diff --git a/packages/bruno-electron/src/ipc/collection.js b/packages/bruno-electron/src/ipc/collection.js
index fd8772f3d..547ac6404 100644
--- a/packages/bruno-electron/src/ipc/collection.js
+++ b/packages/bruno-electron/src/ipc/collection.js
@@ -112,8 +112,9 @@ const getTransientScratchPrefix = () => {
 
 // Check if a path is within the transient directory
 const isTransientPath = (filePath) => {
+  const normalizedFilePath = path.normalize(filePath);
   const transientBase = getTransientDirectoryBase();
-  return filePath.startsWith(transientBase + path.sep) || filePath.startsWith(transientBase);
+  return normalizedFilePath.startsWith(transientBase + path.sep) || normalizedFilePath === transientBase;
 };
 
 const envHasSecrets = (environment = {}) => {
@@ -123,11 +124,14 @@ const envHasSecrets = (environment = {}) => {
 };
 
 const findCollectionPathByItemPath = (filePath) => {
-  const parts = filePath.split(path.sep);
-  const index = parts.findIndex((part) => part.startsWith('bruno-'));
+  const normalizedFilePath = path.normalize(filePath);
 
-  if (isTransientPath(filePath) && index !== -1) {
-    const transientDirPath = parts.slice(0, index + 1).join(path.sep);
+  if (isTransientPath(normalizedFilePath)) {
+    const transientBase = getTransientDirectoryBase();
+    const transientDirName = path.relative(transientBase, normalizedFilePath).split(path.sep)[0];
+    if (!transientDirName) return null;
+
+    const transientDirPath = path.join(transientBase, transientDirName);
     const metadataPath = path.join(transientDirPath, 'metadata.json');
     try {
       const metadataContent = fs.readFileSync(metadataPath, 'utf8');
@@ -152,9 +156,6 @@ const findCollectionPathByItemPath = (filePath) => {
   // Sort by length descending to find the most specific (deepest) match first
   const sortedPaths = allCollectionPaths.sort((a, b) => b.length - a.length);
 
-  // Normalize the file path for comparison
-  const normalizedFilePath = path.normalize(filePath);
-
   for (const collectionPath of sortedPaths) {
     const normalizedCollectionPath = path.normalize(collectionPath);
     if (normalizedFilePath.startsWith(normalizedCollectionPath + path.sep) || normalizedFilePath === normalizedCollectionPath) {