diff --git a/features/plugin-install.feature b/features/plugin-install.feature
index 48941dc37..f8b61ed5a 100644
--- a/features/plugin-install.feature
+++ b/features/plugin-install.feature
@@ -1,5 +1,8 @@
 Feature: Install WordPress plugins
 
+  Background:
+    Given an empty cache
+
   Scenario: Branch names should be removed from Github projects
     Given a WP install
 
diff --git a/features/upgradables.feature b/features/upgradables.feature
index 297781ec4..278f12750 100644
--- a/features/upgradables.feature
+++ b/features/upgradables.feature
@@ -212,3 +212,35 @@ Feature: Manage WordPress themes and plugins
       | type   | type_name | item                    | item_title              | version | zip_file                                                               | file_to_check                                                     |
       | theme  | Theme     | moina                   | Moina                   | 1.1.2   | https://wordpress.org/themes/download/moina.1.1.2.zip                  | {CONTENT_DIR}/moina/style.css                                     |
       | plugin | Plugin    | category-checklist-tree | Category Checklist Tree | 1.2     | https://downloads.wordpress.org/plugin/category-checklist-tree.1.2.zip | {CONTENT_DIR}/category-checklist-tree/category-checklist-tree.php |
+
+  @require-wp-4.5
+  Scenario Outline: Caches certain GitHub URLs
+    Given a WP install
+    And I run `wp plugin delete --all`
+
+    When I run `wp plugin install <zip_file>`
+    Then STDOUT should contain:
+      """
+      Plugin installed successfully
+      """
+    And STDOUT should not contain:
+      """
+      Using cached file '{SUITE_CACHE_DIR}/plugin/<item>-<version>
+      """
+
+    When I run `wp plugin delete --all`
+    And I run `wp plugin install <zip_file>`
+    Then STDOUT should contain:
+      """
+      Plugin installed successfully
+      """
+    And STDOUT should contain:
+      """
+      Using cached file '{SUITE_CACHE_DIR}/plugin/<item>-<version>
+      """
+
+    Examples:
+      | item                   | version | zip_file                                                                                          |
+      | one-time-login         | 0.4.0   | https://github.com/danielbachhuber/one-time-login/releases/latest                                 |
+      | preferred-languages    | 1.8.0   | https://github.com/swissspidy/preferred-languages/releases/download/1.8.0/preferred-languages.zip |
+      | generic-example-plugin | 0.1.1   | https://github.com/wp-cli-test/generic-example-plugin/archive/v0.1.1.zip                          |
diff --git a/src/WP_CLI/CommandWithUpgrade.php b/src/WP_CLI/CommandWithUpgrade.php
index 1d383f583..5c03ae847 100755
--- a/src/WP_CLI/CommandWithUpgrade.php
+++ b/src/WP_CLI/CommandWithUpgrade.php
@@ -227,6 +227,9 @@ public function install( $args, $assoc_args ) {
 					add_filter( 'upgrader_source_selection', $filter, 10 );
 				}
 
+				// Add item to cache allowlist if it matches certain URL patterns.
+				self::maybe_cache( $slug, $this->item_type );
+
 				if ( $file_upgrader->install( $slug ) ) {
 					$slug   = $file_upgrader->result['destination_name'];
 					$result = true;
@@ -841,6 +844,26 @@ private function parse_url_host_component( $url, $component ) {
 		return function_exists( 'wp_parse_url' ) ? wp_parse_url( $url, $component ) : parse_url( $url, $component );
 	}
 
+	/**
+	 * Add versioned GitHub URLs to cache allowlist.
+	 *
+	 * @param string $url The URL to check.
+	 */
+	protected static function maybe_cache( $url, $item_type ) {
+		$matches = [];
+
+		// cache release URLs like `https://github.com/wp-cli-test/generic-example-plugin/releases/download/v0.1.0/generic-example-plugin.0.1.0.zip`
+		if ( preg_match( '#github\.com/[^/]+/([^/]+)/releases/download/v?([^/]+)/.+\.zip#', $url, $matches ) ) {
+			WP_CLI::get_http_cache_manager()->whitelist_package( $url, $item_type, $matches[1], $matches[2] );
+			// cache archive URLs like `https://github.com/wp-cli-test/generic-example-plugin/archive/v0.1.0.zip`
+		} elseif ( preg_match( '#github\.com/[^/]+/([^/]+)/archive/(version/|)v?([^/]+)\.zip#', $url, $matches ) ) {
+			WP_CLI::get_http_cache_manager()->whitelist_package( $url, $item_type, $matches[1], $matches[3] );
+			// cache release URLs like `https://api.github.com/repos/danielbachhuber/one-time-login/zipball/v0.4.0`
+		} elseif ( preg_match( '#api\.github\.com/repos/[^/]+/([^/]+)/zipball/v?([^/]+)#', $url, $matches ) ) {
+			WP_CLI::get_http_cache_manager()->whitelist_package( $url, $item_type, $matches[1], $matches[2] );
+		}
+	}
+
 	/**
 	 * Get the latest package version based on a given repo slug.
 	 *
@@ -871,6 +894,13 @@ protected function get_the_latest_github_version( $repo_slug ) {
 			);
 		}
 
+		if ( 404 === wp_remote_retrieve_response_code( $response ) ) {
+			return new \WP_Error(
+				$decoded_body->status,
+				$decoded_body->message
+			);
+		}
+
 		if ( null === $decoded_body ) {
 			return new \WP_Error( 500, 'Empty response received from GitHub.com API' );
 		}