diff --git a/src/custom-stdio.ts b/src/custom-stdio.ts
index e1c3bb4c..bb5d1de9 100644
--- a/src/custom-stdio.ts
+++ b/src/custom-stdio.ts
@@ -33,8 +33,18 @@ export class FilteredStdioServerTransport extends StdioServerTransport {
   private clientName: string = 'unknown';
   private disableNotifications: boolean = false;
 
+  // Serialised write queue for notification/progress/custom writes.
+  // Ensures at most one `once('drain', ...)` listener is registered at a time,
+  // preventing the MaxListenersExceededWarning on process.stdout (#391).
+  private stdoutQueue: string[] = [];
+  private stdoutDraining: boolean = false;
+
   constructor() {
     super();
+
+    // Allow enough listeners for concurrent MCP response drain waits during
+    // heavy tool usage, without triggering false-positive MaxListeners warnings.
+    process.stdout.setMaxListeners(50);
     
     // Store original methods
     this.originalConsole = {
@@ -123,6 +133,39 @@ export class FilteredStdioServerTransport extends StdioServerTransport {
     return this.messageBuffer.length;
   }
 
+  /**
+   * Write a serialised line to stdout via the notification write queue.
+   * At most one `once('drain', ...)` listener is registered at any time,
+   * preventing MaxListenersExceededWarning during heavy notification load.
+   */
+  private writeNotificationToStdout(data: string): void {
+    this.stdoutQueue.push(data);
+    if (!this.stdoutDraining) {
+      this.flushNotificationQueue();
+    }
+  }
+
+  private flushNotificationQueue(): void {
+    while (this.stdoutQueue.length > 0) {
+      const data = this.stdoutQueue[0];
+      const flushed = this.originalStdoutWrite.call(process.stdout, data);
+      if (flushed) {
+        this.stdoutQueue.shift();
+      } else {
+        // stdout buffer is full — wait for drain before writing more.
+        // Using once() ensures the listener is removed immediately after firing.
+        if (!this.stdoutDraining) {
+          this.stdoutDraining = true;
+          process.stdout.once('drain', () => {
+            this.stdoutDraining = false;
+            this.flushNotificationQueue();
+          });
+        }
+        return;
+      }
+    }
+  }
+
   private setupConsoleRedirection() {
     console.log = (...args: any[]) => {
       if (this.isInitialized) {
@@ -258,8 +301,9 @@ export class FilteredStdioServerTransport extends StdioServerTransport {
         }
       };
 
-      // Send as valid JSON-RPC notification
-      this.originalStdoutWrite.call(process.stdout, JSON.stringify(notification) + '\n');
+      // Route through the serialised write queue to avoid accumulating
+      // drain listeners on process.stdout during heavy notification load.
+      this.writeNotificationToStdout(JSON.stringify(notification) + '\n');
     } catch (error) {
       // Fallback to a simple JSON-RPC error notification if JSON serialization fails
       const fallbackNotification = {
@@ -271,7 +315,7 @@ export class FilteredStdioServerTransport extends StdioServerTransport {
           data: `Log serialization failed: ${args.join(' ')}`
         }
       };
-      this.originalStdoutWrite.call(process.stdout, JSON.stringify(fallbackNotification) + '\n');
+      this.writeNotificationToStdout(JSON.stringify(fallbackNotification) + '\n');
     }
   }
 
@@ -307,7 +351,7 @@ export class FilteredStdioServerTransport extends StdioServerTransport {
         }
       };
 
-      this.originalStdoutWrite.call(process.stdout, JSON.stringify(notification) + '\n');
+      this.writeNotificationToStdout(JSON.stringify(notification) + '\n');
     } catch (error) {
       // Fallback to basic JSON-RPC notification
       const fallbackNotification = {
@@ -319,7 +363,7 @@ export class FilteredStdioServerTransport extends StdioServerTransport {
           data: `sendLog failed: ${message}`
         }
       };
-      this.originalStdoutWrite.call(process.stdout, JSON.stringify(fallbackNotification) + '\n');
+      this.writeNotificationToStdout(JSON.stringify(fallbackNotification) + '\n');
     }
   }
 
@@ -343,7 +387,7 @@ export class FilteredStdioServerTransport extends StdioServerTransport {
         }
       };
       
-      this.originalStdoutWrite.call(process.stdout, JSON.stringify(notification) + '\n');
+      this.writeNotificationToStdout(JSON.stringify(notification) + '\n');
     } catch (error) {
       // Fallback to basic JSON-RPC notification for progress
       const fallbackNotification = {
@@ -355,7 +399,7 @@ export class FilteredStdioServerTransport extends StdioServerTransport {
           data: `Progress ${token}: ${value}${total ? `/${total}` : ''}`
         }
       };
-      this.originalStdoutWrite.call(process.stdout, JSON.stringify(fallbackNotification) + '\n');
+      this.writeNotificationToStdout(JSON.stringify(fallbackNotification) + '\n');
     }
   }
 
@@ -375,7 +419,7 @@ export class FilteredStdioServerTransport extends StdioServerTransport {
         params: params
       };
       
-      this.originalStdoutWrite.call(process.stdout, JSON.stringify(notification) + '\n');
+      this.writeNotificationToStdout(JSON.stringify(notification) + '\n');
     } catch (error) {
       // Fallback to basic JSON-RPC notification for custom notifications
       const fallbackNotification = {
@@ -387,7 +431,7 @@ export class FilteredStdioServerTransport extends StdioServerTransport {
           data: `Custom notification failed: ${method}: ${JSON.stringify(params)}`
         }
       };
-      this.originalStdoutWrite.call(process.stdout, JSON.stringify(fallbackNotification) + '\n');
+      this.writeNotificationToStdout(JSON.stringify(fallbackNotification) + '\n');
     }
   }
 
diff --git a/src/tools/filesystem.ts b/src/tools/filesystem.ts
index 78c2b2de..2214f530 100644
--- a/src/tools/filesystem.ts
+++ b/src/tools/filesystem.ts
@@ -202,6 +202,36 @@ export async function validatePath(requestedPath: string): Promise<string> {
                 });
                 throw new Error(`Failed to resolve symlink for path: ${absoluteOriginal}. Error: ${err.message}`);
             }
+
+            // SECURITY FIX: When the full path doesn't exist (e.g., writing a new file),
+            // resolve the parent directory to detect symlinks in the path chain.
+            // Without this, an attacker could create a symlink inside an allowed directory
+            // pointing to a restricted location, then write to a non-existent file through
+            // that symlink — bypassing the directory restriction check.
+            try {
+                const parentDir = path.dirname(absoluteOriginal);
+                const resolvedParent = await fs.realpath(parentDir, { encoding: 'utf8' });
+                const basename = path.basename(absoluteOriginal);
+                resolvedRealPath = path.join(resolvedParent, basename);
+            } catch {
+                // Parent also doesn't exist — walk up the tree to find
+                // the deepest existing ancestor and resolve it
+                let current = absoluteOriginal;
+                let remaining: string[] = [];
+                while (true) {
+                    const parent = path.dirname(current);
+                    if (parent === current) break; // reached filesystem root
+                    remaining.unshift(path.basename(current));
+                    current = parent;
+                    try {
+                        const resolvedAncestor = await fs.realpath(current, { encoding: 'utf8' });
+                        resolvedRealPath = path.join(resolvedAncestor, ...remaining);
+                        break;
+                    } catch {
+                        // keep walking up
+                    }
+                }
+            }
         }
 
         const pathForNextCheck = resolvedRealPath ?? absoluteOriginal;