diff --git a/src/build.ts b/src/build.ts
new file mode 100644
index 00000000..d4c56749
--- /dev/null
+++ b/src/build.ts
@@ -0,0 +1,103 @@
+// Copyright (c) Microsoft Corporation. All rights reserved.
+// Licensed under the MIT license.
+import * as path from "path";
+import * as vscode from "vscode";
+import { sendError, setErrorCode, setUserError } from "vscode-extension-telemetry-wrapper";
+
+import * as anchor from "./anchor";
+import * as commands from "./commands";
+import * as lsPlugin from "./languageServerPlugin";
+import * as utility from "./utility";
+
+export async function buildWorkspace(): Promise<boolean> {
+    try {
+        await commands.executeJavaExtensionCommand(commands.JAVA_BUILD_WORKSPACE, false);
+    } catch (err) {
+        return handleBuildFailure(err);
+    }
+
+    return true;
+}
+
+async function handleBuildFailure(err: any): Promise<boolean> {
+    if (err instanceof utility.JavaExtensionNotActivatedError) {
+        utility.guideToInstallJavaExtension();
+        return false;
+    }
+
+    const error: Error = new utility.UserError({
+        message: "Build failed",
+    });
+    setErrorCode(error, Number(err));
+    sendError(error);
+
+    if (err === lsPlugin.CompileWorkspaceStatus.WITHERROR || err === lsPlugin.CompileWorkspaceStatus.FAILED) {
+        if (checkErrorsReportedByJavaExtension()) {
+            vscode.commands.executeCommand("workbench.actions.view.problems");
+        }
+
+        const ans = await vscode.window.showErrorMessage("Build failed, do you want to continue?",
+            "Proceed", "Fix...", "Cancel");
+        if (ans === "Proceed") {
+            return true;
+        } else if (ans === "Fix...") {
+            showFixSuggestions();
+        }
+
+        return false;
+    }
+
+    return true;
+}
+
+function checkErrorsReportedByJavaExtension(): boolean {
+    const problems = vscode.languages.getDiagnostics() || [];
+    for (const problem of problems) {
+        const fileName = path.basename(problem[0].fsPath || "");
+        if (fileName.endsWith(".java") || fileName === "pom.xml" || fileName.endsWith(".gradle")) {
+            if (problem[1].filter((diagnostic) => diagnostic.severity === vscode.DiagnosticSeverity.Error).length) {
+                return true;
+            }
+        }
+    }
+
+    return false;
+}
+
+async function showFixSuggestions() {
+    let buildFiles = [];
+    try {
+        buildFiles = await lsPlugin.resolveBuildFiles();
+    } catch (error) {
+        // do nothing
+    }
+
+    const pickitems = [];
+    pickitems.push({
+        label: "Clean workspace cache",
+        detail: "Clean the stale workspace and reload the window",
+    });
+    if (buildFiles.length) {
+        pickitems.push({
+            label: "Update project configuration",
+            detail: "Force the language server to update the project configuration/classpath",
+        });
+    }
+    pickitems.push({
+        label: "Troubleshooting guide",
+        detail: "Find more detail about the troubleshooting steps",
+    });
+
+    const ans = await vscode.window.showQuickPick(pickitems, {
+        placeHolder: "Please fix the errors in PROBLEMS first, then try the fix suggestions below.",
+    });
+    if (ans.label === "Clean workspace cache") {
+        vscode.commands.executeCommand("java.clean.workspace");
+    } else if (ans.label === "Update project configuration") {
+        for (const buildFile of buildFiles) {
+            await vscode.commands.executeCommand("java.projectConfiguration.update", vscode.Uri.parse(buildFile));
+        }
+    } else if (ans.label === "Troubleshooting guide") {
+        utility.openTroubleshootingPage("Build failed", anchor.BUILD_FAILED);
+    }
+}
diff --git a/src/commands.ts b/src/commands.ts
index e1a93e3f..81636136 100644
--- a/src/commands.ts
+++ b/src/commands.ts
@@ -32,6 +32,8 @@ export const JAVA_CHECK_PROJECT_SETTINGS = "vscode.java.checkProjectSettings";
 
 export const JAVA_RESOLVE_ELEMENT_AT_SELECTION = "vscode.java.resolveElementAtSelection";
 
+export const JAVA_RESOLVE_BUILD_FILES = "vscode.java.resolveBuildFiles";
+
 export function executeJavaLanguageServerCommand(...rest) {
     // TODO: need to handle error and trace telemetry
     if (!utility.isJavaExtEnabled()) {
diff --git a/src/configurationProvider.ts b/src/configurationProvider.ts
index fd8ae173..110f0906 100644
--- a/src/configurationProvider.ts
+++ b/src/configurationProvider.ts
@@ -8,6 +8,7 @@ import * as vscode from "vscode";
 
 import { instrumentOperation } from "vscode-extension-telemetry-wrapper";
 import * as anchor from "./anchor";
+import { buildWorkspace } from "./build";
 import * as commands from "./commands";
 import * as lsPlugin from "./languageServerPlugin";
 import { detectLaunchCommandStyle } from "./launchCommand";
@@ -163,22 +164,9 @@ export class JavaDebugConfigurationProvider implements vscode.DebugConfiguration
                 }
 
                 if (needsBuildWorkspace()) {
-                    try {
-                        const buildResult = await commands.executeJavaExtensionCommand(commands.JAVA_BUILD_WORKSPACE, false);
-                    } catch (err) {
-                        if (err instanceof utility.JavaExtensionNotActivatedError) {
-                            utility.guideToInstallJavaExtension();
-                            return undefined;
-                        }
-
-                        const ans = await utility.showErrorMessageWithTroubleshooting({
-                            message: "Build failed, do you want to continue?",
-                            type: Type.USAGEERROR,
-                            anchor: anchor.BUILD_FAILED,
-                        }, "Proceed", "Abort");
-                        if (ans !== "Proceed") {
-                            return undefined;
-                        }
+                    const proceed = await buildWorkspace();
+                    if (!proceed) {
+                        return undefined;
                     }
                 }
 
diff --git a/src/languageServerPlugin.ts b/src/languageServerPlugin.ts
index 9d67f0a3..8b640c66 100644
--- a/src/languageServerPlugin.ts
+++ b/src/languageServerPlugin.ts
@@ -5,6 +5,13 @@ import * as vscode from "vscode";
 
 import * as commands from "./commands";
 
+export enum CompileWorkspaceStatus {
+    FAILED = 0,
+    SUCCEED = 1,
+    WITHERROR = 2,
+    CANCELLED = 3,
+}
+
 export interface IMainClassOption {
     readonly mainClass: string;
     readonly projectName?: string;
@@ -77,3 +84,7 @@ export async function detectPreviewFlag(className: string, projectName: string):
 export function resolveElementAtSelection(uri: string, line: number, character: number): Promise<any> {
     return <Promise<any>>commands.executeJavaLanguageServerCommand(commands.JAVA_RESOLVE_ELEMENT_AT_SELECTION, uri, line, character);
 }
+
+export function resolveBuildFiles(): Promise<string[]> {
+    return <Promise<string[]>>commands.executeJavaLanguageServerCommand(commands.JAVA_RESOLVE_BUILD_FILES);
+}
diff --git a/src/utility.ts b/src/utility.ts
index cdc29fde..66c4dc80 100644
--- a/src/utility.ts
+++ b/src/utility.ts
@@ -86,17 +86,21 @@ export async function showErrorMessageWithTroubleshooting(message: ITroubleshoot
 
 function handleTroubleshooting(choice: string, message: string, anchor: string): string | undefined {
     if (choice === LEARN_MORE) {
-        vscode.commands.executeCommand("vscode.open", vscode.Uri.parse(anchor ? `${TROUBLESHOOTING_LINK}#${anchor}` : TROUBLESHOOTING_LINK));
-        logger.log(Type.USAGEDATA, {
-            troubleshooting: "yes",
-            troubleshootingMessage: message,
-        });
+        openTroubleshootingPage(message, anchor);
         return;
     }
 
     return choice;
 }
 
+export function openTroubleshootingPage(message: string, anchor: string) {
+    vscode.commands.executeCommand("vscode.open", vscode.Uri.parse(anchor ? `${TROUBLESHOOTING_LINK}#${anchor}` : TROUBLESHOOTING_LINK));
+    logger.log(Type.USAGEDATA, {
+        troubleshooting: "yes",
+        troubleshootingMessage: message,
+    });
+}
+
 export async function guideToInstallJavaExtension() {
     const MESSAGE = "Language Support for Java is required. Please install and enable it.";
     const INSTALL = "Install";