diff --git a/src/cli.ts b/src/cli.ts
index 89c8028fc..46a2d9175 100644
--- a/src/cli.ts
+++ b/src/cli.ts
@@ -6,7 +6,7 @@
 import { VSCodeSettings } from '@redhat-developer/vscode-redhat-telemetry/lib/common/vscode/settings';
 import * as cp from 'child_process';
 import { CommandText } from './base/command';
-import { ToolsConfig } from './tools';
+import { ToolNotFoundError, ToolsConfig } from './tools';
 import { ChildProcessUtil, CliExitData } from './util/childProcessUtil';
 import { ExecutionContext } from './util/utils';
 import { VsCommandError } from './vscommand';
@@ -128,6 +128,9 @@ export class CliChannel {
         }
 
         const toolLocation = await ToolsConfig.detect(cmd.command);
+        if (!toolLocation) {
+            throw new ToolNotFoundError(cmd.command);
+        }
         const optWithTelemetryEnv = CliChannel.applyEnv(options, CliChannel.createTelemetryEnv()) as cp.ExecFileSyncOptionsWithStringEncoding;
 
         const result: string = cp.execFileSync(toolLocation, [cmd.parameter, ...cmd.options.map((o)=>o.toString())], optWithTelemetryEnv);
diff --git a/src/tools.ts b/src/tools.ts
index 8cd43fa0c..84c7b2abc 100644
--- a/src/tools.ts
+++ b/src/tools.ts
@@ -13,6 +13,13 @@ import configData from './tools.json';
 import { ChildProcessUtil } from './util/childProcessUtil';
 import { Platform } from './util/platform';
 
+export class ToolNotFoundError extends Error {
+    constructor(public readonly toolName: string) {
+        super(`'${toolName}' tool not found. Install it or enable 'openshiftToolkit.searchForToolsInPath' setting.`);
+        this.name = 'ToolNotFoundError';
+    }
+}
+
 export class ToolsConfig {
 
     public static tools: any = ToolsConfig.loadMetadata(configData, Platform.OS);
diff --git a/src/util/loginUtil.ts b/src/util/loginUtil.ts
index 91b729164..63173b4be 100644
--- a/src/util/loginUtil.ts
+++ b/src/util/loginUtil.ts
@@ -6,6 +6,7 @@
 import { CommandOption, CommandText } from '../base/command';
 import { CliChannel } from '../cli';
 import { Oc } from '../oc/ocWrapper';
+import { ToolNotFoundError } from '../tools';
 import { isOpenShiftCluster } from './kubeUtils';
 
 export class LoginUtil {
@@ -37,9 +38,15 @@ export class LoginUtil {
                 return await CliChannel.getInstance().executeSyncTool(
                         new CommandText('oc', 'api-versions'), { timeout: 5000 })
                     .then((response) => !response || response.trim().length === 0) // Active user is set - no need to login
-                    .catch((error) => true);
+                    .catch((error) => {
+                        if (error instanceof ToolNotFoundError) throw error;
+                        return true;
+                    });
             })
-            .catch((error) => true); // Can't get server - require to login
+            .catch((error) => {
+                if (error instanceof ToolNotFoundError) throw error;
+                return true;
+            });
     }
 
     /**
diff --git a/test/unit/tools.test.ts b/test/unit/tools.test.ts
index 5bd017119..79064f9e6 100644
--- a/test/unit/tools.test.ts
+++ b/test/unit/tools.test.ts
@@ -15,6 +15,7 @@ import sinonChai from 'sinon-chai';
 import * as vscode from 'vscode';
 import { ChildProcessUtil, CliExitData } from '../../src/util/childProcessUtil';
 import { Platform } from '../../src/util/platform';
+import { ToolNotFoundError } from '../../src/tools';
 import * as utils from '../../src/util/utils';
 
 chai.use(sinonChai);
@@ -152,4 +153,28 @@ suite('tools configuration', () => {
             assert.ok(!config.odo);
         });
     });
+
+    suite('ToolNotFoundError', () => {
+        test('extends Error', () => {
+            const error = new ToolNotFoundError('oc');
+            assert.ok(error instanceof Error);
+            assert.ok(error instanceof ToolNotFoundError);
+        });
+
+        test('has correct name property', () => {
+            const error = new ToolNotFoundError('oc');
+            assert.equal(error.name, 'ToolNotFoundError');
+        });
+
+        test('stores toolName', () => {
+            const error = new ToolNotFoundError('oc');
+            assert.equal(error.toolName, 'oc');
+        });
+
+        test('message includes tool name and setting hint', () => {
+            const error = new ToolNotFoundError('oc');
+            assert.ok(error.message.includes('\'oc\''));
+            assert.ok(error.message.includes('searchForToolsInPath'));
+        });
+    });
 });
diff --git a/test/unit/util/loginUtil.test.ts b/test/unit/util/loginUtil.test.ts
new file mode 100644
index 000000000..89f049741
--- /dev/null
+++ b/test/unit/util/loginUtil.test.ts
@@ -0,0 +1,84 @@
+/*-----------------------------------------------------------------------------------------------
+ *  Copyright (c) Red Hat, Inc. All rights reserved.
+ *  Licensed under the MIT License. See LICENSE file in the project root for license information.
+ *-----------------------------------------------------------------------------------------------*/
+
+import * as chai from 'chai';
+import * as sinon from 'sinon';
+import sinonChai from 'sinon-chai';
+import { CliChannel } from '../../../src/cli';
+import { ToolNotFoundError } from '../../../src/tools';
+import { LoginUtil } from '../../../src/util/loginUtil';
+
+const { expect } = chai;
+chai.use(sinonChai);
+
+suite('util/loginUtil.ts', () => {
+    let sandbox: sinon.SinonSandbox;
+    let executeSyncToolStub: sinon.SinonStub;
+
+    setup(() => {
+        sandbox = sinon.createSandbox();
+        executeSyncToolStub = sandbox.stub(CliChannel.getInstance(), 'executeSyncTool');
+    });
+
+    teardown(() => {
+        sandbox.restore();
+    });
+
+    suite('requireLogin()', () => {
+        test('returns false when oc whoami and api-versions succeed', async () => {
+            executeSyncToolStub.onFirstCall().resolves('https://api.cluster:6443\n');
+            executeSyncToolStub.onSecondCall().resolves('apps/v1\nv1\n');
+
+            const result = await LoginUtil.Instance.requireLogin();
+            expect(result).to.be.false;
+        });
+
+        test('returns true when oc whoami fails with regular error', async () => {
+            executeSyncToolStub.rejects(new Error('connection refused'));
+
+            const result = await LoginUtil.Instance.requireLogin();
+            expect(result).to.be.true;
+        });
+
+        test('returns true when api-versions returns empty', async () => {
+            executeSyncToolStub.onFirstCall().resolves('https://api.cluster:6443\n');
+            executeSyncToolStub.onSecondCall().resolves('');
+
+            const result = await LoginUtil.Instance.requireLogin();
+            expect(result).to.be.true;
+        });
+
+        test('propagates ToolNotFoundError from oc whoami', async () => {
+            executeSyncToolStub.rejects(new ToolNotFoundError('oc'));
+
+            try {
+                await LoginUtil.Instance.requireLogin();
+                expect.fail('should have thrown');
+            } catch (error) {
+                expect(error).to.be.instanceOf(ToolNotFoundError);
+                expect((error as ToolNotFoundError).toolName).to.equal('oc');
+            }
+        });
+
+        test('propagates ToolNotFoundError from api-versions', async () => {
+            executeSyncToolStub.onFirstCall().resolves('https://api.cluster:6443\n');
+            executeSyncToolStub.onSecondCall().rejects(new ToolNotFoundError('oc'));
+
+            try {
+                await LoginUtil.Instance.requireLogin();
+                expect.fail('should have thrown');
+            } catch (error) {
+                expect(error).to.be.instanceOf(ToolNotFoundError);
+            }
+        });
+
+        test('returns true when server URI does not match', async () => {
+            executeSyncToolStub.onFirstCall().resolves('https://api.cluster:6443\n');
+
+            const result = await LoginUtil.Instance.requireLogin('https://other.cluster:6443');
+            expect(result).to.be.true;
+        });
+    });
+});