diff --git a/src/debugger/debugAdapterFactory.ts b/src/debugger/debugAdapterFactory.ts
index eca0a3f83..f3c46b6b9 100644
--- a/src/debugger/debugAdapterFactory.ts
+++ b/src/debugger/debugAdapterFactory.ts
@@ -244,7 +244,7 @@ export class LLDBDebugConfigurationProvider implements vscode.DebugConfiguration
     }
 
     async promptForCodeLldbSettingsIfRequired(toolchain: SwiftToolchain) {
-        const libLldbPathResult = await getLLDBLibPath(toolchain);
+        const libLldbPathResult = await getLLDBLibPath(toolchain, this.logger);
         if (!libLldbPathResult.success) {
             const errorMessage = `Error: ${getErrorDescription(libLldbPathResult.failure)}`;
             void vscode.window.showWarningMessage(
diff --git a/src/debugger/lldb.ts b/src/debugger/lldb.ts
index 0a3cf6d80..a47bd5988 100644
--- a/src/debugger/lldb.ts
+++ b/src/debugger/lldb.ts
@@ -17,6 +17,7 @@ import * as fs from "fs/promises";
 import * as path from "path";
 import * as vscode from "vscode";
 
+import { SwiftLogger } from "../logging/SwiftLogger";
 import { SwiftToolchain } from "../toolchain/toolchain";
 import { Result } from "../utilities/result";
 import { IS_RUNNING_UNDER_TEST, execFile } from "../utilities/utilities";
@@ -45,11 +46,15 @@ export function updateLaunchConfigForCI(
  *
  * @returns Library path for LLDB
  */
-export async function getLLDBLibPath(toolchain: SwiftToolchain): Promise<Result<string>> {
+export async function getLLDBLibPath(
+    toolchain: SwiftToolchain,
+    logger?: SwiftLogger
+): Promise<Result<string>> {
     let executable: string;
     try {
         executable = await toolchain.getLLDB();
     } catch (error) {
+        logger?.error(`Failed to get LLDB path from the toolchain, error: ${error}`);
         return Result.makeFailure(error);
     }
     let pathHint = path.dirname(toolchain.swiftFolderPath);
@@ -68,6 +73,7 @@ export async function getLLDBLibPath(toolchain: SwiftToolchain): Promise<Result<
         // should just the version of lldb that comes with CodeLLDB. We return a failure with no message
         // to indicate we want it to fail silently.
         if (process.platform === "win32") {
+            logger?.error(`Failed to get LLDB library path for lldb on Windows, error: ${error}`);
             return Result.makeFailure(undefined);
         }
     }
diff --git a/test/integration-tests/debugger/lldb.test.ts b/test/integration-tests/debugger/lldb.test.ts
index b0a4c1c2c..e70c0d679 100644
--- a/test/integration-tests/debugger/lldb.test.ts
+++ b/test/integration-tests/debugger/lldb.test.ts
@@ -40,7 +40,10 @@ suite("lldb contract test suite", () => {
     });
 
     test("getLLDBLibPath Contract Test, make sure we can find lib LLDB", async () => {
-        const libPath = await getLLDBLibPath(workspaceContext.globalToolchain);
+        const libPath = await getLLDBLibPath(
+            workspaceContext.globalToolchain,
+            workspaceContext.logger
+        );
 
         // Check the result for various platforms
         if (process.platform === "linux") {