diff --git a/features/plugin-install.feature b/features/plugin-install.feature
index 3f7a724d..8943e738 100644
--- a/features/plugin-install.feature
+++ b/features/plugin-install.feature
@@ -168,7 +168,7 @@ Feature: Install WordPress plugins
   Scenario: Paths aren't backslashed when destination folder already exists
     Given a WP install
 
-    When I run `pwd`
+    When I run `wp eval "echo str_replace(chr(92), '/', getcwd());"`
     Then save STDOUT as {WORKING_DIR}
 
     When I run `rm wp-content/plugins/akismet/akismet.php`
diff --git a/features/plugin-list-recently-active.feature b/features/plugin-list-recently-active.feature
index a3eb97f9..cbd97bf5 100644
--- a/features/plugin-list-recently-active.feature
+++ b/features/plugin-list-recently-active.feature
@@ -42,6 +42,8 @@ Feature: List recently active WordPress plugins
       | debug-bar    |
       | site-secrets |
 
+  # Skipped on Windows due to non-portable shell command substitution and newline discrepancies
+  @skip-windows
   Scenario: Use recently active plugin to activate plugins
     Given a WP install
 
@@ -114,6 +116,8 @@ Feature: List recently active WordPress plugins
       | debug-bar    |
       | site-secrets |
 
+  # Skipped on Windows due to non-portable shell command substitution and newline discrepancies
+  @skip-windows
   Scenario: For a MU site, use recently active plugin to activate plugins
     Given a WP multisite install
 
diff --git a/features/plugin-update.feature b/features/plugin-update.feature
index 73577748..771454d6 100644
--- a/features/plugin-update.feature
+++ b/features/plugin-update.feature
@@ -198,7 +198,8 @@ Feature: Update WordPress plugins
       """
 
   # Akismet currently requires WordPress 5.8
-  @require-wp-5.8
+  # Skipped on Windows because chmod does not reliably enforce unwritable files cross-platform
+  @require-wp-5.8 @skip-windows
   Scenario: Plugin updates that error should not report a success
     Given a WP install
     And I run `wp plugin install --force akismet --version=4.0`
@@ -237,7 +238,8 @@ Feature: Update WordPress plugins
       """
     And the return code should be 0
 
-  @require-wp-5.2
+  # Skipped on Windows because of sed usage that would need to be refactored for compatibility.
+  @require-wp-5.2 @skip-windows
   Scenario: Updating all plugins with some of them having an invalid version shouldn't report an error
     Given a WP install
     And I run `wp plugin delete akismet`
@@ -378,7 +380,8 @@ Feature: Update WordPress plugins
       Success: Updated 2 of 2 plugins.
       """
 
-  @require-wp-5.2
+  # Skipped on Windows because of mkdir usage that would need to be refactored for compatibility.
+  @require-wp-5.2 @skip-windows
   Scenario: Skip plugin update when plugin directory is a VCS checkout
     Given a WP install
     And I run `wp plugin install wordpress-importer --version=0.5 --force`
@@ -397,7 +400,8 @@ Feature: Update WordPress plugins
       """
     And the return code should be 1
 
-  @require-wp-5.2
+  # Skipped on Windows because of mkdir usage that would need to be refactored for compatibility.
+  @require-wp-5.2 @skip-windows
   Scenario: Update plugin in VCS checkout when --include-vcs is set
     Given a WP install
     And I run `wp plugin install wordpress-importer --version=0.5 --force`
diff --git a/features/plugin.feature b/features/plugin.feature
index 55839362..69445491 100644
--- a/features/plugin.feature
+++ b/features/plugin.feature
@@ -356,13 +356,13 @@ Feature: Manage WordPress plugins
       Automattic
       """
 
-    When I run `wp eval 'echo get_site_transient("update_plugins")->last_checked;'`
+    When I run `wp eval "echo get_site_transient('update_plugins')->last_checked;"`
     Then save STDOUT as {LAST_UPDATED}
 
     When I run `wp plugin list --skip-update-check`
     Then STDOUT should not be empty
 
-    When I run `wp eval 'echo get_site_transient("update_plugins")->last_checked;'`
+    When I run `wp eval "echo get_site_transient('update_plugins')->last_checked;"`
     Then STDOUT should be:
       """
       {LAST_UPDATED}
@@ -371,7 +371,7 @@ Feature: Manage WordPress plugins
     When I run `wp plugin list`
     Then STDOUT should not be empty
 
-    When I run `wp eval 'echo get_site_transient("update_plugins")->last_checked;'`
+    When I run `wp eval "echo get_site_transient('update_plugins')->last_checked;"`
     Then STDOUT should not contain:
       """
       {LAST_UPDATED}
@@ -467,7 +467,7 @@ Feature: Manage WordPress plugins
     Given a WP install
 
     When I run `rm -rf wp-content/plugins`
-    And I run `if test -d wp-content/plugins; then echo "fail"; fi`
+    And I run `wp eval "if ( is_dir('wp-content/plugins') ) echo 'fail';"`
     Then STDOUT should be empty
 
     When I run `wp plugin install wordpress-importer --activate`
diff --git a/features/theme-update.feature b/features/theme-update.feature
index 09633781..de2eeefd 100644
--- a/features/theme-update.feature
+++ b/features/theme-update.feature
@@ -264,7 +264,7 @@ Feature: Update WordPress themes
     And I run `wp theme path twentytwelve --dir`
     And save STDOUT as {THEME_DIR}
 
-    When I run `mkdir {THEME_DIR}/.git`
+    When I run `wp eval "is_dir( '{THEME_DIR}/.git' ) || mkdir( '{THEME_DIR}/.git', 0777, true ) || exit( 1 );"`
     And I try `wp theme update twentytwelve`
     Then STDERR should contain:
       """
@@ -282,7 +282,7 @@ Feature: Update WordPress themes
     And I run `wp theme path twentytwelve --dir`
     And save STDOUT as {THEME_DIR}
 
-    When I run `mkdir {THEME_DIR}/.git`
+    When I run `wp eval "is_dir( '{THEME_DIR}/.git' ) || mkdir( '{THEME_DIR}/.git', 0777, true ) || exit( 1 );"`
     And I run `wp theme update twentytwelve --include-vcs`
     Then STDOUT should contain:
       """
diff --git a/features/theme.feature b/features/theme.feature
index 53ea0303..ff9c1cc1 100644
--- a/features/theme.feature
+++ b/features/theme.feature
@@ -243,13 +243,13 @@ Feature: Manage WordPress themes
     When I run `wp theme list`
     Then STDOUT should not be empty
 
-    When I run `wp eval 'echo get_site_transient("update_themes")->last_checked;'`
+    When I run `wp eval "echo get_site_transient( 'update_themes' )->last_checked;"`
     Then save STDOUT as {LAST_UPDATED}
 
     When I run `wp theme list --skip-update-check`
     Then STDOUT should not be empty
 
-    When I run `wp eval 'echo get_site_transient("update_themes")->last_checked;'`
+    When I run `wp eval "echo get_site_transient( 'update_themes' )->last_checked;"`
     Then STDOUT should be:
       """
       {LAST_UPDATED}
@@ -258,7 +258,7 @@ Feature: Manage WordPress themes
     When I run `wp theme list`
     Then STDOUT should not be empty
 
-    When I run `wp eval 'echo get_site_transient("update_themes")->last_checked;'`
+    When I run `wp eval "echo get_site_transient( 'update_themes' )->last_checked;"`
     Then STDOUT should not contain:
       """
       {LAST_UPDATED}
@@ -269,7 +269,7 @@ Feature: Manage WordPress themes
     And I run `wp theme delete --all --force`
 
     When I run `rm -rf wp-content/themes`
-    And I run `if test -d wp-content/themes; then echo "fail"; fi`
+    And I run `wp eval "if ( is_dir('wp-content/themes') ) echo 'fail';"`
     Then STDOUT should be empty
 
     When I run `wp theme install twentytwelve --activate`
@@ -283,7 +283,7 @@ Feature: Manage WordPress themes
   Scenario: Attempt to activate or fetch a broken theme
     Given a WP install
 
-    When I run `mkdir -pv wp-content/themes/myth`
+    When I run `wp eval "is_dir( 'wp-content/themes/myth' ) || mkdir( 'wp-content/themes/myth', 0777, true ) || exit( 1 );"`
     Then the wp-content/themes/myth directory should exist
 
     When I try `wp theme activate myth`