diff --git a/packages/opencode/src/filesystem/index.ts b/packages/opencode/src/filesystem/index.ts
index 45231d43f6..01fdcd2e5e 100644
--- a/packages/opencode/src/filesystem/index.ts
+++ b/packages/opencode/src/filesystem/index.ts
@@ -188,13 +188,23 @@ export namespace AppFileSystem {
 
   export function normalizePath(p: string): string {
     if (process.platform !== "win32") return p
+    const resolved = pathResolve(windowsPath(p))
     try {
-      return realpathSync.native(p)
+      return realpathSync.native(resolved)
     } catch {
-      return p
+      return resolved
     }
   }
 
+  export function normalizePathPattern(p: string): string {
+    if (process.platform !== "win32") return p
+    if (p === "*") return p
+    const match = p.match(/^(.*)[\\/]\*$/)
+    if (!match) return normalizePath(p)
+    const dir = /^[A-Za-z]:$/.test(match[1]) ? match[1] + "\\" : match[1]
+    return join(normalizePath(dir), "*")
+  }
+
   export function resolve(p: string): string {
     const resolved = pathResolve(windowsPath(p))
     try {
diff --git a/packages/opencode/src/tool/external-directory.ts b/packages/opencode/src/tool/external-directory.ts
index 66eba438bc..f11455cf59 100644
--- a/packages/opencode/src/tool/external-directory.ts
+++ b/packages/opencode/src/tool/external-directory.ts
@@ -1,7 +1,8 @@
 import path from "path"
+import { Effect } from "effect"
 import type { Tool } from "./tool"
 import { Instance } from "../project/instance"
-import { Filesystem } from "@/util/filesystem"
+import { AppFileSystem } from "../filesystem"
 
 type Kind = "file" | "directory"
 
@@ -15,14 +16,14 @@ export async function assertExternalDirectory(ctx: Tool.Context, target?: string
 
   if (options?.bypass) return
 
-  const full = process.platform === "win32" ? Filesystem.normalizePath(target) : target
+  const full = process.platform === "win32" ? AppFileSystem.normalizePath(target) : target
   if (Instance.containsPath(full)) return
 
   const kind = options?.kind ?? "file"
   const dir = kind === "directory" ? full : path.dirname(full)
   const glob =
     process.platform === "win32"
-      ? Filesystem.normalizePathPattern(path.join(dir, "*"))
+      ? AppFileSystem.normalizePathPattern(path.join(dir, "*"))
       : path.join(dir, "*").replaceAll("\\", "/")
 
   await ctx.ask({
@@ -35,3 +36,11 @@ export async function assertExternalDirectory(ctx: Tool.Context, target?: string
     },
   })
 }
+
+export const assertExternalDirectoryEffect = Effect.fn("Tool.assertExternalDirectory")(function* (
+  ctx: Tool.Context,
+  target?: string,
+  options?: Options,
+) {
+  yield* Effect.promise(() => assertExternalDirectory(ctx, target, options))
+})
diff --git a/packages/opencode/src/tool/read.ts b/packages/opencode/src/tool/read.ts
index a6cb725bea..366993020b 100644
--- a/packages/opencode/src/tool/read.ts
+++ b/packages/opencode/src/tool/read.ts
@@ -10,7 +10,7 @@ import { LSP } from "../lsp"
 import { FileTime } from "../file/time"
 import DESCRIPTION from "./read.txt"
 import { Instance } from "../project/instance"
-import { assertExternalDirectory } from "./external-directory"
+import { assertExternalDirectoryEffect } from "./external-directory"
 import { Instruction } from "../session/instruction"
 
 const DEFAULT_READ_LIMIT = 2000
@@ -96,15 +96,18 @@ export const ReadTool = Tool.defineEffect(
       }
       const title = path.relative(Instance.worktree, filepath)
 
-      const stat = yield* fs.stat(filepath).pipe(Effect.catch(() => Effect.succeed(undefined)))
-
-      yield* Effect.promise(() =>
-        assertExternalDirectory(ctx, filepath, {
-          bypass: Boolean(ctx.extra?.["bypassCwdCheck"]),
-          kind: stat?.type === "Directory" ? "directory" : "file",
-        }),
+      const stat = yield* fs.stat(filepath).pipe(
+        Effect.catchIf(
+          (err) => "reason" in err && err.reason._tag === "NotFound",
+          () => Effect.succeed(undefined),
+        ),
       )
 
+      yield* assertExternalDirectoryEffect(ctx, filepath, {
+        bypass: Boolean(ctx.extra?.["bypassCwdCheck"]),
+        kind: stat?.type === "Directory" ? "directory" : "file",
+      })
+
       yield* Effect.promise(() =>
         ctx.ask({
           permission: "read",
@@ -218,15 +221,7 @@ export const ReadTool = Tool.defineEffect(
       description: DESCRIPTION,
       parameters,
       async execute(params: z.infer<typeof parameters>, ctx) {
-        return Effect.runPromise(
-          run(params, ctx).pipe(
-            Effect.catch((err) =>
-              Effect.sync(() => {
-                throw err
-              }),
-            ),
-          ),
-        )
+        return Effect.runPromise(run(params, ctx).pipe(Effect.orDie))
       },
     }
   }),