diff --git a/src/goDebugConfiguration.ts b/src/goDebugConfiguration.ts
index 6d5fa13a21..1044788f21 100644
--- a/src/goDebugConfiguration.ts
+++ b/src/goDebugConfiguration.ts
@@ -11,9 +11,9 @@ import path = require('path');
 import vscode = require('vscode');
 import { getGoConfig } from './config';
 import { toolExecutionEnvironment } from './goEnv';
-import { promptForMissingTool, promptForUpdatingTool, shouldUpdateTool } from './goInstallTools';
+import { declinedToolInstall, promptForMissingTool, promptForUpdatingTool, shouldUpdateTool } from './goInstallTools';
 import { packagePathToGoModPathMap } from './goModules';
-import { getToolAtVersion } from './goTools';
+import { getTool, getToolAtVersion } from './goTools';
 import { pickProcess, pickProcessByName } from './pickProcess';
 import { getFromGlobalState, updateGlobalState } from './stateUtils';
 import { getBinPath, resolvePath } from './util';
@@ -233,8 +233,15 @@ export class GoDebugConfigurationProvider implements vscode.DebugConfigurationPr
 		const debugAdapter = debugConfiguration['debugAdapter'] === 'dlv-dap' ? 'dlv-dap' : 'dlv';
 		const dlvToolPath = getBinPath(debugAdapter);
 		if (!path.isAbsolute(dlvToolPath)) {
-			await promptForMissingTool(debugAdapter);
-			return;
+			const tool = getTool(debugAdapter);
+
+			// If user has not already declined to install this tool,
+			// prompt for it. Otherwise continue and have the lack of
+			// dlv binary be caught later.
+			if (!declinedToolInstall(debugAdapter)) {
+				await promptForMissingTool(debugAdapter);
+				return;
+			}
 		}
 		debugConfiguration['dlvToolPath'] = dlvToolPath;
 
diff --git a/src/goInstallTools.ts b/src/goInstallTools.ts
index 197d6e45f7..05f3328370 100644
--- a/src/goInstallTools.ts
+++ b/src/goInstallTools.ts
@@ -304,11 +304,18 @@ export async function installTool(
 	return result;
 }
 
+export function declinedToolInstall(toolName: string) {
+	const tool = getTool(toolName);
+
+	// If user has declined to install this tool, don't prompt for it.
+	return !!containsTool(declinedInstalls, tool)
+}
+
 export async function promptForMissingTool(toolName: string) {
 	const tool = getTool(toolName);
 
 	// If user has declined to install this tool, don't prompt for it.
-	if (containsTool(declinedInstalls, tool)) {
+	if (declinedToolInstall(toolName)) {
 		return;
 	}
 
@@ -338,7 +345,9 @@ export async function promptForMissingTool(toolName: string) {
 	const installOptions = ['Install'];
 	let missing = await getMissingTools(goVersion);
 	if (!containsTool(missing, tool)) {
-		return;
+		// If this function has been called, we want to display the prompt whether
+		// it appears in missing or not.
+		missing.push(tool);
 	}
 	missing = missing.filter((x) => x === tool || tool.isImportant);
 	if (missing.length > 1) {
@@ -558,6 +567,17 @@ function getMissingTools(goVersion: GoVersion): Promise<Tool[]> {
 			(tool) =>
 				new Promise<Tool>((resolve, reject) => {
 					const toolPath = getBinPath(tool.name);
+					if (tool.name === 'dlv-dap') {
+						// Check if user already has dlv-dap binary.
+						// If so, it's likely the user may be interested in updating the tool,
+						// so we should mark it as important and return as a missing tool.
+						if (path.isAbsolute(toolPath)) {
+							tool.isImportant = true;
+							resolve(tool);
+							return;
+						}
+						tool.isImportant = false;
+					}
 					resolve(path.isAbsolute(toolPath) ? null : tool);
 				})
 		)
diff --git a/src/goTools.ts b/src/goTools.ts
index b88b33317b..8a61b7b118 100644
--- a/src/goTools.ts
+++ b/src/goTools.ts
@@ -158,6 +158,7 @@ export function getConfiguredTools(
 	// families are 64-bit, so just try to install it and hope for the best.
 	if (process.arch.match(/^(arm64|mips|mipsel|ppc64|s390|s390x|x64)$/)) {
 		maybeAddTool('dlv');
+		maybeAddTool('dlv-dap');
 	}
 
 	// gocode-gomod needed in go 1.11 & higher