diff --git a/lib/commands/debug.ts b/lib/commands/debug.ts
index 33e6d7a18e..922a7fba1f 100644
--- a/lib/commands/debug.ts
+++ b/lib/commands/debug.ts
@@ -135,6 +135,7 @@ export class DebugIOSCommand implements ICommand {
 		private $platformService: IPlatformService,
 		private $options: IOptions,
 		private $injector: IInjector,
+		private $sysInfo: ISysInfo,
 		private $projectData: IProjectData,
 		$iosDeviceOperations: IIOSDeviceOperations,
 		$iOSSimulatorLogProvider: Mobile.IiOSSimulatorLogProvider) {
@@ -161,6 +162,12 @@ export class DebugIOSCommand implements ICommand {
 			this.$errors.fail(`Timeout option specifies the seconds NativeScript CLI will wait to find the inspector socket port from device's logs. Must be a number.`);
 		}
 
+		if (this.$options.inspector) {
+			const macOSWarning = await this.$sysInfo.getMacOSWarningMessage();
+			if (macOSWarning && macOSWarning.severity === SystemWarningsSeverity.high) {
+				this.$errors.fail(`You cannot use NativeScript Inspector on this OS. To use it, please update your OS.`);
+			}
+		}
 		const result = await this.debugPlatformCommand.canExecute(args);
 		return result;
 	}
diff --git a/lib/common/declarations.d.ts b/lib/common/declarations.d.ts
index 914a08681b..8aedd1092c 100644
--- a/lib/common/declarations.d.ts
+++ b/lib/common/declarations.d.ts
@@ -1143,6 +1143,12 @@ interface IDeviceLiveSyncService extends IDeviceLiveSyncServiceBase {
 	afterInstallApplicationAction?(deviceAppData: Mobile.IDeviceAppData, localToDevicePaths: Mobile.ILocalToDevicePathData[]): Promise<boolean>;
 }
 
+interface ISystemWarning {
+	message: string;
+	severity: SystemWarningsSeverity;
+	toString?: () => string;
+}
+
 interface ISysInfo {
 	getSysInfo(config?: NativeScriptDoctor.ISysInfoConfig): Promise<NativeScriptDoctor.ISysInfoData>;
 	/**
@@ -1163,15 +1169,15 @@ interface ISysInfo {
 
 	/**
 	 * Gets all global warnings for the current environment, for example Node.js version compatibility, OS compatibility, etc.
-	 * @return {Promise<string[]>} All warnings. Empty array is returned in case the system is setup correctly.
+	 * @return {Promise<ISystemWarning[]>} All warnings. Empty array is returned in case the system is setup correctly.
 	 */
-	getSystemWarnings(): Promise<string[]>;
+	getSystemWarnings(): Promise<ISystemWarning[]>;
 
 	/**
 	 * Gets warning message for current macOS version.
 	 * @return {Promise<string>} Message in case the current macOS version is deprecated, null otherwise.
 	 */
-	getMacOSWarningMessage(): Promise<string>;
+	getMacOSWarningMessage(): Promise<ISystemWarning>;
 
 	/**
 	 * Returns the value of engines.node key from CLI's package.json file.
diff --git a/lib/common/definitions/logger.d.ts b/lib/common/definitions/logger.d.ts
index 0231f4f238..62338bf6d0 100644
--- a/lib/common/definitions/logger.d.ts
+++ b/lib/common/definitions/logger.d.ts
@@ -16,4 +16,5 @@ interface ILogger {
 	prepare(item: any): string;
 	printInfoMessageOnSameLine(message: string): void;
 	printMsgWithTimeout(message: string, timeout: number): Promise<void>;
+	printOnStderr(formatStr?: any, ...args: any[]): void;
 }
diff --git a/lib/common/host-info.ts b/lib/common/host-info.ts
index accdfa74b9..9fcdd5b825 100644
--- a/lib/common/host-info.ts
+++ b/lib/common/host-info.ts
@@ -57,17 +57,7 @@ export class HostInfo implements IHostInfo {
 		try {
 			const systemProfileOutput = await this.$childProcess.exec(systemProfileCommand);
 
-			// Output of command is similar to:
-			/*
-Software:
-
-    System Software Overview:
-
-      System Version: macOS 10.13.3 (17D47)
-      Kernel Version: Darwin 17.4.0
-      Time since boot: 68 days 22:12
-*/
-			const versionRegExp = /System Version:\s+?macOS\s+?(\d+\.\d+)\.\d+\s+/g;
+			const versionRegExp = /System Version:\s+?macOS\s+?(\d+\.\d+)(\.\d+)?\s+/g;
 			const regExpMatchers = versionRegExp.exec(systemProfileOutput);
 			const macOSVersion = regExpMatchers && regExpMatchers[1];
 			if (macOSVersion) {
diff --git a/lib/common/logger.ts b/lib/common/logger.ts
index 32cad3aca6..e6201a5512 100644
--- a/lib/common/logger.ts
+++ b/lib/common/logger.ts
@@ -148,6 +148,12 @@ export class Logger implements ILogger {
 		this.write(formattedMessage);
 	}
 
+	public printOnStderr(...args: string[]): void {
+		if (process.stderr) {
+			process.stderr.write(util.format.apply(null, args));
+		}
+	}
+
 	private getPasswordEncodedArguments(args: string[]): string[] {
 		return _.map(args, argument => {
 			if (typeof argument === 'string' && !!argument.match(/password/i)) {
diff --git a/lib/common/test/unit-tests/host-info.ts b/lib/common/test/unit-tests/host-info.ts
index 784de59d83..96838ea850 100644
--- a/lib/common/test/unit-tests/host-info.ts
+++ b/lib/common/test/unit-tests/host-info.ts
@@ -65,6 +65,27 @@ describe("hostInfo", () => {
 			assert.equal(calledCommand, "system_profiler SPSoftwareDataType -detailLevel mini");
 		});
 
+		it("returns correct macOS version based on system_profile, when version has two numbers only", async () => {
+			const testInjector = createTestInjector();
+			const hostInfo = testInjector.resolve<IHostInfo>("hostInfo");
+			const childProcess = testInjector.resolve<IChildProcess>("childProcess");
+			let calledCommand = "";
+			childProcess.exec = async (command: string, options?: any, execOptions?: IExecOptions): Promise<any> => {
+				calledCommand = command;
+				return `Software:
+
+    System Software Overview:
+
+      System Version: macOS 10.14 (18A391)
+      Kernel Version: Darwin 18.0.0
+      Time since boot: 1 day 5:52`;
+			};
+
+			const macOSVersion = await hostInfo.getMacOSVersion();
+			assert.deepEqual(macOSVersion, "10.14");
+			assert.equal(calledCommand, "system_profiler SPSoftwareDataType -detailLevel mini");
+		});
+
 		it("returns correct macOS version when system_profile call throws", async () => {
 			const testInjector = createTestInjector();
 			const hostInfo = testInjector.resolve<IHostInfo>("hostInfo");
diff --git a/lib/common/test/unit-tests/stubs.ts b/lib/common/test/unit-tests/stubs.ts
index 71de7170c8..f1f9709623 100644
--- a/lib/common/test/unit-tests/stubs.ts
+++ b/lib/common/test/unit-tests/stubs.ts
@@ -41,6 +41,10 @@ export class CommonLoggerStub implements ILogger {
 	printMarkdown(message: string): void {
 		this.output += message;
 	}
+
+	printOnStderr(...args: string[]): void {
+		// nothing to do here
+	}
 }
 
 export class ErrorsStub implements IErrors {
diff --git a/lib/common/verify-node-version.ts b/lib/common/verify-node-version.ts
index eebfccb408..02dc71872b 100644
--- a/lib/common/verify-node-version.ts
+++ b/lib/common/verify-node-version.ts
@@ -48,12 +48,12 @@ export function verifyNodeVersion(): void {
 	}
 
 	var nodeWarning = getNodeWarning();
-	if (nodeWarning) {
-		console.warn((os.EOL + nodeWarning + os.EOL).yellow.bold);
+	if (nodeWarning && nodeWarning.message) {
+		console.warn((`${os.EOL}${nodeWarning.message}${os.EOL}`).yellow.bold);
 	}
 }
 
-export function getNodeWarning(): string {
+export function getNodeWarning(): ISystemWarning {
 	var verificationOpts = getNodeVersionOpts();
 	var cliName = verificationOpts.cliName;
 	var supportedVersionsRange = verificationOpts.supportedVersionsRange;
@@ -78,6 +78,9 @@ export function getNodeWarning(): string {
 		}
 	}
 
-	return warningMessage;
+	return {
+		message: warningMessage,
+		severity: SystemWarningsSeverity.medium
+	};
 }
 /* tslint:enable */
diff --git a/lib/constants.ts b/lib/constants.ts
index 702024befb..4317535c57 100644
--- a/lib/constants.ts
+++ b/lib/constants.ts
@@ -186,9 +186,10 @@ export class AssetConstants {
 export class MacOSVersions {
 	public static Sierra = "10.12";
 	public static HighSierra = "10.13";
+	public static Mojave = "10.14";
 }
 
-export const MacOSDeprecationStringFormat = "Support for macOS %s is deprecated and will be removed in one of the next releases of NativeScript. Please, upgrade to the latest macOS version.";
+export const MacOSDeprecationStringFormat = "NativeScript does not support macOS %s and some functionality may not work. Please, upgrade to the latest macOS version.";
 export const PROGRESS_PRIVACY_POLICY_URL = "https://www.progress.com/legal/privacy-policy";
 export class SubscribeForNewsletterMessages {
 	public static AgreeToReceiveEmailMsg = "I agree".green.bold + " to receive email communications from Progress Software or its Partners (`https://www.progress.com/partners/partner-directory`)," +
diff --git a/lib/definitions/system-warnings.d.ts b/lib/definitions/system-warnings.d.ts
new file mode 100644
index 0000000000..d02841e093
--- /dev/null
+++ b/lib/definitions/system-warnings.d.ts
@@ -0,0 +1,4 @@
+declare const enum SystemWarningsSeverity {
+	medium = "medium",
+	high = "high"
+}
diff --git a/lib/nativescript-cli.ts b/lib/nativescript-cli.ts
index bbac0422f8..941367fad7 100644
--- a/lib/nativescript-cli.ts
+++ b/lib/nativescript-cli.ts
@@ -26,8 +26,12 @@ import { settlePromises } from "./common/helpers";
 	const $sysInfo = $injector.resolve<ISysInfo>("sysInfo");
 	const macOSWarning = await $sysInfo.getMacOSWarningMessage();
 	if (macOSWarning) {
-		const message = EOL + macOSWarning + EOL ;
-		logger.warn(message);
+		const message = `${EOL}${macOSWarning.message}${EOL}`;
+		if (macOSWarning.severity === SystemWarningsSeverity.high) {
+			logger.printOnStderr(message.red.bold);
+		} else {
+			logger.warn(message);
+		}
 	}
 
 	const commandDispatcher: ICommandDispatcher = $injector.resolve("commandDispatcher");
diff --git a/lib/sys-info.ts b/lib/sys-info.ts
index 5850b92777..6a3a35714e 100644
--- a/lib/sys-info.ts
+++ b/lib/sys-info.ts
@@ -35,15 +35,17 @@ export class SysInfo implements ISysInfo {
 	}
 
 	@exported("sysInfo")
-	public async getSystemWarnings(): Promise<string[]> {
-		const warnings: string[] = [];
+	public async getSystemWarnings(): Promise<ISystemWarning[]> {
+		const warnings: ISystemWarning[] = [];
 		const macOSWarningMessage = await this.getMacOSWarningMessage();
 		if (macOSWarningMessage) {
+			macOSWarningMessage.toString = function() { return this.message; };
 			warnings.push(macOSWarningMessage);
 		}
 
 		const nodeWarning = getNodeWarning();
 		if (nodeWarning) {
+			nodeWarning.toString = function() { return this.message; };
 			warnings.push(nodeWarning);
 		}
 
@@ -57,10 +59,13 @@ export class SysInfo implements ISysInfo {
 		return jsonContent && jsonContent.engines && jsonContent.engines.node;
 	}
 
-	public async getMacOSWarningMessage(): Promise<string> {
+	public async getMacOSWarningMessage(): Promise<ISystemWarning> {
 		const macOSVersion = await this.$hostInfo.getMacOSVersion();
 		if (macOSVersion && macOSVersion < MacOSVersions.HighSierra) {
-			return format(MacOSDeprecationStringFormat, macOSVersion);
+			return {
+				message: format(MacOSDeprecationStringFormat, macOSVersion),
+				severity: SystemWarningsSeverity.high
+			};
 		}
 
 		return null;
diff --git a/test/stubs.ts b/test/stubs.ts
index 38de63aee2..3880b3eeaf 100644
--- a/test/stubs.ts
+++ b/test/stubs.ts
@@ -42,6 +42,10 @@ export class LoggerStub implements ILogger {
 	}
 
 	printMarkdown(message: string): void { }
+
+	printOnStderr(...args: string[]): void {
+		// nothing to do here
+	}
 }
 
 export class ProcessServiceStub implements IProcessService {
diff --git a/test/sys-info.ts b/test/sys-info.ts
index cb7dfbe6f2..5294fd7d5f 100644
--- a/test/sys-info.ts
+++ b/test/sys-info.ts
@@ -32,8 +32,8 @@ describe("sysInfo", () => {
 	};
 
 	describe("getSystemWarnings", () => {
-		const getSystemWarnings = async (opts?: { nodeJsWarning?: string, macOSDeprecatedVersion?: string }): Promise<string[]> => {
-			sandbox.stub(verifyNodeVersion, "getNodeWarning").returns(opts && opts.nodeJsWarning);
+		const getSystemWarnings = async (opts?: { nodeJsWarning?: string, macOSDeprecatedVersion?: string }): Promise<ISystemWarning[]> => {
+			sandbox.stub(verifyNodeVersion, "getNodeWarning").returns(opts && opts.nodeJsWarning ? { message: opts.nodeJsWarning, severity: SystemWarningsSeverity.medium } : null);
 
 			const testInjector = createTestInjector();
 			const $hostInfo = testInjector.resolve<IHostInfo>("hostInfo");
@@ -50,28 +50,31 @@ describe("sysInfo", () => {
 
 		it("returns correct single warning when macOS version is deprecated", async () => {
 			const macOSDeprecatedVersion = MacOSVersions.Sierra;
-			const macOSWarning = format(MacOSDeprecationStringFormat, macOSDeprecatedVersion);
+			const macOSWarning = { message: format(MacOSDeprecationStringFormat, macOSDeprecatedVersion), severity: SystemWarningsSeverity.high };
 			const warnings = await getSystemWarnings({ macOSDeprecatedVersion });
+			_.each(warnings, warning => delete warning.toString);
 			assert.deepEqual(warnings, [macOSWarning]);
 		});
 
 		it("returns correct single warning when Node.js version is deprecated", async () => {
-			const nodeJsWarning = "Node.js Warning";
-			const warnings = await getSystemWarnings({ nodeJsWarning });
+			const nodeJsWarning = { message: "Node.js Warning", severity: SystemWarningsSeverity.medium };
+			const warnings = await getSystemWarnings({ nodeJsWarning: nodeJsWarning.message });
+			_.each(warnings, warning => delete warning.toString);
 			assert.deepEqual(warnings, [nodeJsWarning]);
 		});
 
 		it("returns correct warnings when both Node.js and macOS versions are deprecated", async () => {
 			const macOSDeprecatedVersion = MacOSVersions.Sierra;
-			const macOSWarning = format(MacOSDeprecationStringFormat, macOSDeprecatedVersion);
-			const nodeJsWarning = "Node.js Warning";
-			const warnings = await getSystemWarnings({ macOSDeprecatedVersion, nodeJsWarning });
+			const macOSWarning = { message: format(MacOSDeprecationStringFormat, macOSDeprecatedVersion), severity: SystemWarningsSeverity.high };
+			const nodeJsWarning = { message: "Node.js Warning", severity: SystemWarningsSeverity.medium };
+			const warnings = await getSystemWarnings({ macOSDeprecatedVersion, nodeJsWarning: nodeJsWarning.message });
+			_.each(warnings, warning => delete warning.toString);
 			assert.deepEqual(warnings, [macOSWarning, nodeJsWarning]);
 		});
 	});
 
 	describe("getMacOSWarningMessage", () => {
-		const getMacOSWarning = async (macOSDeprecatedVersion?: string): Promise<string> => {
+		const getMacOSWarning = async (macOSDeprecatedVersion?: string): Promise<ISystemWarning> => {
 			sandbox.stub(verifyNodeVersion, "getNodeWarning").returns(null);
 
 			const testInjector = createTestInjector();
@@ -89,8 +92,9 @@ describe("sysInfo", () => {
 
 		it("returns correct single warning when macOS version is deprecated", async () => {
 			const macOSDeprecatedVersion = MacOSVersions.Sierra;
-			const macOSWarning = format(MacOSDeprecationStringFormat, macOSDeprecatedVersion);
+			const macOSWarning: ISystemWarning = { message: format(MacOSDeprecationStringFormat, macOSDeprecatedVersion), severity: SystemWarningsSeverity.high };
 			const warning = await getMacOSWarning(macOSDeprecatedVersion);
+			delete warning.toString;
 			assert.deepEqual(warning, macOSWarning);
 		});
 	});