diff --git a/lib/definitions/ios-debugger-port-service.d.ts b/lib/definitions/ios-debugger-port-service.d.ts
index 50f156afb0..1b6486a0f5 100644
--- a/lib/definitions/ios-debugger-port-service.d.ts
+++ b/lib/definitions/ios-debugger-port-service.d.ts
@@ -17,7 +17,7 @@ interface IIOSDebuggerPortService {
 	 * Gets iOS debugger port for specified deviceId and appId
 	 * @param {IIOSDebuggerPortInputData} data - Describes deviceId and appId
 	 */
-	getPort(data: IIOSDebuggerPortInputData): Promise<number>;
+	getPort(data: IIOSDebuggerPortInputData, debugOptions?: IDebugOptions): Promise<number>;
 	/**
 	 * Attaches on DEBUGGER_PORT_FOUND event and STARTING_IOS_APPLICATION events
 	 * In case when DEBUGGER_PORT_FOUND event is emitted, stores the port and clears the timeout if such.
diff --git a/lib/services/ios-debug-service.ts b/lib/services/ios-debug-service.ts
index c5f48b7f1a..9ee2412f87 100644
--- a/lib/services/ios-debug-service.ts
+++ b/lib/services/ios-debug-service.ts
@@ -202,7 +202,7 @@ export class IOSDebugService extends DebugServiceBase implements IPlatformDebugS
 		// the VSCode Ext starts `tns debug ios --no-client` to start/attach to debug sessions
 		// check if --no-client is passed - default to opening a tcp socket (versus Chrome DevTools (websocket))
 		if ((debugOptions.inspector || !debugOptions.client) && this.$hostInfo.isDarwin) {
-			this._socketProxy = await this.$socketProxyFactory.createTCPSocketProxy(this.getSocketFactory(debugData, device));
+			this._socketProxy = await this.$socketProxyFactory.createTCPSocketProxy(this.getSocketFactory(device, debugData, debugOptions));
 			await this.openAppInspector(this._socketProxy.address(), debugData, debugOptions);
 			return null;
 		} else {
@@ -211,7 +211,7 @@ export class IOSDebugService extends DebugServiceBase implements IPlatformDebugS
 			}
 
 			const deviceIdentifier = device ? device.deviceInfo.identifier : debugData.deviceIdentifier;
-			this._socketProxy = await this.$socketProxyFactory.createWebSocketProxy(this.getSocketFactory(debugData, device), deviceIdentifier);
+			this._socketProxy = await this.$socketProxyFactory.createWebSocketProxy(this.getSocketFactory(device, debugData, debugOptions), deviceIdentifier);
 			return this.getChromeDebugUrl(debugOptions, this._socketProxy.options.port);
 		}
 	}
@@ -230,9 +230,9 @@ export class IOSDebugService extends DebugServiceBase implements IPlatformDebugS
 		}
 	}
 
-	private getSocketFactory(debugData: IDebugData, device?: Mobile.IiOSDevice): () => Promise<net.Socket> {
+	private getSocketFactory(device: Mobile.IiOSDevice, debugData: IDebugData, debugOptions: IDebugOptions): () => Promise<net.Socket> {
 		const factory = async () => {
-			const port = await this.$iOSDebuggerPortService.getPort({ projectDir: debugData.projectDir, deviceId: debugData.deviceIdentifier, appId: debugData.applicationIdentifier });
+			const port = await this.$iOSDebuggerPortService.getPort({ projectDir: debugData.projectDir, deviceId: debugData.deviceIdentifier, appId: debugData.applicationIdentifier }, debugOptions);
 			if (!port) {
 				this.$errors.fail("NativeScript debugger was not able to get inspector socket port.");
 			}
diff --git a/lib/services/ios-debugger-port-service.ts b/lib/services/ios-debugger-port-service.ts
index 8dac0bb27e..e52f4b509d 100644
--- a/lib/services/ios-debugger-port-service.ts
+++ b/lib/services/ios-debugger-port-service.ts
@@ -14,7 +14,7 @@ export class IOSDebuggerPortService implements IIOSDebuggerPortService {
 		private $projectDataService: IProjectDataService,
 		private $logger: ILogger) { }
 
-	public getPort(data: IIOSDebuggerPortInputData): Promise<number> {
+	public getPort(data: IIOSDebuggerPortInputData, debugOptions?: IDebugOptions): Promise<number> {
 		return new Promise((resolve, reject) => {
 			if (!this.canStartLookingForDebuggerPort(data)) {
 				resolve(IOSDebuggerPortService.DEFAULT_PORT);
@@ -22,7 +22,8 @@ export class IOSDebuggerPortService implements IIOSDebuggerPortService {
 			}
 
 			const key = `${data.deviceId}${data.appId}`;
-			let retryCount: number = 10;
+			const timeout = this.getTimeout(debugOptions);
+			let retryCount = Math.max(timeout * 1000 / 500, 10);
 
 			const interval = setInterval(() => {
 				let port = this.getPortByKey(key);
diff --git a/test/services/ios-debugger-port-service.ts b/test/services/ios-debugger-port-service.ts
index 765d255d11..66d4db19a4 100644
--- a/test/services/ios-debugger-port-service.ts
+++ b/test/services/ios-debugger-port-service.ts
@@ -157,7 +157,7 @@ describe("iOSDebuggerPortService", () => {
 				}
 
 				const promise = iOSDebuggerPortService.getPort({ deviceId: deviceId, appId: appId, projectDir: mockProjectDirObj.projectDir });
-				clock.tick(10000);
+				clock.tick(20000);
 				const port = await promise;
 				assert.deepEqual(port, testCase.emittedPort);
 			});
@@ -171,7 +171,7 @@ describe("iOSDebuggerPortService", () => {
 				}
 
 				const promise = iOSDebuggerPortService.getPort({ deviceId: deviceId, appId: appId, projectDir: mockProjectDirObj.projectDir });
-				clock.tick(10000);
+				clock.tick(20000);
 				const port = await promise;
 				assert.deepEqual(port, testCase.emittedPort);
 			});