diff --git a/CHANGELOG.md b/CHANGELOG.md
index 5425a8d6..89814c6a 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -43,7 +43,9 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
   the container boundary. The visible symptom is that the retry `status`
   itself recommends — `llm-test --provider anthropic-oauth` — fails with a
   missing-token error, because `llm-test` runs client-side in the helper
-  rather than on the server (#379).
+  rather than on the server. The PowerShell wrapper also trims trailing path
+  separators as individual characters, so Windows invocations reach Docker
+  instead of failing during path normalization (#379).
 
 ## [1.24.0] - 2026-08-04
 
diff --git a/bin/ai-memory.ps1 b/bin/ai-memory.ps1
index 4d35670a..f610ae86 100644
--- a/bin/ai-memory.ps1
+++ b/bin/ai-memory.ps1
@@ -44,7 +44,7 @@ $HomePath = (Resolve-Path -LiteralPath $HOME).Path
 $WorkPath = (Get-Location).Path
 $HookHostRoot = ($HomePath -replace '\\', '/') + "/.local/share/ai-memory/hooks"
 
-$HomeRoot = $HomePath.TrimEnd([char[]]@('/', '\\'))
+$HomeRoot = $HomePath.TrimEnd([char[]]@('/', '\'))
 $HomePrefix = $HomeRoot + [IO.Path]::DirectorySeparatorChar
 $InsideHome = $WorkPath.Equals($HomeRoot, [StringComparison]::OrdinalIgnoreCase) -or
     $WorkPath.StartsWith($HomePrefix, [StringComparison]::OrdinalIgnoreCase)
@@ -64,7 +64,7 @@ if ($InsideHome) {
             $ScopeRoot = [IO.Path]::GetFullPath($DetectedScopeRoot.Trim())
         }
     }
-    $ScopeRoot = $ScopeRoot.TrimEnd([char[]]@('/', '\\'))
+    $ScopeRoot = $ScopeRoot.TrimEnd([char[]]@('/', '\'))
     $ScopePrefix = $ScopeRoot + [IO.Path]::DirectorySeparatorChar
     if ($WorkPath.Equals($ScopeRoot, [StringComparison]::OrdinalIgnoreCase)) {
         $ScopeSuffix = ""
diff --git a/crates/ai-memory-cli/tests/packaging.rs b/crates/ai-memory-cli/tests/packaging.rs
index dda9d47a..4a52cf88 100644
--- a/crates/ai-memory-cli/tests/packaging.rs
+++ b/crates/ai-memory-cli/tests/packaging.rs
@@ -1365,6 +1365,21 @@ fn powershell_wrapper_lists_subscription_oauth_tokens_in_its_env_allowlist() {
     }
 }
 
+#[test]
+fn powershell_wrapper_trims_paths_with_single_character_separators() {
+    let wrapper = read_repo("bin/ai-memory.ps1");
+
+    assert_eq!(
+        wrapper.matches(r"TrimEnd([char[]]@('/', '\'))").count(),
+        2,
+        "PowerShell TrimEnd arguments must contain individual characters"
+    );
+    assert!(
+        !wrapper.contains(r"TrimEnd([char[]]@('/', '\\'))"),
+        "a multi-character backslash string cannot be converted to System.Char"
+    );
+}
+
 #[cfg(windows)]
 #[test]
 fn powershell_wrapper_forwards_subscription_oauth_tokens_without_putting_values_in_argv() {