diff --git a/src/services/libs/__tests__/port.test.ts b/src/services/libs/__tests__/port.test.ts
new file mode 100644
index 00000000..d91e34fd
--- /dev/null
+++ b/src/services/libs/__tests__/port.test.ts
@@ -0,0 +1,40 @@
+import { describe, expect, it } from 'vitest';
+import { findAvailablePort, isPortAvailable } from '../port';
+
+describe('Port Utilities', () => {
+  describe('isPortAvailable', () => {
+    it('should return true for available high-numbered port', async () => {
+      const available = await isPortAvailable(59999);
+      expect(available).toBe(true);
+    });
+
+    it('should handle occupied ports gracefully', async () => {
+      const result = await isPortAvailable(80);
+      expect(typeof result).toBe('boolean');
+    });
+  });
+
+  describe('findAvailablePort', () => {
+    it('should return the same port if available', async () => {
+      const testPort = 59998;
+      const result = await findAvailablePort(testPort);
+      expect(result).toBe(testPort);
+    });
+
+    it('should find an available port when starting from a commonly used port', async () => {
+      const testPort = 5212;
+      const result = await findAvailablePort(testPort);
+      expect(result).not.toBeNull();
+      if (result !== null) {
+        expect(result).toBeGreaterThanOrEqual(testPort);
+      }
+    });
+
+    it('should eventually find an available port', async () => {
+      const testPort = 59997;
+      const result = await findAvailablePort(testPort);
+      expect(result).not.toBeNull();
+      expect(typeof result).toBe('number');
+    });
+  });
+});
diff --git a/src/services/libs/port.ts b/src/services/libs/port.ts
new file mode 100644
index 00000000..046f6fb5
--- /dev/null
+++ b/src/services/libs/port.ts
@@ -0,0 +1,62 @@
+import { Server } from 'node:net';
+
+/**
+ * Check if a port is available on the local machine
+ * Optimized for minimal overhead - closes server immediately after binding
+ * @param port The port number to check
+ * @returns true if port is available, false if in use
+ */
+export async function isPortAvailable(port: number): Promise<boolean> {
+  return new Promise((resolve) => {
+    const server = new Server();
+
+    server.once('error', (error: NodeJS.ErrnoException) => {
+      if (error.code === 'EADDRINUSE') {
+        resolve(false);
+      } else {
+        // Other errors treated as unavailable
+        resolve(false);
+      }
+    });
+
+    server.once('listening', () => {
+      // Close with callback to ensure cleanup before resolving
+      server.close(() => {
+        resolve(true);
+      });
+    });
+
+    // Bind to 0.0.0.0 to check all network interfaces
+    server.listen(port, '0.0.0.0');
+  });
+}
+
+/**
+ * Find an available port starting from the given port
+ * First tries port, then port+10, then keeps incrementing by 1
+ * @param startPort The port to start checking from
+ * @param maxAttempts Maximum number of attempts (default 100)
+ * @returns An available port number, or null if none found
+ */
+export async function findAvailablePort(startPort: number, maxAttempts = 100): Promise<number | null> {
+  // First try the original port
+  if (await isPortAvailable(startPort)) {
+    return startPort;
+  }
+
+  // Then try +10
+  const portPlusTen = startPort + 10;
+  if (await isPortAvailable(portPlusTen)) {
+    return portPlusTen;
+  }
+
+  // Then increment by 1 from +10
+  for (let attempt = 1; attempt < maxAttempts; attempt++) {
+    const portToTry = portPlusTen + attempt;
+    if (await isPortAvailable(portToTry)) {
+      return portToTry;
+    }
+  }
+
+  return null;
+}
diff --git a/src/services/wiki/index.ts b/src/services/wiki/index.ts
index e849dc8f..2d870d51 100644
--- a/src/services/wiki/index.ts
+++ b/src/services/wiki/index.ts
@@ -1,3 +1,4 @@
+import { findAvailablePort } from '@services/libs/port';
 import { createWorkerProxy, terminateWorker } from '@services/libs/workerAdapter';
 import { dialog, shell } from 'electron';
 import { attachWorker } from 'electron-ipc-cat/server';
@@ -6,7 +7,8 @@ import { copy, exists, mkdir, mkdirs, pathExists, readdir, readFile } from 'fs-e
 import { inject, injectable } from 'inversify';
 import path from 'path';
 import { Worker } from 'worker_threads';
-// @ts-expect-error - Vite worker import with ?nodeWorker query
+// eslint-disable-next-line @typescript-eslint/ban-ts-comment
+// @ts-ignore - Vite worker import with ?nodeWorker query
 import WikiWorkerFactory from './wikiWorker/index?nodeWorker';
 
 import { container } from '@services/container';
@@ -118,7 +120,8 @@ export class Wiki implements IWikiService {
       logger.error('Try to start wiki, but workspace is not a wiki workspace', { workspace, workspaceID });
       return;
     }
-    const { port, rootTiddler, readOnlyMode, tokenAuth, homeUrl, lastUrl, https, excludedPlugins, isSubWiki, wikiFolderLocation, name, enableHTTPAPI, authToken } = workspace;
+    const { rootTiddler, readOnlyMode, tokenAuth, https, excludedPlugins, isSubWiki, wikiFolderLocation, name, enableHTTPAPI, authToken } = workspace;
+    let { port, homeUrl, lastUrl } = workspace;
     logger.debug('startWiki: Got workspace from workspaceService', {
       workspaceID,
       name,
@@ -131,6 +134,39 @@ export class Wiki implements IWikiService {
       logger.error('Try to start wiki, but workspace is sub wiki', { workspace, workspaceID });
       return;
     }
+
+    // Check if port is available before starting wiki
+    const availablePort = await findAvailablePort(port);
+    if (availablePort === null) {
+      logger.error('Could not find available port for wiki', { workspaceID, requestedPort: port });
+      await workspaceService.updateMetaData(workspaceID, {
+        isLoading: false,
+        didFailLoadErrorMessage: `Could not find available port starting from ${port}`,
+      });
+      return;
+    }
+
+    // Update workspace settings if port changed
+    if (availablePort !== port) {
+      logger.info('Port conflict detected, using alternative port', {
+        workspaceID,
+        originalPort: port,
+        newPort: availablePort,
+      });
+
+      const portChange = {
+        port: availablePort,
+        homeUrl: homeUrl.replace(`:${port}`, `:${availablePort}`),
+        lastUrl: lastUrl?.replace(`:${port}`, `:${availablePort}`) ?? null,
+      };
+
+      await workspaceService.update(workspaceID, portChange, true);
+
+      // Update local variables with new port
+      port = availablePort;
+      homeUrl = portChange.homeUrl;
+      lastUrl = portChange.lastUrl;
+    }
     // wiki server is about to boot, but our webview is just start loading, wait for `view.webContents.on('did-stop-loading'` to set this to false
     await workspaceService.updateMetaData(workspaceID, { isLoading: true });
     if (tokenAuth && authToken) {
@@ -287,16 +323,26 @@ export class Wiki implements IWikiService {
                 logger.info('Realigned view after plugin error', { workspaceID, function: 'startWiki' });
               }
 
-              // fix "message":"listen EADDRINUSE: address already in use 0.0.0.0:5212"
+              // Port availability check should have prevented EADDRINUSE, but handle as fallback
               if (errorMessage.includes('EADDRINUSE')) {
-                const portChange = {
-                  port: port + 1,
-                  homeUrl: homeUrl.replace(`:${port}`, `:${port + 1}`),
-
-                  lastUrl: lastUrl?.replace(`:${port}`, `:${port + 1}`) ?? null,
-                };
-                await workspaceService.update(workspaceID, portChange, true);
-                reject(new WikiRuntimeError(new Error(message.message), wikiFolderLocation, true, { ...workspace, ...portChange }));
+                logger.warn('EADDRINUSE error despite pre-flight port check', {
+                  workspaceID,
+                  port,
+                  errorMessage,
+                });
+                // Try to find another available port as emergency fallback
+                const emergencyPort = await findAvailablePort(port + 1);
+                if (emergencyPort !== null) {
+                  const portChange = {
+                    port: emergencyPort,
+                    homeUrl: homeUrl.replace(`:${port}`, `:${emergencyPort}`),
+                    lastUrl: lastUrl?.replace(`:${port}`, `:${emergencyPort}`) ?? null,
+                  };
+                  await workspaceService.update(workspaceID, portChange, true);
+                  reject(new WikiRuntimeError(new Error(message.message), wikiFolderLocation, true, { ...workspace, ...portChange }));
+                } else {
+                  reject(new WikiRuntimeError(new Error(message.message), wikiFolderLocation, false, { ...workspace }));
+                }
                 return;
               }