diff --git a/mac/Focalboard.xcodeproj/project.pbxproj b/mac/Focalboard.xcodeproj/project.pbxproj
index a991d9d9c..9b930d12a 100644
--- a/mac/Focalboard.xcodeproj/project.pbxproj
+++ b/mac/Focalboard.xcodeproj/project.pbxproj
@@ -7,6 +7,7 @@
 	objects = {
 
 /* Begin PBXBuildFile section */
+		8014951C261598D600A51700 /* PortUtils.swift in Sources */ = {isa = PBXBuildFile; fileRef = 8014951B261598D600A51700 /* PortUtils.swift */; };
 		80D6DEBB252E13CB00AEED9E /* AppDelegate.swift in Sources */ = {isa = PBXBuildFile; fileRef = 80D6DEBA252E13CB00AEED9E /* AppDelegate.swift */; };
 		80D6DEBD252E13CB00AEED9E /* ViewController.swift in Sources */ = {isa = PBXBuildFile; fileRef = 80D6DEBC252E13CB00AEED9E /* ViewController.swift */; };
 		80D6DEBF252E13CD00AEED9E /* Assets.xcassets in Resources */ = {isa = PBXBuildFile; fileRef = 80D6DEBE252E13CD00AEED9E /* Assets.xcassets */; };
@@ -35,6 +36,7 @@
 /* End PBXContainerItemProxy section */
 
 /* Begin PBXFileReference section */
+		8014951B261598D600A51700 /* PortUtils.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = PortUtils.swift; sourceTree = "<group>"; };
 		80D6DEB7252E13CB00AEED9E /* Focalboard.app */ = {isa = PBXFileReference; explicitFileType = wrapper.application; includeInIndex = 0; path = Focalboard.app; sourceTree = BUILT_PRODUCTS_DIR; };
 		80D6DEBA252E13CB00AEED9E /* AppDelegate.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = AppDelegate.swift; sourceTree = "<group>"; };
 		80D6DEBC252E13CB00AEED9E /* ViewController.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = ViewController.swift; sourceTree = "<group>"; };
@@ -103,6 +105,7 @@
 			isa = PBXGroup;
 			children = (
 				80D6DEBA252E13CB00AEED9E /* AppDelegate.swift */,
+				8014951B261598D600A51700 /* PortUtils.swift */,
 				80D6DEBC252E13CB00AEED9E /* ViewController.swift */,
 				80D6DF17252F9BDE00AEED9E /* AutoSaveWindowController.swift */,
 				80D6DEBE252E13CD00AEED9E /* Assets.xcassets */,
@@ -283,6 +286,7 @@
 			isa = PBXSourcesBuildPhase;
 			buildActionMask = 2147483647;
 			files = (
+				8014951C261598D600A51700 /* PortUtils.swift in Sources */,
 				80D6DF18252F9BDE00AEED9E /* AutoSaveWindowController.swift in Sources */,
 				80D6DEBD252E13CB00AEED9E /* ViewController.swift in Sources */,
 				80D6DEBB252E13CB00AEED9E /* AppDelegate.swift in Sources */,
diff --git a/mac/Focalboard/AppDelegate.swift b/mac/Focalboard/AppDelegate.swift
index 6b9b0eff2..ea2f25adb 100644
--- a/mac/Focalboard/AppDelegate.swift
+++ b/mac/Focalboard/AppDelegate.swift
@@ -88,7 +88,16 @@ class AppDelegate: NSObject, NSApplicationDelegate {
         return "su-" + randomNumber
     }
 
+	private func getFreePort() {
+		if PortUtils.isPortFree(in_port_t(serverPort)) {
+			return
+		}
+
+		serverPort = Int(PortUtils.getFreePort())
+	}
+
 	private func startServer() {
+		getFreePort()
 		sessionToken = generateSessionToken()
 
 		let cwdUrl = webFolder()
diff --git a/mac/Focalboard/Base.lproj/Main.storyboard b/mac/Focalboard/Base.lproj/Main.storyboard
index 1ac221a83..be5f285ce 100644
--- a/mac/Focalboard/Base.lproj/Main.storyboard
+++ b/mac/Focalboard/Base.lproj/Main.storyboard
@@ -578,6 +578,13 @@
                                             </connections>
                                         </menuItem>
                                         <menuItem isSeparatorItem="YES" id="hB3-LF-h0Y"/>
+                                        <menuItem title="Diagnostics Info" id="oQB-FY-dcB">
+                                            <modifierMask key="keyEquivalentModifierMask"/>
+                                            <connections>
+                                                <action selector="showDiagnosticsInfo:" target="Ady-hI-5gd" id="hkZ-Xn-3T1"/>
+                                            </connections>
+                                        </menuItem>
+                                        <menuItem isSeparatorItem="YES" id="dRF-4R-egy"/>
                                         <menuItem title="Show Sidebar" keyEquivalent="s" id="kIP-vf-haE">
                                             <modifierMask key="keyEquivalentModifierMask" control="YES" command="YES"/>
                                             <connections>
diff --git a/mac/Focalboard/PortUtils.swift b/mac/Focalboard/PortUtils.swift
new file mode 100644
index 000000000..697f22ac4
--- /dev/null
+++ b/mac/Focalboard/PortUtils.swift
@@ -0,0 +1,52 @@
+// Copyright (c) 2015-present Mattermost, Inc. All Rights Reserved.
+// See LICENSE.txt for license information.
+
+import Foundation
+
+class PortUtils {
+	static func isPortFree(_ port: in_port_t) -> Bool {
+		let socketFileDescriptor = socket(AF_INET, SOCK_STREAM, 0)
+		if socketFileDescriptor == -1 {
+			return false
+		}
+
+		var addr = sockaddr_in()
+		let sizeOfSockkAddr = MemoryLayout<sockaddr_in>.size
+		addr.sin_len = __uint8_t(sizeOfSockkAddr)
+		addr.sin_family = sa_family_t(AF_INET)
+		addr.sin_port = Int(OSHostByteOrder()) == OSLittleEndian ? _OSSwapInt16(port) : port
+		addr.sin_addr = in_addr(s_addr: inet_addr("127.0.0.1"))
+		addr.sin_zero = (0, 0, 0, 0, 0, 0, 0, 0)
+		var bind_addr = sockaddr()
+		memcpy(&bind_addr, &addr, Int(sizeOfSockkAddr))
+
+		if Darwin.bind(socketFileDescriptor, &bind_addr, socklen_t(sizeOfSockkAddr)) == -1 {
+			release(socket: socketFileDescriptor)
+			return false
+		}
+		if listen(socketFileDescriptor, SOMAXCONN ) == -1 {
+			release(socket: socketFileDescriptor)
+			return false
+		}
+		release(socket: socketFileDescriptor)
+		return true
+	}
+
+	private static func release(socket: Int32) {
+		Darwin.shutdown(socket, SHUT_RDWR)
+		close(socket)
+	}
+
+	static func getFreePort() -> in_port_t {
+		var portNum: in_port_t = 0
+		for i in 50000..<65000 {
+			let isFree = isPortFree(in_port_t(i))
+			if isFree {
+				portNum = in_port_t(i)
+				return portNum
+			}
+		}
+
+		return in_port_t(0)
+	}
+}
diff --git a/mac/Focalboard/ViewController.swift b/mac/Focalboard/ViewController.swift
index 96010bf35..02e3d9957 100644
--- a/mac/Focalboard/ViewController.swift
+++ b/mac/Focalboard/ViewController.swift
@@ -45,6 +45,17 @@ class ViewController:
 		WKWebsiteDataStore.default().removeData(ofTypes: websiteDataTypes as! Set<String>, modifiedSince: date, completionHandler:{ })
 	}
 
+	@IBAction func showDiagnosticsInfo(_ sender: NSObject) {
+		let appDelegate = NSApplication.shared.delegate as! AppDelegate
+
+		let alert: NSAlert = NSAlert()
+		alert.messageText = "Diagnostics info"
+		alert.informativeText = "Port: \(appDelegate.serverPort)"
+		alert.alertStyle = .informational
+		alert.addButton(withTitle: "OK")
+		alert.runModal()
+	}
+
 	@objc func onServerStarted() {
 		NSLog("onServerStarted")
 		DispatchQueue.main.asyncAfter(deadline: .now() + 0.5) {