diff --git a/changelog/pending/20221220--cli-plugin--fix-check-of-executable-bits-on-windows.yaml b/changelog/pending/20221220--cli-plugin--fix-check-of-executable-bits-on-windows.yaml
new file mode 100644
index 000000000000..2440b7a6bd4e
--- /dev/null
+++ b/changelog/pending/20221220--cli-plugin--fix-check-of-executable-bits-on-windows.yaml
@@ -0,0 +1,4 @@
+changes:
+- type: fix
+  scope: cli/plugin
+  description: Fix check of executable bits on Windows.
diff --git a/pkg/cmd/pulumi/package.go b/pkg/cmd/pulumi/package.go
index e229d3f5a72b..8218b50febf9 100644
--- a/pkg/cmd/pulumi/package.go
+++ b/pkg/cmd/pulumi/package.go
@@ -20,6 +20,7 @@ import (
 	"io/fs"
 	"os"
 	"path/filepath"
+	"runtime"
 	"strings"
 
 	"github.com/blang/semver"
@@ -109,6 +110,10 @@ func schemaFromSchemaSource(packageSource string) (*schema.Package, error) {
 	}
 
 	isExecutable := func(info fs.FileInfo) bool {
+		// Windows doesn't have executable bits to check
+		if runtime.GOOS == "windows" {
+			return !info.IsDir()
+		}
 		return info.Mode()&0111 != 0 && !info.IsDir()
 	}
 
diff --git a/pkg/cmd/pulumi/plugin_install.go b/pkg/cmd/pulumi/plugin_install.go
index 0ac39e0aa03f..b205d51dbe3e 100644
--- a/pkg/cmd/pulumi/plugin_install.go
+++ b/pkg/cmd/pulumi/plugin_install.go
@@ -233,7 +233,12 @@ func getFilePayload(file string, spec workspace.PluginSpec) (workspace.PluginCon
 		return nil, fmt.Errorf("seeking back in file %s: %w", source, err)
 	}
 	if !encoding.IsCompressed(compressHeader) {
-		if (stat.Mode() & 0100) == 0 {
+		// Windows doesn't have executable bits to check
+		if runtime.GOOS == "windows" {
+			if info.IsDir() {
+				return nil, fmt.Errorf("%s is not executable", source)
+			}
+		} else if (stat.Mode() & 0100) == 0 || info.IsDir() { {
 			return nil, fmt.Errorf("%s is not executable", source)
 		}
 		return workspace.SingleFilePlugin(f, spec), nil