diff --git a/packages/app/src/utils/path-key.ts b/packages/app/src/utils/path-key.ts
index 68d53e91d863..671d2dec319d 100644
--- a/packages/app/src/utils/path-key.ts
+++ b/packages/app/src/utils/path-key.ts
@@ -6,19 +6,13 @@ const isDrive = (value: string) => {
   return value[1] === ":" && ((code >= 65 && code <= 90) || (code >= 97 && code <= 122))
 }
 
-const trimTrailingSlashes = (value: string) => {
-  for (let i = value.length - 1; i >= 0; i--) {
-    if (value[i] !== "/") return value.slice(0, i + 1)
-  }
-  return ""
-}
-
 const isWindowsPath = (value: string) => value[1] === ":" || value.startsWith("\\\\")
 
 export const pathKey = (path: string) => {
-  const value = isWindowsPath(path) ? path.replaceAll("\\", "/") : path
-  const trimmed = trimTrailingSlashes(value)
-  if (!trimmed && value.startsWith("/")) return "/" as PathKey
-  if (isDrive(trimmed)) return `${trimmed}/` as PathKey
+  let value = isWindowsPath(path) ? path.replaceAll("\\", "/") : path
+  if (/^\/+$/.test(value)) return "/" as PathKey
+  if (isDrive(value)) return `${value}/` as PathKey
+  const trimmed = value.replace(/\/+$/, "")
+  if (!trimmed) return "/" as PathKey
   return trimmed as PathKey
 }
diff --git a/packages/opencode/src/session/session.ts b/packages/opencode/src/session/session.ts
index 5e574d9911f5..b84c240f7f48 100644
--- a/packages/opencode/src/session/session.ts
+++ b/packages/opencode/src/session/session.ts
@@ -514,6 +514,14 @@ export const layer: Layer.Layer<Service, never, Bus.Service | Storage.Service |
     const storage = yield* Storage.Service
     const sync = yield* SyncEvent.Service
 
+    const normalizeDirectory = (directory: string) => {
+      const normalized = directory.replaceAll("\\", "/")
+      if (/^\/+$/.test(normalized)) return normalized
+      const driveMatch = normalized.match(/^([A-Za-z]:)\/+$/)
+      if (driveMatch) return `${driveMatch[1]}/`
+      return normalized.replace(/\/+$/, "")
+    }
+
     const createNext = Effect.fn("Session.createNext")(function* (input: {
       id?: SessionID
       title?: string
@@ -531,7 +539,7 @@ export const layer: Layer.Layer<Service, never, Bus.Service | Storage.Service |
         slug: Slug.create(),
         version: InstallationVersion,
         projectID: ctx.project.id,
-        directory: input.directory,
+        directory: normalizeDirectory(input.directory),
         path: input.path,
         workspaceID: input.workspaceID,
         parentID: input.parentID,