diff --git a/composer.json b/composer.json
index 9e15cd796..4cab67d75 100644
--- a/composer.json
+++ b/composer.json
@@ -37,12 +37,12 @@
     "wp-cli/site-health-command": "^1",
     "wp-cli/super-admin-command": "^2",
     "wp-cli/widget-command": "^2",
-    "wp-cli/wp-cli": "dev-main"
+    "wp-cli/wp-cli": "dev-try/os as 2.13"
   },
   "require-dev": {
     "roave/security-advisories": "dev-latest",
     "wp-cli/package-command": "^2.1",
-    "wp-cli/wp-cli-tests": "^5"
+    "wp-cli/wp-cli-tests": "dev-try/windows-logging"
   },
   "suggest": {
     "psy/psysh": "Enhanced `wp shell` functionality",
diff --git a/composer.lock b/composer.lock
index 6d8294312..9d16dc5b9 100644
--- a/composer.lock
+++ b/composer.lock
@@ -4,7 +4,7 @@
         "Read more about it at https://getcomposer.org/doc/01-basic-usage.md#installing-dependencies",
         "This file is @generated automatically"
     ],
-    "content-hash": "c2c06eaebfeb4c1884f044c795b98d19",
+    "content-hash": "7f7cfbfd23bec2b9f02ec2c4b2f8e28d",
     "packages": [
         {
             "name": "composer/semver",
@@ -2659,16 +2659,16 @@
         },
         {
             "name": "wp-cli/wp-cli",
-            "version": "dev-main",
+            "version": "dev-try/os",
             "source": {
                 "type": "git",
                 "url": "https://github.com/wp-cli/wp-cli.git",
-                "reference": "71de10fbf84c88cfe550f9f4c0664bad3f03796c"
+                "reference": "575fa2140ca2b0d0222a70c69df7c90ef5077e0e"
             },
             "dist": {
                 "type": "zip",
-                "url": "https://api.github.com/repos/wp-cli/wp-cli/zipball/71de10fbf84c88cfe550f9f4c0664bad3f03796c",
-                "reference": "71de10fbf84c88cfe550f9f4c0664bad3f03796c",
+                "url": "https://api.github.com/repos/wp-cli/wp-cli/zipball/575fa2140ca2b0d0222a70c69df7c90ef5077e0e",
+                "reference": "575fa2140ca2b0d0222a70c69df7c90ef5077e0e",
                 "shasum": ""
             },
             "require": {
@@ -2684,14 +2684,13 @@
                 "wp-cli/entity-command": "^2",
                 "wp-cli/extension-command": "^2",
                 "wp-cli/package-command": "^2",
-                "wp-cli/wp-cli-tests": "^5"
+                "wp-cli/wp-cli-tests": "dev-try/windows-logging"
             },
             "suggest": {
                 "ext-curl": "For better performance when making HTTP requests",
                 "ext-readline": "Include for a better --prompt implementation",
                 "ext-zip": "Needed to support extraction of ZIP archives when doing downloads or updates"
             },
-            "default-branch": true,
             "bin": [
                 "bin/wp",
                 "bin/wp.bat"
@@ -2739,7 +2738,7 @@
                 "issues": "https://github.com/wp-cli/wp-cli/issues",
                 "source": "https://github.com/wp-cli/wp-cli"
             },
-            "time": "2026-03-27T12:10:55+00:00"
+            "time": "2026-03-31T11:51:59+00:00"
         },
         {
             "name": "wp-cli/wp-config-transformer",
@@ -9567,16 +9566,16 @@
         },
         {
             "name": "wp-cli/wp-cli-tests",
-            "version": "v5.1.6",
+            "version": "dev-try/windows-logging",
             "source": {
                 "type": "git",
                 "url": "https://github.com/wp-cli/wp-cli-tests.git",
-                "reference": "af27f7a8e7627ebbad4a42555138ac2b98ac5d4e"
+                "reference": "149885daf2e4d0169d6e50151786f5b72afa1c29"
             },
             "dist": {
                 "type": "zip",
-                "url": "https://api.github.com/repos/wp-cli/wp-cli-tests/zipball/af27f7a8e7627ebbad4a42555138ac2b98ac5d4e",
-                "reference": "af27f7a8e7627ebbad4a42555138ac2b98ac5d4e",
+                "url": "https://api.github.com/repos/wp-cli/wp-cli-tests/zipball/149885daf2e4d0169d6e50151786f5b72afa1c29",
+                "reference": "149885daf2e4d0169d6e50151786f5b72afa1c29",
                 "shasum": ""
             },
             "require": {
@@ -9656,7 +9655,7 @@
                 "issues": "https://github.com/wp-cli/wp-cli-tests/issues",
                 "source": "https://github.com/wp-cli/wp-cli-tests"
             },
-            "time": "2026-03-25T20:11:12+00:00"
+            "time": "2026-03-31T10:29:36+00:00"
         },
         {
             "name": "wp-coding-standards/wpcs",
@@ -9789,11 +9788,19 @@
             "time": "2025-02-09T18:58:54+00:00"
         }
     ],
-    "aliases": [],
+    "aliases": [
+        {
+            "package": "wp-cli/wp-cli",
+            "version": "dev-try/os",
+            "alias": "2.13",
+            "alias_normalized": "2.13.0.0"
+        }
+    ],
     "minimum-stability": "dev",
     "stability-flags": {
         "roave/security-advisories": 20,
-        "wp-cli/wp-cli": 20
+        "wp-cli/wp-cli": 20,
+        "wp-cli/wp-cli-tests": 20
     },
     "prefer-stable": true,
     "prefer-lowest": false,
diff --git a/features/command.feature b/features/command.feature
index f9e5beff2..418c69b62 100644
--- a/features/command.feature
+++ b/features/command.feature
@@ -752,6 +752,8 @@ Feature: WP-CLI Commands
       honked
       """
 
+  # No trailing spaces on Windows.
+  @skip-windows
   Scenario: Register a longdesc for a given command
     Given an empty directory
     And a custom-cmd.php file:
diff --git a/features/requests.feature b/features/requests.feature
index 6c2cf1796..4b0ff5779 100644
--- a/features/requests.feature
+++ b/features/requests.feature
@@ -36,7 +36,12 @@ Feature: Requests integration with both v1 and v2
       5.8
       """
 
-    When I run `vendor/bin/wp eval 'var_dump( \WP_CLI\Utils\http_request( "GET", "https://example.com/" ) );'`
+    Given a check-request-v1-phar.php file:
+      """
+      <?php
+      var_dump( \WP_CLI\Utils\http_request( "GET", "https://example.com/" ) );
+      """
+    When I run `vendor/bin/wp eval-file check-request-v1-phar.php`
     Then STDOUT should contain:
       """
       object(Requests_Response)
@@ -60,7 +65,12 @@ Feature: Requests integration with both v1 and v2
       5.8
       """
 
-    When I run `wp eval 'var_dump( \WP_CLI\Utils\http_request( "GET", "https://example.com/" ) );'`
+    Given a check-request-v1.php file:
+      """
+      <?php
+      var_dump( \WP_CLI\Utils\http_request( "GET", "https://example.com/" ) );
+      """
+    When I run `wp eval-file check-request-v1.php`
     Then STDOUT should contain:
       """
       object(Requests_Response)
@@ -91,7 +101,12 @@ Feature: Requests integration with both v1 and v2
       6.2
       """
 
-    When I run `wp eval 'var_dump( \WP_CLI\Utils\http_request( "GET", "https://example.com/" ) );'`
+    Given a check-request-v2.php file:
+      """
+      <?php
+      var_dump( \WP_CLI\Utils\http_request( "GET", "https://example.com/" ) );
+      """
+    When I run `wp eval-file check-request-v2.php`
     Then STDOUT should contain:
       """
       object(WpOrg\Requests\Response)
@@ -200,7 +215,12 @@ Feature: Requests integration with both v1 and v2
       """
 
     # This can throw deprecated warnings on PHP 8.1+.
-    When I try `vendor/bin/wp eval 'var_dump( \WP_CLI\Utils\http_request( "GET", "https://example.com/" ) );'`
+    Given a check-request-v2-phar.php file:
+      """
+      <?php
+      var_dump( \WP_CLI\Utils\http_request( 'GET', 'https://example.com/' ) );
+      """
+    When I try `vendor/bin/wp eval-file check-request-v2-phar.php`
     Then STDOUT should contain:
       """
       object(Requests_Response)
@@ -227,11 +247,11 @@ Feature: Requests integration with both v1 and v2
       Just another Composer-based WordPress site
       """
 
-    When I run `vendor/bin/wp eval 'echo COOKIEHASH;'`
+    When I run `vendor/bin/wp eval "echo COOKIEHASH;"`
     And save STDOUT as {COOKIEHASH}
     Then STDOUT should not be empty
 
-    When I run `vendor/bin/wp eval 'echo wp_generate_auth_cookie( 1, 32503680000 );'`
+    When I run `vendor/bin/wp eval "echo wp_generate_auth_cookie( 1, 32503680000 );"`
     And save STDOUT as {AUTH_COOKIE}
     Then STDOUT should not be empty