diff --git a/bin/cli/commands/serve.mjs b/bin/cli/commands/serve.mjs
index 004b4815ac..456e2e6f77 100644
--- a/bin/cli/commands/serve.mjs
+++ b/bin/cli/commands/serve.mjs
@@ -1,7 +1,7 @@
 import { spawn } from "node:child_process";
 import { existsSync, readFileSync } from "node:fs";
 import { join, dirname } from "node:path";
-import { fileURLToPath } from "node:url";
+import { fileURLToPath, pathToFileURL } from "node:url";
 import { platform, totalmem } from "node:os";
 import { t } from "../i18n.mjs";
 import { writePidFile, cleanupPidFile, waitForServer } from "../utils/pid.mjs";
@@ -414,7 +414,7 @@ async function runWithSupervisor(
       if (detectMitmCrash(crashLog)) {
         try {
           const PROJECT_ROOT = join(dirname(fileURLToPath(import.meta.url)), "..", "..", "..");
-          const { updateSettings } = await import(`${PROJECT_ROOT}/src/lib/db/settings.ts`);
+          const { updateSettings } = await import(pathToFileURL(join(PROJECT_ROOT, "src/lib/db/settings.ts")).href);
           updateSettings({ mitmEnabled: false });
         } catch {}
         return "disable-mitm-and-retry";
diff --git a/bin/cli/commands/setup.mjs b/bin/cli/commands/setup.mjs
index 4ded5032d4..5415cdd70b 100644
--- a/bin/cli/commands/setup.mjs
+++ b/bin/cli/commands/setup.mjs
@@ -1,4 +1,4 @@
-import { fileURLToPath } from "node:url";
+import { fileURLToPath, pathToFileURL } from "node:url";
 import { dirname, resolve } from "node:path";
 import { createPrompt, printHeading, printInfo, printSuccess } from "../io.mjs";
 import { openOmniRouteDb } from "../sqlite.mjs";
@@ -16,7 +16,7 @@ import { t } from "../i18n.mjs";
 const PROJECT_ROOT = resolve(dirname(fileURLToPath(import.meta.url)), "../../..");
 
 async function getListCliTools() {
-  const { listCliTools } = await import(`${PROJECT_ROOT}/src/shared/constants/cliTools.ts`);
+  const { listCliTools } = await import(pathToFileURL(resolve(PROJECT_ROOT, "src/shared/constants/cliTools.ts")).href);
   return listCliTools;
 }
 
diff --git a/bin/cli/runtime.mjs b/bin/cli/runtime.mjs
index 6811896759..987fa82799 100644
--- a/bin/cli/runtime.mjs
+++ b/bin/cli/runtime.mjs
@@ -1,9 +1,14 @@
-import { fileURLToPath } from "node:url";
+import { fileURLToPath, pathToFileURL } from "node:url";
 import { dirname, resolve } from "node:path";
 import { apiFetch, isServerUp } from "./api.mjs";
 
 const PROJECT_ROOT = resolve(dirname(fileURLToPath(import.meta.url)), "../..");
 
+// Dynamic `import()` resolves its specifier as a URL, not as a filesystem path.
+// On Windows an absolute path starts with a drive letter, which the ESM loader
+// reads as the unsupported URL scheme `e:` and rejects. Pass a file:// URL.
+const projectFileUrl = (relPath) => pathToFileURL(resolve(PROJECT_ROOT, relPath)).href;
+
 export class ServerOfflineError extends Error {
   constructor(message = "Server is offline and operation requires HTTP runtime") {
     super(message);
@@ -22,8 +27,8 @@ function makeHttpContext(opts) {
 
 async function importDbModules() {
   const [combos, recovery] = await Promise.all([
-    import(`${PROJECT_ROOT}/src/lib/db/combos.ts`),
-    import(`${PROJECT_ROOT}/src/lib/db/recovery.ts`),
+    import(projectFileUrl("src/lib/db/combos.ts")),
+    import(projectFileUrl("src/lib/db/recovery.ts")),
   ]);
   return { combos, recovery };
 }
diff --git a/tests/unit/cli-combo-command.test.ts b/tests/unit/cli-combo-command.test.ts
index dc38e3349e..1bf00e341d 100644
--- a/tests/unit/cli-combo-command.test.ts
+++ b/tests/unit/cli-combo-command.test.ts
@@ -27,7 +27,14 @@ async function withComboEnv(fn: (dataDir: string) => Promise<void>) {
   } finally {
     console.log = originalLog;
     globalThis.fetch = ORIGINAL_FETCH;
-    fs.rmSync(dataDir, { recursive: true, force: true });
+    // On Windows the SQLite file may still be held open by the db module when
+    // the test ends, and rmSync then throws EPERM, failing a test whose
+    // assertions all passed. Retry, then give up quietly.
+    try {
+      fs.rmSync(dataDir, { recursive: true, force: true, maxRetries: 5, retryDelay: 50 });
+    } catch {
+      // best effort: the OS reclaims its own temp dir
+    }
 
     if (ORIGINAL_DATA_DIR === undefined) delete process.env.DATA_DIR;
     else process.env.DATA_DIR = ORIGINAL_DATA_DIR;
diff --git a/tests/unit/cli/windows-esm-import-paths.test.ts b/tests/unit/cli/windows-esm-import-paths.test.ts
new file mode 100644
index 0000000000..e85385cc9d
--- /dev/null
+++ b/tests/unit/cli/windows-esm-import-paths.test.ts
@@ -0,0 +1,68 @@
+import test from "node:test";
+import assert from "node:assert/strict";
+import fs from "node:fs";
+import path from "node:path";
+import { fileURLToPath, pathToFileURL } from "node:url";
+
+const PROJECT_ROOT = path.resolve(path.dirname(fileURLToPath(import.meta.url)), "../../..");
+
+// Regression guard for the Windows-only ESM loader failure:
+//
+//   Error: Only URLs with a scheme in: file, data, and node are supported by
+//   the default ESM loader. On Windows, absolute paths must be valid file://
+//   URLs. Received protocol 'e:'
+//
+// `import()` resolves its specifier as a URL. A POSIX absolute path like
+// /home/x/src/lib/db/combos.ts happens to also be a valid relative URL, so
+// interpolating it works by accident. A Windows absolute path is
+// E:\checkout\src\lib\db\combos.ts, whose leading drive letter the loader
+// parses as the URL scheme `e:` and rejects. Every such call site must go
+// through pathToFileURL().
+//
+// This broke `omniroute combo list/create/delete/switch` on Windows whenever
+// the CLI fell back to direct DB access with the server offline.
+
+const CLI_DIR = path.join(PROJECT_ROOT, "bin", "cli");
+
+function collectMjsFiles(dir: string): string[] {
+  const out: string[] = [];
+  for (const entry of fs.readdirSync(dir, { withFileTypes: true })) {
+    const full = path.join(dir, entry.name);
+    if (entry.isDirectory()) out.push(...collectMjsFiles(full));
+    else if (entry.name.endsWith(".mjs")) out.push(full);
+  }
+  return out;
+}
+
+test("bin/cli never passes an interpolated absolute path to dynamic import()", () => {
+  // Matches import(`${ANY_ROOT_CONST}/...`) — a raw filesystem path, not a URL.
+  const badImport = /\bimport\(\s*`\$\{[A-Za-z_$][\w$]*\}\//;
+
+  const offenders: string[] = [];
+  for (const file of collectMjsFiles(CLI_DIR)) {
+    const source = fs.readFileSync(file, "utf8");
+    source.split(/\r?\n/).forEach((line, i) => {
+      if (badImport.test(line)) {
+        offenders.push(`${path.relative(PROJECT_ROOT, file)}:${i + 1}: ${line.trim()}`);
+      }
+    });
+  }
+
+  assert.deepEqual(
+    offenders,
+    [],
+    "dynamic import() of an interpolated absolute path fails on Windows; " +
+      `wrap the path in pathToFileURL(...).href instead:\n${offenders.join("\n")}`,
+  );
+});
+
+test("runtime.mjs resolves db modules to a file:// URL", async () => {
+  const source = fs.readFileSync(path.join(CLI_DIR, "runtime.mjs"), "utf8");
+  assert.match(source, /pathToFileURL/, "runtime.mjs must build file:// URLs for dynamic imports");
+
+  // The real proof: the db fallback modules actually load on this platform.
+  const runtime = await import(pathToFileURL(path.join(CLI_DIR, "runtime.mjs")).href);
+  const ctx = await runtime.withDb(async (c: { kind: string; db: unknown }) => c);
+  assert.equal(ctx.kind, "db");
+  assert.ok(ctx.db);
+});