
index 99887d3607..3a17482c56 100644
--- a/wp-admin/update-core.php
+++ b/wp-admin/update-core.php
@@ -146,7 +146,7 @@ function core_upgrade_preamble() {
 		echo '<h3>';
 		_e('You have the latest version of WordPress.');
 
-		if ( wp_http_supports( 'ssl' ) ) {
+		if ( wp_http_supports( array( 'ssl' ) ) ) {
 			require_once ABSPATH . 'wp-admin/includes/class-wp-upgrader.php';
 			$upgrader = new WP_Automatic_Updater;
 			$future_minor_update = (object) array(
diff --git a/wp-includes/update.php b/wp-includes/update.php
index 9979ae9944..bc666fd225 100644
--- a/wp-includes/update.php
+++ b/wp-includes/update.php
@@ -93,8 +93,8 @@ function wp_version_check( $extra_stats = array() ) {
 	if ( $extra_stats )
 		$post_body = array_merge( $post_body, $extra_stats );
 
-	$url = 'http://api.wordpress.org/core/version-check/1.7/?' . http_build_query( $query, null, '&' );
-	if ( wp_http_supports( array( 'ssl' ) ) )
+	$url = $http_url = 'http://api.wordpress.org/core/version-check/1.7/?' . http_build_query( $query, null, '&' );
+	if ( $ssl = wp_http_supports( array( 'ssl' ) ) )
 		$url = set_url_scheme( $url, 'https' );
 
 	$options = array(
@@ -108,6 +108,10 @@ function wp_version_check( $extra_stats = array() ) {
 	);
 
 	$response = wp_remote_post( $url, $options );
+	if ( $ssl && is_wp_error( $response ) ) {
+		trigger_error( __( 'An unexpected error occurred. Something may be wrong with WordPress.org or this server&#8217;s configuration. If you continue to have problems, please try the <a href="http://wordpress.org/support/">support forums</a>.' ) . ' ' . '(WordPress could not establish a secure connection to WordPress.org. Please contact your server administrator.)', headers_sent() || WP_DEBUG ? E_USER_WARNING : E_USER_NOTICE );
+		$response = wp_remote_post( $http_url, $options );
+	}
 
 	if ( is_wp_error( $response ) || 200 != wp_remote_retrieve_response_code( $response ) )
 		return false;
@@ -246,11 +250,15 @@ function wp_update_plugins() {
 		'user-agent' => 'WordPress/' . $wp_version . '; ' . get_bloginfo( 'url' )
 	);
 
-	$url = 'http://api.wordpress.org/plugins/update-check/1.1/';
-	if ( wp_http_supports( array( 'ssl' ) ) )
+	$url = $http_url = 'http://api.wordpress.org/plugins/update-check/1.1/';
+	if ( $ssl = wp_http_supports( array( 'ssl' ) ) )
 		$url = set_url_scheme( $url, 'https' );
 
 	$raw_response = wp_remote_post( $url, $options );
+	if ( $ssl && is_wp_error( $raw_response ) ) {
+		trigger_error( __( 'An unexpected error occurred. Something may be wrong with WordPress.org or this server&#8217;s configuration. If you continue to have problems, please try the <a href="http://wordpress.org/support/">support forums</a>.' ) . ' ' . '(WordPress could not establish a secure connection to WordPress.org. Please contact your server administrator.)', headers_sent() || WP_DEBUG ? E_USER_WARNING : E_USER_NOTICE );
+		$raw_response = wp_remote_post( $http_url, $options );
+	}
 
 	if ( is_wp_error( $raw_response ) || 200 != wp_remote_retrieve_response_code( $raw_response ) )
 		return false;
@@ -382,11 +390,15 @@ function wp_update_themes() {
 		'user-agent'	=> 'WordPress/' . $wp_version . '; ' . get_bloginfo( 'url' )
 	);
 
-	$url = 'http://api.wordpress.org/themes/update-check/1.1/';
-	if ( wp_http_supports( array( 'ssl' ) ) )
+	$url = $http_url = 'http://api.wordpress.org/themes/update-check/1.1/';
+	if ( $ssl = wp_http_supports( array( 'ssl' ) ) )
 		$url = set_url_scheme( $url, 'https' );
 
 	$raw_response = wp_remote_post( $url, $options );
+	if ( $ssl && is_wp_error( $raw_response ) ) {
+		trigger_error( __( 'An unexpected error occurred. Something may be wrong with WordPress.org or this server&#8217;s configuration. If you continue to have problems, please try the <a href="http://wordpress.org/support/">support forums</a>.' ) . ' ' . '(WordPress could not establish a secure connection to WordPress.org. Please contact your server administrator.)', headers_sent() || WP_DEBUG ? E_USER_WARNING : E_USER_NOTICE );
+		$raw_response = wp_remote_post( $http_url, $options );
+	}
 
 	if ( is_wp_error( $raw_response ) || 200 != wp_remote_retrieve_response_code( $raw_response ) )
 		return false;