diff --git a/features/plugin-install.feature b/features/plugin-install.feature
index 319c0787..7eae2b28 100644
--- a/features/plugin-install.feature
+++ b/features/plugin-install.feature
@@ -305,3 +305,77 @@ Feature: Install WordPress plugins
       """
       active
       """
+
+  Scenario: Install with --activate on already-active plugin should keep it activated
+    Given a WP install
+
+    When I run `wp plugin install hello-dolly --activate`
+    Then STDOUT should contain:
+      """
+      Plugin 'hello-dolly' activated.
+      """
+    And the return code should be 0
+
+    When I run `wp plugin list --name=hello-dolly --field=status`
+    Then STDOUT should be:
+      """
+      active
+      """
+
+    When I try `wp plugin install hello-dolly --activate`
+    Then STDERR should contain:
+      """
+      Warning: hello-dolly: Plugin already installed.
+      """
+    And STDOUT should contain:
+      """
+      Activating 'hello-dolly'...
+      """
+    And STDOUT should contain:
+      """
+      Plugin 'hello-dolly' activated.
+      """
+    And the return code should be 0
+
+    When I run `wp plugin list --name=hello-dolly --field=status`
+    Then STDOUT should be:
+      """
+      active
+      """
+
+  Scenario: Install with --activate-network on already-network-active plugin should keep it activated
+    Given a WP multisite install
+
+    When I run `wp plugin install hello-dolly --activate-network`
+    Then STDOUT should contain:
+      """
+      Plugin 'hello-dolly' network activated.
+      """
+    And the return code should be 0
+
+    When I run `wp plugin list --name=hello-dolly --field=status`
+    Then STDOUT should be:
+      """
+      active-network
+      """
+
+    When I try `wp plugin install hello-dolly --activate-network`
+    Then STDERR should contain:
+      """
+      Warning: hello-dolly: Plugin already installed.
+      """
+    And STDOUT should contain:
+      """
+      Network-activating 'hello-dolly'...
+      """
+    And STDOUT should contain:
+      """
+      Plugin 'hello-dolly' network activated.
+      """
+    And the return code should be 0
+
+    When I run `wp plugin list --name=hello-dolly --field=status`
+    Then STDOUT should be:
+      """
+      active-network
+      """
diff --git a/src/Plugin_Command.php b/src/Plugin_Command.php
index 06875d73..68cb819b 100644
--- a/src/Plugin_Command.php
+++ b/src/Plugin_Command.php
@@ -391,7 +391,8 @@ public function activate( $args, $assoc_args = [] ) {
 				// If force flag is set, deactivate and reactivate to run activation hooks.
 				if ( $force ) {
 					deactivate_plugins( $plugin->file, false, true );
-				} else {
+				} elseif ( ! $this->chained_command ) {
+					// Only skip if not part of a chained command.
 					WP_CLI::warning( "Plugin '{$plugin->name}' is already network active." );
 					continue;
 				}
@@ -401,7 +402,8 @@ public function activate( $args, $assoc_args = [] ) {
 				// If force flag is set, deactivate and reactivate to run activation hooks.
 				if ( $force ) {
 					deactivate_plugins( $plugin->file, false, false );
-				} else {
+				} elseif ( ! $this->chained_command ) {
+					// Only skip if not part of a chained command.
 					WP_CLI::warning( "Plugin '{$plugin->name}' is already active." );
 					continue;
 				}
@@ -415,22 +417,30 @@ public function activate( $args, $assoc_args = [] ) {
 			$result = activate_plugin( $plugin->file, '', $network_wide );
 
 			if ( is_wp_error( $result ) ) {
-				$message = $result->get_error_message();
-				$message = (string) preg_replace( '/<a\s[^>]+>.*<\/a>/im', '', $message );
-				$message = wp_strip_all_tags( $message );
-				$message = str_replace( 'Error: ', '', $message );
-				WP_CLI::warning( "Failed to activate plugin. {$message}" );
-				// If the error is due to unexpected output, display it for debugging
-				if ( 'unexpected_output' === $result->get_error_code() ) {
-					/**
-					 * @var string $output
-					 */
-					$output = $result->get_error_data();
-					if ( ! empty( $output ) ) {
-						WP_CLI::debug( "Unexpected output: {$output}", 'plugin' );
+				// When called from a chained command, treat 'already_active' as success.
+				// This handles race conditions where WordPress may have preserved activation
+				// status during the install process.
+				if ( $this->chained_command && 'plugin_already_active' === $result->get_error_code() ) {
+					$this->active_output( $plugin->name, $plugin->file, $network_wide, 'activate' );
+					++$successes;
+				} else {
+					$message = $result->get_error_message();
+					$message = (string) preg_replace( '/<a\s[^>]+>.*<\/a>/im', '', $message );
+					$message = wp_strip_all_tags( $message );
+					$message = str_replace( 'Error: ', '', $message );
+					WP_CLI::warning( "Failed to activate plugin. {$message}" );
+					// If the error is due to unexpected output, display it for debugging
+					if ( 'unexpected_output' === $result->get_error_code() ) {
+						/**
+						 * @var string $output
+						 */
+						$output = $result->get_error_data();
+						if ( ! empty( $output ) ) {
+							WP_CLI::debug( "Unexpected output: {$output}", 'plugin' );
+						}
 					}
+					++$errors;
 				}
-				++$errors;
 			} else {
 				$this->active_output( $plugin->name, $plugin->file, $network_wide, 'activate' );
 				++$successes;