diff --git a/orchestrate/skills/orchestrate/scripts/__tests__/comment-cli.test.ts b/orchestrate/skills/orchestrate/scripts/__tests__/comment-cli.test.ts
index e3c6954d4..f8c736a92 100644
--- a/orchestrate/skills/orchestrate/scripts/__tests__/comment-cli.test.ts
+++ b/orchestrate/skills/orchestrate/scripts/__tests__/comment-cli.test.ts
@@ -2,14 +2,15 @@ import { describe, expect, test } from "bun:test";
 import { spawnSync } from "node:child_process";
 import { mkdtempSync, rmSync, writeFileSync } from "node:fs";
 import { tmpdir } from "node:os";
-import { join } from "node:path";
+import { dirname, join } from "node:path";
+import { fileURLToPath } from "node:url";
 
 import { loadKickoffThreadTsOrBail } from "../cli/comments.ts";
 
 const TEST_SLACK_CHANNEL = "C123TEST";
 
-const CLI_PATH = new URL("../cli.ts", import.meta.url).pathname;
-const SCRIPTS_DIR = new URL("..", import.meta.url).pathname;
+const CLI_PATH = fileURLToPath(new URL("../cli.ts", import.meta.url));
+const SCRIPTS_DIR = dirname(CLI_PATH);
 
 describe("comment CLI", () => {
   test("Refuses to post without --task or --thread-ts", () => {
diff --git a/orchestrate/skills/orchestrate/scripts/__tests__/kickoff-dedupe.test.ts b/orchestrate/skills/orchestrate/scripts/__tests__/kickoff-dedupe.test.ts
index 586c4aa39..81d12185e 100644
--- a/orchestrate/skills/orchestrate/scripts/__tests__/kickoff-dedupe.test.ts
+++ b/orchestrate/skills/orchestrate/scripts/__tests__/kickoff-dedupe.test.ts
@@ -1,7 +1,11 @@
 import { describe, expect, test } from "bun:test";
 import { spawnSync } from "node:child_process";
+import { dirname } from "node:path";
+import { fileURLToPath } from "node:url";
 
-const SCRIPTS_DIR = new URL("..", import.meta.url).pathname;
+const SCRIPTS_DIR = dirname(
+  fileURLToPath(new URL("../cli.ts", import.meta.url))
+);
 
 import {
   findActiveRootPlanner,
diff --git a/orchestrate/skills/orchestrate/scripts/__tests__/prompt-plan-validation.test.ts b/orchestrate/skills/orchestrate/scripts/__tests__/prompt-plan-validation.test.ts
index 033abcb9e..c852dda11 100644
--- a/orchestrate/skills/orchestrate/scripts/__tests__/prompt-plan-validation.test.ts
+++ b/orchestrate/skills/orchestrate/scripts/__tests__/prompt-plan-validation.test.ts
@@ -3,12 +3,13 @@ import { spawnSync } from "node:child_process";
 import { mkdtempSync, rmSync, writeFileSync } from "node:fs";
 import { tmpdir } from "node:os";
 import { join } from "node:path";
+import { fileURLToPath } from "node:url";
 
 function runPromptWithPlan(plan: unknown): ReturnType<typeof spawnSync> {
   const workspace = mkdtempSync(join(tmpdir(), "orchestrate-plan-migration-"));
   writeFileSync(join(workspace, "plan.json"), JSON.stringify(plan, null, 2));
 
-  const cliPath = new URL("../cli.ts", import.meta.url).pathname;
+  const cliPath = fileURLToPath(new URL("../cli.ts", import.meta.url));
   try {
     return spawnSync(
       process.execPath,