diff --git a/package.json b/package.json
index 81128aa16bb6..5de98e8a3bcb 100644
--- a/package.json
+++ b/package.json
@@ -1768,8 +1768,8 @@
         "unicode": "^10.0.0",
         "untildify": "^3.0.2",
         "unzip": "^0.1.11",
-        "vscode-debugadapter": "^1.0.1",
-        "vscode-debugprotocol": "^1.0.1",
+        "vscode-debugadapter": "^1.28.0",
+        "vscode-debugprotocol": "^1.28.0",
         "vscode-extension-telemetry": "^0.0.14",
         "vscode-languageclient": "^3.1.0",
         "vscode-languageserver": "^3.1.0",
diff --git a/src/client/debugger/mainV2.ts b/src/client/debugger/mainV2.ts
index 53f4d60d17cd..bcb9a9d26e8c 100644
--- a/src/client/debugger/mainV2.ts
+++ b/src/client/debugger/mainV2.ts
@@ -69,6 +69,10 @@ export class PythonDebugger extends DebugSession {
         body.supportsConditionalBreakpoints = true;
         body.supportsSetVariable = true;
         body.supportsExceptionOptions = true;
+        body.supportsEvaluateForHovers = true;
+        body.supportsModulesRequest = true;
+        body.supportsValueFormattingOptions = true;
+        body.supportsSetExpression = true;
         body.exceptionBreakpointFilters = [
             {
                 filter: 'raised',
diff --git a/src/test/debugger/capabilities.test.ts b/src/test/debugger/capabilities.test.ts
new file mode 100644
index 000000000000..8052b5f6f2dc
--- /dev/null
+++ b/src/test/debugger/capabilities.test.ts
@@ -0,0 +1,103 @@
+// Copyright (c) Microsoft Corporation. All rights reserved.
+// Licensed under the MIT License.
+
+'use strict';
+
+// tslint:disable:no-suspicious-comment max-func-body-length no-invalid-this no-var-requires no-require-imports no-any
+
+import { expect } from 'chai';
+import { ChildProcess, spawn } from 'child_process';
+import * as getFreePort from 'get-port';
+import { connect, Socket } from 'net';
+import * as path from 'path';
+import { PassThrough } from 'stream';
+import { Message } from 'vscode-debugadapter/lib/messages';
+import { DebugProtocol } from 'vscode-debugprotocol';
+import { EXTENSION_ROOT_DIR } from '../../client/common/constants';
+import { createDeferred } from '../../client/common/helpers';
+import { ProtocolParser } from '../../client/debugger/Common/protocolParser';
+import { ProtocolMessageWriter } from '../../client/debugger/Common/protocolWriter';
+import { PythonDebugger } from '../../client/debugger/mainV2';
+import { sleep } from '../common';
+import { IS_MULTI_ROOT_TEST, TEST_DEBUGGER } from '../initialize';
+
+class Request extends Message implements DebugProtocol.InitializeRequest {
+    // tslint:disable-next-line:no-banned-terms
+    public arguments: any;
+    constructor(public command: string, args: any) {
+        super('request');
+        this.arguments = args;
+    }
+}
+
+suite('Debugging - Capabilities', () => {
+    let disposables: { dispose?: Function; destroy?: Function }[];
+    let proc: ChildProcess;
+    setup(async function () {
+        if (!IS_MULTI_ROOT_TEST || !TEST_DEBUGGER) {
+            this.skip();
+        }
+        disposables = [];
+    });
+    teardown(() => {
+        disposables.forEach(disposable => {
+            try {
+                disposable.dispose!();
+                // tslint:disable-next-line:no-empty
+            } catch { }
+            try {
+                disposable.destroy!();
+                // tslint:disable-next-line:no-empty
+            } catch { }
+        });
+        try {
+            proc.kill();
+            // tslint:disable-next-line:no-empty
+        } catch { }
+    });
+    test('Compare capabilities', async () => {
+        const protocolWriter = new ProtocolMessageWriter();
+        const initializeRequest: DebugProtocol.InitializeRequest = new Request('initialize', { pathFormat: 'path' });
+
+        const debugClient = new PythonDebugger(undefined as any);
+        const inStream = new PassThrough();
+        const outStream = new PassThrough();
+        disposables.push(inStream);
+        disposables.push(outStream);
+        debugClient.start(inStream, outStream);
+        const debugClientProtocolParser = new ProtocolParser();
+        debugClientProtocolParser.connect(outStream);
+        disposables.push(debugClientProtocolParser);
+        const expectedResponsePromise = new Promise<DebugProtocol.InitializeResponse>(resolve => debugClientProtocolParser.once('response_initialize', resolve));
+        protocolWriter.write(inStream, initializeRequest);
+        const expectedResponse = await expectedResponsePromise;
+
+        const host = 'localhost';
+        const port = await getFreePort({ host });
+        const env = { ...process.env };
+        env.PYTHONPATH = path.join(EXTENSION_ROOT_DIR, 'pythonFiles', 'experimental', 'ptvsd');
+        proc = spawn('python', ['-m', 'ptvsd', '--server', '--port', `${port}`, '--file', 'someFile.py'], { cwd: __dirname, env });
+        // Wait for the socket server to start.
+        // Keep trying till we timeout.
+        let socket: Socket | undefined;
+        for (let index = 0; index < 1000; index += 1) {
+            try {
+                const connected = createDeferred();
+                socket = connect({ port, host }, () => connected.resolve(socket));
+                socket.on('error', connected.reject.bind(connected));
+                await connected.promise;
+                break;
+            } catch {
+                await sleep(500);
+            }
+        }
+        const protocolParser = new ProtocolParser();
+        protocolParser.connect(socket!);
+        disposables.push(protocolParser);
+        const actualResponsePromise = new Promise<DebugProtocol.InitializeResponse>(resolve => protocolParser.once('response_initialize', resolve));
+        protocolWriter.write(socket!, initializeRequest);
+        const actualResponse = await actualResponsePromise;
+
+        expect(actualResponse.body).to.deep.equal(expectedResponse.body);
+    });
+});
diff --git a/yarn.lock b/yarn.lock
index 19893afaaa94..7027a7bdcfbc 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -1826,7 +1826,7 @@ gulp-untar@^0.0.6:
     tar "^2.2.1"
     through2 "~2.0.3"
 
-gulp-util@^3.0.0, gulp-util@^3.0.7, gulp-util@~3.0.0, gulp-util@~3.0.7, gulp-util@~3.0.8:
+gulp-util@^3.0.0, gulp-util@^3.0.7, gulp-util@~3.0.8:
   version "3.0.8"
   resolved "https://registry.yarnpkg.com/gulp-util/-/gulp-util-3.0.8.tgz#0054e1e744502e27c04c187c3ecc505dd54bbb4f"
   dependencies:
@@ -3904,7 +3904,7 @@ ret@~0.1.10:
   version "0.1.15"
   resolved "https://registry.yarnpkg.com/ret/-/ret-0.1.15.tgz#b8a4825d5bdb1fc3f6f53c2bc33f81388681c7bc"
 
-retyped-diff-match-patch-tsd-ambient@^1.0.0-1:
+retyped-diff-match-patch-tsd-ambient@^1.0.0-0:
   version "1.0.0-1"
   resolved "https://registry.yarnpkg.com/retyped-diff-match-patch-tsd-ambient/-/retyped-diff-match-patch-tsd-ambient-1.0.0-1.tgz#26482bf4915c7ed9f8300bb5cbec48fd4ff5bc62"
 
@@ -4835,16 +4835,21 @@ vscode-debugadapter-testsupport@^1.27.0:
   dependencies:
     vscode-debugprotocol "1.27.0"
 
-vscode-debugadapter@^1.0.1:
-  version "1.27.0"
-  resolved "https://registry.yarnpkg.com/vscode-debugadapter/-/vscode-debugadapter-1.27.0.tgz#0688f7d03d7568efd653003ecdb402b7ba37231e"
+vscode-debugadapter@^1.28.0:
+  version "1.28.0"
+  resolved "https://registry.yarnpkg.com/vscode-debugadapter/-/vscode-debugadapter-1.28.0.tgz#ebd6653e3f41db324d9547595375571a8732e966"
   dependencies:
-    vscode-debugprotocol "1.27.0"
+    vscode-debugprotocol "1.28.0"
+    vscode-uri "1.0.1"
 
-vscode-debugprotocol@1.27.0, vscode-debugprotocol@^1.0.1:
+vscode-debugprotocol@1.27.0:
   version "1.27.0"
   resolved "https://registry.yarnpkg.com/vscode-debugprotocol/-/vscode-debugprotocol-1.27.0.tgz#735a43a3cc1235fe587c0ef93fe4e328def7b17c"
 
+vscode-debugprotocol@1.28.0, vscode-debugprotocol@^1.28.0:
+  version "1.28.0"
+  resolved "https://registry.yarnpkg.com/vscode-debugprotocol/-/vscode-debugprotocol-1.28.0.tgz#b9fb97c3fb2dadbec78e5c1619ff12bf741ce406"
+
 vscode-extension-telemetry@^0.0.14:
   version "0.0.14"
   resolved "https://registry.yarnpkg.com/vscode-extension-telemetry/-/vscode-extension-telemetry-0.0.14.tgz#17454705b6bb8757351b955d812923f02ee895bf"
@@ -4879,6 +4884,10 @@ vscode-languageserver@^3.1.0:
     vscode-languageserver-protocol "3.5.1"
     vscode-uri "^1.0.1"
 
+vscode-uri@1.0.1:
+  version "1.0.1"
+  resolved "https://registry.yarnpkg.com/vscode-uri/-/vscode-uri-1.0.1.tgz#11a86befeac3c4aa3ec08623651a3c81a6d0bbc8"
+
 vscode-uri@^1.0.1:
   version "1.0.3"
   resolved "https://registry.yarnpkg.com/vscode-uri/-/vscode-uri-1.0.3.tgz#631bdbf716dccab0e65291a8dc25c23232085a52"