diff --git a/.changeset/thick-oranges-smoke.md b/.changeset/thick-oranges-smoke.md
new file mode 100644
index 000000000..95dd8b20f
--- /dev/null
+++ b/.changeset/thick-oranges-smoke.md
@@ -0,0 +1,5 @@
+---
+"@opennextjs/cloudflare": patch
+---
+
+fix: shell quoting on windows machines to avoid upload errors for routes with `[...path]` segments
diff --git a/packages/cloudflare/src/cli/commands/helpers.ts b/packages/cloudflare/src/cli/commands/helpers.ts
index 4f1149ec1..85b6a0ecd 100644
--- a/packages/cloudflare/src/cli/commands/helpers.ts
+++ b/packages/cloudflare/src/cli/commands/helpers.ts
@@ -83,6 +83,18 @@ export async function getEnvFromPlatformProxy(options: GetPlatformProxyOptions,
  * @returns escaped arg
  */
 export function quoteShellMeta(arg: string) {
+	if (process.platform === "win32") {
+		if (arg.length === 0) {
+			return '""';
+		}
+		const needsEscaping = /[&|<>^()%!"]/;
+		const needsQuotes = /\s/.test(arg) || needsEscaping.test(arg);
+		let escaped = arg.replace(/"/g, '""');
+		if (/[&|<>^()%!]/.test(arg)) {
+			escaped = escaped.replace(/[&|<>^()%!]/g, "^$&");
+		}
+		return needsQuotes ? `"${escaped}"` : escaped;
+	}
 	if (/["\s]/.test(arg) && !/'/.test(arg)) {
 		return `'${arg.replace(/(['\\])/g, "\\$1")}'`;
 	}