diff --git a/packages/cli/src/commands/agent/delete.ts b/packages/cli/src/commands/agent/delete.ts
index e5bc6a5d1..a3d9672e2 100644
--- a/packages/cli/src/commands/agent/delete.ts
+++ b/packages/cli/src/commands/agent/delete.ts
@@ -1,5 +1,6 @@
 import type { Command } from "commander";
 import { connectToDaemon, getDaemonHost } from "../../utils/client.js";
+import { isSameOrDescendantPath } from "../../utils/paths.js";
 
 export function addDeleteOptions(cmd: Command): Command {
   return cmd
@@ -69,12 +70,9 @@ export async function runDeleteCommand(
     if (options.all) {
       agents = agents.filter((a) => !a.archivedAt);
     } else if (options.cwd) {
-      const filterCwd = options.cwd;
       agents = agents.filter((a) => {
         if (a.archivedAt) return false;
-        const agentCwd = a.cwd.replace(/\/$/, "");
-        const targetCwd = filterCwd.replace(/\/$/, "");
-        return agentCwd === targetCwd || agentCwd.startsWith(targetCwd + "/");
+        return isSameOrDescendantPath(options.cwd!, a.cwd);
       });
     } else if (id) {
       const fetchResult = await client.fetchAgent(id);
diff --git a/packages/cli/src/commands/agent/ls.ts b/packages/cli/src/commands/agent/ls.ts
index 29e2a9b71..866869672 100644
--- a/packages/cli/src/commands/agent/ls.ts
+++ b/packages/cli/src/commands/agent/ls.ts
@@ -3,6 +3,7 @@ import type { AgentSnapshotPayload } from "@getpaseo/server";
 import { connectToDaemon, getDaemonHost } from "../../utils/client.js";
 import type { CommandOptions, ListResult, OutputSchema, CommandError } from "../../output/index.js";
 import { collectMultiple } from "../../utils/command-options.js";
+import { isSameOrDescendantPath } from "../../utils/paths.js";
 
 export function addLsOptions(cmd: Command): Command {
   return cmd
@@ -193,11 +194,7 @@ export async function runLsCommand(
 
     // Optional cwd filter.
     if (options.cwd) {
-      const targetCwd = options.cwd.replace(/\/$/, "");
-      agents = agents.filter((a) => {
-        const agentCwd = a.cwd.replace(/\/$/, "");
-        return agentCwd === targetCwd || agentCwd.startsWith(targetCwd + "/");
-      });
+      agents = agents.filter((a) => isSameOrDescendantPath(options.cwd!, a.cwd));
     }
 
     // Apply label filtering only when explicitly requested.
diff --git a/packages/cli/src/commands/agent/stop.ts b/packages/cli/src/commands/agent/stop.ts
index 5f4c4903c..13366eb06 100644
--- a/packages/cli/src/commands/agent/stop.ts
+++ b/packages/cli/src/commands/agent/stop.ts
@@ -1,5 +1,6 @@
 import { Command } from "commander";
 import { connectToDaemon, getDaemonHost } from "../../utils/client.js";
+import { isSameOrDescendantPath } from "../../utils/paths.js";
 import type {
   CommandOptions,
   SingleResult,
@@ -75,12 +76,9 @@ export async function runStopCommand(
       agents = agents.filter((a) => !a.archivedAt);
     } else if (options.cwd) {
       // Stop agents in directory
-      const filterCwd = options.cwd;
       agents = agents.filter((a) => {
         if (a.archivedAt) return false;
-        const agentCwd = a.cwd.replace(/\/$/, "");
-        const targetCwd = filterCwd.replace(/\/$/, "");
-        return agentCwd === targetCwd || agentCwd.startsWith(targetCwd + "/");
+        return isSameOrDescendantPath(options.cwd!, a.cwd);
       });
     } else if (id) {
       // Stop specific agent
diff --git a/packages/cli/src/commands/daemon/local-daemon.ts b/packages/cli/src/commands/daemon/local-daemon.ts
index 2ab0c596a..f2c92ad1d 100644
--- a/packages/cli/src/commands/daemon/local-daemon.ts
+++ b/packages/cli/src/commands/daemon/local-daemon.ts
@@ -294,7 +294,8 @@ export function resolveTcpHostFromListen(listen: string): string | null {
     normalized.startsWith("/") ||
     normalized.startsWith("unix://") ||
     normalized.startsWith("pipe://") ||
-    normalized.startsWith("\\\\.\\pipe\\")
+    normalized.startsWith("\\\\.\\pipe\\") ||
+    /^[A-Za-z]:[/\\]/.test(normalized)
   ) {
     return null;
   }
diff --git a/packages/cli/src/commands/worktree/archive.ts b/packages/cli/src/commands/worktree/archive.ts
index 695fc90f4..f75350fd4 100644
--- a/packages/cli/src/commands/worktree/archive.ts
+++ b/packages/cli/src/commands/worktree/archive.ts
@@ -1,3 +1,4 @@
+import path from "path";
 import type { Command } from "commander";
 import { connectToDaemon, getDaemonHost } from "../../utils/client.js";
 import type {
@@ -77,7 +78,7 @@ export async function runArchiveCommand(
 
     // Find the worktree by name or branch
     const worktree = listResponse.worktrees.find((wt) => {
-      const name = wt.worktreePath.split("/").pop();
+      const name = path.basename(wt.worktreePath);
       return name === nameArg || wt.branchName === nameArg;
     });
 
@@ -105,7 +106,7 @@ export async function runArchiveCommand(
       throw error;
     }
 
-    const worktreeName = worktree.worktreePath.split("/").pop() ?? nameArg;
+    const worktreeName = path.basename(worktree.worktreePath) || nameArg;
 
     return {
       type: "single",
diff --git a/packages/cli/src/utils/client.ts b/packages/cli/src/utils/client.ts
index 6517c0c74..22ce604d9 100644
--- a/packages/cli/src/utils/client.ts
+++ b/packages/cli/src/utils/client.ts
@@ -45,10 +45,15 @@ export function normalizeDaemonHost(raw: string): string | null {
     return trimmed.startsWith("\\\\.\\pipe\\") ? `pipe://${trimmed}` : trimmed;
   }
 
-  if (path.isAbsolute(trimmed)) {
+  if (trimmed.startsWith("/") || trimmed.startsWith("~")) {
     return `unix://${trimmed}`;
   }
 
+  // Windows absolute paths (e.g. C:\Users\foo) are filesystem paths, not TCP or IPC targets.
+  if (/^[A-Za-z]:[/\\]/.test(trimmed)) {
+    return null;
+  }
+
   if (/^\d+$/.test(trimmed)) {
     return `127.0.0.1:${trimmed}`;
   }
diff --git a/packages/cli/src/utils/paths.ts b/packages/cli/src/utils/paths.ts
new file mode 100644
index 000000000..e8339e1e6
--- /dev/null
+++ b/packages/cli/src/utils/paths.ts
@@ -0,0 +1,27 @@
+/**
+ * Path utilities for cwd filtering in agent commands.
+ */
+
+/**
+ * Check if `candidatePath` is the same directory as `basePath` or a descendant of it.
+ *
+ * Handles both Unix (/) and Windows (\) path separators, including mixed separators.
+ * This is important because agent cwd paths come from the agent's OS (could be Windows)
+ * while the CLI filter path comes from the user (could also be Windows or Unix).
+ */
+export function isSameOrDescendantPath(basePath: string, candidatePath: string): boolean {
+  // Normalize both paths: replace all backslashes with forward slashes, strip trailing separator
+  let normalizedBase = basePath.replace(/\\/g, "/").replace(/\/$/, "");
+  let normalizedCandidate = candidatePath.replace(/\\/g, "/").replace(/\/$/, "");
+
+  // Windows paths are case-insensitive — detect by drive letter prefix (e.g. "C:/")
+  if (/^[a-zA-Z]:\//.test(normalizedBase) || /^[a-zA-Z]:\//.test(normalizedCandidate)) {
+    normalizedBase = normalizedBase.toLowerCase();
+    normalizedCandidate = normalizedCandidate.toLowerCase();
+  }
+
+  return (
+    normalizedCandidate === normalizedBase ||
+    normalizedCandidate.startsWith(normalizedBase + "/")
+  );
+}
diff --git a/packages/cli/tests/18-local-daemon-utils.test.ts b/packages/cli/tests/18-local-daemon-utils.test.ts
index 81a1886ab..89780a673 100644
--- a/packages/cli/tests/18-local-daemon-utils.test.ts
+++ b/packages/cli/tests/18-local-daemon-utils.test.ts
@@ -42,4 +42,12 @@ console.log("=== Local Daemon Utility Helpers ===\n");
   console.log("✓ rejects empty and non-host listen values\n");
 }
 
+{
+  console.log("Test 5: rejects Windows absolute paths (not TCP endpoints)");
+  assert.strictEqual(resolveTcpHostFromListen("C:\\Users\\foo\\.paseo\\paseo.sock"), null);
+  assert.strictEqual(resolveTcpHostFromListen("D:\\project\\socket"), null);
+  assert.strictEqual(resolveTcpHostFromListen("C:\\paseo.sock"), null);
+  console.log("✓ rejects Windows absolute paths\n");
+}
+
 console.log("=== All local daemon utility tests passed ===");
diff --git a/packages/cli/tests/28-client-ipc-targets.test.ts b/packages/cli/tests/28-client-ipc-targets.test.ts
index ad9511237..09b999ba6 100644
--- a/packages/cli/tests/28-client-ipc-targets.test.ts
+++ b/packages/cli/tests/28-client-ipc-targets.test.ts
@@ -41,6 +41,13 @@ console.log("=== CLI IPC Target Helpers ===\n");
   console.log("✓ local unix socket paths normalize into IPC daemon targets\n");
 }
 
+{
+  console.log("Test 3b: Windows absolute paths are NOT treated as unix sockets");
+  assert.strictEqual(normalizeDaemonHost("C:\\Users\\foo\\.paseo\\paseo.sock"), null);
+  assert.strictEqual(normalizeDaemonHost("D:\\project\\socket"), null);
+  console.log("✓ Windows absolute paths are not treated as unix sockets\n");
+}
+
 {
   console.log("Test 4: default host resolution tries local IPC first, then localhost fallback");
   const paseoHome = mkdtempSync(path.join(os.tmpdir(), "paseo-client-targets-"));
diff --git a/packages/cli/tests/30-cwd-filter-paths.test.ts b/packages/cli/tests/30-cwd-filter-paths.test.ts
new file mode 100644
index 000000000..939adc7b6
--- /dev/null
+++ b/packages/cli/tests/30-cwd-filter-paths.test.ts
@@ -0,0 +1,213 @@
+#!/usr/bin/env npx tsx
+
+/**
+ * CWD Filter Path Tests
+ *
+ * Tests that cwd filtering in agent commands works correctly
+ * with both Unix and Windows-style paths.
+ *
+ * Bug: The original code used hardcoded "/" separators for:
+ *   1. Stripping trailing separators (only stripped "/", not "\")
+ *   2. Descendant matching (appended "/" instead of platform separator)
+ *
+ * This causes Windows paths like "C:\Users\dev\project" to fail matching
+ * against "C:\Users\dev\project\sub" because the code appends "/" instead
+ * of "\" for the startsWith check.
+ */
+
+import assert from "node:assert";
+import { isSameOrDescendantPath } from "../src/utils/paths.ts";
+
+console.log("=== CWD Filter Path Tests ===\n");
+
+// Test 1: Unix exact match
+{
+  console.log("Test 1: Unix exact match");
+  assert.strictEqual(
+    isSameOrDescendantPath("/home/user/project", "/home/user/project"),
+    true,
+    "exact Unix paths should match",
+  );
+  console.log("✓ Unix exact match\n");
+}
+
+// Test 2: Unix descendant match
+{
+  console.log("Test 2: Unix descendant match");
+  assert.strictEqual(
+    isSameOrDescendantPath("/home/user/project", "/home/user/project/src"),
+    true,
+    "Unix descendant should match",
+  );
+  console.log("✓ Unix descendant match\n");
+}
+
+// Test 3: Unix non-match (sibling)
+{
+  console.log("Test 3: Unix non-match (sibling)");
+  assert.strictEqual(
+    isSameOrDescendantPath("/home/user/project", "/home/user/other"),
+    false,
+    "sibling directories should not match",
+  );
+  console.log("✓ Unix non-match (sibling)\n");
+}
+
+// Test 4: Unix prefix overlap (project vs project2)
+{
+  console.log("Test 4: Unix prefix overlap (project vs project2)");
+  assert.strictEqual(
+    isSameOrDescendantPath("/home/user/project", "/home/user/project2"),
+    false,
+    "prefix overlap without separator should not match",
+  );
+  console.log("✓ Unix prefix overlap\n");
+}
+
+// Test 5: Unix trailing slash on base
+{
+  console.log("Test 5: Unix trailing slash on base");
+  assert.strictEqual(
+    isSameOrDescendantPath("/home/user/project/", "/home/user/project/src"),
+    true,
+    "trailing slash on base should still match descendants",
+  );
+  console.log("✓ Unix trailing slash on base\n");
+}
+
+// Test 6: Unix trailing slash on candidate
+{
+  console.log("Test 6: Unix trailing slash on candidate");
+  assert.strictEqual(
+    isSameOrDescendantPath("/home/user/project", "/home/user/project/"),
+    true,
+    "trailing slash on candidate should match as same dir",
+  );
+  console.log("✓ Unix trailing slash on candidate\n");
+}
+
+// Test 7: Windows exact match
+{
+  console.log("Test 7: Windows exact match");
+  assert.strictEqual(
+    isSameOrDescendantPath("C:\\Users\\dev\\project", "C:\\Users\\dev\\project"),
+    true,
+    "exact Windows paths should match",
+  );
+  console.log("✓ Windows exact match\n");
+}
+
+// Test 8: Windows descendant match
+{
+  console.log("Test 8: Windows descendant match");
+  assert.strictEqual(
+    isSameOrDescendantPath("C:\\Users\\dev\\project", "C:\\Users\\dev\\project\\src"),
+    true,
+    "Windows descendant should match",
+  );
+  console.log("✓ Windows descendant match\n");
+}
+
+// Test 9: Windows non-match (sibling)
+{
+  console.log("Test 9: Windows non-match (sibling)");
+  assert.strictEqual(
+    isSameOrDescendantPath("C:\\Users\\dev\\project", "C:\\Users\\dev\\other"),
+    false,
+    "Windows sibling directories should not match",
+  );
+  console.log("✓ Windows non-match (sibling)\n");
+}
+
+// Test 10: Windows prefix overlap (project vs project2)
+{
+  console.log("Test 10: Windows prefix overlap (project vs project2)");
+  assert.strictEqual(
+    isSameOrDescendantPath("C:\\Users\\dev\\project", "C:\\Users\\dev\\project2"),
+    false,
+    "Windows prefix overlap without separator should not match",
+  );
+  console.log("✓ Windows prefix overlap\n");
+}
+
+// Test 11: Windows trailing backslash on base
+{
+  console.log("Test 11: Windows trailing backslash on base");
+  assert.strictEqual(
+    isSameOrDescendantPath("C:\\Users\\dev\\project\\", "C:\\Users\\dev\\project\\src"),
+    true,
+    "trailing backslash on base should still match descendants",
+  );
+  console.log("✓ Windows trailing backslash on base\n");
+}
+
+// Test 12: Windows trailing backslash on candidate
+{
+  console.log("Test 12: Windows trailing backslash on candidate");
+  assert.strictEqual(
+    isSameOrDescendantPath("C:\\Users\\dev\\project", "C:\\Users\\dev\\project\\"),
+    true,
+    "trailing backslash on candidate should match as same dir",
+  );
+  console.log("✓ Windows trailing backslash on candidate\n");
+}
+
+// Test 13: Mixed separators (agent might use \ while CLI sends /)
+{
+  console.log("Test 13: Mixed separators");
+  assert.strictEqual(
+    isSameOrDescendantPath("C:/Users/dev/project", "C:\\Users\\dev\\project\\src"),
+    true,
+    "mixed separators should still match",
+  );
+  console.log("✓ Mixed separators\n");
+}
+
+// Test 14: Deep Windows descendant
+{
+  console.log("Test 14: Deep Windows descendant");
+  assert.strictEqual(
+    isSameOrDescendantPath(
+      "C:\\Users\\dev\\project",
+      "C:\\Users\\dev\\project\\src\\components\\Button.tsx",
+    ),
+    true,
+    "deep Windows descendant should match",
+  );
+  console.log("✓ Deep Windows descendant\n");
+}
+
+// Test 15: Case-insensitive Windows descendant match
+{
+  console.log("Test 15: Case-insensitive Windows descendant match");
+  assert.strictEqual(
+    isSameOrDescendantPath("C:\\Users\\Dev\\Project", "c:\\users\\dev\\project\\src"),
+    true,
+    "Windows paths with different casing should match (case-insensitive)",
+  );
+  console.log("✓ Case-insensitive Windows descendant match\n");
+}
+
+// Test 16: Case-insensitive Windows exact match
+{
+  console.log("Test 16: Case-insensitive Windows exact match");
+  assert.strictEqual(
+    isSameOrDescendantPath("c:\\repo", "C:\\Repo"),
+    true,
+    "Windows paths with different casing should match exactly (case-insensitive)",
+  );
+  console.log("✓ Case-insensitive Windows exact match\n");
+}
+
+// Test 17: Parent should not match
+{
+  console.log("Test 15: Parent should not match");
+  assert.strictEqual(
+    isSameOrDescendantPath("/home/user/project/src", "/home/user/project"),
+    false,
+    "parent directory should not match (only same-or-descendant)",
+  );
+  console.log("✓ Parent should not match\n");
+}
+
+console.log("=== All CWD filter path tests passed ===");
diff --git a/packages/desktop/src/daemon/daemon-manager.ts b/packages/desktop/src/daemon/daemon-manager.ts
index f3055b357..607ac91a4 100644
--- a/packages/desktop/src/daemon/daemon-manager.ts
+++ b/packages/desktop/src/daemon/daemon-manager.ts
@@ -189,7 +189,8 @@ function resolveTcpHostFromListen(listen: string): string | null {
     normalized.startsWith("/") ||
     normalized.startsWith("unix://") ||
     normalized.startsWith("pipe://") ||
-    normalized.startsWith("\\\\.\\pipe\\")
+    normalized.startsWith("\\\\.\\pipe\\") ||
+    /^[A-Za-z]:[/\\]/.test(normalized)
   ) {
     return null;
   }
diff --git a/packages/server/src/server/agent/agent-storage.test.ts b/packages/server/src/server/agent/agent-storage.test.ts
index 43f0ab527..00db5a635 100644
--- a/packages/server/src/server/agent/agent-storage.test.ts
+++ b/packages/server/src/server/agent/agent-storage.test.ts
@@ -1,7 +1,7 @@
 import { describe, expect, test, beforeEach, afterEach } from "vitest";
 import os from "node:os";
 import path from "node:path";
-import { mkdtempSync, rmSync } from "node:fs";
+import { mkdtempSync, readdirSync, rmSync } from "node:fs";
 import { promises as fs } from "node:fs";
 
 import { createTestLogger } from "../../test-utils/test-logger.js";
@@ -352,6 +352,24 @@ describe("AgentStorage", () => {
     expect(records[0]?.internal).toBe(true);
   });
 
+  test("Windows drive-letter paths produce valid directory names", async () => {
+    await storage.applySnapshot(
+      createManagedAgent({
+        id: "win-agent",
+        cwd: "D:\\Users\\dev\\MyProject",
+      }),
+    );
+
+    const record = await storage.get("win-agent");
+    expect(record).not.toBeNull();
+
+    // The persisted directory must not contain a colon (invalid on Windows)
+    const dirs = readdirSync(storagePath);
+    expect(dirs).toHaveLength(1);
+    expect(dirs[0]).not.toContain(":");
+    expect(dirs[0]).toBe("D-Users-dev-MyProject");
+  });
+
   test("remove deletes all duplicate record files across project directories", async () => {
     const agentId = "agent-duplicate";
 
diff --git a/packages/server/src/server/agent/agent-storage.ts b/packages/server/src/server/agent/agent-storage.ts
index 75c7ac843..6c0ebd54d 100644
--- a/packages/server/src/server/agent/agent-storage.ts
+++ b/packages/server/src/server/agent/agent-storage.ts
@@ -335,11 +335,16 @@ export class AgentStorage {
 }
 
 function projectDirNameFromCwd(cwd: string): string {
-  const trimmed = cwd.replace(/^[\\/]+/, "").replace(/[\\/]+$/, "");
-  if (!trimmed) {
-    return "root";
+  // path.win32.parse handles drive letters, UNC roots, and Unix roots on all platforms
+  const { root } = path.win32.parse(cwd);
+  const withoutRoot = cwd.slice(root.length).replace(/[\\/]+$/, "");
+  // Sanitize root: strip colons and separators, keep letters (e.g. "C:\" → "C", "\\server\share\" → "server-share")
+  const sanitizedRoot = root.replace(/[:\\/]+/g, "-").replace(/^-+|-+$/g, "");
+  const prefix = sanitizedRoot ? sanitizedRoot + "-" : "";
+  if (!withoutRoot) {
+    return sanitizedRoot || "root";
   }
-  return trimmed.replace(/[\\/]+/g, "-");
+  return prefix + withoutRoot.replace(/[\\/]+/g, "-");
 }
 
 async function writeFileAtomically(targetPath: string, payload: string) {
diff --git a/packages/server/src/server/bootstrap.smoke.test.ts b/packages/server/src/server/bootstrap.smoke.test.ts
index 70c951520..ee2b4e520 100644
--- a/packages/server/src/server/bootstrap.smoke.test.ts
+++ b/packages/server/src/server/bootstrap.smoke.test.ts
@@ -122,6 +122,23 @@ describe("paseo daemon bootstrap", () => {
     }
   });
 
+  test("parses whitespace-padded numeric port strings", () => {
+    expect(parseListenString(" 6767 ")).toEqual({
+      type: "tcp",
+      host: "127.0.0.1",
+      port: 6767,
+    });
+  });
+
+  test("rejects Windows absolute paths that are not named pipes", () => {
+    // A Windows drive path like C:\daemon must NOT be silently parsed as TCP
+    // (split(":") would yield host="C" and port="\\daemon" which is nonsensical).
+    expect(() => parseListenString(String.raw`C:\daemon`)).toThrow();
+    expect(() => parseListenString(String.raw`D:\Users\foo\.paseo\daemon.sock`)).toThrow();
+    // Single-letter "host" with no valid port is not a valid listen string
+    expect(() => parseListenString(String.raw`C:\some\path`)).toThrow();
+  });
+
   test("parses Windows named pipes as managed IPC listen targets", () => {
     expect(parseListenString(String.raw`\\.\pipe\paseo-managed-test`)).toEqual({
       type: "pipe",
diff --git a/packages/server/src/server/bootstrap.ts b/packages/server/src/server/bootstrap.ts
index 2485db8d0..0027fedb8 100644
--- a/packages/server/src/server/bootstrap.ts
+++ b/packages/server/src/server/bootstrap.ts
@@ -35,34 +35,43 @@ function resolveBoundListenTarget(
   };
 }
 
+// Matches a Windows drive-letter path like C:\ or D:\
+const WINDOWS_DRIVE_RE = /^[A-Za-z]:\\/;
+
 export function parseListenString(listen: string): ListenTarget {
+  // 1. Windows named pipes: \\.\pipe\... or pipe://...
   if (listen.startsWith("\\\\.\\pipe\\") || listen.startsWith("pipe://")) {
     return {
       type: "pipe",
       path: listen.startsWith("pipe://") ? listen.slice("pipe://".length) : listen,
     };
   }
-  // Unix socket: starts with / or ~ or contains .sock
-  if (listen.startsWith("/") || listen.startsWith("~") || listen.includes(".sock")) {
-    return { type: "socket", path: listen };
-  }
-  // Explicit unix:// prefix
+  // 2. Explicit unix:// prefix
   if (listen.startsWith("unix://")) {
     return { type: "socket", path: listen.slice(7) };
   }
-  // TCP: host:port or just port
+  // 3. Reject Windows absolute drive paths — they are not Unix sockets
+  if (WINDOWS_DRIVE_RE.test(listen)) {
+    throw new Error(`Invalid listen string (Windows path is not a valid listen target): ${listen}`);
+  }
+  // 4. POSIX absolute path (/ or ~) — Unix socket
+  if (listen.startsWith("/") || listen.startsWith("~")) {
+    return { type: "socket", path: listen };
+  }
+  // 5. Pure numeric — TCP port on 127.0.0.1
+  const trimmed = listen.trim();
+  if (/^\d+$/.test(trimmed)) {
+    const port = parseInt(trimmed, 10);
+    return { type: "tcp", host: "127.0.0.1", port };
+  }
+  // 6. host:port — TCP
   if (listen.includes(":")) {
     const [host, portStr] = listen.split(":");
-    const port = parseInt(portStr, 10);
-    if (!Number.isFinite(port)) {
+    const parsedPort = parseInt(portStr, 10);
+    if (!Number.isFinite(parsedPort)) {
       throw new Error(`Invalid port in listen string: ${listen}`);
     }
-    return { type: "tcp", host: host || "127.0.0.1", port };
-  }
-  // Just a port number
-  const port = parseInt(listen, 10);
-  if (Number.isFinite(port)) {
-    return { type: "tcp", host: "127.0.0.1", port };
+    return { type: "tcp", host: host || "127.0.0.1", port: parsedPort };
   }
   throw new Error(`Invalid listen string: ${listen}`);
 }
diff --git a/packages/server/src/terminal/terminal-manager.test.ts b/packages/server/src/terminal/terminal-manager.test.ts
index f1033e4e1..20dadc4e7 100644
--- a/packages/server/src/terminal/terminal-manager.test.ts
+++ b/packages/server/src/terminal/terminal-manager.test.ts
@@ -73,6 +73,12 @@ describe("TerminalManager", () => {
       await expect(manager.getTerminals("tmp")).rejects.toThrow("cwd must be absolute path");
     });
 
+    it("accepts Windows absolute paths", async () => {
+      manager = createTerminalManager();
+      await expect(manager.getTerminals("C:\\Users\\foo\\project")).resolves.not.toThrow();
+      await expect(manager.getTerminals("D:\\MyProject")).resolves.not.toThrow();
+    });
+
     it("creates separate terminals for different cwds", async () => {
       manager = createTerminalManager();
       const tmpTerminals = [await manager.createTerminal({ cwd: "/tmp" })];
@@ -121,6 +127,18 @@ describe("TerminalManager", () => {
       );
     });
 
+    it("does not reject Windows absolute paths as relative", async () => {
+      manager = createTerminalManager();
+      // Should pass path validation (not throw "cwd must be absolute path").
+      // The terminal may or may not spawn successfully on non-Windows hosts,
+      // so we only assert the validation error is absent.
+      try {
+        await manager.createTerminal({ cwd: "C:\\Users\\foo\\project" });
+      } catch (error) {
+        expect((error as Error).message).not.toBe("cwd must be absolute path");
+      }
+    });
+
     it("inherits registered env for the worktree root cwd", async () => {
       await withShell("/bin/sh", async () => {
         manager = createTerminalManager();
diff --git a/packages/server/src/terminal/terminal-manager.ts b/packages/server/src/terminal/terminal-manager.ts
index dc243b681..22e016875 100644
--- a/packages/server/src/terminal/terminal-manager.ts
+++ b/packages/server/src/terminal/terminal-manager.ts
@@ -1,5 +1,5 @@
 import { createTerminal, type TerminalSession } from "./terminal.js";
-import { resolve, sep } from "node:path";
+import { resolve, sep, win32, posix } from "node:path";
 
 export interface TerminalListItem {
   id: string;
@@ -37,7 +37,7 @@ export function createTerminalManager(): TerminalManager {
   const defaultEnvByRootCwd = new Map<string, Record<string, string>>();
 
   function assertAbsolutePath(cwd: string): void {
-    if (!cwd.startsWith("/")) {
+    if (!posix.isAbsolute(cwd) && !win32.isAbsolute(cwd)) {
       throw new Error("cwd must be absolute path");
     }
   }
diff --git a/packages/server/src/utils/checkout-git.test.ts b/packages/server/src/utils/checkout-git.test.ts
index 8ded45d91..2edeef819 100644
--- a/packages/server/src/utils/checkout-git.test.ts
+++ b/packages/server/src/utils/checkout-git.test.ts
@@ -18,6 +18,9 @@ import {
   NotGitRepoError,
   pushCurrentBranch,
   resolveRepositoryDefaultBranch,
+  parseWorktreeList,
+  isPaseoWorktreePath,
+  isDescendantPath,
 } from "./checkout-git.js";
 import { createWorktree } from "./worktree.js";
 import { getPaseoWorktreeMetadataPath } from "./worktree-metadata.js";
@@ -812,4 +815,73 @@ const x = 1;
     ).rejects.toThrow(/base/i);
     await expect(mergeToBase(worktree.worktreePath, {}, { paseoHome })).rejects.toThrow(/base/i);
   });
+
+  describe("parseWorktreeList", () => {
+    it("parses porcelain worktree output", () => {
+      const output = [
+        "worktree /home/user/repo",
+        "branch refs/heads/main",
+        "",
+        "worktree /home/user/.paseo/worktrees/feature",
+        "branch refs/heads/feature",
+        "",
+      ].join("\n");
+
+      const entries = parseWorktreeList(output);
+      expect(entries).toHaveLength(2);
+      expect(entries[0]).toEqual({ path: "/home/user/repo", branchRef: "refs/heads/main" });
+      expect(entries[1]).toEqual({
+        path: "/home/user/.paseo/worktrees/feature",
+        branchRef: "refs/heads/feature",
+      });
+    });
+
+    it("detects bare repos", () => {
+      const output = ["worktree /home/user/repo.git", "bare", ""].join("\n");
+      const entries = parseWorktreeList(output);
+      expect(entries).toHaveLength(1);
+      expect(entries[0]?.isBare).toBe(true);
+    });
+  });
+
+  describe("isPaseoWorktreePath", () => {
+    it("matches Unix .paseo/worktrees/ paths", () => {
+      expect(isPaseoWorktreePath("/home/user/.paseo/worktrees/feature")).toBe(true);
+    });
+
+    it("matches Windows .paseo\\worktrees\\ paths", () => {
+      expect(isPaseoWorktreePath("C:\\Users\\dev\\.paseo\\worktrees\\feature")).toBe(true);
+    });
+
+    it("rejects paths without .paseo/worktrees segment", () => {
+      expect(isPaseoWorktreePath("/home/user/repo")).toBe(false);
+      expect(isPaseoWorktreePath("C:\\Users\\dev\\repo")).toBe(false);
+    });
+  });
+
+  describe("isDescendantPath", () => {
+    it("detects children with Unix separators", () => {
+      expect(isDescendantPath("/home/user/repo/child", "/home/user/repo")).toBe(true);
+    });
+
+    it("detects children with Windows separators", () => {
+      expect(isDescendantPath("C:\\repos\\child", "C:\\repos")).toBe(true);
+    });
+
+    it("rejects the parent itself", () => {
+      expect(isDescendantPath("/home/user/repo", "/home/user/repo")).toBe(false);
+    });
+
+    it("rejects siblings that share a prefix", () => {
+      expect(isDescendantPath("/home/user/repo-extra", "/home/user/repo")).toBe(false);
+    });
+
+    it("handles mixed separators", () => {
+      expect(isDescendantPath("C:/repo/child", "C:\\repo")).toBe(true);
+    });
+
+    it("is case insensitive on Windows paths", () => {
+      expect(isDescendantPath("c:\\repo\\child", "C:\\repo")).toBe(true);
+    });
+  });
 });
diff --git a/packages/server/src/utils/checkout-git.ts b/packages/server/src/utils/checkout-git.ts
index 6685934ae..ded5c96cd 100644
--- a/packages/server/src/utils/checkout-git.ts
+++ b/packages/server/src/utils/checkout-git.ts
@@ -603,20 +603,39 @@ async function getMainRepoRoot(cwd: string): Promise<string> {
   });
   const worktrees = parseWorktreeList(worktreeOut);
   const nonBareNonPaseo = worktrees.filter(
-    (wt) => !wt.isBare && !wt.path.includes("/.paseo/worktrees/"),
+    (wt) => !wt.isBare && !isPaseoWorktreePath(wt.path),
   );
-  const childrenOfBareRepo = nonBareNonPaseo.filter((wt) => wt.path.startsWith(normalized + "/"));
+  const childrenOfBareRepo = nonBareNonPaseo.filter((wt) => isDescendantPath(wt.path, normalized));
   const mainChild = childrenOfBareRepo.find((wt) => basename(wt.path) === "main");
   return mainChild?.path ?? childrenOfBareRepo[0]?.path ?? nonBareNonPaseo[0]?.path ?? normalized;
 }
 
-type GitWorktreeEntry = {
+export type GitWorktreeEntry = {
   path: string;
   branchRef?: string;
   isBare?: boolean;
 };
 
-function parseWorktreeList(output: string): GitWorktreeEntry[] {
+/** Check whether a path contains a `.paseo/worktrees/` segment (both `/` and `\`). */
+export function isPaseoWorktreePath(p: string): boolean {
+  return /[/\\]\.paseo[/\\]worktrees[/\\]/.test(p);
+}
+
+/** True when `child` is strictly inside `parent` (handles both `/` and `\`). */
+export function isDescendantPath(child: string, parent: string): boolean {
+  let c = child.replace(/\\/g, "/").replace(/\/+$/, "");
+  let p = parent.replace(/\\/g, "/").replace(/\/+$/, "");
+  // Case-insensitive on Windows (drive letter like C: or D:)
+  if (/^[A-Za-z]:/.test(c) || /^[A-Za-z]:/.test(p)) {
+    c = c.toLowerCase();
+    p = p.toLowerCase();
+  }
+  if (!c.startsWith(p)) return false;
+  if (c.length === p.length) return false;
+  return c[p.length] === "/";
+}
+
+export function parseWorktreeList(output: string): GitWorktreeEntry[] {
   const entries: GitWorktreeEntry[] = [];
   let current: GitWorktreeEntry | null = null;
   for (const line of output.split("\n")) {