diff --git a/CHANGELOG.md b/CHANGELOG.md
index 41e9669f..e7230d4a 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,22 @@
 
 All notable changes to this project will be documented in this file. See [standard-version](https://github.com/conventional-changelog/standard-version) for commit guidelines.
 
+## [3.15.0](https://github.com/soulcraftlabs/brainy/compare/v3.14.2...v3.15.0) (2025-09-26)
+
+### Bug Fixes
+
+* **vfs**: Ensure Contains relationships are maintained when updating files
+* **vfs**: Fix root directory metadata handling to prevent "Not a directory" errors
+* **vfs**: Add entity metadata compatibility layer for proper VFS operations
+* **vfs**: Fix resolvePath() to return entity IDs instead of path strings
+* **vfs**: Improve error handling in ensureDirectory() method
+
+### Features
+
+* **vfs**: Add comprehensive tests for Contains relationship integrity
+* **vfs**: Ensure all VFS entities use standard Brainy NounType and VerbType enums
+* **vfs**: Add metadata validation and repair for existing entities
+
 ## [3.0.1](https://github.com/soulcraftlabs/brainy/compare/v2.14.3...v3.0.1) (2025-09-15)
 
 **Brainy 3.0 Production Release** - World's first Triple Intelligence™ database unifying vector, graph, and document search
diff --git a/docs/vfs/TROUBLESHOOTING.md b/docs/vfs/TROUBLESHOOTING.md
new file mode 100644
index 00000000..d3c75144
--- /dev/null
+++ b/docs/vfs/TROUBLESHOOTING.md
@@ -0,0 +1,257 @@
+# VFS Troubleshooting Guide
+
+## Common Issues and Solutions
+
+### Issue: "VFSError: Not a directory: /"
+
+**Symptoms:**
+- `readdir('/')` throws "Not a directory" error
+- Root directory exists but isn't recognized as directory
+- Files can be written but not listed
+
+**Root Cause:**
+The root directory entity exists but doesn't have the proper metadata structure.
+
+**Solution (v3.15.0+):**
+This issue has been fixed in v3.15.0. The VFS now:
+1. Ensures root directory has `vfsType: 'directory'` metadata
+2. Adds compatibility layer for entities with malformed metadata
+3. Automatically repairs metadata on entity retrieval
+
+**Manual Fix (if needed):**
+```javascript
+// Force re-initialization of root directory
+await vfs.init()  // Will repair root if needed
+
+// Or manually update root entity
+const rootId = vfs.rootEntityId
+await brain.update({
+  id: rootId,
+  metadata: {
+    path: '/',
+    vfsType: 'directory',
+    // ... other metadata
+  }
+})
+```
+
+---
+
+### Issue: "readdir() returns empty array despite files existing"
+
+**Symptoms:**
+- Files are successfully written to VFS
+- Files can be read individually
+- `readdir()` returns `[]` for directories with files
+
+**Root Cause:**
+Contains relationships are missing between parent directories and files.
+
+**Solution (v3.15.0+):**
+This issue has been fixed. The VFS now:
+1. Creates Contains relationships when writing new files
+2. Ensures Contains relationships exist when updating files
+3. Repairs missing relationships automatically
+
+**Manual Fix (if needed):**
+```javascript
+// Repair missing Contains relationship
+const parentId = await vfs.resolvePath('/directory')
+const fileId = await vfs.resolvePath('/directory/file.txt')
+
+await brain.relate({
+  from: parentId,
+  to: fileId,
+  type: VerbType.Contains
+})
+```
+
+---
+
+### Issue: "VFS not initialized" error
+
+**Symptoms:**
+- Any VFS operation throws "VFS not initialized"
+- Operations fail even after creating VFS instance
+
+**Root Cause:**
+The VFS `init()` method wasn't called after getting the VFS instance.
+
+**Solution:**
+```javascript
+// ✅ CORRECT
+const vfs = brain.vfs()  // Get instance
+await vfs.init()         // Initialize (REQUIRED!)
+
+// ❌ WRONG
+const vfs = brain.vfs()
+// Missing: await vfs.init()
+```
+
+---
+
+### Issue: Files disappear after process restart
+
+**Symptoms:**
+- Files exist during session
+- All files gone after restart
+- Fresh VFS each time
+
+**Root Cause:**
+Using in-memory storage instead of persistent storage.
+
+**Solution:**
+```javascript
+// ✅ Use persistent storage
+const brain = new Brainy({
+  storage: {
+    type: 'filesystem',  // Persistent
+    path: './brainy-data'
+  }
+})
+
+// ❌ Don't use memory for production
+const brain = new Brainy({
+  storage: { type: 'memory' }  // Data lost on restart!
+})
+```
+
+---
+
+### Issue: Infinite recursion when listing directories
+
+**Symptoms:**
+- Directory appears as its own child
+- Stack overflow errors
+- UI freezes
+
+**Root Cause:**
+Using path-based filtering instead of graph relationships.
+
+**Solution:**
+```javascript
+// ✅ CORRECT - Use graph relationships
+const children = await vfs.getDirectChildren('/directory')
+
+// ❌ WRONG - Path prefix matching causes recursion
+const allNodes = await brain.find({})
+const children = allNodes.filter(n =>
+  n.metadata.path.startsWith('/directory/'))  // Directory matches itself!
+```
+
+---
+
+### Issue: Can't find files by content
+
+**Symptoms:**
+- Semantic search returns no results
+- Only exact filename matches work
+
+**Root Cause:**
+Files aren't being properly embedded or indexed.
+
+**Solution:**
+```javascript
+// Ensure files have content for embedding
+await vfs.writeFile('/doc.txt', 'Actual content here')  // Not empty!
+
+// Use semantic search correctly
+const results = await vfs.search('machine learning', {
+  path: '/documents',  // Search within path
+  limit: 10,
+  type: 'file'
+})
+```
+
+---
+
+## Debugging Tips
+
+### 1. Check VFS Initialization
+```javascript
+console.log('VFS initialized:', vfs.initialized)
+console.log('Root entity ID:', vfs.rootEntityId)
+```
+
+### 2. Verify Entity Metadata
+```javascript
+const entity = await vfs.getEntity('/path/to/file')
+console.log('Entity metadata:', entity.metadata)
+console.log('VFS type:', entity.metadata.vfsType)
+```
+
+### 3. Check Relationships
+```javascript
+const parentId = await vfs.resolvePath('/directory')
+const relations = await brain.getRelations({
+  from: parentId,
+  type: VerbType.Contains
+})
+console.log('Child count:', relations.length)
+```
+
+### 4. Enable Debug Logging
+```javascript
+const brain = new Brainy({
+  storage: { type: 'filesystem' },
+  logger: {
+    level: 'debug',
+    enabled: true
+  }
+})
+```
+
+---
+
+## Performance Tips
+
+### 1. Use Caching
+```javascript
+// Enable caching in VFS config
+const vfs = brain.vfs({
+  cache: {
+    enabled: true,
+    ttl: 300000,  // 5 minutes
+    maxSize: 1000
+  }
+})
+```
+
+### 2. Batch Operations
+```javascript
+// Write multiple files efficiently
+const files = [
+  { path: '/file1.txt', content: 'content1' },
+  { path: '/file2.txt', content: 'content2' }
+]
+
+await Promise.all(
+  files.map(f => vfs.writeFile(f.path, f.content))
+)
+```
+
+### 3. Limit Directory Depth
+```javascript
+// Don't traverse too deep
+const tree = await vfs.getTreeStructure('/', {
+  maxDepth: 3,  // Limit recursion
+  includeHidden: false
+})
+```
+
+---
+
+## Getting Help
+
+If you encounter issues not covered here:
+
+1. Check the [VFS API Guide](./VFS_API_GUIDE.md)
+2. Review [VFS Examples](./VFS_EXAMPLES_SCENARIOS.md)
+3. Look at [test files](../../tests/vfs/) for working examples
+4. Report issues at [GitHub Issues](https://github.com/soulcraftlabs/brainy/issues)
+
+Remember: Most VFS issues are related to:
+- Missing initialization (`await vfs.init()`)
+- Using memory storage instead of filesystem
+- Missing Contains relationships
+- Incorrect path handling
\ No newline at end of file
diff --git a/docs/vfs/VFS_GRAPH_TYPES.md b/docs/vfs/VFS_GRAPH_TYPES.md
new file mode 100644
index 00000000..54270395
--- /dev/null
+++ b/docs/vfs/VFS_GRAPH_TYPES.md
@@ -0,0 +1,199 @@
+# VFS Graph Type Usage Guide
+
+## Standard Type System
+
+The Brainy VFS uses Brainy's standard graph type system for all entities and relationships. This ensures compatibility with the broader Brainy ecosystem and enables powerful cross-domain queries.
+
+## Entity Types (NounType)
+
+### Directory Entities
+- **Type:** `NounType.Collection`
+- **Purpose:** Represents directories/folders that contain other entities
+- **Metadata:** Includes `vfsType: 'directory'` for VFS-specific operations
+
+```javascript
+// Directories are created as Collections
+await brain.add({
+  type: NounType.Collection,
+  metadata: {
+    path: '/documents',
+    vfsType: 'directory',
+    // ... other metadata
+  }
+})
+```
+
+### File Entities
+
+The VFS intelligently selects the appropriate NounType based on file content:
+
+- **`NounType.Document`** - Text files, JSON, source code, markdown
+- **`NounType.Media`** - Images, videos, audio files
+- **`NounType.File`** - Generic/binary files
+
+```javascript
+// Automatic type selection based on MIME type
+function getFileNounType(mimeType) {
+  if (mimeType.startsWith('text/') || mimeType.includes('json')) {
+    return NounType.Document
+  }
+  if (mimeType.startsWith('image/') ||
+      mimeType.startsWith('video/') ||
+      mimeType.startsWith('audio/')) {
+    return NounType.Media
+  }
+  return NounType.File
+}
+```
+
+## Relationship Types (VerbType)
+
+### Core VFS Relationships
+
+#### Parent-Child Structure
+- **Type:** `VerbType.Contains`
+- **Direction:** Parent → Child
+- **Purpose:** Represents the hierarchical file system structure
+
+```javascript
+// Creating directory structure
+await brain.relate({
+  from: parentDirectoryId,
+  to: childFileOrDirectoryId,
+  type: VerbType.Contains
+})
+```
+
+#### Custom File Relationships
+
+You can add custom relationships between files using any VerbType:
+
+```javascript
+// Document references another
+await vfs.addRelationship('/doc1.md', '/doc2.md', VerbType.References)
+
+// Code file depends on library
+await vfs.addRelationship('/app.js', '/lib/utils.js', VerbType.DependsOn)
+
+// Image derived from original
+await vfs.addRelationship('/edited.jpg', '/original.jpg', VerbType.DerivedFrom)
+```
+
+## VFS-Specific Metadata
+
+While using standard graph types, VFS adds domain-specific metadata for efficient file operations:
+
+```javascript
+{
+  // Standard Brainy fields
+  type: NounType.Document,  // Standard noun type
+
+  // VFS-specific metadata
+  metadata: {
+    path: '/documents/report.pdf',
+    name: 'report.pdf',
+    vfsType: 'file',  // VFS-specific: 'file' or 'directory'
+    size: 1024000,
+    mimeType: 'application/pdf',
+    permissions: 0o644,
+    owner: 'user',
+    group: 'users',
+    accessed: Date.now(),
+    modified: Date.now(),
+    // ... custom metadata
+  }
+}
+```
+
+## Benefits of Standard Types
+
+### 1. Cross-Domain Queries
+```javascript
+// Find all documents (including VFS files) about "machine learning"
+const results = await brain.search('machine learning', {
+  where: { type: NounType.Document }
+})
+```
+
+### 2. Graph Traversal
+```javascript
+// Find all entities contained in a directory
+const contained = await brain.getRelations({
+  from: directoryId,
+  type: VerbType.Contains
+})
+
+// Find what contains a file (parent directories)
+const parents = await brain.getRelations({
+  to: fileId,
+  type: VerbType.Contains
+})
+```
+
+### 3. Semantic Understanding
+```javascript
+// Files are automatically embedded based on their content type
+// Documents get text embeddings
+// Media files get metadata embeddings
+// This enables semantic search across all file types
+```
+
+## Best Practices
+
+### DO:
+✅ Use `NounType.Collection` for directories
+✅ Use appropriate file NounTypes based on content
+✅ Use `VerbType.Contains` for parent-child relationships
+✅ Add custom relationships with standard VerbTypes
+✅ Include `vfsType` metadata for VFS operations
+
+### DON'T:
+❌ Use string literals for types (use enums)
+❌ Create custom noun/verb types for VFS
+❌ Mix graph relationships with metadata-only queries
+❌ Forget to create Contains relationships
+
+## Example: Complete File Creation
+
+```javascript
+// Creating a file with proper types
+const fileEntity = await brain.add({
+  type: NounType.Document,  // Standard noun type
+  data: 'File content for embeddings',
+  metadata: {
+    path: '/docs/guide.md',
+    vfsType: 'file',  // VFS-specific metadata
+    mimeType: 'text/markdown',
+    size: Buffer.byteLength('File content for embeddings')
+  }
+})
+
+// Create Contains relationship with parent
+await brain.relate({
+  from: parentDirectoryId,
+  to: fileEntity.id,
+  type: VerbType.Contains  // Standard verb type
+})
+```
+
+## Migration from Legacy Code
+
+If you have legacy code using strings for types:
+
+```javascript
+// ❌ OLD (strings)
+await brain.relate({
+  type: 'contains'  // Wrong!
+})
+
+// ✅ NEW (enums)
+await brain.relate({
+  type: VerbType.Contains  // Correct!
+})
+```
+
+Always import and use the type enums:
+
+```javascript
+import { NounType, VerbType } from '@soulcraft/brainy'
+```
\ No newline at end of file
diff --git a/src/vfs/VirtualFileSystem.ts b/src/vfs/VirtualFileSystem.ts
index 7c12c2b4..6083fa73 100644
--- a/src/vfs/VirtualFileSystem.ts
+++ b/src/vfs/VirtualFileSystem.ts
@@ -113,17 +113,38 @@ export class VirtualFileSystem implements IVirtualFileSystem {
    * Create or find the root directory entity
    */
   private async initializeRoot(): Promise<string> {
-    // Check if root already exists
+    // Check if root already exists - search using where clause
     const existing = await this.brain.find({
       where: {
-        path: '/',
-        vfsType: 'directory'
+        'metadata.path': '/',
+        'metadata.vfsType': 'directory'
       },
       limit: 1
     })
 
     if (existing.length > 0) {
-      return existing[0].entity.id
+      const rootEntity = existing[0]
+      // Ensure the root entity has proper metadata structure
+      const entityMetadata = (rootEntity as any).metadata || rootEntity
+      if (!entityMetadata.vfsType) {
+        // Update the root entity with proper metadata
+        await this.brain.update({
+          id: rootEntity.id,
+          metadata: {
+            path: '/',
+            name: '',
+            vfsType: 'directory',
+            size: 0,
+            permissions: 0o755,
+            owner: 'root',
+            group: 'root',
+            accessed: Date.now(),
+            modified: Date.now(),
+            ...entityMetadata  // Preserve any existing metadata
+          }
+        })
+      }
+      return rootEntity.id
     }
 
     // Create root directory
@@ -940,6 +961,41 @@ export class VirtualFileSystem implements IVirtualFileSystem {
       throw new VFSError(VFSErrorCode.ENOENT, `Entity not found: ${id}`)
     }
 
+    // Ensure entity has proper VFS metadata structure
+    // Handle both nested and flat metadata structures for compatibility
+    if (!entity.metadata || !entity.metadata.vfsType) {
+      // Check if metadata is at top level (legacy structure)
+      const anyEntity = entity as any
+      if (anyEntity.vfsType || anyEntity.path) {
+        entity.metadata = {
+          path: anyEntity.path || '/',
+          name: anyEntity.name || '',
+          vfsType: anyEntity.vfsType || (anyEntity.path === '/' ? 'directory' : 'file'),
+          size: anyEntity.size || 0,
+          permissions: anyEntity.permissions || (anyEntity.vfsType === 'directory' ? 0o755 : 0o644),
+          owner: anyEntity.owner || 'user',
+          group: anyEntity.group || 'users',
+          accessed: anyEntity.accessed || Date.now(),
+          modified: anyEntity.modified || Date.now(),
+          ...entity.metadata  // Preserve any existing nested metadata
+        }
+      } else if (entity.id === this.rootEntityId) {
+        // Special case: ensure root directory always has proper metadata
+        entity.metadata = {
+          path: '/',
+          name: '',
+          vfsType: 'directory',
+          size: 0,
+          permissions: 0o755,
+          owner: 'root',
+          group: 'root',
+          accessed: Date.now(),
+          modified: Date.now(),
+          ...entity.metadata
+        }
+      }
+    }
+
     return entity as VFSEntity
   }