diff --git a/packages/ui/src/components/chat/FileAttachment.tsx b/packages/ui/src/components/chat/FileAttachment.tsx
index 5949164f..158a78f8 100644
--- a/packages/ui/src/components/chat/FileAttachment.tsx
+++ b/packages/ui/src/components/chat/FileAttachment.tsx
@@ -471,7 +471,7 @@ export const ActiveEditorFileSuggestion = memo(() => {
       ? `${selection.startLine}`
       : `${selection.startLine}-${selection.endLine}`
   }
-  const selectionLabel = selection ? `${fileName}:${selectionRange}` : ''
+  const selectionLabel = selection ? `${relativePath}:${selectionRange}` : ''
   const isSelectionAttached = !!selectionLabel && attachedFiles.some(
     (f) => f.source === 'vscode' && f.vscodeSource === 'selection' && f.filename === selectionLabel && f.vscodePath === filePath
   )
diff --git a/packages/vscode/src/extension.ts b/packages/vscode/src/extension.ts
index 1fd80b94..8fbdec8c 100644
--- a/packages/vscode/src/extension.ts
+++ b/packages/vscode/src/extension.ts
@@ -297,13 +297,14 @@ export async function activate(context: vscode.ExtensionContext) {
       }
 
       // Get file info for context
-      const filePath = vscode.workspace.asRelativePath(editor.document.uri);
+      // false matches the relativePath broadcast for the active editor, so this attachment dedupes against the pin-selection suggestion.
+      const filePath = vscode.workspace.asRelativePath(editor.document.uri, false);
       // Get line numbers (1-based for display)
       const startLine = selection.start.line + 1;
       const endLine = selection.end.line + 1;
       const lineRange = startLine === endLine ? `${startLine}` : `${startLine}-${endLine}`;
 
-      const filename = `${editor.document.fileName.split(/[\\/]/).pop() || filePath}:${lineRange}`;
+      const filename = `${filePath}:${lineRange}`;
       const contextSelection = {
         filePath: editor.document.uri.fsPath,
         filename,