diff --git a/src/shared/session-directory-resolver.test.ts b/src/shared/session-directory-resolver.test.ts
index 717d9f90..da1903f0 100644
--- a/src/shared/session-directory-resolver.test.ts
+++ b/src/shared/session-directory-resolver.test.ts
@@ -15,6 +15,17 @@ describe("session-directory-resolver", () => {
       expect(result).toBe(true)
     })
 
+    test("returns true when path ends with AppData directory segment", () => {
+      //#given
+      const directory = "C:/Users/test/AppData/Local"
+
+      //#when
+      const result = isWindowsAppDataDirectory(directory)
+
+      //#then
+      expect(result).toBe(true)
+    })
+
     test("returns false when path is outside AppData", () => {
       //#given
       const directory = "D:/projects/oh-my-opencode"
@@ -25,6 +36,17 @@ describe("session-directory-resolver", () => {
       //#then
       expect(result).toBe(false)
     })
+
+    test("returns false for lookalike non-AppData segment", () => {
+      //#given
+      const directory = "D:/projects/appdata/local-tools"
+
+      //#when
+      const result = isWindowsAppDataDirectory(directory)
+
+      //#then
+      expect(result).toBe(false)
+    })
   })
 
   describe("resolveSessionDirectory", () => {
diff --git a/src/shared/session-directory-resolver.ts b/src/shared/session-directory-resolver.ts
index bc76f1a5..16d38944 100644
--- a/src/shared/session-directory-resolver.ts
+++ b/src/shared/session-directory-resolver.ts
@@ -1,4 +1,4 @@
-const WINDOWS_APPDATA_SEGMENTS = ["\\appdata\\local\\", "\\appdata\\roaming\\", "\\appdata\\locallow\\"]
+const WINDOWS_APPDATA_SEGMENTS = ["\\appdata\\local", "\\appdata\\roaming", "\\appdata\\locallow"]
 
 function normalizeWindowsPath(directory: string): string {
   return directory.replaceAll("/", "\\").toLowerCase()
@@ -6,7 +6,9 @@ function normalizeWindowsPath(directory: string): string {
 
 export function isWindowsAppDataDirectory(directory: string): boolean {
   const normalizedDirectory = normalizeWindowsPath(directory)
-  return WINDOWS_APPDATA_SEGMENTS.some((segment) => normalizedDirectory.includes(segment))
+  return WINDOWS_APPDATA_SEGMENTS.some((segment) => {
+    return normalizedDirectory.endsWith(segment) || normalizedDirectory.includes(`${segment}\\`)
+  })
 }
 
 export function resolveSessionDirectory(options: {